sailboat rides portland maine

Sailing daily out of Portland's East End!

Relax and enjoy the best views of Portland aboard Nautilus

Grab your favorite bottle of wine and step aboard for an experience you'll always remember. Sail past lighthouses, the historic Fort Gorges, and learn about the rich history of Portland Harbor from our seasoned and passionate crew.

Sail on Casco Bay with us!

Book a sailing adventure for a day trip, sunset cruise or your own private charter in Portland, Maine!

DAY SAILS &

PRIVATE CHARTERS

11:00 AM - 1:00 PM | Morning Sail

3:00 PM - 5:00 PM | Afternoon Sail

$80 per Person | $450 Private Charter

Hop on one of our 2-hour morning or afternoon sails to explore Maine’s diverse and scenic Portland Harbor.

Choose our first trip for a calm morning outing, or join us in the afternoon when the wind picks up. Get on the water with Nautilus Sailing Company for a uniquely memorable Portland, Maine excursion.

SUNSET SAILS & PRIVATE CHARTERS

6:00 - 8:00 PM | Sunset Sail

Fall Hours May Vary

$95 per Person | $550 Private Charter

Sunset sails depart each evening for 2 hours to enjoy golden hour views of Maine’s diverse and scenic Portland Harbor.

Bring your camera and favorite cocktail and get on the water with Nautilus Sailing Company to enjoy the best sunset views of Portland, Maine.

CUSTOM CHARTERS

Starting at $450 |  Call for a Quote

Need an extra hour or some additional flexibility? From intimate wedding ceremonies, to memorable anniversary celebrations, to unique bachelor and bachelorette parties, to corporate outings, our custom private charters are fully customizable to meet your needs.

Call to plan your ideal Portland Harbor sail charter and make your next special event epic!

BOOKING CALENDAR

Have a date in mind? View our Booking Calendar below:

Designed and built to look and feel like the sailing vessels of days gone by, our 37' ketch Nautilus perfectly combines traditional form and modern function.

With a large cockpit and wide cabin tops, you'll find plenty of comfortable seating options for all. Guests are free to move up to the bow for a great view while we're underway. The spacious cabin offers ample space for lounging, eating, or a brief respite from the elements. The galley has all the amenities of home, including an ice box and stove, and there is also a large head (bathroom) with push button facilities-- everything you need to create your ideal Portland excursion. Join us! We're certain you'll be glad you did.

Step aboard the sailboat Nautilus and experience the real magic of Casco Bay.

Relax and unwind as we silence the motor and let the wind take us sailing past lighthouses, between the islands, past historic forts, and even alongside playful porpoises and seals. With Captain Sam and first mate Crow as your seasoned guides, sit back and enjoy the view while you learn about our treasured Maine coast.

• What is the maximum passenger capacity? Nautilus's passenger capacity is 6 people maximum. This is determined by the U.S. Coast Guard so it is not flexible.
• Do infants count towards passenger capacity? Yes. The passenger limit is based on the number of human lives aboard, rather than by seating room.
• Do you take same-day bookings? YES we do! Our booking software with FareHarbor allows for same-day bookings. If a sail during a time slot you are interested in appears to be greyed out, you can give us a call to see if there are any seats remaining. One important thing to note: if the crew are not currently on the boat, it will take us roughly one hour to arrive at the boat and complete an all-systems safety check, so please call as far in advance as possible.
• Will we tip (heel) over? As a sailboat, the Nautilus is designed to lean to one side or the other with the pressure of the wind in her sails, with the extent of that heeling depending on the strength of the wind. If you’d like a more spirited sail, we recommend checking the forecast for winds of 13 knots (roughly 15 miles per hour) or higher. Morning and Sunset Sails tend to be the calmest, while Afternoon Sails are generally more lively. In Portland we usually receive the strongest winds in May, June, September, and October, while July and August are the calmest months.
• Is there a bathroom on board? Yes! We have a marine toilet, also called a head. The marina also has facilities for all guests in the form of 3 single-stall restrooms.
• Are life jackets required to be worn? Due to Federal law, anyone under 13 years of age is required to wear a life jacket on board any commercial vessel that is off the dock. Adults can choose to wear one if it would make them feel comfortable, but it is not required.
• What is your general cancellation policy? Please cancel one week in advance of your sail to receive a full refund. Cancellations made with under one week’s notice will not receive a refund unless they are due solely to sudden illness (see covid-19 policy below).
• What happens if it rains? Nautilus will still depart in mist, light rain, and passing showers. In the event of poor weather or unsafe conditions determined by the Captain at the time of the sail, we will offer to rebook your sail to a more pleasant day or provide you with a refund.
• Do you have a covid-19 / illness refund policy? If you become sick with covid-19, the flu, or any other contagious illness and need to cancel, you will receive a full refund. We appreciate your help in not spreading any illnesses to the crew!

Portland, Maine Historic Fort & Lighthouse Tours

Family friendly civil war fort tours, maine’s iconic lighthouses tour, and 21+ sunset cruises. a local craft beer, canned cocktail, or wine is included for every guest.

• Most Popular!
• User All Ages
• Hour Glass 2 Hours

Fort Tour on a Private Island

Casco Bay’s stone fortresses are captivating characters in the story of Maine history. For the first time, SeaPortland is bringing you to the historic site Fort Scammel via the Elizabeth Grace . Join us for a boat tour no other Portland harbor tour company can offer.    

