Key West Sailing

Morning Sail, Snorkel & Kayak Excursion

The Morning Half Day Excursion is a great way to start your day off. This trip is a 4.5 hour trip on one of our shallow draft schooners. It includes snorkeling, kayaking, and sailing.

• Relax on a historic schooner

• Limited to 20 people or less

• Sail in the pristine waters of Key West

• Kayak and snorkel - no experience necessary

• Enjoy complimentary non-alcoholic and alcoholic drinks

• Fresh fruit, chips, salsa, and hummus

Premium Day Sail, Snorkel &, Kayak with Lunch

The Full Day Excursion is the perfect trip for you all that love being out on the water. It’s got everything the half day does and then some. We will spend plenty of time snorkeling as well as kayaking around one of the mangrove islands. Weather permitting we will stop at an island with a beach or a sandbar while taking in all the beauty of our Florida Keys Ecosystem. Between activities, we will provide a full lunch while you relax and take in some sailing. Beer, wine, water, sodas, and snacks are also provided.

• Relax on a historic schooner

• Limited to 20 people or less

• Sail in the pristine waters of Key West

• Kayak and snorkel - no experience necessary

• Enjoy complimentary non-alcoholic and alcoholic drinks

• Sunbathe or relax under our canopy

Afternoon Sail, Snorkel, Kayak & Sunset Excursion

The Afternoon Half Day Excursion is similar to the morning excursion but gives you a chance to sleep in a little later if you choose. On the afternoon trip, you will enjoy the same activities as the morning, kayaking, snorkeling, and sailing. Snacks and drinks will also be provided along the way. One of many great things that stands out with this trip though is the Key West sunset seen from the water on the way home. Truly one of the best ways to end your day.

• Relax on a historic schooner

• Limited to 20 people or less

• Sail in the pristine waters of Key West

• Kayak and snorkel - no experience necessary

• Enjoy complimentary non-alcoholic and alcoholic drinks

• Enjoy Key West Sunset

Key West Wind & Wine Sunset Sail

Danger’s Wind and Wine sunset sail features an array of fine wines and upscale beers from around the world, complemented by bountiful hors-d'oeuvres that will arouse your palate. All this while sailing under a cloud of canvas aboard our Historic Key West Schooners.

Coastal Living Magazine ranked Danger Charter’s Wind and Wine Sail one of the top two Sunset Sails in all of North America. Danger Charter’s Wind and Wine Cruise is unparalleled for folks who want an upscale, yet relaxed and intimate, sunset sail. Sailing nightly, we serve eight different fine wines from all over the world, usually four red, three white, and a Champagnoise. Wine drinkers love this cruise since it is virtually the only sailing excursion in the U.S. that serves “real” wine. In addition, an array of quality beer, and hors-d'oeuvres are also served, making the evening an unforgettable start to a great Key West night!

• Up to 8 different varieties of wine

• Craft and domestic beers available

• Hors d'oeuvres complementing the wines

• Top rated sunset sail

• 2 hours

• Explore the calm waters of the island's west coast

• Departs from Danger Chandlery Store

Stock Island Wind & Wine Sunset Sail

Danger’s Wind and Wine sunset sail features an array of fine wines and upscale beers from around the world, complemented by bountiful hors-d'oeuvres that will arouse your palate. All this while sailing under a cloud of canvas aboard our Historic Key West Schooners.

Coastal Living Magazine ranked Danger Charter’s Wind and Wine Sail one of the top two Sunset Sails in all of North America. Danger Charter’s Wind and Wine Cruise is unparalleled for folks who want an upscale, yet relaxed and intimate, sunset sail. Sailing nightly, we serve eight different fine wines from all over the world, usually four red, three white, and a Champagnoise. Wine drinkers love this cruise since it is virtually the only sailing excursion in the U.S. that serves “real” wine. In addition, an array of quality beer, and hors-d'oeuvres are also served, making the evening an unforgettable start to a great Key West night!

• Up to 8 different varieties of wine

• Craft and domestic beers available

• Hors d'oeuvres complementing the wines

• Top rated sunset sail

• 2 hours

• Adventure along the east side of Key West

• Departs from Perry Marina

Private Sunset Sail

Danger’s Wind and Wine sunset sail features an array of fine wines and upscale beers from around the world, complemented by bountiful hors-d'oeuvres that will arouse your palate. All this while sailing under a cloud of canvas aboard our Historic Key West Schooners.

