Cookies!

We use cookies to improve your browsing experience. And dolphins make us happy. Find out more about our cookies policy here.

All listings in Clearwater

Great sailboat rentals near Clearwater, Florida.

Page 1 of 14 listings

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
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
Set Sail aboard the Most Photographed Boat in the Tampa Bay Region!
Sailing in Treasure Island · 28 guests

Set Sail aboard the Most Photographed Boat in the Tampa Bay Region!

New
$695/hour

Sailing Reviews in Clearwater

  1. 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!!

  2. 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!

  3. 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!

  4. 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

  5. GM

    Gary

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

    Nick was a very experienced and knowledgeable skipper who truly welcomed us aboard. This is a beautiful sailing vessel that provides a fun, safe and comfortable ride for everyone aboard. We had a super trip with Nick and would love to book a whole day with him next time we are in town.

  6. BC

    Brian

    2017 Robertson and Caine Leopard 40 - Luxury Catamaran

    We highly recommend this fabulous father/daughter team for an amazing sail or scenic cruise on a clean, newer catamaran with great toys and amenities. Amazing experience we will be sure to repeat with family and friends.