Great sailboat rentals near Clearwater, Florida.

Average of 9 reviews in this area.
5 listings

Step onboard a sailboat for an unforgettable experience in Clearwater, Florida.

Get ready for a fun adventure when you hit the open water onboard a sailboat in Clearwater, Florida. Rent or charter a sailboat with or without a captain and experience the joy of exploring the water by wind power. From hourly, half-day, full-day or multi-day sailing excursions, you are sure to create memories that will last a lifetime. Clearwater, Florida is a wonderful sailboat rental destination.

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 customer reviews for Sailing in Clearwater.

  1. AK
    Atta
    2 to 2 1/2 hr. Public Sunset Sailing Excursions from St. Pete Beach, Florida!

    Wonderful experience! Boats are beautiful and the captains are very knowledgeable and fun. The sunset is amazing, even though it was cloudy, we were able to get some great colors. We also had a pod of dolphins following the boats and jumping next to us. Great experience, good value, they offer water/sodas on the boat for free. Good overall experience and will def. do it again! Thank you!

  2. EP
    Erika
    2 hours Dolphin Watch Sailing Excursion on Boca Ciega Bay and the Greater Tampa Bay

    I loved everything about the sail boat ride with Captain Cecil, and Rick ! It was an amazing time and my family from Alabama enjoyed every second .

  3. SR
    Santiago
    Day Sails and Sunset Cruises with Nick and Kelly aboard 44' Sailboat in St. Petersburg, FL

    Sailing with Satori was an experience out of this world! Nick is an amazing captain who goes above and beyond. Clear communication, humble man and excellent sailing. Thank you and we'll be back for round 2! Cheers!

  4. GM
    Gary
    Day Sails and Sunset Cruises with Nick and Kelly aboard 44' Sailboat in St. Petersburg, FL

    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.

  5. KA
    Kahlea
    Day Sails and Sunset Cruises with Nick and Kelly aboard 44' Sailboat in St. Petersburg, FL

    Nick was an AMAZING captain!! Such a valuable and fun experience. My fiancé and I had the best time on the boat. HIGHLY recommend sailing with Nick!

  6. MS
    Michelle
    Day Sails and Sunset Cruises with Nick and Kelly aboard 44' Sailboat in St. Petersburg, FL

    Nick was a wonderful captain and was especially considerate to my friend that was worried about getting sea sick. We enjoyed a beautiful sunset sail, and we all left smiling and relaxed!