Coastal Living Magazine ranked Danger Charter’s Wind and Wine Sail one of the top two Sunset Sails in all of North America. Danger Charter’s Wind and Wine Cruise is unparalleled for folks who want an upscale, yet relaxed and intimate, sunset sail. Sailing nightly, we serve eight different fine wines from all over the world, usually four red, three white, and a Champagnoise. Wine drinkers love this cruise since it is virtually the only sailing excursion in the U.S. that serves “real” wine. In addition, an array of quality beer, and hors-d'oeuvres are also served, making the evening an unforgettable start to a great Key West night!

• Up to 30 Passengers

• Up to 8 different varieties of wine

• Craft and domestic beers available

• Hors d'oeuvres complementing the wines

• Non-alcoholic beverages

• Top rated sunset sail

• Departure locations vary

Private Charter Sail, Snorkel & Kayak

The Private Charter Sail, Snorkel & Kayak is a great way to start your day. This trip is a 4.5 hour trip on one of our shallow draft schooners. It includes snorkeling, kayaking, and sailing.

• Limited to 22 people or less

• Sail in the pristine waters of Key West

• Kayak and snorkel - no experience necessary

• Enjoy complimentary non-alcoholic and alcoholic drinks

• Fresh fruit, chips, salsa, and hummus

• Departure locations vary

Private Harbor Cruise Day Sail

This 2-hour, customizable day sail allows you to experience the pristine Florida Keys water upon one of our historic schooners. A selection of sodas, beer, and wine are included. We will also provide fresh fruit, chips, salsa, and hummus, though numerous other options are available for additional catering. Birthdays, reunions, graduations, engagements, company outings, or any other special occasion is sure to be memorable on this day sail!

Floridays • 2 Hour Private Sail

The best option for wedding parties, family gatherings, and memorial services. Price varies by number of guests, 6 people included in base price. Every private charter is unique and we make it special for your occasion!

Enjoy your private 2 hour sunset cruise around the beautiful waters of Key West

• Complimentary champagne and beverages will be served on board

Java Cat • 2 hr Sunset Sail Private

Enjoy an exclusive and intimate sunset cruise on the Java Cat. Departing from the Key West Historic Seaport, your captain sails the surrounding waters with the Key West sunset as the main event. The best value in Key West for a private sunset Key West charter! A group of up to 6 guests can “own the boat” for a fabulous Key West sunset sail.

Private Charter Sunset Sail

A perfect end to an island day. Sunset sails are the thing to do in Key West. Capture the magic of it all without being on a boat crowded with people. At Sunset Sail Key West we strive to revive the romance and charm without the crowds. Sit back while the captain and mate raise the sails, shut off the engine and sail off into the sunset!
Take the wheel or take in the sights as we sail you through a tour of Key West harbor, sail past the crowds at Mallory square and cross the line of the Gulf of Mexico to the Atlantic Ocean! Look seaward and dream of sailing far away, take in the sea stories of our crew and plan your next sail with Sunset Sail Key West. With frequent sailor discounts and custom sailing packages available, we cherish our return customers.

Sunset Sail on When and If

"When the war is over, and if I live through it, Bea and I are going to sail around the world" declared General George S Patton of his beloved custom built yacht.

When and If was the peacetime dream of an American war hero, and at 82 years old she is open to the public as part of a fund-raising programme to preserve her flag, keep her in her current excellent condition and fulfil her destiny to sail around the world.

Come and be part of her story as we sail into the sunset, enjoying the unspoiled view and blue water sailing to be had off the Keys' Atlantic coast. Help raise sail, take a turn at the helm or simply relax and enjoy the ride as our captain and crew sail you out to catch the breeze!

1.5hr Key West Harbor Day Sail

Catch that warm keys breeze as you head for a sun-soaked daysail out of Downtown Key West. Enjoy the view from the aqua water as you pick out the city's most famous landmarks and sail around the harbor islands before returning to the dock 1.5 hours later.

Starlight Sail

Relax as you sail out beyond the lights and sounds of Key West and get a clear view of the spectacular nighttime sky. Gaze into the night to spot the seasonal celestial highlights as we shut the engine off and take a peaceful sail through the starlight.

Full Day Private Luxury Charter

Our full day, 8-hour charter is just right for those of you who want to stop at multiple locations for snorkeling the only barrier reef in the US, explore our surrounding uninhabited islands, or just float and relax their day away in the most peaceful and stunning waters in all of Florida.

3/4 Day Private Luxury Charter

Just the right amount of time for some groups, our 6 hour day charter provides enough time for those who wish to spend a little extra time exploring the waters of Key West.

Choose from activities such as:

• Snorkeling and swimming

• Lounging in calm waters on our 6 ft x 12 ft Lily Pad

• Tours of Key West Harbor.

Half Day Private Luxury Charter

Our 4-hour charter may be customized for your choice of activities, including snorkeling the reef, sailing, or just lounging in the water on our 6 ft x 12 ft Lily Pad!