• Hour Glass 1.5 Hours

Sunset Lighthouse Harbor Cruise

 There is nothing quite like a Maine sunset, especially from the water . Aboard the Elizabeth Grace , with local craft beers in hand, we will take you on a stunning journey through the waters of Casco Bay. Don’t miss this tour!

Scenic Lighthouse Harbor Tour

This epic tour is the best way to take in the historic lighthouses, stone forts, and rocky islands that make Casco Bay a world-renowned destination.

Limited Edition Tour

• Limited Time - Monthly Tour

Maine Island Rum Tasting and Boat Tour

Embark on a one-of-a-kind rum tasting adventure with Sea Portland and Three of Strong Spirits. Cruise Casco Bay to House Island aboard the Elizabeth Grace for a 90-min journey through Portland’ Maine’s candid history with prohibition and rum.

SeaPortland brings you straight into the heart of authentic Maine.

Aboard the Elizabeth Grace and other vessels in our fleet, we show you the parts of Casco Bay unseen by most. We provide experiences that strike at the heart of what makes this part of the world so magical.

Join us for boat tours of previously unexplored early nineteenth-century forts. Bathe in the warm lights of a summer sunset over the water. Breathe in the ocean air while viewing Maine’s famous lighthouses. Toast local craft beverages. What could be better?

Join us for a tour today.

• Chevron down Is there a head (bathroom) on the boat?

There is no bathroom on the boat. We highly recommend using the facilities before boarding. If you are on the Private Island Fort Tour there is a bathroom on the island.

• Chevron down Can I purchase more drinks on the boat?

Yes! Every SeaPortland tour includes 1 canned alcoholic beverage per person (local beer, hard seltzer, wine, canned cocktails). We have complimentary non-alcoholic beverages stocked aboard.

Following the first included beverage, additional beverages can be purchased via credit / debit card on the boat.

• Chevron down Should I tip the crew?

Yes. The boat crew is there to help keep you safe and to tell you about the sights in the harbor. They work hard to make it a great experience! The crew will split tips and for those wondering 20% is the common amount.

• Chevron down Can we bring our own alcohol on board?

No, we have our own license that prohibits guests from bringing their own alcohol on the boat.

• Chevron down Can we bring food on board?

Yes, feel free to bring food on board. We just ask that you also take any trash away with you as well.

• Chevron down Do we have to be 21 to take a tour?

Both our Sunset Tour and Rum Tasting Cruise are 21+.

Our daytime Lighthouse Tour and morning Fort Scammel Tour are for all ages!

• Chevron down What should I wear?

Dress appropriately for the weather. We will have a canopy which will protect you from direct sunlight and rain, however it can be significantly cooler out on the water so we recommend bringing a jacket. On the Fort Tour we highly encourage closed toed shoes.

• Chevron down What is your Cancellation Policy?

All ticket sales are final without Ticket Protection.

Tours cannot be exchanged, rescheduled, or refunded.

Ticket Protection allows you to cancel or reschedule your tour with at least 24 hours’ notice. We will reschedule or reimburse you for your full tour ticket price (minus booking and ticket protection fees).

We operate rain and shine as long as the waters are safe and we have met our minimum number of guests to operate the tour

• Lobstering Schedule
• Special Excursions
• Private Charters
• Gift Certificates
• Vessel Info
• Testimonials
• Order Lobsters

Maine Lobstering Tours

Come join us for an unforgettable excursion on the waters of Casco Bay while we guide you through the daily routines of a Maine Lobsterman. Participate in the excitement of hauling up the traps or sit back and relax as we cruise near picturesque lighthouses, historic civil war forts, and the “Seal Rocks”.

Each of our lobster tours lasts for 80-90 minutes and passenger numbers are limited to ensure that everyone gets an up-close and personal Maine lobstering experience.

You’ll see how these tasty treats get from the bottom of the ocean to your dinner plate and learn about lobster habits, conservation efforts and the difference between hard shells, shedders, shorts, culls, and keepers. Any lobsters we catch can be purchased after the cruise for wholesale “boat” price, and if you don’t have a pot at home, take them across the pier to the Portland Lobster Company restaurant for the freshest lobster dinner anywhere.

*Click here to book online*

A diverse variety of marine life will enter a lobster trap, and some common visitors include rock crabs, snails, starfish, and hermit crabs. Our see-thru “live tank” offers a chance to watch these little creatures until the end of the day when all are thrown back into the sea.

In addition to lobstering, the Lucky Catch can provide a wide selection of private charters including birthdays, corporate outings, cocktail cruises, bird watching and island dining transportation. If you have an idea for a custom charter, let us know and we’ll try to make it work for you!

Casco Bay Custom Charters

Embark on an unforgettable journey: customizable private boat charters & tours of casco bay, celebrating a decade on the water.

Experience Casco Bay’s Splendor with Our Private Boat Charters & Tours. 

At Casco Bay Custom Charters, we invite you to explore the captivating beauty of Maine from the unique vantage point of our classic wooden vessels. For the past decade, we’ve shared more than just boat tours. Our charters are personal introductions to the coastal landscapes, lighthouses, and culinary delights that define our region. 

With a focus on customization, each voyage with us is tailored to uncover the genuine essence of Casco Bay, enhanced by our commitment to exceptional service. Led by experienced crews passionate about sharing their knowledge and love for Maine, we ensure your journey is not only enjoyable but truly memorable.

SEARCH CHARTERS BY GROUP SIZE

Designed for exclusivity, our charters accommodate intimate groups of up to 6 guests or larger gatherings of 7-16. Our friendly captains and knowledgeable stewards ensure a personalized boating experience.

