small sailboat rental florida

Beachside Sailing

Sailing Lessons and Rentals

Sailboat Rentals

Sailboat Rentals in Port Canaveral and Merritt Island, Florida, near Cape Canaveral, Cocoa Beach and Orlando, FL.

Our sailboat rentals are affordable and conveniently located near many Orlando and Central Florida attractions, just a short drive from Walt Disney World.  We have boats available in Port Canaveral and Merritt Island, located near Cape Canaveral, Cocoa Beach and Titusville, Florida. Our locations allow quick access to the Indian River, Banana River, and Atlantic Ocean.  Our sailboats can accommodate multiple persons, so please click here or call us at (321) 624-5537 for more information about our sailboat rentals, sailing school and other Sailing events.

Sailboats Unlimited

Bareboat and Crewed Sailing Charters

Bareboat and Crewed Sailing Charters in Naples, Florida since 1985!

Crewed Sailing Charters

Choose from a 2 hour “taste of sailing”, a half-day “jaunt along the beach” sailing the wind, a full day “adventure to Marco Island” sightseeing or romantic sunset or moonlight cruise.

Bareboat Charters

Let us help you plan a complete Florida sailing vacation from a simple overnight to a couple of weeks

Types of Charters

Choose your desired charter.

When choosing a sailing charter, you want to choose with confidence. Established in Naples in 1985, providing romantic getaways, sunset/sunrise trips, once in a lifetime sailing experiences for families on vacation, and corporate team building adventures.

About sailboats unlimited, naples most trusted sailboat chartering company since 1985.

The best experience you will have while visiting beautiful Naples, Florida

Located in sunny Naples, Fl, we have specialized in crewed sailing charters, bareboat sailing charters, yacht deliveries, and yacht maintenance since 1985.

When visiting Naples, FL or any of the surrounding areas, you have the opportunity to take our sailboats out onto the beautiful gulf. Let us charter you and your guest, or reserve the entire yacht for your guest. Sunset and moonlight cruises, half day and full day cruises. We have something for every scenario.

Our bareboat yacht charters are on boats ranging from 34′ to 42′. Half day to weekly bareboat charters are available. Preliminary checkout available by phone or fax. Prices vary depending on vessel. 34′ ocean racers and up to 42′ luxury cruising yachts. Large parties can be accommodated, with up to 16 on the Danmark, a 40′ Sloop U.S. Coast Guard inspected vessel.

Enjoy the unique Florida experience sightseeing and watching the dolphins at play. Kick back and be pampered or you take the helm. Free sailing instruction during the charter.

• Best listings 1st
• Price - Low to high
• Average Rating - Highest rated 1st

Our charter advisors are here to assist you.

An expert will find you the best offers

The state of Florida in the United States is home to some of the most popular boating destinations and cities such as Miami and Fort Lauderdale. While these areas offer many boats, Miami and the Florida Keys have some beautiful sailing conditions, which makes sailboat rental in Florida particularly popular.

Pricing and Info on renting a sailboat in Florida.

To rent a sailboat in Florida, prices cost around £500 for the day, while renting a sailboat in Florida for a week will average at around £4000. These prices vary however, due to the type of boat and the time of year you want to go.

Sailboat availability in Florida

Because Florida is sunny year-round, it does not follow the conventional sailing season. The peak season will typically run from December deep into February, but sailing still goes strong into May. If you’re looking to avoid the influx of tourists, then sailing in the months of April and May is perfect for you. Outside of this period, you’ll still have plenty of sunshine, but you’ll also have heavier periods of rain and humidity. Even in the low season sailing is very popular in Florida, and so you should always book far in advance.

Do I need a license to rent a sailboat in Florida?

To rent a sailboat in Florida, you do not need a license, however, if you were born on or after January 1st of 1988 you will need to obtain a Boating Safety Education Identification Card, which will require you to complete an approved Boating Safety Course. Also, if you are 18 years old or younger, you cannot rent any sort of watercraft.

If you do not have a licence or sailing experience, you can rent any of our sailboats with a skipper from our catalogue. When you rent a skippered sailboat, you can relax and enjoy your trip. The skippers help you to get to know the places you visit by boat in depth.

Overview of Florida

Undoubtedly one of the best areas to sail in the USA is Florida. With the sunshine year-round, you’ll always have perfect conditions to explore this beautiful state by boat. Due to its geographical position, it’s a sailor's paradise with an endless coastline that is available. If you’re living in the US, it’s the perfect place close to home; if you live abroad, it is more than recommended to make the trip.

In Florida, you’ll have several options for where to rent a boat. One of the most popular destinations to sail in Florida is the Florida Keys. Rent a boat in Key West, here you will have access to some of the best island hopping and you will be able to create a unique journey. Seeing the different islands and several coves is a highlight of any vacation. If you plan on sailing in the Florida Keys, chartering a yacht for at least is the right way to go.

Besides the Florida Keys, you’ll also be able to rent a boat in Fort Lauderdale. Fort Lauderdale is the perfect departure point for seeing the coast of Florida. Because of its location, you’ll have access to hot spots like Miami or sail down to the Florida Keys. Either way, you’ll surely have the perfect sailing holiday in Florida.

Due to the popularity of sailing in Florida, it is no wonder sailboat rental is so popular, as the sailing conditions are some of the bests you will find in the US, particularly in the Bay of Florida, with Miami and the Florida Keys, in particular, being a popular area to rent a sailboat.

Sailing areas around Florida:

• Florida Keys
• Fort Lauderdale

Our other types of boats

Best deals at sea.

Find the best prices for boat rentals & yacht charters with or without a skipper.

Quality control

Boat listings are checked regularly to guarantee the highest standards possible

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Verified third party to secure your payments and security deposits

Customer Care

A team of charter experts to help you seven days a week

• 305-619-0140

Private Liveaboard Classes

Florida keys sailing, come sail with us.

