orange beach catamaran

Sailing & Catamaran Cruises

In gulf shores & orange beach.

Imagine gliding across crystal-clear turquoise waters, catching glimpses of dolphins or pausing to fish and enjoy the views of sugar-white sand and beautiful foliage. Those who embark on Gulf Shores and Orange Beach sailing adventures get the opportunity to do just that. From the large expanses of Gulf waters to the tucked away back bays, there are many places in the area to explore by boat when on a sailing vacation.

Find Sailing Adventures

• Orange Beach (4)
• Wheelchair accessible (1)

Cetacean Dolphin and Sailing Cruises

For over twenty years, people have found the entertainment and relaxation they've been searching for with us. We offer several...

Back Bay Sailing Adventures

Let’s cast off the lines and sail whichever way the wind takes us. Explore the beautiful back bays of Gulf...

Sail Wild Hearts

Sail Wild Hearts offers a variety of daily options to the general public. We offer Family Adventure sails, Kayak Adventure...

Sail OB An Orange Beach Sailing Adventure

Come experience true offshore sailing just 10 minutes from our dock. We offer Gulf sailing adventures specializing in family day...

SAILING ACTIVITIES

Gulf Shores and Orange Beach are excellent areas to sail from. The Alabama Coastal region is pristine and the waters are teeming with sea life. There are many options for getting out onto the water and each has its own benefit. Chartered tours allow you to see hidden pockets or special local gems. The cruise captains also know where the action is—whether it’s dolphin sightings, diving or the best fishing holes.

While sailing is an activity in of itself, there are also many other options during your time on Gulf waters.

Fishing   – Fishing is prolific in Alabama's Gulf Coast. It’s also a straightforward process to find out about regulations, permits, what’s in season, and more. If you go the  fishing charter  route, guides will provide you with the information you need to kick off a successful trip. Some popular “catches” include grouper, shrimp, crab, king mackerel and mullet.

Diving  – It’s a true adventure to explore what lives under the surface.  Diving  is a popular sailing activity in the Gulf Shores area. During a sailing/diving excursion, you can check out wrecks, sea life and other treasures hidden in the depths.

Nature viewing  – From  Perdido Key  to Dauphin Island, Gulf Shores and Orange Beach holds many species of  gulf coast birds , fish and wildlife in the water, air and on land. Alabama’s Gulf Coast is popular with birders who come to see numerous species and abundant seabirds here year-round. In the water, you’ll find dolphins, fish and maybe even a manatee. On the shores, you'll be sure to spot some sea turtles, butterfly migrations and alligators!

Bring Your Own Boat

Or Rent One

For some people, bringing their own boat is considered the perfect vacation. Luckily for them, Gulf Shores and Orange Beach are boat-friendly areas. With 11 boat launches and plenty of parking, bringing your sailboat is easy. You’ll find many maintenance and repair shops as well as  marinas  stocked with the essentials for boating. The Gulf Shores sailing community is friendly and will surely send you to some stunning spots.

Sailing Charters

Several outfitters offer sailing excursions with a captain. Some guides will whisk you across the bay and allow you to bring your own cooler of food and drink. Others take you on nature excursions, which are designed to show you the areas that have abundant wildlife viewing. You’ll also find different times for Gulf Shores sailing tours. Dinner sailing is popular and catching an epic sunset is often the goal. However, all of the tours are ideal for capturing those picture-perfect scenes, so don’t leave your camera behind.

Boat Rentals

If you have experience on the water, you may want to choose a sailboat rental instead of a cruise. Gulf Shores and Orange Beach have outfitters that offer  boat rentals  for the experienced captains. Sailboat rentals are an excellent way to explore the Gulf without a timeline. Talk to the locals about great spots and spend full days or more discovering the Gulf.

You May Also Like

• Subscribe to Enews
• Vacation Guide
• Chat With Us

The Experience

Elevate your vacation with the wild hearts experience.

What makes a spectacular sail? At Wild Hearts, we believe it’s creating every cruise for the comfort and pleasure of our passengers. That’s why we have one of the most spacious and seaworthy sailboats operating on the Alabama Gulf Coast. It’s why our trips are designed to treat you to some of the best scenes and activities available in our area. Most importantly, it’s why our coast guard-licensed crew is committed to handling every step of the sail – leaving you free to relax and enjoy the ride.

No matter which excursion you choose, you can trust that Wild Hearts will deliver the ultimate Gulf Shores, Perdido Key or Orange Beach sailing experience. Here’s what to expect on your next Wild Hearts adventure.

A 53 ft Sailing Catamaran

Wild Hearts is a Gold Coast 53-foot catamaran sailboat designed for open-ocean sailing. Public cruises and private sailing charters depart from Orange Beach, Perdido Key, and Gulf Shores.

A Seaworthy Ride

Built in St. Croix USVI, this US Coast Guard certified vessel is made of strip planked cedar and epoxy for unrelenting strength and durability. Her spacious decks and cabin spaces are designed to provide you with premium comfort as we ride the cresting waves. With a mast that rises 53ft in the air and a sail area of over 1000 square feet, she will easily whisk you away at double digit speeds – even as her wide 30-foot beam ensures you have a safe, smooth, and seaworthy sail.

Why Wait for Someday?

From its hull to its heart, Wild Hearts was crafted to provide our passengers with the ultimate sailing experience. It’s not just the quality craftsmanship that makes this vessel so spectacularly seaworthy – it’s the little details in her design that bring something amazing to every adventure.

A spacious 53-foot deck comfortably accommodates up to 49 passengers

Her multi-level design provides an opportunity to meet in groups or break away for peaceful privacy., a covered cabin below deck gives shelter from the elements., an onboard bar provides a space for complimentary refreshments and snacks, an accommodating and professional crew is included., two restrooms are on the boat for your convenience..

The Wild Hearts crew is aware of your safety, comfort, and enjoyment at all times. You’re in good hands with our Coast Guard-licensed master skipper and crew – who are always ready to serve and sail!

Come Aboard Wild Hearts with Captain Zach Smith

Captain Zach Smith – also known as Captain Zach “Sparrow” – may not be a pirate, but he shares the love of wind, salt and sea that often lies in a sailor’s heart.

Zach is a homegrown ‘Bama boy raised in Auburn, Alabama. Alabama fans beware: Capt. Zach may make you walk the plank.

Feeling the pull to explore island life, Capt. Zach eventually moved to the Virgin Islands. He spent five years in St. John where he spent his spare time learning to sail, paddleboard, dive and wind surf. He loved it so much that when he finally headed back to Alabama, he sought out a job that would keep him on the water. His coastal home took some of the stress out of his search – at his first job interview he was told to sail a small Hobie Cat through the beach surf and back again. He sailed through with flying colors and has never looked back.