Small Groups aboard MONHEGAN

Intimate cruises for up to 6 on a vintage lobster boat

Learn More »

Large Groups aboard MARIE L

Classic coastal tours for up to 16

DINING CHARTERS

The best way to eat locally-sourced Maine cuisine is aboard our Dining Charters. Specialty menu dining charters, chef’s dinner sunset cruises, and bottomless mimosa brunch cruises available. Local catering and all-inclusive drink upgrades are available aboard EVERY Casco Bay Custom Charter!

Private Sunset Dinner Cruise

Small Groups (up to 6 guests) aboard MONHEGAN

Bottomless Mimosas & Croissant Brunch

Large Groups (7-16 guests) aboard MARIE L

ELOPE ON A PRIVATE ISLAND

Experience the magic of saying ‘I do’ on a private island with our Fortland Elopement Package. Escape to Fortland for an intimate, and unique wedding ceremony set against the backdrop of a stunning coastal landscape. An unforgettable way to share your vows and begin your new adventure in love

FORTLAND ISLAND ELOPEMENT PACKAGE

Unique, intimate wedding ceremonies on Fortland.

SAIL WITH GLEAM

For a limited-time, we’re partnering with GLEAM to offer sailing charters off the coast of Maine. GLEAM is a fully restored vintage 12 meter yacht that hosts up to 13 guests. Each captivating sailing excursion includes captain and crew for an effortless Maine summer sail.

GLEAM Private Sailing Charters

Sailing Excursions along Maine's Coast

CREATE YOUR OWN CUSTOM CHARTER

Tailor any of our curated tours and experiences for your group’s needs, from corporate bleisure to family-friendly outings and celebrations. Collaborate with our team to craft your perfect day, selecting from diverse food, beverage, and tour itinerary options. Your bespoke Maine adventure awaits.

Unforgettable 5-Star Maine Experiences ⭐⭐⭐⭐⭐

Embrace authentic maine with casco bay custom charters.

Journey with us and unlock the essence of Maine on our signature boat tours. Enjoy the serenity of coastal cruises while indulging in gourmet locally-sourced food and craft beverages. Our classic wooden vessels offer a truly authentic Maine experience for unforgettable memories.

Eager for an unparalleled experience? Book your private boat charters and coastal tours to navigate the beautiful waters of Casco Bay!

Your Guide to the BEST Maine Sailing Tours | Windjammers, Sailboats, & Schooner Tours

Everyone knows that Maine has a stunning coastline and breathtaking views of the Atlantic Ocean from pristine beaches to rugged cliff walks. But, have you ever considered seeing Maine from the water? Set sail on an exciting adventure on one of the best Maine sailing tours onboard a windjammer, sailboat, or schooner.

We think it’s the best way to view the Maine coast , and what could be more exhilarating than setting sail out of a Maine harbor aboard a tall-masted schooner? Down the coastline from the Downeast & Acadia region to the Southern Maine Coast , there are so many sailing excursions to choose from.

The best part? You can sit back and relax while someone else does the sailing and navigating. Or, you may lend a hand and hoist a sail if you prefer. There’s no better way to experience the beauty of Maine than on a historic sailing trip, so check out these options for your next visit to Maine.

Downeast & Acadia Sailing Tours

Downeast windjammer cruise lines.

If you’re looking for a variety of options for sailing, Downeast Windjammer Cruise Lines in Bar Harbor has you covered. Offering a Sunset Sail, a Morning Sail, and an Afternoon Sail, there’s a wonderful experience no matter the time of day. Each sail has its own vibe.

The Sunset Sail is the most popular cruise that Downeast offers. It includes live folk music, beer, and wine for sale. Or, enjoy sailing in Frenchman Bay during the Morning Sail, which is more relaxed but still offers breathtaking views of Acadia National Park .

The Afternoon Sail is perfect for those looking for a narration during the sail. The captain will point out points of interest, regale you with the local history, and discuss wildlife.

No matter the sail, you can bring a picnic of snacks along, and most sails are pet-friendly.

Downeast Sailing Adventures

Southwest Harbor

Step aboard the Real Maine for an unforgettable experience sailing around the Cranberry Islands, Acadia, and Somes Sound. This tour will take you by lighthouses, past gorgeous homes on the shore, and by working fishing boats.

Book a private charter or a group day sailing adventure for up to six passengers. Downeast Sailing Adventures has daily sails on its 33-foot boat Surprise and its 38-foot boat Swan .

Sail Acadia

Northeast Harbor & Southwest Harbor

Sail Acadia offers trips out of two harbors, Northeast Harbor and Southwest Harbor . Sailing trips can be either shared or privately chartered. Private charters can be catered to your preferences with sailing instructions or a stop at an island for a picnic included.

Book a morning sail for calm waters with gentle sea breezes and good opportunities to view local wildlife. The morning sail is suggested for first-timers and children.

Or, book an afternoon sail for stronger winds that will make the sailboat cruise faster. This sail typically sees seals along the route, and the captain will often give a narration of the wildlife and history of the area.

Another option is a sunset sail for a romantic experience. This sail will have you seeing gorgeous sunset views on calm waters.

Schooner Tours in MidCoast Maine

Schooner stephen taber.

If you’re looking for an all-inclusive overnight experience, book a sail aboard the 150-year-old Stephen Taber . Each sail includes accommodations in one of 12 cabins, meals, wine (on evening sails), a lobster bake and barbecue on the beach, and evening entertainment.