Proud Member of the ASA

At Florida Keys Sailing our specialty is: Private Live Aboard Sailing Classes and Sailing Vacations with just you and your spouse or friends. “Learn to Sail” or take an Advanced Class to develop your skills. Qualified sailors can Charter our boats. A Captain will happily take you and your family on a Day Sailing Trip if you need one. Many sailing classes offered elsewhere crowd you on a boat with a group of total strangers.

At Florida Keys Sailing ALL of our Sailing Classes, Day Sailing Trips, and Private Charters are exactly that…PRIVATE.

No one else except YOUR Party is ever on-board. This means you will learn more by having more time DOING, not WATCHING someone else sail. Dollar for dollar you will find more VALUE in taking your Sailing Courses at Florida Keys Sailing.

Or download the form here

Fun on the Waves

Our Classes

To learn more about the liveaboard classes we offer, visit our classes page

2 DAY BASIC FUNDAMENTALS OF SAILING

Designed for beginners who want the best introduction to the exciting sport of sailing. Students will receive a good understanding of all the “Basic Fundamentals of Sailing”. They will leave as very competent Crew Members.

3 DAY BASIC KEELBOAT “LEARN TO SAIL CLASS”

Beginner students will learn to responsibly be the Skipper of a Day Sailing Keelboat in familiar waters in moderate wind and sea conditions. Classes available are year round on demand based on your travel plans.

5 DAY BASIC COASTAL CRUISING OR 101 & 103

Students will learn to responsibly skipper and crew an auxiliary powered cruising sailboat during daylight hours within sight of land in moderate wind conditions. This Private Live Aboard Class is taught aboard our Catalina 30' or Irwin 34 Offered all year on demand based on your travel plans.

5 DAY BAREBOAT CRUISING OR 103 & 104

Charter a cruising sailboat during daylight hours in most wind and sea conditions. This Private Live Aboard Class is taught aboard our Irwin 34. Offered all year on demand based on your travel plans. 5 Days and 4 Nights…Privately Living aboard at our Dock

3/1 DAY ADVANCED COASTAL CRUISING OR 106

Cruise a sailboat during nighttime hours in most wind and sea conditions. A Private Live Aboard Class is held aboard our Catalina 30 or Irwin 34. Offered all year on demand based on your travel plans. 3 Days and 3 Nights…Privately Living Aboard

7 DAY BAREBOAT CRUISING OR 101, 103 &104

Charter a cruising sailboat during daylight hours in most wind and sea conditions. This Private Live Aboard Class is taught aboard our Irwin 34 This is the Class the Bareboat Charter Companies want you to have. Offered all year long on demand based on your travel plans. 7 Days and 6 Nights…Privately Living Aboard at our Dock

3 DAY FAST TACK TO CRUISING ASA 101 & 103

It’s the fastest and least expensive way to get the first 2 – ASA Certifications. Both combined into a 3 Day / 2 Night Live aboard Class. Prior sailing experience before enrolling is advised. Only $2,039 per student! And better yet…a second student enrolls for FREE!

5 - DAY FAST TACK TO BAREBOAT CRUISING ASA 101, 103 & 104

It’s the fastest and least expensive way to get these 3 - ASA Certifications. All 3 are combined into a 5 Day / 4 Night – Live aboard Class. Prior sailing experience before enrolling is advised. Only $3,599 per student! And better yet…a second student enrolls for FREE!

Testimonials

Daysailing & charters, we offer both daysailing and charters, click below to learn more.

• SAILING LOCATION: Keys Fisheries & Marina 35th St Gulfside, MM 49 Marathon, FL 33050
• By Mail: Florida Keys Sailing 5171 Overseas Hwy #504407 Marathon, FL 33050
• By E-Mail: [email protected]
• By Telephone: 305-619-0140
• Marathon Chamber of Commerce
• Get Knotted - Animated Knots
• Sombrero Lighthouse Data and Marine Forecast

Copyright© 2020 Florida Keys Sailing™, LLC

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The Best Sailboat Rentals in Florida

Browse, book, and get out onto the water with local captains and boat owners., our favorite sailboat rentals in florida.

4.9 (895 reviews)

• Boat Rentals

the United States

Relaxing Catamaran Adventure: Snorkel, Sail, Dolphins

50ft Catamaran Charter with Water Toys - Boca Raton, FL

2017 Robertson and Caine Leopard 40 - Luxury Catamaran

22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!

Stiletto 30 Catamaran for Dolphin Watching, Sunsets, Snorkeling in Destin

51ft Trimaran-Catamaran Sailing Yacht Charter in Miami, Florida

Crab Island/Dolphins/Snorkeling on a Captained Pontoon Boat

This Catamaran Party Boat accommodates up to 49 people with a captain and crew!

Suggested searches, types of boats popular in florida.

From mid-size to mega yachts, these luxury boats are great for groups and celebrations

₽7,380-₽118,540

Perfect for casual cruising, sandbar stops, swimming, and parties

₽4,610-₽41,510

Explore local waters with a boat rental dedicated to sightseeing and exploration

₽4,610-₽59,960

• Fishing Charters

Let a captain do the driving while you do the fishing

₽4,610-₽46,130

Fishing Boats

Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts

₽4,610-₽49,820

Fast, fun, and easy to operate, these are a guaranteed good time on the water

₽5,540-₽43,820

All the comforts of home out on the water, for multi-day boat trips

₽5,540-₽118,540

Who says you need a motor to have fun on the water?