Today, Captain Zach spends his days sailing Wild Hearts around the spectacular waters of Orange Beach and Perdido Key. He knows the local waters and enjoys introducing people to his passion for sailing. He and his crew welcome you aboard and sincerely hope you have an adventure you’ll keep in your heart forever.

When asked why he sails Captain Zach answers, “Sailing gives me such freedom; I feel at home on the water, and it is never the same twice.”

Sail away with Deckhand Brittney Vandiver

Brittney Vandiver joined the crew of the Wild Hearts for the 2020 season. Although relatively new to the Wild Hearts, she earned her status as a boating and tourism industry veteran long ago. The daughter of a boat captain, life on the water came naturally. Brittney could be found tagging along with her father at the marina while still in diapers. She began her journey as a deckhand in 1999 at the age of 12 by helping her parents start a dining and dolphin cruise business in Orange Beach, Alabama. She will be entering her 24th season in 2022!

Brittney is married with two children. Avery, her son, is 11, and her daughter, Haley, is 7. Her husband, Daniel, unsurprisingly is also a U.S. Coast Guard licensed captain. Brittney was born and raised on the Gulf Coast. Boating and the Gulf of Mexico are deeply rooted parts of her life. Helping guests experience the joy of boating, and the beauty of the Gulf Coast is what makes her the happiest.

RESERVATIONS

251-981-6700.

WILD HEARTS is located in Orange Beach, Alabama directly across the street from the PERDIDO BEACH RESORT 27101 Perdido Beach Blvd. (Hwy 182) Latitude: 30.278934 Longitude: -87.561368

BACK BAY SAILING ADVENTURES

Sailing cruises in orange beach, alabama.

• MOST POPULAR!

SUNSET ESCAPE

Bring your own spirits and escape with us on our signature sunset cruise! Book your cruise and let the sound of the wind and water relax you!

• Hour Glass 2 hours
• Clock 6 p.m.

Buy Gift Certificate

Private 2 hour sailing trip for up to six guest.

FEATURED ACTIVITIES

• Clock 2 p.m.

PRIVATE DAY CRUISE

Book this private day cruise and enjoy the peaceful sounds of the wind and the water. Watch for dolphins playing and pelicans flying over the bay.

• Hour Glass 4 hours
• Clock 11 p.m.

BACK BAY ADVENTURE SAIL

Book your Back Bay Adventure Sail to explore the back bays of Alabama and Florida! We most always see dolphins. Learn basic sailing navigation or kick back and relax.

• Clock 11 a.m.

11AM 2 Hour Day Sail

Enjoy your 2 hour cruise in the Back Bays of Orange Beach, Alabama!

BEST SUNSET OR DAY SAILING TRIP IN ORANGE BEACH & GULF SHORES!

Sailing in Orange Beach, Alabama and Gulf Shores, Alabama is a one-of-a-kind experience. Whether you choose a family day cruise or a relaxing sunset sail, you will not be disappointed. Back bay sailing is a top ten thing to do while on vacation. Sit back and relax to the soothing sounds of the breeze in the sails and the water beneath you.

Keep a lookout for wildlife. We almost always see dolphins playing and swimming with the boat. Back Bay Sailing Adventures offers a unique opportunity to observe eagles nesting, osprey fishing, pelicans coasting across the bays and the occasional otter in the bayou. Sunset sailing with Back Bay Sailing Adventures in Orange Beach is an unforgettable experience and family-friendly adventure. We are located at Bear Point Harbor in Orange Beach, Alabama.

HAPPY VACATIONERS RATE US 5 STARS!

We very much enjoyed our Sunset Sailing cruise. What a wonderful way to spend our special anniversary! Thank you to Captain Harold and Melanie who were great hosts on their beautiful yacht! It was such a relaxing sail, beautiful sunset ...calm waters... it was a very special evening. We highly recommend sailing with Back Bay Sailing Adventures when vacationing in Orange Beach/Gulf Shores and can’t wait to return for another sail!

Our family of 4 adults and an 8 year old boarded at 5:45 pm for a beautiful, relaxing and enjoyable sunset cruise. Although the wind was not always cooperative we had a great trip. Probably the highlight of the trip was when Darryl let Ava “captain” the ship. Thanks to all

Booked back bay sailing with 5 of my girlfriends for something different for our annual beach trip. Highlight of our trip!! Perfect day. Hosts were SO accommodating and made it a blast. 5 stars all around!! Can’t wait to come back!!!

One of the best things I’ve ever done on a vacation. Melanie and Harold were the perfect hosts. It was a wonderful experience being able to spend an evening on the water and having the sailboat to ourselves. Great with our 9 year old, too!

This was absolutely an awesome evening with family and friends! Capt. Harold was very knowledgeable of the area and a joy to sail with. Very relaxing!

Orange Beach Sailing Charters

Sailing charters in gulf shores, alabama, welcome to orange beach sailing charters....

We are excited about this upcoming summer and we are ready to take you, your loved ones and family on the best “private” sailing charter on the Alabama Gulf Coast. Come along with Captain Ryan or Captain Randy on our fabulous sailing yachts, “ Sailob ” and “ Attitude “. We are the premier sailing cruise line serving Orange Beach and Gulf Shores, Alabama. Take one of our Gulf Shores sailing charters out on the water today!

Book Your Sailing Charters Online!

• most popular!
• User All ages
• Users Up to 6 passengers
• Hour Glass 2 hours

2-Hour Getaway Sail

Sail out to the Gulf of Mexico or the Bay (depending on conditions and customer preference). You will be able to see the Perdido Pass bridge, the pass and the jetties. Book your sailing charter in Orange Beach today!

• Hour Glass 4 hours

4-Hour Adventure Sail

The four-hour Adventure Sail goes to the Gulf under the Perdido Pass Bridge and down the beach either towards Gulf Shores, passing all of Orange Beach, or sail down to Florida depending on the wind direction and customer preference. Book your sailing charter online!

• Hour Glass 8 hours

All Day Sailing Charter

The ALL DAY sailing charter in Gulf Shores is a great way to experience sailing Orange Beach and Pensacola to the fullest. Book your charter online today!

Sunset Sailing Charter

Let your imagination take you away on this luxurious sailing yacht and sunset sail in Orange Beach, AL. Coastal Alabama has some of the most romantic and beautiful views that you can see from the water while on a cruise. Book your sunset cruise in the Gulf Shores online today!

Book Your Orange Beach Sailing Charters Online!

All day and overnight adventures give you time to relax and take in the beautiful coastline.

