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Awesome sailboat rentals near Sarasota, Florida.

4.9(Average of 229 reviews in this area)
View our Sarasota sail boating guide
1 - 24 of 61 listings
"Tropic Whisper" Beneteau 473Sailing in Punta Gorda6 guests

"Tropic Whisper" Beneteau 473

New
Superowner
$448hour
34' Island Packet Sailboat in NaplesSailing in Naples4 guests

34' Island Packet Sailboat in Naples

5.0
$120hour
Hunter Marine Sailing Yacht in Delray Beach to Lake BocaSailing in Delray Beach12 guests

Hunter Marine Sailing Yacht in Delray Beach to Lake Boca

New
Superowner
$36person
SAIL RIGHT FROM MIAMI RIVER IN A 36' FT YACHT!!Events in Miami12 guests

SAIL RIGHT FROM MIAMI RIVER IN A 36' FT YACHT!!

5.0
$199hour
Spa Austin Whaler Sailboat Rental in MiamiSailing in Everglades2 guests

Spa Austin Whaler Sailboat Rental in Miami

New
$10hour
38’ Morgan Sailboat Rental in Miami Beach, FloridaSailing in Miami Beach6 guests

38’ Morgan Sailboat Rental in Miami Beach, Florida

5.0
Superowner
$100hour
2019 HOBIE MIRAGE ADVENTURE ISLAND SAILBOATSailing in Jacksonville2 guests

2019 HOBIE MIRAGE ADVENTURE ISLAND SAILBOAT

New
$40hour
45’ Beneteau Oceanis Sailing in Destin FloridaSailing in Destin6 guests

45’ Beneteau Oceanis Sailing in Destin Florida

5.0
$200hour
2022 Lexington Pontoon Boat rental in Fort Walton Beach/ Destin FL.Powerboats in Fort Walton Beach5 guests

2022 Lexington Pontoon Boat rental in Fort Walton Beach/ Destin FL.

5.0
$93hour
PIRATE Tall Ship (Private Charters) in NassauEvents in Nassau300 guests

PIRATE Tall Ship (Private Charters) in Nassau

4.0
$2,100hour
Catamaran 38' Private tour to Isla Mujeres / Cancun / Playa del CarmenSailing in Centro - Supmza. 00116 guests

Catamaran 38' Private tour to Isla Mujeres / Cancun / Playa del Carmen

5.0
$200hour
4 Persons 24' Cruising Catamaran in Cancún, Mexico For CharterTours in Cancún4 guests

4 Persons 24' Cruising Catamaran in Cancún, Mexico For Charter

5.0
$115hour
40ft. Black Sea Ray Yacht for 13 pax in Cancún, Quintana RooEvents in Cancún13 guests

40ft. Black Sea Ray Yacht for 13 pax in Cancún, Quintana Roo

New
$225hour
Boat Island Historical Tour in AtlanticSailing in Nags Head1 guest

Boat Island Historical Tour in Atlantic

New
$45person
Pearson 26 Coastal Sailboat in NorfolkSailing in Chesapeake Bay6 guests

Pearson 26 Coastal Sailboat in Norfolk

5.0
$60hour
Get away for a day or weekend! Charter 44' Catalina Sailboat!Sailing in Potomac River6 guests

Get away for a day or weekend! Charter 44' Catalina Sailboat!

5.0
$490day
Annapolis Sailing a 34' Beneteau Sloop! SEVERN RIVER & Chesapeake BAYSailing in Potomac River6 guests

Annapolis Sailing a 34' Beneteau Sloop! SEVERN RIVER & Chesapeake BAY

5.0
$150hour
Learn to Sail in Havre de Grace, MD (Minutes off of I95 in Historic Havre de Grace, MD)Tours in Havre de Grace2 guests

Learn to Sail in Havre de Grace, MD (Minutes off of I95 in Historic Havre de Grace, MD)

New
$200person
Starratt & Jenks Morgan 45ft Sailing Charter in Havre de Grace, MD - USCG Licensed CaptainSailing in Havre de Grace6 guests

Starratt & Jenks Morgan 45ft Sailing Charter in Havre de Grace, MD - USCG Licensed Captain

