Stock Island Wind & Wine Sunset Sail Aboard Classic Schooner

The Stock Island Wind & Wine Sunset Sail promises an enchanting experience aboard a classic schooner. Departing from the Perry Hotel & Marina, guests can indulge in a selection of fine wines, premium beers, and gourmet appetizers while taking in the breathtaking sunset views. Recognized as one of North America’s top sunset sails, this upscale yet relaxed excursion offers a perfect opportunity for social mingling or a romantic evening. With limited spots available, it’s a chance to savor the magic of the open waters and witness a stunning sunset spectacle.

This experience made our article of 12 Best Wine Tours In Key West.

Key Points

• The classic schooner journey lasts for 2 hours and departs from the Perry Hotel & Marina.
• Guests can enjoy a selection of fine wines, premium beers, and gourmet appetizers during the sunset sail.
• Pricing starts at $128.89 per person with a free cancellation policy up to 24 hours in advance.
• The sail is ranked among the top Sunset Sails in North America and serves "real" wine.
• Recommended items for the sail include a sweatshirt, sunglasses, camera, and photo ID.

You can check availability for your dates here:

Experience Overview

The Stock Island Wind & Wine Sunset Sail offers guests a unique opportunity to embark on a classic schooner for a 2-hour journey.

Departing from the Perry Hotel & Marina, the sail takes place aboard a scenic schooner, allowing participants to experience the beauty of Key West’s coastal waters.

Guests can check-in 30 minutes prior at the Bad Boy Taqueria & Tequila, ensuring a smooth start to their experience.

Throughout the sail, guests can indulge in a selection of fine wines, premium beers, and gourmet appetizers, all while taking in the breathtaking sunset views.

Pricing and Reservation

Although the Stock Island Wind & Wine Sunset Sail starts at $128.89 per person, guests can take advantage of the free cancellation policy up to 24 hours in advance for a full refund.

Travelers can also reserve their spot without any upfront payment, allowing them to pay later. This flexible booking process caters to those who want to secure their place on the classic schooner without immediately committing funds.

With these convenient options, guests can ensure they experience the renowned sunset sail and wine tasting in Key West without financial constraints.

Culinary Offerings

Along With the flexible booking options, the Stock Island Wind & Wine Sunset Sail offers guests an array of culinary delights.

Onboard, patrons can indulge in:

• 8 varieties of fine wines, including 4 reds, 3 whites, and 1 Champagne

• 5 premium beers, featuring both imported and domestic options

• Gourmet appetizers, such as charcuterie boards with a selection of meats, cheeses, crackers, fruit, and crudités, complemented by decadent chocolate

• Refreshing sodas and bottled water to quench any thirst

The experience focuses on an upscale yet relaxed atmosphere, making it the only sailing excursion in the U.S. to serve "real" wine.

Unique Features and Recognition

Coastal Living Magazine ranked the Wind and Wine Sail among the top two Sunset Sails in North America, highlighting its focus on an upscale yet relaxed atmosphere.

This sailing excursion in the U.S. is the only one serving "real" wine, elevating the experience beyond typical sunset cruises. Passengers can mingle with friends or enjoy a romantic evening while watching the crew hoist the sails, creating a unique and memorable outing.

The Wind and Wine Sail’s recognition as one of the best in North America reflects its commitment to providing an exceptional coastal experience.

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Amenities and Recommendations

To help passengers make the most of their experience, the Wind and Wine Sail offers several amenities and recommendations.

Restrooms are available for use before boarding and on the schooners. Passengers are advised to bring a sweatshirt for cooler winter evenings, sunglasses to enjoy the stunning sunset, and a camera to capture the picturesque coastal views. Guests are also encouraged to bring a valid photo ID.

The relaxed atmosphere allows passengers to mingle with friends or enjoy a romantic evening while watching the crew expertly hoist the sails.

The relaxed atmosphere allows passengers to mingle with friends or enjoy a romantic evening while watching the crew expertly hoist the sails.