₽1,380-₽55,350

Wakeboarding Boats

A high-octane powerboat designed and outfitted for wakeboard towing

₽6,460-₽27,680

Get off the boat and into the water with offshore snorkeling trips

₽9,230-₽73,340

Explore the ocean depths with trained boat operators

₽6,000-₽11,530

A high-energy adventure for the whole family

₽5,070-₽6,920

Top Sailboat Rental Locations Near Florida

Miami , Florida

945 listings

Miami Beach , Florida

453 listings

Tampa , Florida

437 listings

Hollywood , Florida

297 listings

Saint Petersburg , Florida

259 listings

Tampa Bay , Florida

256 listings

Most Popular Yacht Rentals in Florida

ENJOY MIAMI IN 57FT FAIRLINE FLYBRIDGE!!! One hour free mon-thurs 🎸

38' Mini-Yacht!! - Large "Ultra Luxury" Adventure & Activity Vessel 🏖

Enjoy Miami In Luxury Silverton Flybridge 48ft!

FREE Hour when you book 4 on Rinker Fiesta V 340 Yacht!!!

BEAUTIFUL 38’ SUNDANCER 12 GUEST

48ft Princes Yacht W/1Jet Skis included for up to 12 people in Miami

Welcome Aboard Our Beautiful 38' Chris Craft Launch OPA BIER!

ENJOY MIAMI IN NEW SUNSEEKER PREDATOR 60FT!!! 🌊

Most popular pontoon rentals in florida.

20ft Pontoon Suntracker Party Barge in St. Petersburg. Gas included!

Fast Luxury Barletta Tritoon! Perfect for Destin! 13 passenger, free amenities!

Naples Private Boat Charter on a NEW Godfrey - All you need included!

LUXURIOUS AND SPACIOUS PARTY BOAT - BRAND NEW TRITOON

Brand New Spacious, Clean and Comfortable Affordable Luxury Tritoon for 12

"Fine Tooning" Charter in St.Petersburg, FL

Awesome Pontoon Party Boat up to 12 people!

Suncatcher G3 Pontoon 24ft in Orange Beach, Alabama

Most popular boat tours in florida.

ENJOY MIAMI In 64' LUXURY AZIMUT!!!

AMUSING MIAMI BOAT TOURS!! 30’ Sundeck! Free Hour when you book 4!!!

50 FT SeaRay Flybridge- 1 FREE Jetski or $100 OFF!!

ENJOY MIAMI IN 60FT SEA RAY!!

Enjoy Miami With Luxury Atlantis 64ft Power Mega Yacht!!One hour free mon-thurs

20' Bennington pontoon, Yamaha 70HP, up to 9 people - gas included! Bay Pines

ENJOY MIAMI IN NEW 48FT GALEON!!

ENJOY MIAMI IN 57FT AZIMUT!!! One hour free mon-thurs 🎸

Recent reviews in florida.

March, 2024

Celebrated my 40th alongside my family on David and Emma’s catamaran and it turned out better than I would’ve ever imagined! Emma was the best captain and she was even more awesome with the kids. We went during spring break and their recommendations on where to go with the kids was just perfect. David was great with communicating with me since before I even booked the trip, and answered all the questions I had promptly. We all had such a great time, made so many memories and will definitely be booking with David and Emma again!!

We booked David's boat for a bachelorette/30th birthday party and had a BLAST. David, and his daughter, Emma, were absolutely amazing. They were easy to get in contact with and responded promptly. Their boat was modern and perfect for what we were looking for. They even added some decorations and heart shaped sunglasses! We thought that was so thoughtful. If you're looking for a boat in St. Pete beach, I highly recommend this one!

We had an amazing day on board with Kristal & Captain Deren's ship. They truly enjoy what they do and it shows in their hospitality, attention to details, and the vibe they created on board. Thank you again and see you soon for another great sail. ❤️

My family and I had an absolutely amazing time with David & his daughter! The took us to see dolphins, we got to jump off the boat, it was just wonderful. 10/10 would recommend. I can’t wait to book again!!

February, 2024

Spring Break special w/ FREE Champagne & Fuel included!

I had an amazing time with my friends on this boat! It was exactly how I wanted to celebrate my birthday! The boat was super clean and perfect size for the six of us, and the sound system was amazing so we danced so much lol Everything was super seamless, including booking and communicating with Brandon; I could tell he really wanted me to have the best celebration and I appreciated that! Spending time at the sandbar was so nice too. Seriously, just book this! You‘ll be so happy you did!

Private Catamaran Charter in Marathon

We had the most beautiful day on the water with Jack. Weather was perfect. So relaxing. Just sat back and enjoyed. We saw dolphins a few times. We got to take in the most beautiful sunset ever. Highly recommend Jack as your captain!!

Top Sailboat Rental Locations in the United States

Los Angeles , California

405 listings

Marina del Rey , California

168 listings

San Francisco , California

66 listings

Honolulu , Hawaii

63 listings

New York , New York

84 listings

Oakland , California

38 listings

How To Book on Getmyboat

Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.

Inquire & Book

Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.

Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!

Dive into Our Journal

March 04, 2024

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Getmyboat Is Boating Together, Everywhere

February 21, 2024

The Top 10 Most Popular Cities in Florida for Boating

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Getmyboat Introduces an All-New Affiliate Program

January 05, 2024

Risky Reservoirs: States Where Aging Dams Pose the Greatest Threat

December 13, 2023

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Bareboat Charters

Bareboat charters. your sailboat. your experience.

Sail Away to Tropical Paradise: Explore the Florida Keys on a Well-Equipped Sailing Vacation

Picture this: a gentle breeze brushes against your face as you navigate the calm, turquoise waters of the Florida Keys. You’re at the helm of a beautiful sailing vessel, equipped with all the amenities you need to make your sailing vacation unforgettable. Whether you choose the Catalina 22′ for a day sail or the Morgan 33′ Out Island for an overnight trip, you can rest assured that your boat is well-equipped for your chosen adventure.

As you board your boat, you feel a sense of excitement and freedom wash over you. You’re in charge of your vacation – you get to plot your course and sail into tropical paradise at your own pace. The warm sun beats down on you, and you can’t help but feel grateful for this opportunity to escape the stresses of everyday life.