Guests can choose from a themed trip or a private charter from Rockland Maine . Themed trips are a lot of fun and span from three to six nights, depending on your preference.

Enjoy trips such as Culinary Explorations; ‘Wine, Dine, and Chocolate;’ Yacht Racing Regatta; Penobscot Bay’s Hidden Gems; and more. These trips are sure to be memorable experiences, and by the end of the trips, you’ll feel like family with the other guests on board.

Here are more MidCoast Maine boat tours that are part of the Maine Windjammer Association like the Schooner Stephen Taber : Schooner American Eagle | Captain Tyler King | Rockland, ME Windjammer Angelique | Captain Dennis Gallant & Candace Kuchinski | Camden ME Schooner Grace Bailey | Captain Sam Sikkema | Rockland, ME Schooner Heritage | Captains Sean Grims & Ben Welzenbach | Rockland, ME Schooner Ladona | Captain J.R. Braugh  | Rockland, ME Schooner Lewis R. French | Captain Becky Wright and Nathan Sigouin | Camden, ME Schooner Mary Day | Captain Barry King and Jen Martin | Camden, ME

A Morning in Maine

If you’re strapped for time and want a shorter sail, A Morning in Maine’s sailing trips are a wonderful experience. The two-hour sailing adventures take place aboard a 55-foot ketch that passes lighthouses and other schooners.

The morning trip is perfect for those looking for calm sailing. The mid-afternoon sail has windier conditions for a faster sail. Evening and sunset sails feature beautiful sunset views and a relaxing ride. Guests are often given the chance to try to steer the boat as well.

Schooner Surprise

The Schooner Surprise has been sailing for over 105 years, with 30 of those years setting sail out of Camden Maine . Guests can book a two-hour sail with views of the lighthouse, summer houses and views of Penobscot Bay .

These family-friendly sails let guests, including children, take the wheel while out at sea. Special sails include a Full Moon Sail that features live music during sunset and a trip lasting two hours into the night. Or, book a fireworks view sail or a Birding and Marine Life Tour with an ornithologist.

Portland & Casco Bay Sailing Tours

Portland schooner co..

Portland Schooner Co. sets sail from Portland Maine and cruises through Casco Bay for a delightful trip along the coastline and past lighthouses and ocean life, like seals. On the two-hour sail, bring your own picnic and even alcoholic beverages for a relaxing, scenic time on the water.

These sails are perfect for all ages. Sails take place throughout the day on one of the five historic wooden schooners. The sails are relaxing and do not include narration, but the crew is available to answer any questions that guests may have.

Maine Sailing Adventures

Maine Sailing Adventures offers traditional two-hour and themed sails through Casco Bay . What sets it apart from other sailing companies is its unique themed sails. Try an acoustic sail that features live music. Or, try a wine sail that includes a wine tasting for adults.

Have you ever heard of a yoga sail? This ship can accommodate up to 12 guests for a yoga class that you won’t experience anywhere else. Enjoy amazing views of the water while working on your poses.

Sail Portland Maine

If you’re looking for an intimate sailing adventure, Sail Portland Maine has you covered. Guests can choose a private charter or a public trip. The public trips’ capacity is 12 people, so you know that your sail won’t be too crowded.

Day and sunset trips are two hours in length and pass by all of the famous Casco Bay features — like historic forts, lighthouses, and if you’re lucky to spot them, seals. Guests are welcome to bring their own food and drinks, while bottled water is complimentary on board.

Schooner Tours on the Southern Maine Coast

The pineapple ketch.

Kennebunkport

There’s no better way to see the Kennebunk River than sailing on it. The Pineapple Ketch departs from Nonantum Resort for a dazzling trip along the river and the Kennebunkport coastline.

You’ll see gorgeous seasonal cottages, including the famous cottage of President George H.W. Bush. Enjoy views of the Goat Island Lighthouse, local harbors, seabirds, and seals.

Each sail includes complimentary bottled water and sodas, but guests are also welcome to bring their own food and beverages.

Silverlining Sailing

Silverlining Sailing offers one of the most intimate sails in Ogunquit Maine . Each boat has the capacity for up to six passengers, making for a small group sail. Sails typically last two hours, departing from the quaint Perkins Cove village.

There are five trips daily (weather permitting) from early morning through to a sunset sail in the evening. Enjoy stunning ocean views, gorgeous waterfront homes, views of local beaches, and harbors.

Since this is a smaller group sail, guests get the opportunity to try their hand at taking the wheel and steering the schooner.

Broad Reach Adventures

Broad Reach Adventures has two-hour sails, half-day and full-day sails, and chartered sails from Saco Maine , so there’s a sail to accommodate your busy schedule.

Each one allows guests to see beautiful views of the Saco River, Saco Bay, Biddeford Pool, Old Orchard Beach , and lighthouses along the way. Longer sails provide guests with the opportunity to disembark and explore uninhabited islands.

A unique feature that Broad Reach Adventures offers is the opportunity to add a massage or professional photographer. These experiences are available on certain dates and times, so book ahead if you’re interested in these add-ons.

Sailing Lessons & Boat Rentals

If you want to learn to sail, sailing instruction is often available as part of your charter package.  Private charters  of sailboats on the Maine coast allow experienced sailors to explore the coastline on their own.

Private sailors will find  hotel marinas  for lodging in Maine’s best harbors. If you time your sailing cruise right, you might witness seals, porpoises, whales, or other tall ships.