New
$200hour
Catalina 22 Sailboat for rent in Gravois Mills, MissouriLake of the Ozarks4 guests

Catalina 22 Sailboat for rent in Gravois Mills, Missouri

New
$99day
"Class Action" Hunter LegendSailing in Lake Michigan6 guests

"Class Action" Hunter Legend

New
Superowner
$321hour
#1 Manhattan Luxury Sailboat, Champagne & Catering Service, 5-Star AccommodationsSailing in Manhattan6 guests

#1 Manhattan Luxury Sailboat, Champagne & Catering Service, 5-Star Accommodations

5.0
Superowner
$325hour
Jeanneau 39i Julia Sailing Yacht in NY HarborSailing in Manhattan6 guests

Jeanneau 39i Julia Sailing Yacht in NY Harbor

5.0
$350hour
Amazing Sailing Trip in NYC !!! The Most beautiful Sailboat in NYCSailing in Manhattan6 guests

Amazing Sailing Trip in NYC !!! The Most beautiful Sailboat in NYC

5.0
$330hour

Sail Reviews in Sarasota

  1. NR
    Nicholas
    45’ Beneteau Oceanis Sailing in Destin Florida

    The experience with Captain Chris was amazing. The crews knowledge of the local area to the adventure that is charters sailing it was a blast! We were blessed to have quite literally perfect conditions so you're mileage may vary due to weather but se la vie. We saw all kinds of wildlife and found time to watch the sunset on the water after taking dip near the beach. If you're looking for a great time on a proper sail boat check them out.

  2. KC
    Kathryn
    38’ Morgan Sailboat Rental in Miami Beach, Florida

    Alexi was fantastic and was able to get our trip in before the hurricane hit. He was very knowledgeable and a great tour guide. 10/10 would book this trip again!

  3. Aja
    Aja
    2022 Lexington Pontoon Boat rental in Fort Walton Beach/ Destin FL.

    Our captain was great! We had so much fun. The boat was well equipped and comfortable. The price is unbeatable for the area. Our captain made sure we got some nice photos throughout the tour and saw all the hotspots! The captain also provided us with floaties and waterproof phone cases. We couldn't have asked for a better trip or captain.

  4. Marco
    Marco
    Amazing Sailing Trip in NYC !!! The Most beautiful Sailboat in NYC

    Perfect place to start in Manhattan for a cruise to the Statue of Liberty or under the Brooklyn Bridge. Amazing sailboat, absolutely up to date, with comfort and speed as well, it is a pleasure to sail with Captain Paul!

  5. DB
    Daniel
    Amazing Sailing Trip in NYC !!! The Most beautiful Sailboat in NYC

    Paul and Melissa are fantastic. They went to absolutely every length possible to make our trip as incredible as it was. The boat is in immaculate condition and it was a fantastic day. Definitely do choose this boat as it was a day not to forget!

  6. Rachel
    Rachel
    45’ Beneteau Oceanis Sailing in Destin Florida

    We loved our awesome day on the water with Captain Chris! We felt so comfortable and loved our time on the boat. We also got to do some sightseeing and fishing- we spotted multiple dolphins as well as pulling in some Spanish mackerel. 10/10 recommend!

Boating Guide - Sarasota Sail

Explore Sarasota, Florida onboard a sailboat rental.

Looking for a fun boating experience on your next trip to Sarasota, Florida? Renting or chartering a sailboat is a great way to explore for a day, bringing your friends and family together onboard. A sailboat rental or charter is the perfect choice for a special event or during a vacation and for touring a new area. Sailboats are great for a day trip on a lake or river near Sarasota, Florida, for a relaxed sailing experience, or if you're taking lessons to become a skipper on your own.

Using GetMyBoat to rent your next sailboat.

Experiencing the water has never been easier thanks to GetMyBoat. GetMyBoat allows you to quickly search, compare prices, submit rental inquiries, and pay for your rental or charter from the convenience of your phone or computer. We offer a secure platform for renters to facilitate a seamless rental transaction. For boat owners, we connect millions of renters to their boat and provide the security and safe checks on each rental transaction.

Search for the perfect experience now and book your dream day out on the water.

GetMyBoat has 61 listings for Sail experiences in Sarasota with 229 reviews.

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