If you’re planning a multiple night charter, you can provision at one of the local chain supermarkets and enjoy your fully-equipped galley at your leisure. Or, if you’re just renting for the day, you can grab a packed lunch and set off on your adventure.

The Florida Keys offer a plethora of activities for sailors of all levels. From visiting underwater or land-based state and national parks to local beach bars and restaurants, there’s something for everyone. Take a dip in the crystal-clear waters, explore the mangrove islands, or relax on a secluded beach – the choice is yours.

Whether you choose the Catalina 22′, the Morgan 33′ Out Island, or one of our catamarans, you can rest assured that your boat is well-equipped for your chosen adventure. So go ahead, captain your sailing vacation in the Florida Keys and create memories that will last a lifetime.

Meet your yacht at our home in Soper’s Hole

“Know your charter is going to be perfect, without any drama.”

Experience exhilarating Sailing and Nature.

“Discover the Islands of the Florida Keys.”

“Morning Star Charters.”

Let the day Start and stop when and where you desire.

“The Perfect Getaway”

“Enjoy the feeling of being welcomed into the Morning Star sailing family”

Sailing at it’s best

“Morning Star Sailing Charters is the longest established Sailing snorkeling Charter company in the Florida Keys.”

Enjoy self-prepared meals from your well equipped galley while surrounded by incredible beauty

“All the water toys you could want, available to rent right here at Morning Star Charters.”

Morning Star Charters, Sailing, Snorkeling, Kayaking, Sunset Sails, Cottages and Sailboat Rentals in the Florida Keys / Key Largo. Sailing and land based Sailing Vacations.

• CHARTER YACHTS
• CREWED YACHTS
• Bareboat Charter
• Skippered Charters
• Crewed Yacht Rentals
• POWERBOAT or MOTORYACHT CRUISING
• HOUSEBOATING
• SAILBOAT CHARTERS
• CATAMARAN CHARTERS
• SAILING DESTINATIONS & ITINERARIES
• CHARTER GUIDE

Sailing Yacht Charter Florida Sailboat Charters & Rentals

Top-rated yacht charters in florida - preselected yacht rentals:.

Sailboat Sun Odyssey 410 for rent in Vinoy Resort Marina

• Sun Odyssey 410 [Yacht Price incl. Taxes]
• Barbeque Grill
• Yacht Insurance
• Bahamas charter tax
• Final cleaning
• Damage waiver
• Cancellation insurance
• Virgin Islands Search and Rescue (VISAR)
• Cruising tax
• Fuel (for outboarder)
• Maryland Amusement Tax
• VAT or sales tax

Sailboat Dufour 430 for rent in Saint Petersburg

• Dufour 430 [Yacht Price incl. Taxes]

Yacht Dufour 430 available for charter in Saint Petersburg

Yacht Sun Odyssey 440 for hire in Key West

• Sun Odyssey 440 [Yacht Price incl. Taxes]
• Cockpit cushion
• Outboard engine for dinghy
• Barbeque Grill (gas)

Sailboat Dufour 470 for rent in Saint Petersburg

• Dufour 470 [Yacht Price incl. Taxes]
• Skipper (food not included)

Yacht Catalina 309 for rent in Saint Petersburg

• Catalina 309 [Yacht Price incl. Taxes]

Yacht Hunter 290 for hire in Tarpon Point Marina

• Hunter 290 [Yacht Price incl. Taxes]
• Rubber Dinghy

Sailing yacht Catalina 350 for charter in Vinoy Resort Marina

• Catalina 350 [Yacht Price incl. Taxes]

Sailing boat Hunter 31 for hire in Saint Petersburg

• Hunter 31 [Yacht Price incl. Taxes]

Sailboat Hunter 40 available for charter in Saint Petersburg

• Hunter 40 [Yacht Price incl. Taxes]

Sailing yacht Catalina 350 available for charter in Saint Petersburg

Sailing boat Island Packet 31 for rent in Tarpon Point Marina

• Island Packet 31 [Yacht Price incl. Taxes]
• Cape Coral (6)
• Dania Beach (1)
• Key Largo (1)
• Key West (4)
• Saint Petersburg (30)
• Biscayne Bay (1)
• Caloosahatchee River (6)
• Florida Bay (1)
• Florida Keys (5)
• Glover Bight (6)
• Intracoastal Waterway (2)
• Key West Island (4)
• Tampa Bay (30)
• Treasure Island (2)

TOP Yacht Charters - Yacht Rentals

• Sailboat Charter North Atlantic Ocean
• Sailboat Charter Gulf of Mexico
• Sailboat Charter Straits of Florida
• Sailboat Charter United States of America
• Sailboat Charter US Atlantic Coast
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Rent the best Florida Keys sailboats

• Sailboat Rentals
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• Florida Keys

Our top sailboat rentals

Luxury Sailing Catamaran in Brickell

Key Biscayne, FL

Best and most Relaxing Sail in Miami! Join Us!!

Marathon, FL

Florida Keys Catamaran Cruise

Luxury 47 feet Beneteau Yacht - Miami

Sailing Cataraman 48ft "Bubble" | Sound-bath, Yoga and Meditation

Key Largo, FL

Set Sail on a 22' Catalina Adventure in the Florida Keys

Miami Beach, FL

Explore the waters of Miami aboard 60' Leopard 2021

Sailing Adventures and Relaxing Cruises

Key Largo Sail The Everglade & More

60' Catana for sailing in Miami, FL!

Relentless -35' Edel Sailing Cat

Catamaran Sailing Cruiser Lagoon

How to rent a sailboat in florida keys, find the perfect boat.

Enter your desired location and date to explore our fleet of sailboats.

Select a captain

Choose to drive yourself or select a USCG licensed captain.

Book with ease

Connect with your boat owner and complete your booking online.

Enjoy your day on the water with friends and family!

