Sailing in Florida
Where to sail, charter types and lessons. Sailing charters coming soon.
Steady trade winds, warm water and protected bays make Florida a great place to learn to sail or charter a boat for the day. Here are the best sailing areas, the types of charters, and what to know before you go.
Where is the best sailing in Florida?
The Florida Keys (Key West sunset sails and reef trips), Biscayne Bay off Miami, Tampa Bay and St. Petersburg, and Charlotte Harbor near Fort Myers are the top areas. Winter and spring bring the most reliable breezes and the mildest weather.
New to sailing? A crewed charter lets you relax while a licensed captain sails; a lesson from an accredited sailing school teaches you to sail yourself. See Sail boating: let us do the work.
Charter types
| Type | Best for |
|---|---|
| Sunset or day sail | Couples and families, 2 to 3 hours, no experience needed |
| Private crewed charter | Groups who want their own boat and captain for a half or full day |
| Sailing lessons | Learning to sail with a certified instructor |
| Bareboat charter | Experienced sailors with a sailing résumé or certification |
Out of Port Canaveral? Read about offshore trolling out of Port Canaveral, safety at sea and your charter and the Florida sailfish tournament.
Sailing charters: coming soon
We are talking with licensed sailing captains in Florida. Tell us where and when you want to sail and we will let you know as soon as charters open.
Get notified when trips open
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Florida sailing FAQ
When is the best time to sail in Florida?
November through May, when breezes are steady and summer thunderstorms and hurricanes are less of a concern.
Do I need experience to go on a sailing charter?
No. On a crewed charter the captain sails the boat and you can help as much or as little as you like.
Where can I take a sunset sail in Florida?
Key West is the classic spot; sunset sails also run in Miami, St. Petersburg and Naples.
Does iOutdoors offer sailing charters?
Sailing charters are coming soon. Use the form above or call or text (407) 392-4593.