Watching the sunrise from the deck of a schooner is one of life’s simplest, most satisfying pleasures. Of course, the spectacular Maine scenery is always included on your sail.

Set Sail on Sailboat & Schooner Tours From Maine This Season

Now that you know about all of the sailing trip options, it’s time to set sail into the open waters of Maine. From two-hour trips of the bays and harbors to overnight excursions, there’s an experience awaiting you on your next getaway.

Each Maine sailing company offers its own unique trips aboard safe, well-maintained schooners. Relax, unwind, and feel the ocean breeze in your hair as you cruise through the lapping waves of Maine’s Atlantic shoreline.

The VisitMaine.Net team is the small team of authors and editors that research and write our in-depth guides throughout the site and update past articles to make sure they're still super valuable to you. We have one goal: to help you fall more in love with the state of Maine!

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Travel+Discover Maine – The unofficial guide to exploring the great state of Maine. Not affiliated with any official tourism entities.

Copyright Travel+Discover Maine 2024 Images Courtesy Greg and Heather Burke unless otherwise noted.

Guided Tours + Cruises

Sample the sights and sounds of the region.

When you visit the Greater Portland, Maine region you get a hands-on experience. Get up close and personal with our rocky coastline and sandy beaches. The region is your oyster and you can take on everything from kayak trips to lobstering tours to brews cruises.

Learn More On The Blog

Portland Discovery Land & Sea Tours

The perfect way to experience the coastal and inland areas of Greater Portland Maine.

Offering specialty food cruises, harbor tours, and private charters. Complimentary beer and wine with all cruises!

Visiting Maine and want to see whales, puffins, or the sights? Cap’n Fish is the way to experience Boothbay Harbor.

Portland's iconic ferry system with year-round ferry services, specialty cruises and private charters to the islands of Casco Bay.

Discover the wonder of Casco Bay with Fogg's Water Taxi & Charters, offering a diverse range of services across our seven boats.

Join us for a guided tour, pedicab ride, or explore the region at your own pace with a worksman bike rental.

Private sightseeing tours are available for couples and all size groups, from minivan to motor coach.

Highly interactive tours that will educate and entertain you all along the way. Foodie tours, history tours, and more!

Come aboard Frances, our 74’ traditional British cutter for a day sail, evening sail, wine sail, or an acoustic sunset series sail. Private charter available.

Home to the best tours and activities in Maine. Authentic experiences led by locals. Your gateway to an unforgettable Maine.

Jump aboard New England Eco Adventure’s small, intimate excursions that blend adventure and education into one amazing trip.

Experience unforgettable storytelling—rich with heart, humor, and humanity—on a walking tour with Maine's top-rated guide!

Don't just see Portland- Discover it! Offer a wide variety of sightseeing and charter options by Land and Sea.

Operate a unique multimedia history tour aboard a Vintage Fire Engine. We explore the peninsula of Portland.

Refresh your spirit with a two-hour sail on Casco Bay and witness first-hand the forts, lighthouses, sea life and rugged coastline.

Hosted on a traditional lobster boat, Rugosa’s lobster tour offers the most exclusive, personal, and educational cruise in Kennebunkport.

For 20 years we have been offering cycling, walking, and multi-sport vacations in the most beautiful places in Maine.

Portland's #1 party boat! Join us on the water for a fully immersive way to experience Casco Bay and the islands, all while live bands set the soundtrack.

Explore the best of Maine with private sightseeing tours featuring chef prepared local cuisine and drinks. Unforgettable experiences await on our historic boats.

A unique island experience within Fort Scammel on the private House Island in Casco Bay. Camp and tour the historic island!

A lobstering excursion for all ages while enjoying close-up views of historic lighthouses, civil war forts, and seals.

Maine’s first human-powered party boat. Book individual seats or the whole boat for a private tour of Portland.

All-inclusive tours providing guests a behind-the-scenes look at Maine’s breweries, distilleries, wineries, and more.

Land & sea adventures aboard a modern amphibious vehicle. A quacktastic historical tour of the Old Port and Harbor.

Scenic train ride along beautiful Casco Bay. Activities, historic railroad cars & exhibits.

Experience the Old Port's rich history since 1632. Over 50 historic stops! Memorable tour experiences not to miss!

Join our family owned and operated tour company for unforgettable explorations. Customized year-round tours.

Residents and guides, with enthusiasm and expertise in Portland’s history, food, drinks, art, music, and literature.

A day in the life of a lobsterman from pulling traps and setting traps to examining sea life and selling the catch.

We offer unique boat-based tours and experiences on the beautiful waters of Casco Bay!

City & 3 lighthouses Historical Sightseeing Tour with a REAL local, born & raised in Portland!

A family-owned and operated tour company sharing what we love about our charming city and the state of Maine.

“The Best Harbor Charters in Portland, ME”

Join Sail Portland Maine for a more intimate trip around the waters of Casco Bay aboard our 6 passenger sailing vessel, the Eleanor Hawkes, or our 12 passenger Classic Motor Yacht Picnic Boat, the Calista Ann.

Eleanor Hawkes → Set Sail on the Eleanor Hawkes

The Eleanor Hawkes is a Friendship sloop, a beautiful traditional-style sailboat that glides effortlessly over the water. With space for up to 6 guests , this is the most private sail you can get in Portland shy of owning a boat!