Why Boatsetter?

As the global leader in peer-to-peer boat rentals, Boatsetter offers an easy, safe and accessible way to experience on-the-water adventure. With boat rentals in 600+ locations, finding a boat is easy and with the option to tap into the largest network of USCG licensed captains, boating experience is not required.

Get out on the water worry-free, knowing our insurance covers every boating trip

Choosing the right boat rental platform is essential to your peace of mind while on the water. That's why we've gone the extra mile to focus on safety through our exclusive partnership with GEICO Marine and BoatUS. As the first and only boat rental marketplace to offer insurance on every peer-to-peer rental, you are protected during all rentals with insurance coverage and on-water assistance through TowBoatUS.

Got questions?

Frequently asked questions

What makes Boatsetter different from other boat rental platforms?

What makes Boatsetter different is peace of mind. Boatsetter is the first and only boat rental marketplace to offer insurance on every peer-to-peer boat rental. We know choosing the right boat rental platform is essential to your experience while on the water. That's why we've gone the extra mile to focus on safety through our exclusive partnership with GEICO Marine and BoatUS. As the first and only boat rental marketplace to offer insurance on every peer-to-peer rental, you are protected during all rentals with insurance coverage and on-water assistance through TowBoatUS.

How to rent a boat on Boatsetter?

At Boatsetter, our mission is to make getting out on the water as easy as possible. With our intuitive booking system, you can rent a boat as soon as today. -First, you must determine your budget and the type of boat you want to rent. -Next, decide where you would like to boat and the kind of boat you would like to spend the day on. -Finally, determine if you will be needing a boat captain and reach out to the boat owner. That’s it! You’re officially on your way to a fantastic day out on the water.

How much does it cost to rent a boat?

The cost to rent a boat depends on whether you are renting for a half-day or a full day, the boat features and the boat size can impact your boat rental price. Rental prices can range from $200 to $1,000 plus depending on the boat rental itself and the length of time of the rental.

How many people can fit on the boat rental?

The number of people who can fit on boat rental largely depends on the boat’s size and how many life jackets are on board. Currently the coast guard allows a maximum of 10-12 people on a Boatsetter boat rental.

How much does it cost to rent a yacht?

The cost of renting a yacht depends on the boat’s size and the amount of time you’ll use the yacht. The onboard amenities and luxurious accommodations also dictate the price. You can contact our yacht specialists for a custom quote by visiting https://www.boatsetter.com/luxury-yacht-charters .

How old do you have to be to rent a boat?

You must be 18 years old to rent a captained boat and 25 years old if you would like to rent a bareboat charter.

Do I need a boating license to rent a boat?

Boating license requirements vary from state to state. As a renter, you are responsible for understanding local state requirements.

Can you rent a yacht for the day?

Boatsetter allows you to rent a yacht for the day. Single-day yacht rentals are available for a select number of yachts. To chat with a yacht specialist please visit https://www.boatsetter.com/luxury-yacht-charters .

Can you rent a yacht for the week?

Boatsetter allows its customers to rent a yacht for the week. Renting a yacht for a week gives you more access to the wide range of yachts available on our platform. You can either book a rental directly through the site or connect with one of our charter specialists to plan your trip here: https://www.boatsetter.com/luxury-yacht-charters .

Can you rent a yacht for the month?

Booking a month-long yacht rental is a detailed and hands-off process when working with our team of yacht charter specialists. We tailor each yacht charter to our client's specific wants and needs. Our luxury yacht charter specialists can be reached at (954) 715-4114 or by visiting https://www.boatsetter.com/luxury-yacht-charters .

How to rent a private yacht?

Renting a private yacht is a very detailed experience that caters to your exact needs while onboard one of our luxury yachts. To plan your private yacht rentals experience please visit https://www.boatsetter.com/luxury-yacht-charters .

How much does it cost to rent a pontoon boat?

The cost of renting a pontoon boat depends on the size, location, and rental time of the boat. Prices can range anywhere from $200 for a half-day rental or just under a $1,000 for longer rentals.

How much does it cost to charter a yacht?

The cost to charter a yacht varies depending on the boat size and the length of the charter. Prices typically range from less than $1,000 to $5,000 plus if you’re wanting to charter the yacht overnight.

How much does it cost to rent a boat for the day?

The cost of renting a boat for the day on average ranges from $200 to $1200. The cost to rent a boat varies depending on the size of the boat and the length of time that you will be using the boat.

How does the boat insurance work?

Boat insurance typically covers loss caused by things such as fire, sinking, storms, and collisions. The extent of the coverage varies depending on the policy.

Do I need my own insurance to rent a boat?

You do not need boat insurance when renting with Boatsetter. Coverage is provided under the Peer-to-Peer Boat Rental Policy, which is underwritten by GEICO Marine Insurance Company. The policy was written from the ground up as a stand-alone recreational boat rental insurance policy covering the period of time that the boat is being rented and is available for all non-commercially insured boats.

Does Boatsetter screen renters?

Yes. We use a system called Cognito to ensure that payment information matches the renter's identity. We also require renters taking out a captained boat to be at least 18 years old and on a bareboat to be at least 25 years old.

Is listing my boat on Boatsetter free?

Yes! Listing a boat is completely free. We only take a commission when your boat is rented. We only make money when you do!

What if I'm not comfortable having a renter drive my boat?

If you are not comfortable having a renter drive your boat, we have an expansive network of licensed and experienced captains. Once your boat is listed, you can filter through our network of captains and favorite captains in your area that you would like to operate your boat.

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Top sailboat rentals reviews in Florida Keys, FL

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Amazing experience all around!

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We had a great time on the boat! Beautiful day, beautiful weather, nice boat!

We had a great time. Aaron was a wonderful captain. Highly recommend.

Aaron was awesome! We had a great day on the water. The boat was in great shape and Aaron took care of everything we...