• Restrooms available pre-boarding and on the schooners

• Suggested items: sweatshirt, sunglasses, camera, photo ID

• Opportunity to mingle with friends or enjoy a romantic evening

• Crew hoists the sails for an authentic sailing experience

• Relaxed atmosphere to make the most of the sunset sail

The Schooner

The classic schooner that hosts the Wind and Wine Sunset Sail is the focal point of this unique excursion.

Adorned with traditional sails and masts, the schooner exudes an air of nautical elegance. Guests can admire the classic craftsmanship and imagine sailing the high seas as the crew effortlessly maneuvers the vessel.

The schooner provides ample space for mingling, with comfortable seating and unobstructed views of the stunning Key West sunset.

Whether seeking a romantic evening or a lively social gathering, the schooner sets the stage for an unforgettable sunset experience.

Sailing the Open Waters

As the schooner sets sail, guests are treated to a captivating journey across the open waters surrounding Key West. The crew expertly navigates the vessel, allowing passengers to take in the stunning vistas of the Gulf of Mexico and the Florida Keys.

The sail offers a unique perspective, as the schooner glides effortlessly over the gently rolling waves.

• Soak in the serene atmosphere as the sails billow in the wind.

• Spot local marine life, including dolphins, seabirds, and other coastal creatures.

• Enjoy the complimentary wine, beer, and gourmet appetizers while admiring the breathtaking sunset.

• Capture the magic of the moment with stunning photographs of the open water and the approaching dusk.

• Relax and unwind as the schooner carries you back to the marina, completing the unforgettable Wind and Wine Sunset Sail experience.

Sunset Spectacle

As the schooner glides across the open waters, guests are treated to a breathtaking sunset spectacle.

The sun dips below the horizon, casting a warm, golden glow across the shimmering sea. Vibrant hues of orange, pink, and purple fill the sky, reflecting off the gentle waves.

Passengers gather on the deck, cameras in hand, eager to capture the mesmerizing display. The sails billow in the evening breeze, adding to the serene ambiance.

Sipping fine wines and savoring gourmet appetizers, guests savor the tranquil moment, captivated by the natural beauty unfolding before them.

Frequently Asked Questions

Can I Bring My Own Food and Beverages on Board?

Bringing your own food and beverages aboard is not allowed. The sail offers a selection of fine wines, premium beers, and gourmet appetizers as part of the experience. Outside food and drinks are typically prohibited to maintain the upscale atmosphere.

Do the Schooners Have Wi-Fi or Charging Stations Available?

The schooners don’t offer Wi-Fi or charging stations. They provide a disconnected experience, allowing passengers to fully enjoy the sail and surrounding scenery without digital distractions.

Is There a Dress Code or Any Special Attire Requirements?

There’s no formal dress code, but guests are advised to dress comfortably in casual attire. Lightweight, breathable fabrics are recommended as the sails can get a bit breezy. No special attire is required for this relaxed, upscale sailing experience.

Can I Request Specific Wines or Beers to Be Served?

While guests can’t request specific wines or beers, the tour offers a wide selection of fine wines and premium beers. The staff give you an upscale yet relaxed experience tailored to each group’s preferences.

Are There Any Age Restrictions or Child Policies for the Sail?

There’s a minimum age of 21 to participate, and the sail isn’t recommended for children. Guests under 21 aren’t allowed to consume alcohol on board. The experience is designed for adults to enjoy an upscale, relaxed sunset sail.

The Sum Up

The Stock Island Wind & Wine Sunset Sail offers an unforgettable experience. Guests can savor fine wines, gourmet appetizers, and breathtaking sunset views from the comfort of a classic schooner. Recognized as a top sunset sail by Coastal Living Magazine, this excursion provides an upscale yet relaxed atmosphere, perfect for social mingling or a romantic evening. Don’t miss the opportunity to reserve your spot and embark on this enchanting adventure.

You can check availability for your dates here: