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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
$175/hour
Instant Book
2017 Robertson and Caine Leopard 40 - Luxury Catamaran
Sailing in Treasure Island · 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
Luxurious 40ft Leopard Catamaran - Captain Included
Sailing in Treasure Island · 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
55ft "Poseidon SR" Sea Ray Flybridge Power MegaYacht Charter in Tampa, Florida
Events in Tampa · 13 guests

55ft "Poseidon SR" Sea Ray Flybridge Power MegaYacht Charter in Tampa, Florida

New
$801/hour
Single Paddle  Kayak
Adventures in Ellenton · 1 guest

Single Paddle Kayak

New
$25/hour

Sailing Reviews in Tampa Bay

  1. 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!

  2. 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.

  3. Shajira

    Shajira

    2017 Robertson and Caine Leopard 40 - Luxury Catamaran

    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!!

  4. Meghan

    Meghan

    2017 Robertson and Caine Leopard 40 - Luxury Catamaran

    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!

  5. BT

    Brian

    2017 Robertson and Caine Leopard 40 - Luxury Catamaran

    Dave and Emma were excellent captains!! I booked them for a private sunset cruise to propose to my girlfriend and they were so accommodating, responsive and personable. The boat was beautiful and I would highly recommend them! We will definitely book another trip with them. 10/10 everything!

  6. Robert

    Robert

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

    If you're looking for a professional to take you sailing but you don't want it to feel like a tour boat, take a ride on Nick's personal boat. Bring along something cold to drink and enjoy the peace and quiet of being out on the water. My only regret is I should have made it a full day