Sailaway Charters
Florida, USA sailing area

Florida · USA

Sail Florida.

Charter from Key West and Burnt Store Marina — 6 yachts on the dock right now.

See yachts in FloridaTalk to an expert
6 yachts6 bareboat

Why sail Florida

Florida is flat-water cruising in warm water, and that suits people who want an easy first bareboat week or a family charter without big passages. From Key West you drop south into the reef line and out to the Marquesas; from Punta Gorda you have the sheltered sweep of Charlotte Harbour and the barrier islands off Fort Myers. Distances are short, the holding is mostly good sand, and you can plan a week around lunch stops rather than tide gates. It isn't a place for serious distance sailors chasing weather — it's a place for shallow-draft gunkholing, snorkelling off the boat, and pulling into a marina bar by late afternoon. We sail it because the season runs long and the water stays swimmable when the Med has gone cold.

Live fleet

Yachts available in Florida.

6 yachts

Florida questions

Asked and answered.

How much does a yacht charter in Florida cost?
A bareboat week sits in the mid-range for a modern monohull or catamaran, with the security deposit, damage waiver, fuel, end clean and any marina nights on top. Fuel is a small line because legs are short and you motor little. Rates shift with season and boat, so we quote per request rather than post a figure — message us on WhatsApp with your dates and base for a firm number.
Do I need a licence to charter a bareboat in Florida?
The US doesn't run a national recreational sailing licence, but our base will want evidence you can handle the boat — a recognised sailing certification (ASA, RYA or equivalent) plus a logbook showing coastal miles. If your paperwork is light or you're new to the grounds, take a skipper for the week or the first day or two. Tell us on WhatsApp and we'll sort it.
When is the best time to sail Florida?
November to May is the settled window. Winter brings the easterly trades and swimmable water, broken by cold fronts every week or so that clock the wind north-west for a day. Summer is hot, storm-prone in the afternoons, and hurricane season — most weeks book either side of it. December through April gives you the steadiest breeze and driest decks.
Where should I start — Key West or Charlotte Harbour?
First charterers should start at Charlotte Harbour, out of Burnt Store Marina or Punta Gorda: wide protected water, forgiving depths, and sheltered anchorages behind the barrier islands. Key West suits sailors comfortable reading thin backcountry water and the reef line to the south. Both grounds sail short legs, so neither is a long-passage week — pick by depth and confidence, not distance.
Is Florida good for a family sailing holiday?
Yes, especially Charlotte Harbour. Short legs mean nobody's stuck on a long beat, the anchorages are calm, and there are Gulf beaches, state parks and a lunch stop most days. Warm water means swimming and snorkelling straight off the boat. Keep everyone in sun cover and hats — the heat and glare are the real hazards here, not the sailing.
How shallow is the water and does it matter?
It matters a lot. The Keys backcountry runs a metre or two over grass and sand, and Charlotte Harbour has its own thin patches. You navigate by the chart and by reading the colour of the water — dark is deep, pale green and brown are trouble. Take a shallow-draft boat, keep polarised sunglasses on, and you'll gunkhole happily. It's part of what makes the sailing here relaxed.
How do I get to the charter bases?
For Charlotte Harbour, fly into Fort Myers (RSW) — under an hour to Punta Gorda and Burnt Store; Punta Gorda's own airport works too. For Key West, fly direct into EYW where you can, or into Miami and drive the Overseas Highway down, roughly three to four hours. Non-US visitors should check ESTA or visa rules and carry passports before travelling.
How many yachts can I charter in Florida?
Right now there are 6 active yachts in Florida, based out of Key West and Burnt Store Marina. The fleet list above is live from our operator system.
Bareboat or crewed in Florida?
6 of the boats here are bareboat. Tell us your experience level and we'll match you.
How do I get a quote?
Send us your dates, your group and roughly the boat you want. Same day, we reply with three real options, three prices and the honest trade-offs.

By the cabin

Cabin cruises in Florida

Scheduled crewed cruises — book by the cabin and share the yacht with a small group.

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Real people

Talk to a human

A real person reads every message and replies within 24 hours — no bots, no auto-replies.

  • Honest advice from sailors, not salespeople
  • We reply within 24 hours
  • No spam, ever

Talk to an expert

Get three options.

Real sailors who run the trips — tell us your week, your group and your vibe. Same day, we send three boats, three prices and the honest trade-offs. Boats we would put our own families on.

Real humans on every channel — WhatsApp, email, phone. No call centre.

Final boarding call

Why not you?

New sailors, beginners or seasoned skippers — tell us when, where and how many. We send three real options the same day. No spam, no fluff, no commitment.

60 seconds. No payment until you choose a boat.
Yacht under sail at sunset

Free quote

Get three real options.

Tell us roughly when and where. We'll send three real boats, three prices, the trade-offs — usually within the hour.