Dolphin Sightings

We see dolphins! No noise from the engine means more happy dolphins in the water.

Family Day Trips

Children love our two and four hour day trips. Perfect escape from the beach and shopping.

Romantic Sunsets

Sunset trips make for an unforgettable experience on the Alabama coast.

Our Gulf Shores sailing charters are professionally operated with an experienced crew. We offer convenience and save you time by allowing you to book your sailing charter online. We are also conveniently located in Orange Beach so it does not take long to get you offshore and sailing the calm seas of the Gulf of Mexico. We make your life easier than it was before you found us. Don’t panic if you forgot drinks, we have water to keep you hydrated. We encourage you to bring your camera, bathing suit, and sunglasses.  Flip flops are always optional with Orange Beach Sailing Charters .

Our sailing yachts can accommodate up to six passengers while sailing in Orange Beach and Gulf Shores. Orange Beach Sailing Charters specializes in small group sailing charters and family eco tours. Young and older couples also frequent our yachts to share romantic moments together. Your kids will love our Orange Beach sailing charters. Children enjoy learning about local marine life like dolphins, sea turtles, seagulls, pelicans, cormorants, manatees and gain nautical knowledge about sailing the boat. When you charter your sailing trip with us, you are chartering the boat for only your group. Book your charter to start your sailing in Gulf Shores, Alabama today!

500+ 5-Star Reviews Of Our Excursions In Orange Beach, Al!

Excellent trip with Captain Randy. We did the sunset cruise which was excellent. We even saw several dolphins in the bay. Highly recommend as Captain Randy runs a professional and safe operation.

Having previously sailed with Captain Ryan and loved it; we got the opportunity to sail with Captain Randy on a 4 hour charter. Highly recommended. Focused on making sure you have the experience you are looking for. Very knowledgeable and enjoyable to chat with. Orange Beach Sailing Charters is great!

This was our first private sailboat ride in Orange Beach Al. And we had a blast! Captain Randy was great. Funny, informative, and very accommodating. There were six of us. Mema, gramps, mom, dad, and two teenagers. Captain Randy showed us some of the most valuable properties in Alabama. We were very happy with our sunset cruise. And we highly recommend This sailboat experience.

Great sunset cruise the other night. Randy is a fantastic captain and host. We booked the private sunset cruise for our anniversary. Our 1st try was rained out, but Randy was great at trying to accommodate and we made it at the end of the week. Thanks Randy. We will be back.

Would recommend anyone new to sailing to try the Orange Beach Sailing Charters. They provided good customer service up front and a better experience out on the water. My wife and I selected the 2 hour tour during the afternoon and thoroughly enjoyed being out on the water. Captain Randy was an excellent guide and offered much information about the area. Hope to get out there again in the future for a longer session.

Great experience. We took the sunset cruise. Private charter for 6 people. Hard pressed to find a better value. This was a relaxing cruise in the Gulf. Captain Randy is friendly, entertaining, and professional. So much better than riding in a boat with 60 strangers. Zero complaints. Couldn’t have been better.

We had a wonderful time sailing with Captain Randy. What an experience! We enjoyed his knowledge and great stories. We will see you next time we are in town Capt!

Captain Randy was a delight to sail with. He was very knowledgeable and had lots of experience. We all felt extremely comfortable and safe in his hands. Our trip was mid-day and we had a bit of an un-sure weather pattern. But, Captain Randy still made our trip adventurous and fun!! We can't wait to sail with Captain Randy on our next trip.

Orange Beach Sun and Sailing Cruise aboard Catamaran

• All Fees and Taxes
• Full-service cocktail bar available for purchase. Bring valid ID
• 4673 Wharf Pkwy W, Orange Beach, AL 36561, USA Find us in Orange Beach, Alabama, at The Wharf Entertainment District, we are located directly in front of The Springhill Suites by Marriot on the West End Side of the Marina. Our address is 4673 Wharf Parkway West, Orange Beach, Alabama 36561.
• Infants must sit on laps
• Near public transportation
• Not wheelchair accessible
• Confirmation will be received at time of booking
• Not recommended for travelers with back problems
• No heart problems or other serious medical conditions
• Travelers should have a moderate physical fitness level
• We have been able to accommodate most requests. Please call us at 251-550-8000 to discuss your needs with our staff.
• Minimum of 18 pounds in order to board. Infants weighing less than 18 pounds will not be permitted to board.
• This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund
• This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund
• This tour/activity will have a maximum of 40 travelers
• For a full refund, cancel at least 24 hours in advance of the start date of the experience.

Similar experiences

• You'll start at 4673 Wharf Pkwy W 4673 Wharf Pkwy W, Orange Beach, AL 36561, USA Find us in Orange Beach, Alabama, at The Wharf Entertainment District, we are located directly in front of The Springhill Suites by Marriot on the West End Side of the Marina. Our address is 4673 Wharf Parkway West, Orange Beach, Alabama 36561. See address & details
• 1 Orange Beach Stop: 2 hours Have you ever experienced a sailing adventure aboard a two-hull sailboat? Two hulls provide stability, ensuring a smooth, relaxing ride. Come enjoy a two-hour sail in Orange Beach aboard the Cetacean, a 52-foot Hawaiian catamaran. With the wind in our sails, the Cetacean skims along the waters of Orange Beach, Alabama and Perdido Key, Florida. While out sailing, watch the mesmerizing sight of wildlife in their natural habitat as schools of fish surround the boat, our playful dolphins come to say hello, and marine birds dive into the water for breakfast or lunch. We also often spot bald eagles, egrets, herons, osprey, and seagulls flying by! This relaxing Alabama cruise is perfect for couples, families, and groups of friends. Read more
• You'll return to the starting point

