Private Sailing Cruise

Private Key West Sailing • 3 Hours • Morning, Afternoon & Sunset Options

From$599
Group sizeMax 6 people

What to Expect

Set sail from Stock Island and enjoy a private cruise through the clear waters of the Florida Keys. This 3-hour sailing experience is a laid-back way to get out on the water, whether guests are starting the day with a morning sail, catching the afternoon breeze, or heading out for a classic Key West sunset.

Each cruise is private for the group and offers time to relax, enjoy the views, and experience Key West from the water with an experienced local captain. Island Sailing and Excursions has over 30 years of charter experience and helps guests connect with the best of the Key West waterfront.

About the Boat ⛵

Guests will sail aboard Leona, a classic Passport 40 sailboat designed for comfortable cruising. With spacious deck areas, timeless sailboat lines, and a relaxed private-charter feel, Leona offers a smooth and scenic way to experience the waters around Key West. The boat is ideal for guests looking for an intimate sailing experience without the crowds of a larger tour boat.

Includes

Private sailing cruise aboard Leona, a Passport 40 sailboat
Experienced captain
Required safety gear on board
Bottled water and sparkling water
Chips and salsa

Duration

3 hours

Address

6000 Peninsular Avenue, Key West, FL, 33040

Pricing

Private Sail 3 hours$599
Sunset Private Sail$699

Prices are typical; see the booking calendar for live availability and rates.

Cancellation Policy

Cancel up to 2 days before the start time.

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