Paul, Chris, Lime Key Boat Rentals and Boatsetter were AWESOME!

I own a well equipped C-22, and the one I rented...

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Perfect boat. Great crew. Truly excellent experience!

The staff were great and provided a fun atmosphere. The boat was amazing, very clean and comfortable. Thank you, Juan.

Aaron was so nice and amazing! My husband and I just got married that morning and we wanted to do a sunset sail with...

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Thanks Capt. John! Your boat was a beauty and we appreciate all the individual attention you and Tina provided me...

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Sailboat Rentals in Florida Keys, FL

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Sailing boat rentals

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Dufour - Dufour 45 Classic | 12 people (14m)

From $492 per day.

Atlantic - 49 | 13 people (14.93m)

From $783 per day.

Dufour - Gib Sea 51 | 12 people (16m)

From $1,209 per day.

Alfa - 56 | 8 people (16.4m)

From $1,612 per day.

Bavaria - Cruiser 50 | 10 people (15.57m)

From $1,958 per day.

Dufour Yachts - Classic | 6 people (10m)

From $260 per day.

Beneteau - Cyclades 50.5 | 10 people (15.7m)

From $224 per day.

Atlantic - Deluxe 61 | 25 people (20m)

From $1,679 per day.

Ocean yachts - Ocean star 51,2 | 12 people (16m)

From $184 per day.

Wooden Traditional-Style Boat - 2018 | 21 people (14.85m)

From $592 per day.

PARASCHOS SAILING YACHT - 52FT. | 12 people (15.8m)

From $1,570 per day.

Bavaria - Bavaria 49 | 10 people (15m)

From $1,388 per day.

Bavaria - 50ft | 10 people (15m)

From $799 per day.

Wooden - Sailing boat Trehandiri | 6 people (10.7m)

From $1,727 per day.

Traditional Cycladic - Sailing Boat | 1 person (15m)

From $3,357 per day.

BAVARIA - Bavaria 50 | 12 people (14.99m)

From $1,407 per day.

From $475 per day

Wauquiez - PILOT SALOON 48 (NEW) | 7 people (14.7m)

From $312 per day, why should i rent a sailing boat.

A sailing boat is an ideal way to discover new gems on land while cruising on the sea and allowing the wind to carry you. Sailing boats are safe and marvelous boats, which you can use for relaxation, or also for going on an adventure and experiencing the thrill of sailing on the waves.

Spend time with friends or relax with family. Renting a sailing boat can be the best way to make the most of your holiday! Look forward to sunbathing aboard your boat and enjoying a drink or two in the sun. If you’re ever seeking shade then don’t forget you can take a break and relax in your cool cabin below deck.

How much does a sailing boat rental cost?

A sailboat rental has different price ranges depending on the number of cabins, the length, season, the year the boat was built, if it is chartered with or without a skipper, etc. You can rent a sailboat for a day starting from $250 during low season. Bigger sailing yacht rentals with 6 cabins can cost from $11,000 per week. Rent a sailboat for a week during low season for $1,000 per week. Depending on the owner’s listing, there may be different included or additional costs so make sure you read all of the additional costs and options.

Additional options such as air conditioning, power generator, and water toys raise the price. One last thing to take into account is whether or not you will be sleeping on board and if so, how many people will want a cabin or are okay with sleeping in other living spaces? This decision can greatly influence the price.

Do I need a boat license to rent a sailing boat?

A sailboat charter may require a boating license depending on the legislation of the location, where you are going to sail and the boat owner’s listing. Some owners choose to not have their sailing boat for rent available without a license due to risks of damage. For example, in Spain, a permit is only required for those up to 6 meters in length. Meaning you can sail your boat rental in  Barcelona  without worrying about a permit so long as the boat meets regulations.

Don’t have a boating license? Then you should charter a sailboat with a skipper! A professional sailor will help you set sail and make your sailing holidays unforgettable. Your luxury sailing experience is waiting for you! These special offers allow you to learn from the skipper in your own personal sailing school.

What are the best destinations to rent a sailing boat?

Among the possible sailing boat charter destinations,  Cabo San Lucas  is definitely worth mentioning, as well as  the Bahamas and all of its many islands. Other places to visit are the Spanish Balearic Islands, including Mallorca and Ibiza , Mexico , Italy,  and  Caribbean  destinations, such as  Puerto Rico . The best time of year to sail will depend on your destination and the winds in that area. Places in Europe usually have the best sailing conditions in the summer. Don't miss out on our favorite European spots,  Valencia ,  Corfu ,  Cinque Terre , and  Split . If you are planning to go to places in the Caribbean, Mexico, and South America, these are excellent destinations all year round!

With a sailing boat, you can sail between beaches with spectacular scenery and swim in clear turquoise waters, all whilst making the most of the opportunity to captain your very own boat (if you have the required license). Otherwise, a skipper will be available to help you discover new places and make the experience that extra bit special. From your sailboat, you can dive, snorkel, scuba dive, or use a surfboard to discover the most hidden spots! If you’re feeling extra adventurous then why not test the canoe out?!

What should I consider when renting a sailing boat?

Some things that you should consider when renting a sailing boat:

• Dates of travel
• Destination
• Additional charges

The first things to consider when renting a sailing boat are the capacity you will need, the dates of travel, and the destination you want to start your sailing experience in. The capacity is especially important if you are choosing to stay on the boat. The capacity will also depend on if you decide to hire a crew and a skipper. A skipper may be mandatory for your sailing yacht charter if you do not have a valid nautical license. Make sure you count the correct number of people including crew!

There are also additional charges depending on if you want to add certain features for the trip. You may also choose to bring your pet on board! If you choose this option then you will most likely need to pay an extra price per rental.

What is included in a sailing boat charter and what additional expenses can I expect?