• Linda J 0 contributions 5.0 of 5 bubbles Dolphins! This was a good tour. We saw dolphins and the captain spent enough time in the area of the sightings to ensure that all passengers were given opportunities to see/watch them. The captain and crew were entertaining during the cruise which livened things up a bit. Read more Written March 19, 2024
• NYWanderer 0 contributions 5.0 of 5 bubbles Lots of Dolphins Very pleasant hour and a half cruise. Saw lots of dolphins. As they are in a restricted area, chances are good that you will see some dolphins. We saw loads. They are small so you don't see a lot of their bodies but what we saw was good. Snacks (chips, cookies, etc.) and drinks (soda and alcohol) are offered on board for a cost. Staff was anxious for everyone to have a good time. It was a lovely, interesting boat ride. Read more Written March 17, 2024
• dec0shah 0 contributions 4.0 of 5 bubbles Sugar Beach ⛱️🏖️ Convince to the places we planned for rooms were really nice with balcony only concern was the dryer in room was really loud need to be serviced Read more Written March 17, 2024
• William J 0 contributions 5.0 of 5 bubbles Sunset Cruise We had a wonderful time on the sun set cruise!! It was definitely a great experience and topped it off with getting to see some dolphins as a bonus. Captain Johnny was amazing and so were all the bartenders!! Read more Written March 15, 2024
• P2733PSbettyc 0 contributions 5.0 of 5 bubbles Great The captain and the crew were very good It was a great experience It was our honeymoon and the first time that we were in Orange Beach. My husband thought that I had wasted my money because he didn't think that we would see any dolphins. When he saw a lot of them he was surprised he even told the captain that he was surprised. We had a great experience. We can't wait to come back again. Thanks Betty Cumbie Read more Written March 15, 2024
• Christine T 0 contributions 5.0 of 5 bubbles Great experience and would recommend The staff and captain were very friendly. We were able to see several dolphins. Enjoyed the facts shared. Was nice to have the drinks and snacks. Read more Written March 14, 2024
• G9530OEsheilas 0 contributions 5.0 of 5 bubbles Great Tour! We took this tour to celebrate my husband's birthday. We had such a great time! The crew was so much fun. We saw lots of birds and dolphins. Would defintely take this tour again next time we're in town. Read more Written March 13, 2024
• Y9829DAanonymous 0 contributions 5.0 of 5 bubbles Great experience for all ages! This is a great experience for all ages. My kids 13&11 enjoyed seeing all the dolphins. My son even got to “drive” the boat. Well worth the money. They do offer beverages on board and snacks for a fee. Because it is a smaller boat it's not over crowded which is a huge bonus. Highly recommend. Read more Written March 13, 2024
• 452carat 0 contributions 5.0 of 5 bubbles Loved it! LOVED everything about this experience! Captain was very personable, crew very friendly, drinks delish, very relaxing and we saw pods of dolphins 🐬 Read more Written March 12, 2024
• nicoleromerodesign 0 contributions 5.0 of 5 bubbles So much fun! My husband and I are local and decided to give this Sunset Dolphin and Nature cruise a shot for our 10th Anniversary. After we signed up we received a text with clear directions as well as instructions to follow upon arrival. Check in was quick and easy. The captain was a lot of fun and knowledgeable and the crew/bartenders were also upbeat and friendly. We were fortunate, it was gorgeous weather and there was no shortage of dolphins. We even had them jumping behind us in the waves created by the boat. The drinks and music created a fun and relaxed atmosphere. We would love to do this cruise again or one of the other ones in the near future. If you’re wondering there are bathrooms before you leave and a small one on board for emergencies. I highly recommend this to anyone who is looking for something fun and unique to do with family, friends, or on a date. Read more Written March 8, 2024
• jeaninem820 0 contributions 5.0 of 5 bubbles Wild Weber Women went on the Water The crew was incredibly welcoming, the dolphins were fun, and the Wild Weber Women had a blast celebrating milestone birthdays on The Explorer. We will definitely bring additional friends and family for more experiences! Read more Written March 7, 2024
• Brian R 0 contributions 5.0 of 5 bubbles Dolphin Sunset cruise at Orange, Beach, Alabama Best cruise to go on if you want to see lots of dolphins and an eagle or two. The boat crew were a lot of fun and helped us to have an enjoyable tour. Read more Written March 7, 2024
• BKSP813 0 contributions 5.0 of 5 bubbles The dolphins were showing off Although the mostly overcast skies made for a less than magnificent beach sunset, the dolphins were making their appearance around the catamaran-beside and in front of it! Service & servers/mates were friendly and attentive. Beautiful evening. Read more Written March 7, 2024
• allifromWI 0 contributions 3.0 of 5 bubbles Main goal delivered, I guess, but not the best experience We encountered a fair number of dolphins, which was the selling point for the tour. I probably would have given them a 4 or 5 if it weren't for two things: they encourage people to get up & walk around, which was really chaotic with a full boat and made it harder to actually see the dolphins. Secondly, when we were heading back, they were encouraging everyone to feed the birds Cheez Its and other stuff that really isn't healthy for humans, but it's really unhealthy for the birds. That was really disappointing, especially since the captain seemed to have a lot of knowledge about and cared about the birds. He should have known that encouraging close human interaction and feeding the birds garbage isn't healthy for the birds. Read more Written March 6, 2024
• gbendure98 0 contributions 5.0 of 5 bubbles Geo and Mindy Loved the dolphins great weather and captain and crew. Fun time great sunset smooth sailing. First time my wife was on a sailboat. She loved the whole experience Read more Written March 6, 2024

More to explore in Orange Beach

Most Recent: Reviews ordered by most recent publish date in descending order.

Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as wait time, length of visit, general tips, and location information.

Orange Beach Sun and Sailing Cruise aboard Catamaran provided by Cetacean Cruises

• Sunset Cruise
• Bachelorette/Bachelor
• Ft. Mcree/Blue Angels Trips
• Dolphin Cruise
• Kayak Tours
• Book Online

About the Daedalus

The Daedalus takes her name from a legendary figure in Greek mythology. Daedalus* was a brilliant architect, inventor, builder, and puzzle-solver. He designed and built the Labyrinth, a maze used to imprison the half-man, half-bull Minotaur.

Sailing Charter in Gulf Shores & Orange Beach, AL

You can leave your worries behind when you set sail on the Daedalus for a gorgeous Gulf Coast sailing trip. The Daedalus cruises the gulf waters of Orange Beach and Gulf Shores Alabama with a warm ocean breeze and a beautiful sunset as a backdrop. We offer the most affordable trips in the Gulf Coast […]

Call Us to Reserve a Trip Today!

251.987.1228

Or http://www.sailthedaedalus.com/dating-berkshire/ .

Sailing Charters in Gulf Shores & Orange Beach, AL

Photo gallery.

Trip Options

• Day Cruises
• Sunset Cruises
• Bachelorette/Bachelor Trips
• Wedding, Anniversary Event Cruises
• Twilight Cruises
• Ft. McRee Trips
• Shrimping Cruises
• Private Cruises

Copyright © 2015 - All Rights Reserved JimBills.com

Dolphins Down Under

The best glass bottom dolphin cruise in oba, choose your adventure.

• Most Popular!
• Hour Glass 1.5 hours , Dolphins Guaranteed

Glass Bottom Dolphin Cruise

Explore the Gulf Coast and experience wild dolphins in their natural environment on our popular glass bottom dolphin cruise in Orange Beach. Reserve your spot today!

