Incredible sailboat rentals in Florida, United States.

Average of 208 reviews in this area.
1 - 18 of 109 listings

Rent or charter a sailboat for a memorable experience in Florida.

Are you ready for a fun adventure out on the open water onboard a sailboat in 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. Florida is a wonderful sailboat rental destination.

Using GetMyBoat to book your next sailing experience.

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 Florida.

  1. JS
    Jaida
    Luxurious, Spacious 38ft Sailing Catamaran

    I absolutely loved this trip! Aaron was a great captain and he offered to take great pictures for me and my friends! I went for my 21st birthday and we had an absolute blast. The boat was beautiful and the pictures shown do not do it justice. I will certainly book this again!

  2. LB
    Lisa
    Sailing Charter On 39' Catalina Sailboat In Fort Lauderdale, Florida

    We felt so blessed that we found Charles! He was the best Captain/host with extensive knowledge of the area, including the history of various houses and buildings. He accommodated my kids’ constant requests and is so funny!! A real pleasant experience. Worth every penny.

  3. CA
    Chrystelle
    64' Sailing Ketch for Charter in Jacksonville area

    What a fun day we had! We chartered Tom’s magnificent sail boat for our daughter’s 18th birthday. She will definitely remember this special day forever! Tom, our captain was so easy going from the second we talked on the phone- great communication. We all had an amazing time especially our teenagers (from jumping off the boat to swinging off the boat like monkeys lol). I definitely recommend Nepenthe Sails and Tom (captain/owner). We have gained a new friend in the process! 😄

  4. RH
    Racquel
    Sailing Charter On 39' Catalina Sailboat In Fort Lauderdale, Florida

    This was an amazing experience. Our extremely accommodating captain ensured we had everything right at our fingertips, he made us feel very safe and welcomed and gave us an unforgettable day.

  5. NN
    Natosha
    Captained Charter On 34' Gemini 105 Cruising Catamaran in Shalimar, Florida

    I booked a trip for an anniversary gift and Karl was very accommodating. My sister and brother in law truly enjoyed their experience. Would definitely book again...thanks for everything!

  6. SZ
    Sam
    Luxurious, Spacious 38ft Sailing Catamaran

    We had an excellent time on this boat. Captain Aaron took some killer sunset photos of us jumping into the ocean. Plenty of room to hang out. Good times. Will book again!