The Eleanor Hawkes is based on the Friendship sloop, also known as a Muscongus Bay sloop or lobster sloop, which is a traditional style of gaff-rigged sloop that originated in Friendship, Maine around 1880. Fishermen in Friendship and neighboring Bremen collectively originated the design, one influenced by the fishing sailboats of Gloucester, Massachusetts, particularly the schooner Fredonia of 1889.

Although familiar as a pleasure craft today, the Friendship sloop was the traditional fishing boat used off the coast of Maine, especially for lobstering, until the introduction of the gasoline engine early in the 20th century. Friendship-area boat builder Wilbur A. Morse produced many examples from the 1880s and into the early 1900s.

Calista Ann → Go for a Cruise on the Calista Ann

The Calista Ann is our newest addition to the Sail Portland Maine fleet! This motor vessel, also sometimes referred to as a picnic boat or cocktail cruiser, has slightly more seating and space to move about, so if you’re looking for a private cruise for a larger party, Calista Ann is the boat for you!

We offer cruises for up to 12 guests on public and private charters to keep the intimate feel for your group.

We provide multiple trip options to ensure that your Portland, Maine boat cruise fits into your schedule. You can see all our available charter times here !

Harbor Charters in Portland, Maine

Want to learn more about the history of Portland and the ships of its past? Come join us! You’ll experience the most scenic harbor charters in Portland, Maine, aboard the Eleanor Hawkes or Calista Ann. Sit back, relax and enjoy the cruise of a lifetime through the glassy waters of Casco Bay with the best sailing Portland has to offer. Book your trip with us today!

Choose Which Harbor Charter is Right for You

BOOK YOUR KENNEBUNK OR PORTLAND TOUR BEFORE SUMMER SLIPS AWAY!

Portland, Maine Boating Adventures

Explore casco bay in a custom-built rib boat where everyone gets a front-row seat see the crown jewel of maine on our exciting, adventure boat tours and excursions.

Your family doesn’t want to be crammed onto a crowded big boat tour of  Casco Bay. You want to have the time of your life zipping around Maine’s most postcard-perfect lighthouses, forts, wildlife,  and surrounding islands, with a small, select group and a front-row seat.

Only New England EcoAdventures blends education, excitement, and adventure into each Casco Bay adventure and offers first-class accommodations that let you see and sustain the stunning Southern Maine ecosystem.

We get there faster. We stay longer. And we go places other boat tours can’t reach—in a style they can’t match.

Upcoming Portland Boat Tour Adventures

• Most Popular!
• Map Marker Portland, Maine
• Hour Glass 1.5 hours
• Star Outline Seal watching , Lighthouse tour , Scenic cruise

Best of Casco Bay

Depart with us from bustling Portland Harbor as we tour one of Maine’s most picturesque boating destinations. Casco Bay is littered with islands, historic forts, wildlife, birds, and lighthouses in our unique 14-passenger RIB boat.

• Hour Glass 3 hours
• Star Outline Whale watching

Adventure Whale Watch – Portland

Experience the breathtaking beauty of the Atlantic Ocean on our whale-watching tour departing from Portland, Maine. Set sail from the historic harbor, where you’ll board a comfortable vessel equipped for a thrilling marine adventure.

• Hour Glass 2.5 hours
• Star Outline Oyster Farm Tour

Mere Point Oyster Farm Tour

Join us on a scenic ride of Casco Bay on our way to tour one of Maine’s premier oyster farms. Along the way we will cruise through some of Casco Bay’s less visited waters for great wildlife viewing before arriving at Mere Point Oyster Farm.

• Hour Glass 2.25 hours
• Star Outline Lighthouse tour

Portland’s Ultimate Lighthouse Tour

Experience the picturesque beauty of the Maine coastline with our exhilarating boat tour from Portland, Maine. This guided adventure will take you on a breathtaking journey along the rugged shoreline to view more lighthouses than any other tour in the state!

• Star Outline Scenic cruise

Small Group Adults-Only Sunset Adventure

Grab your favorite adult beverage and join us on an adults-only, intimate, sunset adventure that you won’t soon forget!

Portland, Maine and Casco Bay New England EcoAdventures let you learn, live, and love the Maine life like a local.

Our premium RIB boat takes you through Portland’s working waterfront where you’ll enjoy the islands, forts, lighthouses, vibrant seal colonies and seabirds.

Salty breezes and brilliant sunsets. Fresh, buttery lobster, blueberry pie, and craft beers. Shoals of playful dolphins and pods of majestic whales. Gentle cruises through scenic vistas and adrenaline-fueled, wind-whipped speedboat runs across sparkling waves.

We give you so many wonderful ways to truly experience the southern Maine lifestyle—and every guest gets a front-row, 360-degree view and in-depth insight into the wonders all around you.

Our Customers Rave About Us

The boat ride was so much fun and so much more intimate than a big boat. It can def. get a bit choppy at times but the seats are well cushioned which makes for a great adventure. Captain and staff are very nice and experienced. We saw some seals and 2 humpbacks which def. gave us a great show smacking their fins into the water. We would highly recommend this adventure. Regardless of what wildlife you will sight the boat ride on its own is worth the trip. Thx again.

It included stopping at an area to watch seals, a lighthouse and the history, seeing the Bush estate and their boat, and tons of thrills riding the waves! It was not rough as we thought and you don't get soaked; just a little bit of sea spray which was nice on a hot day. Captain Gary was knowledgeable and fun by throwing in humor now and then. We were glad for the little pockets in front of our seats to put our phones and jackets. We'll be back for another tour next summer and we really want to experience their Hampden Beach location.