• Hour Glass 1.25 hours

Sunset Dolphin Cruise

Enjoy the last light of the day as you look for dolphins and other marine life aboard our gorgeous glass bottom boat. You just can’t beat an Orange Beach sunset on the water!

• Hour Glass 1.5 hours

Private Boat Charter

You can charter a private boat for anything from a birthday party to a company outing, church outing, school event, or even a family reunion.

DDU Exclusive Adult Cruise

Join us on our NEW Adult Only Adventure while seeing fantastic views and new faces to mingle with!

Orange Beach's Best Guided Dolphin Tours

"Absolutely Wonderful Experience!!! Captain Schmidty and 1st mate Bill were so kind and knowledgeable!!!Highly Recommend !!!! Sunset tour was so enjoyable and Beautiful!!! Saw several dolphins!!!!! Thanks So Much Dolphins Down Under.... Bill also made a yummy Pink Dolphin drink for us "

"Dolphins Down Under was a fantastic experience. My wife and I went on the sunset cruise and we both felt you couldn't beat the value of an amazing guided tour and beautiful sunset background. We saw several dolphins and really had a wonderful time. The team of guys that run this charter are fantastic and they truly make the ride an awesome experience."

"My kids, my parents and I went out on a dolphin cruise and had a wonderful time! I highly recommend! The staff was wonderful and my son loved being about to drive the boat! We saw lots of dolphins and even saw a baby dolphin! Great time for family of all ages! We will definitely be back! Thanks again captain Schmidty and Zoe for a great time!"

"My family loved both the dolphin cruise and the snorkeling adventure. Staff went out of their way to find dolphins (which we saw lots of) and even made my children feel comfy while snorkeling. We will surely book with them again! Thanks for the memories!"

Sail Wild Hearts Blu Horizon

27200 Perdido Beach Blvd , Orange Beach , Alabama

Wild Hearts is setting sail for gulf adventures on the Alabama Gulf Coast. Come board this 53-foot, open-ocean catamaran and sail the turquoise waters of Orange Beach and Gulf Shores, Alabama and Perdido Key, Florida. Daily cruises are available with excursions just off the shore, offering views of white-sand beaches. 

Why choose an ordinary dolphin cruise when you can lift anchor and set sail with us? You'll enjoy an island stop where kayaks, paddleboards and snorkeling await you. 

Parasail aboard the Sky Surfer - from the Perdido Beach Resort Dock.

Alabama Extreme Watersports - Facebook

Aquatic Adventures and Adrenaline Rushes on the Alabama Gulf Coast

Experience a wide range of thrilling maritime ventures. From dolphin encounters, to jet skiing and airborne expeditions, we’ve got plenty of ways to play.

© 2024 Coast360

• Sunset Charters
• 2 Hour Getaway Sail
• 4 Hour Adventure Sail
• All Day Sailing Fun Package
• Reservations

Orange Beach & Gulf Shores Alabama Sunset Sailing Charters

Welcome back for spring & summer.

Sunset sailing charters in Orange Beach, Alabama is the most popular afternoon activity on the entire Gulf Coast.  Let your imagination take you away on the Gulf Shores island's most luxurious sailing yacht and sunset charter.  Coastal Alabama has some of the most romantic and beautiful views that you can see from the water while on a sailing cruise.  Whether you are a young couple just getting started in life or have been together for 25 years or longer, let us take you and your loved one to a place where you can cherish the memory for a lifetime.

Orange Beach Sunset Sailing Charters offers year-round private and shared expense sailing charters for vacationers staying in Fort Morgan, Gulf Shores, Orange Beach, Alabama and Perdido Key, Florida.   We carry a maximum of 6 people on our sailboat, The SAILob.  OB is for Orange Beach and our name is pronounced "Sail Oh Bee."   Most of our sunset sailing charters are made up of people just like you and your family.  Watching the sun set over the Alabama coastal waters while you are sailing is a breathtaking experience.  There is nothing better than sharing that sailing experience with the one you love or your family.

Most recent photo!

Sailob is easy to find and are just minutes away, no matter where you are staying on the Alabama coastline.  For those of you with a GPS, we set sail from our pier located at the Hudson Marina - 4575 South Wilson Boulevard in Orange Beach, Alabama 36561

Fill up your senses with a sunset sailing charter

Orange Beach Sailing Charters offers laid back sailing charters that stimulates the entire family.  You can relax and unwind as the gentle ocean breeze fills our main sail and catapults you into one of the quietest places you have ever been.  You feel the wind blowing over our upper deck and through your hair.  Imagine closing your eyes for a moment.  You will feel the warmth of the afternoon sun touching your face and taking you away to another place in time.  Sunset sailing allows you watch the Summer Sun as it sinks below the Gulf Shores horizon.  The smell of the salt air and the sounds of nature are two of senses that will be stimulated when you join us on one of our sunset sailing adventures.

Escape, relax, rejuvenate and unwind with us

So, turn off your cell phone and leave it in your Orange Beach condo or hotel room for a few hours.  Come along with Orange Beach Sailing Adventures and let us help you escape reality and enter into a whole new world of Gulf Shores vacations.  You will be amazed how good you will feel while you are spending some private time with the ones you love.

Benefits of sunset sailing in Orange Beach along Alabama's Gulf Shores

The most beautiful white sandy beaches are located on the Alabama Gulf Coast.  We have 32 miles of pristine beaches you can look at from a whole new perspective from the water.  Sailing with us, will allow you to see the Alabama beaches from a whole new perspective.  You will see first hand all of the amazing things that makes Orange Beach Sailing Charters unique.

• We are Orange Beach's truly green business and are eco friendly to the environment
• The privacy you get while sailing with us is priceless
• The intimacy you can have with the one you love is amazing
• See marine birds like Seagulls, Pelicans, Ospreys and Herrons
• See marine mammals like Wild Dolphins and Manatees
• See marine reptiles like Sea Turtles
• See marine life like Jelly Fish and large schools of Fish breaking the waters surface

© 1998 - 2024 | View Our Privacy Policy | This site last updated on 3/19/2024

We are open! Providing a safe and clean environment per CDC guidelines for customer and staff safety

DOLPHIN & SAILING CRUISES

Orange beach, alabama, space is limited book online today.

Aboard The Explorer, dolphin sightings are guaranteed, or your next trip is free!

Reservations for our Orange Beach, AL dolphin and nature cruises or our sailing trips are not required, but are STRONGLY recommended as they are the only way to guarantee your seat on the boat.  Please arrive 30 minutes prior to departure and register your group at our kiosk. The captain invites guests to board the boat when all groups have arrived. Our two-hour dolphin and nature cruise in Orange Beach combines all the features of the dolphin cruise with extra floating time through the hidden creeks of the back bays. We spend the entire time locating and observing our local dolphin pod and other wildlife.