Each sailing boat charter has different additional and included costs, so if you are not sure of what costs are included make sure to ask the boat owner of your rental. Included costs can include mooring in the home port, sometimes skippers may be also included.

You can expect different additional expenses depending on the boat owner’s listing. The skipper may be a mandatory cost and included or can be optional and at an additional cost. Skippers normally range from $180 per day. Items such as extra cleaning, pets on board, early boarding, water sports equipment such as paddle surf, snorkeling gear, and more.

How can I rent a sailboat?

Our website offers a wide range of sailing boats, and you can find the one that suits you best by using our filters. For example, you can choose the size of your boat, the number of people that will be with you, the dates of your trip, whether you require a skipper, and much more! Don't forget to check the time and available dates of each sailing boat and don't hesitate to contact the owner if you have any doubts. Prices range from $1,000 per week in low season, and around $10,000 per week in high season for sailing boats required for more people and with more cabins.

What are the most popular brands for sailing boat rentals?

The most popular brands for sailing boat charters are Bavaria and Jeanneau.

How much does it cost to rent a sailboat for a day?

The cost of a sailing boat charter for a day depends on the destination, the capacity, boat features, season and lastly the boat owner’s listing. For example a sailing boat charter in Barcelona costs around $200/day with 6 places in low season and the boat is 6-8m in length. 

How much does it cost to rent a sailboat for a week?

A sailboat rental for a week depends on the destination, capacity of the boat, boat features, season, and the boat owner’s listing. For example, a sailing boat rental in Barcelona costs starting from $2,500/week in low season. The boat listing has a capacity of 10 people and is 40ft in length. A sailing rental in Miami instead can cost from $1,600/week with the boat having a capacity of 6 people and a length of 41ft.

What is included in a sailboat charter and what additional expenses can I expect?

Usually, there is a base price for the charter period and a flat rate for the additional mandatory costs. Pay particular attention here to decide if you want to include only the final cleaning or also add bedding, towels, and an engine for the auxiliary boat. Other costs include mooring fees, of course, which can vary greatly depending on the size of the ship, the port, and the country. For gas and fresh water, you can expect to pay between $150 and $300 per week.

Do you need a license for a sailing boat rental?

If you want to charter a sailboat without a skipper, most countries require a navigation license. In France and the Caribbean, however, you can charter a sailboat without one. The decisive factor in such cases is the "past history sailing experience" of those who wish to charter the sailboat, which is a sheet that details the entire navigational experience of the interested party.

Where to charter a sailboat?

Spain and Italy offer many beautiful sailing spots. Croatia is an ideal place for beginners. For experienced sailors, we recommend chartering a sailboat in Martinique, Seychelles, Greece, or in the Canary Islands. Choose your favorite destination and we will send you an offer!

Can I move to different places with my sailing boat charter?

Yes. A sailboat charter is an excellent and affordable way to spend a holiday at sea discovering different places. You will feel at ease on board and can anchor in quiet bays or explore a new beach or cove every day. If you rent for more than one day you should know that weekly rentals nearly always start on Saturday afternoon and require you to return to the port of origin the following Friday afternoon. The last night is usually spent on board since check-out will take place on Saturday morning around 9 am.

Welcome to Bimini Bay Sailing Lessons

Small sailboat sailing school.

I sold my last sailboat in July, 2023. I will still give occasional lessons for individuals who own their own small powerboat or sailboat.

Have a new Keelboat or Powerboat? I give small keelboat and small motorboat lessons on your boat, covering such topics as docking, backing up, pivot turns, and more as I share local knowledge of our waterways...

Bimini Bay is a beautiful, sheltered body of water nestled inside Anna Maria Island. It is the perfect, safe place to learn to sail -- and we often see dolphins! Bimini Bay Sailing is just minutes from Holmes Beach, Longboat Key, and Bradenton, snuggled between Tampa Bay and the Gulf of Mexico. During the last part of your saling lesson we usually sail just off the shore of Anna Maria Island into Tampa Bay, with a clear view of the Sunshine Skyway, Egmont Key and the Anna Maria Pier.

Take Sailing Lessons on the very stable WindRider 17 Trimaran, with a quiet electric motor for uncertain breezes. Or at your location on your own small dinghy sailboat or keelboat. I also offer powerboat docking lessons on your own boat.

Learn how to use a mainsheet, jib sheets, and a furling line. learn how to tack, jibe, and how to rig a sailboat. learn your basic points of sail. students usually sail at least half of the time on their own..

If you already know how to sail and you want to rent a Trimaran, for your safety and pleasure, I will still do a skills and safety review. Then I'll go out with you as your coach/guide, on the same sailboat, but you will do almost all of the sailing. This is to make your experience as safe and pleasant as possible.

Captain Floyd Jay Winters , an instructor for Bimini Bay Sailing since 2012, has taken over the helm of the Anna Maria Island small sailing school. (He is fully vaccinated.) To schedule a sailing lesson, you can reach Coach Jay Winters at 941.730.2719 or click on the [ Contact ] link.

I encourage a follow up session to refine your skills and have to opportunity to get more sailing time on your own. Parents or spouses are welcome to watch the sailing class and take photos of their kids or spouse as they learn to sail. Click the [ Lessons ] link for more information on what is covered.

Click the [ Photos ] link to see beautiful photos of Sunfish at Bimini Bay Sailing School.

A Father and Son Tacking a Sunfish (29 seconds)

For the past 11 years, Bimini Bay Sailing has offered a sailing summer camp through the Anna Maria Island Community Center. And once again this past June 2022, fourteen young sailors had the opportunity to safely experience the excitement of their first exposure to sailing during our mini sailing camps at Bimini Bay.

Receive sailing lessons at our small sailing school or just refresh your sailing skills in beautiful Bimini Bay. The magical waters around Anna Maria Island are warm, clear, and uncrowded.