We had a great time on our hour long scenic thrill ride! My husband and I took my dad as a belated Father’s Day gift (he loves a good rush) and we were not disappointed. The seats were neat. They were three vertical rows that you had to straddle. There was a handle bar in front of you. We felt safe and comfortable. It was a tremendous thrill. My only complaint is that I wish it lasted longer! Because of this, I’m excited to book another trip with them in the coming years, whether it’s the whale watch or the lighthouse tour. My family and I stay in Ogunquit nearly every year and this was a great new activity to try in the area! Highly recommend!! Thank you for a great time!

• Chevron down What To Expect
• A first-class adventure tour without any crowds
• A narrated ocean adventure
• Amazing wildlife and scenery
• Amazing photo opportunities
• Custom POD seats for maximum comfort
• 360 Degree views for everyone
• Educational face to face interactions
• A knowledgeable captain
• Chevron down What's Included
• Complimentary water
• Cooler with ice
• Motions sickness wristbands
• Chevron down What You Need to Bring
• Your camera (make sure it’s charged)
• Warm clothing (dressing in layers is always smart)
• Sturdy Footwear (flip flops are fine)
• Chevron down What Not to Bring
• We also recommend NOT wearing a dress
• Chevron down Important Information

After you Book your Tour

• You will be emailed a receipt immediately after you book. The receipt will contain all the necessary information that you will need.
• YOU DO NOT NEED A PHYSICAL TICKET.
• Please meet at the picnic tables outside of Fore Points Marina 20 minutes before your scheduled tour for check-in and wait for the first mate. Fore Points Marina is located at 1 Marina Way in Portland, Maine.
• There is very little storage aboard the boat – please no large bags or coolers.
• If you are taking a child, we have life jackets for children that are between 50lbs and 90lbs.
• If you are pregnant or have a history of back or neck problems, we recommend another tour.

Parking – Traffic can be very bad in Southern Maine in the Summer, please give yourself plenty of time. Parking options are below…

(1) We recommend using the Thames St. Parking Lot which is located directly in front of Fore Points Marina. The address to the lot is Eastern Promenade Trail, Portland, ME 04101. The rates are $5 an hour.

(2) There is also a parking garage on Thames St. It sits on the left before you get to the parking lot. It’s a little further of a walk but it’s sheltered. The rates are $5 an hour.

(3) Walking is always a great option! We’re just a 5 – minute walk from the hustle and bustle of Commercial St.

• Chevron down Additional Information

Browse our  Frequently Asked Questions for any additional information you may need or call us at 207-502-8040.

We look forward to serving you in 2024!

Maine Duck Tours

Duck Tours In Portland, Maine

Experience Portland by Land and Sea

Land & sea historical tour of portland and casco bay.

On our history and sightseeing tour of Portland, we’ll travel by land & by sea to explore many different points of interest.

Fun for all ages aboard a modern amphibious vehicle!

As you twist and turn through the Old Port aboard Maine’s famous, modern land and sea vehicle, or “Duck”, we’ll tell you about the legends and lore that have shaped Portland into one of the most historical cities in the nation.

Learn about places of interest to visit and many little known facts about the city that is nicknamed “The Phoenix.” Then, hold onto your tail feathers as we DRIVE into the waters of Casco Bay to view Portland’s working waterfront, Calendar Islands and marine wildlife.  This is Maine sightseeing at it’s best!

For all of our tour details, please visit our Portland Maine Tour page.

Top 10 Boat Tours & Water Sports in Portland!

We did it as a part of our Portland trip with small kids aged 3-7. We all enjoyed the tour of the city as well as the boat time as well. Dugan was very helpful in getting us oriented after the ride as well. Highly recommend this!

What a fun tour, we enjoyed our trip on land and water. Truly, it quacked us up! I would recommend this tour on the beginning of your stay in Portland, it will give you a nice overview of the area.

Dugan and captain Mike did an excellent job. Both were very professional. Dugan was a great host, he was very knowledgeable and friendly-I would highly recommend this tour if you are in Portland.

The Maine Duck Tours is a good way to oversee the city. You get taken on land and water so it is entertaining and fun!

• Mailboat Run

Hop on the Mailboat Run! The locals’ favorite way to experience Casco Bay – this true working boat carries passengers, mail and freight to Little Diamond, Great Diamond, Long, Cliff and Chebeague Islands. Year-round availability. Check out our blog for more information!

Narration provided with 10 or more cruise passengers.

Duration : 2.5-3.5 hrs. (times vary based upon route and cargo volume)            Runs : Daily

• Sunrise Run
• Diamond Pass Run
• 2024 Cruising Casco Bay Concert Series

Private Lighthouse Sightseeing Charter on a Vintage Lobster Boat

TICKET PRICES STARTING FROM

Taxes and fees will be calculated at checkout

100% PRIVATE TOUR! Step aboard a vintage Maine Lobster Boat for a private, 2-hour lighthouse viewing & sightseeing charter.  Leave the crowds behind as we tour the islands of Casco Bay and pass by 4 lighthouses, historic 19th century forts, and the scenic Maine Coast.   Charters depart from Portland's Old Port. This authentic Maine experience is perfect for families and small groups. Each charter is private for groups of up to 6 and all ages are welcome!

Ticket Options

1 Option Available

2024 MONHEGAN: $102.5

Ticket Information

• Mobile or paper ticket accepted
• One per booking

What's not Included

• No food or drinks included, but beer/wine available for purchase on board.
• Parking in the Old Port is not included

Cancellation Policy

• For a full refund, cancel at least 24 hours before the scheduled departure time.

