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All listings in Clearwater

Great sailboat rentals near Clearwater, Florida.

Page 1 of 110 listings

Limited Availability
Luxury Bali 4.2 Catamaran | All-Inclusive Private Charters in St. Pete
Sailing in Saint Petersburg · 6 guests

Luxury Bali 4.2 Catamaran | All-Inclusive Private Charters in St. Pete

5.0
$238+/hour
Beautiful 45’ Sailboat - Private Charter
Sailing in Madeira Beach · 6 guests

Beautiful 45’ Sailboat - Private Charter

5.0
$225/hour
22ft Pontoon Suntracker Party Barge DLX 10 people in Bay Pines. Gas included!
Powerboats in Bay Pines · 10 guests

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

4.7
$59/hour
Day Sails and Sunset Cruises in Downtown St. Petersburg,  44' Morgan Sailboat
Sailing in Saint Petersburg · 6 guests

Day Sails and Sunset Cruises in Downtown St. Petersburg, 44' Morgan Sailboat

5.0
$206+/hour
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
45' Luxury Sailing Catamaran Charter
Sailing in Saint Petersburg · 6 guests

45' Luxury Sailing Catamaran Charter

5.0
$300+/hour
40’ Fountaine Pajot Sailing Catamaran - Explore the Beauty of Tampa Bay
Sailing in Saint Petersburg · 12 guests

40’ Fountaine Pajot Sailing Catamaran - Explore the Beauty of Tampa Bay

New
$350+/hour
Day Sails & Sunset Cruises – Downtown St. Petersburg, FL – 36’ Catalina Yacht
Sailing in Saint Petersburg · 6 guests

Day Sails & Sunset Cruises – Downtown St. Petersburg, FL – 36’ Catalina Yacht

New
$206+/hour
Beautiful 45’ Sailboat - Private Charter
Sailing in Madeira Beach · 6 guests

Beautiful 45’ Sailboat - Private Charter

New
$225/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 Clearwater

  1. Nicole

    Nicole

    Luxury Bali 4.2 Catamaran | All-Inclusive Private Charters in St. Pete

    We loved our experience on this absolutely breathtaking catamaran. It fit us all perfectly and the lounging area was so perfect to get out of the sun. We all wished we booked for a longer time.

  2. KP

    Kym

    Luxury Bali 4.2 Catamaran | All-Inclusive Private Charters in St. Pete

    We had an amazing experience celebrating a birthday aboard Sweet Escape! We booked a 3-hour private charter, and they really went out of their way to insure sure we enjoyed every part of it. When we arrived, Jonas had a Happy Birthday sign waiting for us, along with a beautiful charcuterie platter and sandwich spread ready for us to enjoy. We spent some time sailing with the motors off, relaxing in the water on a floating mat and we even got to try a new activity they had never done on one of their charters before, making our experience even more memorable! The Sweet Escape was beautiful, clean and very comfortable. Jonas and the captain were attentive while also giving us plenty of time and space to enjoy the boat and celebrate together. They did everything they could to make our day enjoyable, special, and amazing. I would absolutely recommend them for anyone looking for a fun, relaxing and personalized private catamaran experience. Thank you, Jonas and Captain, for helping us create such a wonderful birthday memory!

  3. AL

    Amy

    Beautiful 45’ Sailboat - Private Charter

    Loved how beautiful the boat is, and the opportunity to learn more about sailing, and other adventures that they offer like yoga on an island, night adventures out into the Gulf to see celestial events, sailing school and more.

  4. RR

    Roberto

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

    We had a blast and got lost in the finger islands but we made it back to the dock

  5. MO

    Milena

    Luxury Bali 4.2 Catamaran | All-Inclusive Private Charters in St. Pete

    Had an amazing time on this charter today! The crew was incredibly nice, communicated everything clearly, and made the whole experience easy and enjoyable from start to finish!! The trip itself was fantastic, and you can tell they really care about their guests having a great time. I would absolutely recommend this boat to anyone looking for a fun and stress-free experience on the water!

  6. TE

    Tate

    Luxury Bali 4.2 Catamaran | All-Inclusive Private Charters in St. Pete

    Jonas and Captain Carlos took top care of my family and I! I was so impressed with the amenities and cleanliness of the boat. They were both extremely knowledgeable about the area and sailing in whole. My nephew had a blast and they showed him patience and earned the respect of an 8 year old in addition to all of the "adults". Thank you so much, Jonas and Captain Carlos!