*Please note: we are not handicapped accessible, and we do not permit strollers onboard*

• Most Popular Cruises!
• Hour Glass 2 Hours

Dolphin and Nature Eco Tour

The Dolphin and Nature Eco Tour is a fan favorite! Get to know our resident dolphins and enjoy other wildlife sightings on this family-friendly cruise!

Sunset Dolphin & Nature Cruise

This 2 hour cruise offers the same experience as our Dolphin and Nature Eco tour, with all the ambiance of a beautiful, bay sunset! What a great way to end your day!

Sunset Sailing Cruise

Sail off into the sunset on our stable and comfortable catamaran as we experience the bays of Orange Beach! Keep a lookout for dolphins and Orange Beach’s local wildlife on this relaxing sailing excursion.

Dolphin Eco Tour

The best highlight of your afternoon in Gulf Shores and Orange Beach is on our dolphin cruise! Spot our playful friends and get to know who’s who in the pod with our expert guides. On this tour, we focus solely on dolphins!

Sun & Sailing Cruise

You can enjoy one of our signature cocktails while getting some sun. With the wind in our sails, the Cetacean skims along the waters of Orange Beach, Alabama and Perdido Key, Florida. While out sailing, you see coastal wildlife and marine life all around.

• Hour Glass 1.5 hours

Early Bird Private Cruise

This is the ultimate social distancing private cruise! Join us, exclusively, on our pontoon-style vessel for a morning 1.5 hour dolphin excursion aboard the Explorer. The Explorer features a full-service cocktail bar, onboard restroom, and bench-style seating throughout.

Private Custom Wedding Cruises

Call: (251) 550-8000 | What better way to commemorate a marriage or other special event than at sail! Private charters are available for groups of up to 40 guests.

Private Sailing Cruises

Call: (251) 550-8000 | Have you ever experienced a sailing adventure aboard a two-hull sailboat? Two hulls provide stability for a smooth ride without leaning to one side.

Local News | Four-day expo at fairgrounds all about getting…

Share this:.

• Click to share on Facebook (Opens in new window)
• Click to share on Twitter (Opens in new window)
• Click to share on Reddit (Opens in new window)
• Click to print (Opens in new window)
• Orange County
• Things to Do

Local News | Four-day expo at fairgrounds all about getting outdoors

Children dropped lines, hoping to catch a trout, while standing in the middle of the county fairgrounds in Costa Mesa on Thursday, March 7.

It was the opening day of the Pacific Coast Sportfishing Tackle, Boat, Travel and Outdoors Show, visiting for the 14th year.

Michael Bravo, 5, center, reels in a rainbow trout with the assistance of Jonathon Shute of Offishial Business Outdoors, left, and his father Roger Bravo at the Kid’s Trout Pond at the 14th annual Pacific Coast Sportfishing Tackle, Boat, Travel and Outdoor show at the OC Fair and Events Center in Costa Mesa on Thursday, March 7, 2024. After being caught the fish are then released back into the pool. (Photo by Leonard Ortiz, Orange County Register/SCNG)

Visitors examine fishing yachts at the 14th annual Pacific Coast Sportfishing Tackle, Boat, Travel and Outdoor show at the OC Fair and Events Center in Costa Mesa on Thursday, March 7, 2024. The show runs from March 2-5. (Photo by Leonard Ortiz, Orange County Register/SCNG)

Fishing and boating enthusiast checkout the 47-foot Freeman 47 fishing catamaran at the 14th annual Pacific Coast Sportfishing Tackle, Boat, Travel and Outdoor show at the OC Fair and Events Center in Costa Mesa on Thursday, March 7, 2024. The show runs from March 2-5. (Photo by Leonard Ortiz, Orange County Register/SCNG)

Visitors at the 14th annual Pacific Coast Sportfishing Tackle, Boat, Travel and Outdoor show at the OC Fair and Events Center in Costa Mesa on Thursday, March 7, 2024 are dwarfed by the giant outboard motors. The show runs from March 2-5. (Photo by Leonard Ortiz, Orange County Register/SCNG)

An excited Emily Villavicencio, 5, left, reels in a rainbow trout with the assistance of Jonathon Shute of Offishial Business Outdoors at the kid’s trout pound at the 14th annual Pacific Coast Sportfishing Tackle, Boat, Travel and Outdoor show at the OC Fair and Events Center in Costa Mesa on Thursday, March 7, 2024. After being caught the fish are then released back into the pool. (Photo by Leonard Ortiz, Orange County Register/SCNG)

Rainbow trout swim in a pool at the Kid’s Fishing Pond, sponsored by Offishial Business Outdoors at the 14th annual Pacific Coast Sportfishing Tackle, Boat, Travel and Outdoor show at the OC Fair and Events Center in Costa Mesa on Thursday, March 7, 2024. The show runs from March 2-5. (Photo by Leonard Ortiz, Orange County Register/SCNG)

Claire Chamberlain, 5, of Costa Mesa examines a Peregrine falcon from Adam’s Falconry Service at the 14th annual Pacific Coast Sportfishing Tackle, Boat, Travel and Outdoor show at the OC Fair and Events Center in Costa Mesa on Thursday, March 7, 2024. The show runs from March 2-5. (Photo by Leonard Ortiz, Orange County Register/SCNG)

Giavanna Baham holds a Harris hawk named Fawkes at the Adam’s Falconry Service booth at the 14th annual Pacific Coast Sportfishing Tackle, Boat, Travel and Outdoor show at the OC Fair and Events Center in Costa Mesa on Thursday, March 7, 2024. The show runs from March 2-5. (Photo by Leonard Ortiz, Orange County Register/SCNG)

Men talk boats at the 14th annual Pacific Coast Sportfishing Tackle, Boat, Travel and Outdoor show at the OC Fair and Events Center in Costa Mesa on Thursday, March 7, 2024. The show runs from March 2-5. (Photo by Leonard Ortiz, Orange County Register/SCNG)

Visitors pass by fishing yachts at the 14th annual Pacific Coast Sportfishing Tackle, Boat, Travel and Outdoor show at the OC Fair and Events Center in Costa Mesa on Thursday, March 7, 2024. The show runs from March 2-5. (Photo by Leonard Ortiz, Orange County Register/SCNG)

The family-friendly event features manufacturers and dealers of outdoor products, tons of boats, travel lodges and more, as well as kids’ activities, live music and expert seminars. There are two trout fishing ponds set up for kids to try for a catch – which they will also release.