Additional Info

• Public transportation options are available nearby
• Suitable for all physical fitness levels

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Maine Maritime Academy

A college of engineering, management, science, and transportation, 2024 summer training cruise, cruise return to portland and livestream.

The TSSOM will arrive in Portland, Maine, on July 16, 2024, at the Portland Ocean Terminal. This is the final stop of the 2024 Summer Training Cruise, and students will begin disembarking on Thursday, July 18, starting at 12:00. Please join us in welcoming back everyone aboard after a successful voyage, either in person or via the livestream. The livestream event will begin at approximately 7:15 a.m. and will include prerecorded student interviews about their experiences this summer.

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Tri for a cure team arrives at starting line in south portland by boat.

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Maine's Total Coverage spotted a unique arrival at the Tri for a Cure starting area in South Portland.

Jen Belesca and her two teammates arrived by boat Sunday morning from her home on Chebeague Island.

"That's the logistically sound way to get here from Chebeague," Belesca said. "That's the way I've always done it. I don't know any other way to get here."

Belesca, a nineteen-year breast cancer survivor, is competing in her ninth Tri for a Cure, the Maine Cancer Foundation's all-women's triathlon fundraiser.

Before the event began, Belesca was honored as one of the top-five fundraisers at this year's triathlon by raising $15,653 for the MCF.

"My goal is to raise as much money as I can, and I have an amazing group of friends and family that support me," Belesca said. "It's really humbling."

This year's Tri for a Cure has raised a record-breaking $2.13 million for the Maine Cancer Foundation. The event has raised more than $22 million overall for cancer research.

"It is the highest fundraising number we have ever seen in 17 years," said Julie Marchese , who co-founded Tri for a Cure in 2008 and is serving as race director for the final time.

The Tri for a Cure triathlon consists of a 1/3-mile swim, 15-mile bike ride and 3-mile run.

Bangor Daily News

Maine news, sports, politics, election results, and obituaries

GLEAM Sailing to partner with Casco Bay Custom Charters to offer exciting excursions aboard a historic 12-meter racing yacht out of Portland

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Casco Bay Custom Charters, Portland’s premiere private boat charter company, is excited to announce a partnership with GLEAM Sailing from Newport, Rhode Island. This collaboration offers an unparalleled sailing excursion of Casco Bay aboard GLEAM, a historic Newport racing yacht.

This beautifully restored 1937 12-meter yacht has enthralled generations of sailors with her competitive spirit and beauty. Designed by renowned naval architect Clinton Crane, GLEAM was intended to be both his personal yacht, and a majestic racer serving as a trial horse for America’s Cup challengers..

According to Casco Bay Custom Charters owner Jim Gallea, “GLEAM offers a truly unique sailing experience that is distinct from other sailing offerings in Casco Bay. She’s a lively, quick boat on the water, offering a real sense of adventure and fun while maintaining a graceful elegance that evokes the golden age of wooden sailing yachts from a century ago. If you have any affinity for sailing, you can’t pass up a chance to sail aboard GLEAM.”

Casco Bay Custom Charters partnership with GLEAM Sailing is a natural fit as both companies value the restoration and preservation of classic boats, and are dedicated to creating truly special experiences on the water. For the past 10 years, Casco Bay Custom Charters has offered private sightseeing and dining excursions aboard historic Maine-built wooden boats, including Portland’s most distinctive dining experience: a 6-course dinner charter prepared and served onboard by Chef Keith Castro.

GLEAM will be making limited stops in Portland during the months of July and August between appearances in regattas along the Maine coast.

All charters aboard GLEAM are private charters that can accommodate groups of up to 13 passengers. Each sailing excursion includes captain and crew for an effortless Maine summer sail. Charters are typically 3 hours in length, assuring ample time to explore beyond Portland Harbor and experience GLEAM to her fullest.

GLEAM Sailing offers onboard catering available from local provisioners, Pepperell Provisions and Charcutemarie. Guests are allowed to bring aboard food and drinks to enjoy while on the water, if preferred. All sailing charters are customizable, and can accommodate corporate group retreats. As a family-owned local business, we frequently combine our boating experiences with other local hospitality partners and welcome the opportunity to collaborate to create your perfect Maine day.

For more information and reservations, please visit cascobaycustomcharters.com or call 207-205-5796.

Blog post – https://www.cascobaycustomcharters.com/blog/gleam-sailing-partnership .

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Make a plan to attend the Maine Lobster Festival, July 31 to Aug. 4

The annual event takes place in Rockland.

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A fresh batch of lobster at the food tent during the 2018 Maine Lobster Festival in Rockland. Ariana van den Akker/Staff Photographer

You’ll have a shell of a good time celebrating the state’s star crustacean during the annual Maine Lobster Festival, happening July 31 to Aug. 4 at Harbor Park in Rockland.

The festival’s five-day schedule features an arts and crafts show, parade and tasting event.

Other highlights of the Maine Lobster Festival include the International Great Crate Race, during which participants attempt to race across a string of lobster traps in Rockland Harbor. There’s also a seafood cooking contest, road race and plenty of kids’ activities.

Some of the musical acts performing over the five days are Paddy Mills, Rigometrics, Charlie and The Hustle and Julia Gagnon.

Don’t forget about the actual lobsters. You’ll have plenty of chances to eat your fill.

For the full schedule, head to mainelobsterfestival.com .

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