Private Catamaran Sailing: Ten Thousands Islands, Naples

Crew a stiletto catamaran built for speed, or sit back while the captain handles the sails.

A private 2-hour sailing tour through the Ten Thousands Islands near Naples, Florida, aboard a stiletto catamaran: a high-performance vessel known for speed and shallow-water access. You can actively help crew the sails or simply watch from the deck while the captain points out local flora and fauna. Bottled water is included. The captain speaks English and guides the experience throughout.

The experience

The stiletto catamaran is built differently from standard sailing boats. Designed in the early 1980s, these vessels are known in the sailing community for being the fastest, driest, and most beachable catamarans available: meaning they can reach shallow waters and handle rough conditions better than conventional hulls. You'll spend 2 hours sailing around the Ten Thousands Islands, a maze of mangrove-lined waterways and small islands that form one of Florida's most distinctive ecosystems.

The tour is structured around your preference. If you want to participate, the captain will teach you how to help crew the sails and handle the boat's systems. If you'd rather observe, you can sit back and let the captain manage everything while you watch the water and shoreline. Either way, the captain points out the wildlife and plant life you pass: herons, dolphins, and the dense mangrove forests that define this region. Bottled water is provided throughout the sail.

This is a private charter, so it's just you and your group with the captain. There are no other passengers, which means the pace and focus stay on what interests you. The boat's shallow-draft design lets it access narrow channels and shallow areas that larger vessels cannot reach, opening up parts of the islands most tours miss.

What’s included

• Bottled water.
• captain guide in English.
• private charter with no other passengers.

Options for this experience

3 options

Two-hour private sailing tripGuide in English · 6 departure times: the first at 08:30, the last at 15:00

Private sunset sailingGuide in English · 16:00 and 17:30

Private half-day sail and beach tripGuide in English · 08:30, 10:00, 11:30 and 13:00Lasts 4 hours

You see the exact price of each option when you check availability.See dates & prices

Before you book

Days and timesEvery day10 departure times: the first at 08:30, the last at 17:30

GroupPrivate

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Cancellation and refundsNo refund if you cancel.It may be canceled due to bad weather. If that happens, you're offered another date or a refund.

Prices and times updated 3 days ago

Good to know

Moderate physical levelPets welcomePublic transport nearbyNot for heart conditionsNot for back problemsInfants must sit on laps

Operated by Easy Breezy Charters

Is this one for you?Choose the 2-hour sail if you want the core experience of the islands without a full-day commitment. Pick the half-day option if you'd like a beach stop added to your time on the water. The sunset departure suits anyone who prefers evening light and a different pace of wildlife viewing.

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Top questions

What happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. No refund if you cancel.

What's the difference between the three sailing options you offer?

The Private 2 Hour Sail is the core tour through the Ten Thousands Islands. The Private 1/2 Day Sail/Beach Trip extends the experience and adds a beach stop, while the Private Sunset Sailing departs in the evening to catch the light over the water and islands. All three use the same stiletto catamaran and include a captain guide.

Can I actually help sail the boat, or is it just watching?

You can actively crew the sails if you want to. The captain will show you how to help manage the boat's systems and sails. If you prefer to relax and observe instead, that's equally fine. The captain handles everything and narrates what you're seeing.

What wildlife might I see in the Ten Thousands Islands?

The Ten Thousands Islands are home to herons, dolphins, and other coastal birds and marine life. The mangrove forests that line the waterways are the main feature of the landscape, and the captain points out what appears during your sail.

Is this tour suitable for someone who's never sailed before?

Yes. You don't need sailing experience to join. If you want to participate in crewing, the captain teaches you what to do. If you've never sailed and prefer not to, you can simply enjoy the ride and the scenery while the captain manages the boat.

How does a stiletto catamaran differ from a regular sailboat?

Stiletto catamarans are known for being faster, drier, and able to reach shallower waters than conventional sailboats. This design lets the boat access narrow channels and shallow areas of the Ten Thousands Islands that larger vessels cannot navigate.