Organizers said this year’s show will feature more boat buying opportunities and several new manufacturers and retail shops. It is spanning seven of the fairground’s halls, making for  217,000 square feet of show experience that continues through Sunday.

“My husband is a big fisherman. We have a boat and we go out pretty often, but he wants to get into kite fishing so he wanted to come and scout it out,” said Samantha Villavicencio of Escondido, who was at the kid’s fishing pond with her two children Logan, 3, and Villavicencio, 5.

“This is my first time to the show, but my husband mentioned there were activities for the kids,” she said, “so we all came because we want to make sure our kids get into fishing.”

When: Noon to 7 p.m. on March 8; 10 a.m. to 7 p.m. on March 9; and 10 a.m. to 5 p.m. on  March 10

Where: OC Fair & Event Center, 88 Fair Drive, Costa Mesa

Cost: $20 general admission, free for children 12 and younger and active duty military with ID, $12 parking

Information: sportfishingfestival.com, ocfair.com

• Newsroom Guidelines
• Report an Error

More in Local News

Local News | Irvine considers new trails to connect hikers to Crystal Cove

Local News | Anaheim demolishes motel on Beach Boulevard, plans to build affordable housing

Local News | Mission San Juan Capistrano welcomes the Return of the Swallows

Local News | Santiago Canyon College dean driven to empower students to ensure success

• Share full article

Frugal Traveler

A Cheapskate in Monterey

We put the California county, known for its exclusive towns and fancy golf courses, to the frugal test, combining a hefty dose of stunning nature with affordable restaurants, budget lodgings and a few splurges.

The jellyfish exhibit at the Monterey Bay Aquarium in Monterey, Caif. At $59.95 for admission, the aquarium, the author writes, “is a worthy splurge, offering opportunities to encounter creatures large, small, wondrous and rare.” Credit... Jason Henry for The New York Times

Supported by

By Elaine Glusac

Elaine Glusac is the Frugal Traveler columnist, focusing on budget-friendly tips and journeys.

• March 20, 2024

My first view of Monterey Bay on California’s Central Coast was thrilling — a raft of 40-something sea otters — and free. The next time I would get close to them, at the Monterey Bay Aquarium , it cost nearly $60. That split between free access to outdoor wonders and investment-grade attractions epitomized my experience in the area.

Like so much of coastal California, the Monterey Peninsula, home to famous Pebble Beach golf courses and exclusive towns like Carmel-by-the-Sea (known simply as Carmel), connotes wealth. It is encompassed by Monterey County, a roughly 3,300-square-mile area, which includes Big Sur, where accommodations at luxury resorts like the Post Ranch Inn start at around $1,500 a night.

With a budget of less than half of that for three days, I put Monterey — the town and the county — to the frugal test. In January, a quiet and thrifty time of year, I trusted parks and preserves, unsung hotels and small businesses to keep things economical, even if sampling the variety of Monterey — ranging from historic cities to redwood forests, tide pools and vineyards — required renting a car ($175).

Seeking Steinbeck

My introduction to Monterey, John Steinbeck’s 1945 classic novel “Cannery Row,” describes its waterfront lined in sardine canneries as “a poem, a stink, a grating noise, a quality of light, a tone, a habit, a nostalgia, a dream.” It’s hard to find that gritty romance along today’s Cannery Row , which boomed in the 1930s and ’40s, before overfishing killed supply.

Now chains such as Bubba Gump Shrimp Co. and Sunglass Hut replace “weedy lots and junk heaps,” though a central plaza with bronze sculptures of Steinbeck and some of his characters pays tribute to the past.

Still, the spirit of the book’s protagonist, Doc — a marine biologist based on the real-life scientist Ed Ricketts — lives on at the Monterey Bay Aquarium, which is housed in the former Hovden Cannery. At $59.95 for admission, the aquarium is a worthy splurge, offering opportunities to encounter creatures large, small, wondrous and rare.

“We bring the ocean to people to inspire them with things they might not get to see otherwise,” said Madi Frazier, an aquarium naturalist, as she guided me to a kelp forest modeled on the one found just beyond the bayfront building’s glass walls.

A wing devoted to deepwater ecology held bright red bloody-belly comb jellyfish, stringy bioluminescent siphonophores and four-foot-high Japanese spider crabs that inched along in the gloom. A dune-style aviary offered opportunities to observe a normally skittish red knot at close range. Bat rays glided beneath tentative fingers in shallow touch tanks.

A few blocks away, Katie Blandin named her five-year-old cocktail bar Pearl Hour after “the hour of the pearl,” described in “Cannery Row” as “the interval between day and night when time stops and examines itself.”

We met during happy hour — 6 to 8 p.m. Wednesday through Sunday — when classic cocktails such as the Corpse Reviver No. 2 go for $10 (normally $13). Ms. Blandin plants the bar’s back patio in succulents, flowers and herbs, many of which make their way into her cocktails.

“I think even a cocktail should have a sense of terroir,” she said.

Old Monterey

The oldest part of Monterey — an outpost of Spain and then Mexico dating back to the 17th century — lies just over a mile south of Cannery Row in a pedestrian-friendly downtown where signs flag historic adobe buildings.

Among several modestly priced hotels there, I booked the Hotel Abrego , where my $130-a-night room included a Keurig coffee machine and spacious glassed-in shower. Its $20 nightly resort fee, included in the room total, covered parking, a hot breakfast buffet and a glass of wine.

It was easy walking distance to lively Alvarado Street, lined in restaurants and shops. A 19th-century complex, the Cooper Molera Adobe , includes an orchard, barn and house museum (free) behind its walls, and the Alta Bakery and Cafe , where I sipped coffee ($3) on the tranquil patio.

Down the block, Ad Astra Bread Co . sells aromatic loaves of sourdough ($10 each) from Ron Mendoza, the former pastry chef at the Michelin-starred Aubergine in nearby Carmel.

“For the last five years, some of our leading chefs have abandoned fine dining and opened artisanal food businesses,” said Deborah Luhrman, the editor and publisher of the food magazine Edible Monterey Bay , who recommended both bakeries.

The brewpub Alvarado Street Brewery was buzzing when I stopped in for a quinoa bowl ($16) and a Mai Tai tropical I.P.A. for $8. Nearby, my favorite cheap find, El Charrito Express , served substantial barbacoa wraps stuffed with marinated beef, beans and rice for $6.99.

Chancing it in Carmel

From the outset, it felt like a losing bet to take my penny-pinching budget to chic Carmel-by-the-Sea, the one-square-mile seaside town where the actor Clint Eastwood was once mayor.

Even getting there comes at a price: 17-Mile Drive , the coastal scenic route, costs $12 to drive. Fortunately, it’s free to cyclists, which helped take the edge off the cost of the bike I rented to explore some of Monterey’s celebrated cycling routes .