Arial Map 1    Arial Map 2

Bimini Bay Sailing, Anna Maria Island , Florida

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Small Boat Cruising in the Florida Keys

• By Bianca Dumas
• July 12, 2022

We were tied to the fuel dock in Marathon, the midpoint of the Florida Keys, in the early part of 2022, when I realized our mistake. 

Other cruisers traveling the Great Loop were on the loop’s southern stretch of the route, while some bluewater cruisers were starting to stage for passage to the Bahamas and beyond. I asked the dockmaster if any slips were available, and learned that it’s perpetually high season in the Keys, including at that moment. Along with cruisers and sailors, fish migrations change throughout the year, calm summer conditions attract divers, and festivals bring in the party crowds.

“We’re always booked out,” he said, shaking his head. Then he paused, perhaps realizing that he’d just sold us a total of 6 gallons of diesel. “Wait, what size is your sailboat?”

We were on Jackalope , a Nor’Sea 27. He shifted into a smile. “Oh yeah, we can probably squeeze you in down there,” he said, pointing to the inner harbor. 

We were grateful for the offer, but in the end, we stuck with our plan to anchor out. We had stayed on a dock—at Bahia Honda State Park—only once during our monthlong Keys cruise. While a lot of people on bigger boats doing the loop preferred marinas, anchoring out seemed to fit with our small-boat cruising style. We were basically camping, which required few amenities and created a lot of options. We took bucket baths when we couldn’t go ashore for showers. We cooked from simple ingredients that didn’t have to be refrigerated: lentils, rice and pasta. We paddled our inflatable kayak to shore for an occasional restaurant meal. 

We laughed when we were once mistaken for homeless people on a resupply walk, but how could we argue? We don’t have the same look as those who can blow-dry their hair and pull clothes off a hanger. 

But our small boat makes for a big adventure. We crossed the Gulf of Mexico from Fort Myers Beach directly to Key West, and because the 90-mile crossing took us three days and two nights, we had the experience of a much bigger, more challenging passage than other boats would. Our sails go up quickly and easily, so we take advantage of every quarter-hour of good wind that we can find.

Moving slow and low, we don’t fear crab pots; they’re easy to see and steer around, even in the dark. And since a keel-hung rudder protects our small propeller, hitting a crab-pot float head-on doesn’t cause trouble. At our top motoring speed of 4 knots, we can see dolphins, turtles and manatees before they dive for cover. 

We can’t avoid getting tan because we steer from an open center cockpit. Nor can we avoid getting exercise because we have to paddle ashore rather than motor. ( Jackalope ’s canoe stern means we don’t have a motorized dinghy on davits.) 

Like the mythical Western creature that shares its name, Jackalope has a small stature. Just right for us.

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In addition to the best offers we have for boat and yacht charters in Florida, see also options available for rent in these nearby locations:

• 1084 boat rentals in Pompano Beach, FL
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How to Rent a Boat in Florida, USA on Sailo

Choosing a yacht rental in Florida? Enjoy a one-of-a kind experience on the water with Sailo's private yacht charter in Florida. Whatever your sailing style; from experienced skipper, fishing fanatic or thrill seeker, to those who just want to relax on deck with your family or friends, you’ll be spoiled for choice. Rent a boat in Florida with Sailo for a memorable day trip or a sailing vacation to remember!

Our prime selection of private yacht charters in Florida

Step aboard your private yacht charter in Florida, with a choice over 893 boats to rent from Sailo. We offer a selection of boats for all tastes, including 55 sailboat charters in Florida . You can also choose from 46 Florida catamaran rentals . Want to see the State in style? Choose from one of our 731 Florida motor yachts on Sailo.If you’re looking to host a party or a reception for more than 13 guests, you’ll also find 60 party boat rentals in Florida , for a truly memorable event.

How to find the right Florida yacht rental?

Sailo offers beautiful yacht rentals in Florida at various price points. Use our advanced filters to narrow your search by date, group size, and trip duration: 2 hrs, 4 hrs or full day boat charters in Florida. You can also choose the type of boat (sailboat, motorboat, catamaran) you want and go even further and look for a particular length, manufacturer and model. The price filter will help you see the available boats within your budget and the crew option is useful when you want to see boats with a skipper/captain included or only bareboats. Do you see a boat that you would like to rent in Florida? Click on it to go to the next page to read more about it, see more photos, send a direct message to the owner to ask more questions or start creating your booking request right away!

How much does it cost to rent a yacht in Florida?

You can charter a boat in Florida for a day, for an average of $1100. The average price for a weekly boat rental in Florida is $18489. Your total budget for a sailing trip in Florida depends on many factors such as: trip duration, if captain and crew are included in the price or their cost have to be paid separately, fuel cost (which could be significantly higher on a motorboat compared to a sailboat) and other extras you choose to customize your experience by boat charter in Florida.

Do I need a licence to rent a yacht in Florida on Sailo?

No, you do not need a license to rent a boat in Florida on Sailo as long as you are renting a boat with a captain included. There are two types of boat rentals and yacht charters available on our website: bareboat and captained charters. If you rent a bareboat yacht, then your charter comes without any crew, and you or someone in your group will need a license. The boat owner will require you to upload the boating resume or license of the person who will drive the boat. Most of our boat owners might also like to test your boating skills before you take your bareboat charter out on the water. When you charter a yacht with a captain included or add the captain and/or crew as an extra to your sailing adventure, then a certified skipper will be provided.

Tips for responsible boating

If you’re looking to explore our beautiful planet, a yacht charter in Florida is a great place to start. Explore coral reefs with your snorkel, discover hidden bays and islands and generally enjoy the view of nature. Remember, that sailing motto:  'Take only photos, leave only wake'  (OK, so we paraphrased). To be a responsible sailor, remember:

• Don’t disturb coral or sealife
• Take your trash home (and don’t throw anything in the sea)
• Respect the locals and their customs wherever you go

Read more about responsible boating.

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