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All listings in Tampa Bay

Incredible sailboat rentals in Tampa Bay, United States.

Page 1 of 18 listings

Sunset Sails: Explore the Open Waters of Tampa, Florida
Sailing in Tampa · 6 guests

Sunset Sails: Explore the Open Waters of Tampa, Florida

5.0
$225/hour
2017 Robertson and Caine Leopard 40 - Luxury Catamaran
Sailing in Saint Petersburg · 12 guests

2017 Robertson and Caine Leopard 40 - Luxury Catamaran

5.0
Superowner
Best of 2025
$300+/hour
Day Sails and Sunset Cruises - Downtown St. Petersburg, FL - 44' Yacht
Sailing in Saint Petersburg · 6 guests

Day Sails and Sunset Cruises - Downtown St. Petersburg, FL - 44' Yacht

5.0
$205+/hour
2022 BAYLINER DX2000!!! Spacious and perfect for cruising around AMI!
Powerboats in Holmes Beach · 8 guests

2022 BAYLINER DX2000!!! Spacious and perfect for cruising around AMI!

4.9
$372+/day
Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat
Sailing in Saint Pete Beach · 6 guests

Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat

5.0
$110/hour
Instant Book
Luxurious 40ft Leopard Catamaran - Captain Included
Sailing in Saint Petersburg · 6 guests

Luxurious 40ft Leopard Catamaran - Captain Included

5.0
Superowner
Best of 2025
$315+/hour
44ft Aquila "A Lil Bit Nauti" Yacht Charter in Palmetto, FL
Sailing in Palmetto · 13 guests

44ft Aquila "A Lil Bit Nauti" Yacht Charter in Palmetto, FL

New
$590/hour
St. Pete Sunset Sails - 34ft Sailboat
Sailing in Saint Petersburg · 4 guests

St. Pete Sunset Sails - 34ft Sailboat

New
$160/hour

Sailing Reviews in Tampa Bay

  1. Zach

    Zach

    2017 Robertson and Caine Leopard 40 - Luxury Catamaran

    Could not recommend this vessel and crew more. We rented it for the 4th of July and it was an unforgettable experience for our group. Despite some shaky weather we still had a blast. The boat is incredible and such a fair rate compared to other similar listings. Captain Dave and Joe were AWESOME. Would book again in a heartbeat!

  2. LP

    Leeann

    Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat

    Oleg was an awesome captain! He went above and beyond to accommodate us!

  3. Deja

    Deja

    2017 Robertson and Caine Leopard 40 - Luxury Catamaran

    We can’t thank Captains Dave & Joe enough. From the communication with Bailey, to the overall experience.. everything went smooth and easy. I booked for my friend’s Bachelorette Party and they made our time worth while. I definitely recommend for any occasion. Both Captains Dave and Joes made sure we were equipped with everything and comfortable during our sailing. My favorite part was swimming and lounging on the floatable pools.. oh, and seeing dolphins! Overall 10/10 experience!

  4. Leah

    Leah

    Sunset Sails: Explore the Open Waters of Tampa, Florida

    Such an amazing experience! From the day I inquired to the moment we got off the boat , Arlo was a great person and made the experience unforgettable! Highly recommend, you won’t regret it and you’ll have the best memories to hold on to. Thank you again!

  5. JR

    Jeremy

    Sunset Sails: Explore the Open Waters of Tampa, Florida

    Whether you’re considering your first adventure out at sea or perhaps taken a few adventures, Arlo is your guy for a great sailing experience, kind heartedness, and very experienced in boats and adventures out at sea. He ensured that we were taken care of, well attended, and was an excellent host. I highly recommend Arlo. He gave a great experience.

  6. Kieron

    Kieron

    2017 Robertson and Caine Leopard 40 - Luxury Catamaran

    Bailey's luxury catamaran was gorgeous and the sunset cruise we took for my husband's 40th birthday with family was a very special experience. Captain Dave and Emma were so nice and accommodating for our group of 12. They provided us with ice and beverages as well as utensils and napkins for the catered platters we brought. We were also able to connect to the sound system to play our music for the entire trip. We had perfect weather and got to see dolphins frolicking prior to heading out into the Gulf for a gorgeous sail and stunning sunset!