From the bike shop Mad Dogs & Englishmen in Monterey, I rented an electric bike ($40 for four hours) to assist in the long ride — about 28 miles round-trip — and its hills. The deal included free valet parking for my car at the adjacent Monterey Place Hotel & Spa.

On a cool January morning, frothy aquamarine waves broke on the granite rocks that barricaded the coast, tempting me to stop every half mile or so to admire their churn. A thick fog blew in as I reached the area’s renowned shorefront links, dramatizing their sand bunkers and wind-shorn cypress trees. I passed a landscape painter and jaw-dropping Pebble Beach mansions before coasting into Carmel.

Amid luxury retailers like Tiffany and Bottega Veneta I found the new Korean restaurant Jeju Kitchen in the outdoor Carmel Plaza . My salmon rice bowl was not cheap at $26, but it was delicious, substantial and only a few dollars more than food truck options at the Carmel Farmers Market across the street.

Monarchs, redwoods and waterfalls

It was far easier to stretch my budget seeking nature in Monterey, home to 99 miles of coastline.

I started at the 2.4-acre Pacific Grove Monarch Sanctuary , where mature Monterey pine trees attract overwintering butterflies that are known to cluster in groups of up to 1,000 from November through February (free).

Using binoculars, I spied bright orange monarchs catching early-morning rays from the tips of pine boughs like mini-solar panels. A pair of deer grazed in the shade below while a set of acorn woodpeckers chattered in the treetops. The abundant bird life drew the attention of two red-shouldered hawks, which glided in silently.

Continuing south along the coast, I spent a sunny afternoon at Point Lobos State Natural Reserve (admission $10). The craggy headland has been the setting for classic Hollywood films, including Alfred Hitchcock’s “Rebecca,” and attracted the photographers Edward Weston and Ansel Adams .

The reserve, which has a special conservation status within the state park system, was created by a land donation to protect its cypress grove, according to Kathleen Lee, the executive director of the nonprofit Point Lobos Foundation , which supports the park with fund-raising and docent training. In a phone interview, she directed me to the forest, noting that it is “one of only two native Monterey cypress groves remaining in California.”

Atop vertiginous cliffs, a trail wound bravely through the wind-sculpted trees. Below them, harbor seals appeared in the backwash of coves. A short drive south, I scrambled over wet rocks at Weston Beach — named for the photographer — to find tide pools filled with sea stars, anemones and hermit crabs.

Waning light chased me from the park as I set out south, eager to make the drive down famously curvy Highway 1 in Big Sur before dark. The rugged coast of towering redwoods and mountains that plunge into the ocean was named El Sur Grande , or the Big South, by Mexican colonizers as an unmapped wilderness.

Twenty-two miles south of Point Lobos, Ripplewood Resort got its start when the highway was being built in the 1920s. I booked a rustic but comfortable cabin there for $135 a night and woke to find it ideally located just a few miles north of Big Sur Bakery , a beacon of artisanal baking that seemed impossible in such a remote location (a Cheddar-and-chive scone cost $5.50).

Ripplewood also lies close to a series of coastal parks, including Pfeiffer Big Sur State Park , where the four-mile Buzzard’s Roost Trail ascended amid redwoods to ridge-top ocean views (admission, $10, good at all state parks for the day). Nine more wiggly miles south, McWay Falls cascades onto a pristine beach at Julia Pfeiffer Burns State Park . Between them, I stopped at frequent turnouts to scan for migrating gray whales exhaling telltale spouts.

A safari and a tasting

The survival of southern sea otters in California is a comeback story. Hunted nearly to extinction for their thick pelts, sea otters managed to hang on in the most remote coves and crags of Big Sur, where a few individuals were discovered in 1938. Now numbering about 3,000, the endangered marine mammals are some of the most charismatic residents in the Central Coast’s kelp beds.

They also thrive in Elkhorn Slough , a coastal wetland preserve in Moss Landing, about 27 miles north of Monterey. There, I boarded an electric catamaran from Monterey Bay Eco Tours to troll the calm waters on a 90-minute cruise ($45).

Within minutes, we spotted harbor seals hauled out on muddy banks shared by marbled godwits, black-necked stilts and whimbrel, some of the park’s more than 300 species of birds. Mother otters fed their babies sea cucumbers, gave them swimming lessons and carried sleeping pups as they floated on their backs.

“Elkhorn Slough is a low-stress environment for them,” said Cindy Rice, a naturalist guide leading the tour.

The drive to my last stop — Monterey’s vineyards — took me through the agricultural flats surrounding Salinas, which grows 70 percent of the nation’s salad greens, some 20 miles to the Salinas Valley , which nurtures pinot noir and chardonnay grapes in the foothills of the Santa Lucia range.

Attracted by vintage tractors, I turned into the family-owned Rustiqué Wines and found its convivial tasting room lodged in a former dairy barn filled not with hushed aficionados swirling and evaluating wine, but with a sociable crowd enjoying glasses of estate pinot noir and oaked chardonnay in the spirit of happy hours everywhere.

The winemaker Chad Silacci and two other family members worked the bar and the crowd. The winery, established in 2006, has built a following through concerts, events and warm hospitality (tastings cost $20, waived with a two-bottle purchase).

“We want it to be comfortable,” Mr. Silacci said, indicating the tasting room’s sofas and chairs arrayed around a wood-burning stove. “It’s kind of like walking into our family’s living room.”

I finished an earthy pinot, thinking the investment, like so many in Monterey, paid unanticipated returns.

Follow New York Times Travel on Instagram and sign up for our weekly Travel Dispatch newsletter to get expert tips on traveling smarter and inspiration for your next vacation. Dreaming up a future getaway or just armchair traveling? Check out our 52 Places to Go in 2024 .

Open Up Your World

Considering a trip, or just some armchair traveling here are some ideas..

Italy :  Spend 36 hours in Florence , seeking out its lesser-known pockets.

Southern California :  Skip the freeways to explore the back roads between Los Angeles and Los Olivos , a 100-mile route that meanders through mountains, canyons and star-studded enclaves.

Mongolia : Some young people, searching for less curated travel experiences, are flocking to the open spaces of this East Asian nation .

Romania :  Timisoara  may be the most noteworthy city you’ve probably never heard of , offering just enough for visitors to fill two or three days.

India: A writer fulfilled a lifelong dream of visiting Darjeeling, in the Himalayan foothills , taking in the tea gardens and riding a train through the hills.

52 Places:  Why do we travel? For food, culture, adventure, natural beauty? Our 2024 list has all those elements, and more .

Advertisement