As the sun dips below the horizon, the gentle sway of a classic schooner sets the stage for an unforgettable evening on the waters of Stock Island. Passengers aboard the Wind & Wine Sunset Sail are in for a treat, indulging in a carefully curated selection of premium wines and gourmet appetizers while taking in the stunning ‘Floribbean’ scenery. With knowledgeable guides providing local insights, this two-hour voyage promises to be a top-rated experience, offering a unique opportunity to escape the everyday and take in the captivating beauty of the Florida Keys. The only question that remains is what enchanting sights and flavors await those who embark on this captivating journey.
Key Points

- Classic schooner experience with 2-hour sunset sail, starting at $128.89 per person, including premium wines, cold beers, and gourmet appetizers.
- Ranked among top two sunset sails in North America, offering an unforgettable sensory experience with nature’s beauty and culinary delight.
- Wide selection of eight premium wines and five craft beer options, enjoyed while witnessing the sunset over the Florida Keys.
- Unique offering as the only U.S. sailing excursion serving genuine wine, elevating the experience with a sophisticated wine selection.
- Captivating experience enhanced by graceful movements of sails and crew, with knowledgeable guides sharing insights and stories during the sail.
Overview and Pricing

Embarking on the Stock Island Wind & Wine Sunset Sail offers visitors a classic schooner experience, with prices starting from a reasonable $128.89 per person for the 2-hour voyage.
The sunset sail promises to be an unforgettable journey, as guests are invited to step aboard a historic schooner and sail into the stunning ‘Floribbean’ sunset.
Complimentary premium wines, cold beers, and gourmet appetizers heighten the luxurious experience.
Travelers can make the most of the journey, with the option to cancel up to 24 hours in advance for a full refund.
What’s more, the ability to reserve now and pay later allows guests to secure their spot without any upfront costs.
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Experience Highlights

Sailing into the ‘Floribbean’ sunset aboard a classic schooner, guests can expect an unforgettable experience that captivates the senses.
Complementing the scenic coastal views are premium wines, cold beers, and gourmet appetizers that elevate the nautical journey.
A knowledgeable guide leads the way, sharing insights and stories that enhance the experience.
Ranked among the top two sunset sails in North America by Coastal Living Magazine, this unique offering is the only sailing excursion in the U.S. that serves ‘real’ wine, providing an unparalleled pairing of nature’s beauty and culinary delight.
From the moment the sails catch the wind to the final sunset glow, guests are immersed in an enchanting exploration of the Florida Keys.
Wine and Food Offerings

Guests aboard the Stock Island Wind & Wine Sunset Sail are treated to an array of premium wines, crisp beers, and gourmet hors-d’oeuvres that elevate the nautical experience.
The selection of eight wines includes four reds, three whites, and a sparkling Champagne, offering a diverse range of flavors to please every palate.
Alongside the wines, five premium beer options, both imported and domestic, provide a refreshing counterpoint.
The culinary offerings are no less impressive, with charcuterie boards featuring an artful selection of meats, cheeses, crackers, fruits, and crudités, complemented by indulgent chocolate.
Sipping world-class libations while taking in the breathtaking sunset over the Florida Keys creates an unforgettable sensory journey.
Meeting and Departure Details

Visitors for the Stock Island Wind & Wine Sunset Sail meet 30 minutes prior to departure at the Bad Boy Taqueria & Tequila. A friendly captain escorts them through the picturesque Perry Hotel & Marina to the waiting schooner docked at Slip J5.
The journey to the boat is part of the experience, as guests wander past swaying palms, the salty breeze ruffling their hair, and the sound of lapping waves all around.
Once aboard, guests can:
- Soak in the stunning views of the Florida Keys sunset.
- Relax with a glass of premium wine or cold beer.
- Savor delectable gourmet appetizers.
- Chat with the knowledgeable crew about the area’s history and ecology.
Recommendations and Amenities

With the sights, sounds, and salty air of the Florida Keys as the backdrop, the Stock Island Wind & Wine Sunset Sail offers a delightful array of amenities to enhance the experience.
Participants are encouraged to bring along a cozy sweatshirt for the cooler winter months, as well as sunglasses and a camera to capture the breathtaking sunset vistas.
Conveniently, bathroom facilities are available both before boarding and aboard the elegant schooners.
Whether guests choose to mingle with friends or enjoy a romantic evening, they’ll be captivated by the graceful movements of the sails and the crew as they hoist them, creating an unforgettable journey along the tranquil waters.
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Sail Into the "Floribbean" Sunset

Sailing into the ‘Floribbean’ sunset aboard the classic schooner, guests embark on a captivating journey, as the wind whispers through the sails and the gentle waves lap against the hull. The vessel glides effortlessly across the glistening waters, offering a front-row seat to nature’s breathtaking display.
Guests are immersed in the following delights:
- Vibrant hues of orange, pink, and purple paint the sky, creating a mesmerizing backdrop for the sailing adventure.
- The scent of sea air and the salty breeze caress the senses, transporting guests to a serene oasis.
- The gentle rocking of the boat and the soothing sounds of the water create a tranquil ambiance.
- Guests can savor the moment, sipping premium wine and enjoying gourmet appetizers as they witness the sun’s descent into the horizon.
Premium Wine and Gourmet Appetizers

As guests settle into the classic schooner, they’re greeted with an array of premium wine and gourmet appetizers, elevating the sunset sailing experience.
The wine selection features four rich red varietals, three crisp whites, and a sparkling Champagne – a unique offering for a sailing excursion. Alongside the wines, five premium beers, both imported and domestic, provide additional refreshment.
The gourmet hors-d’oeuvres include tempting charcuterie boards laden with an array of meats, cheeses, crackers, fresh fruit, and crudités. Guests can savor each bite while sipping their preferred libation and taking in the breathtaking views as the schooner glides across the tranquil waters of the ‘Floribbean’ sunset.
Only Sailing Excursion Serving "Real" Wine
This sailing excursion is the only one in the United States that serves genuine wine, elevating the sunset cruise experience with a touch of sophistication. Unlike the typical beer-and-soda options found on many sunset sails, the Stock Island Wind & Wine Sail offers an impressive selection of eight wine varietals, from bold reds to crisp whites and a sparkling Champagne.
The wine lineup includes:
- Four red wines: a Cabernet Sauvignon, Merlot, Pinot Noir, and Malbec.
- Three white wines: a Chardonnay, Sauvignon Blanc, and Pinot Grigio.
- One Champagne.
- Five premium beer options, both domestic and imported.
This unique offering elevates the journey, allowing guests to sip and savor the sunset while immersed in the classic ambiance of a schooner sailboat.
Frequently Asked Questions

Is the Boat Equipped With Restrooms During the Sailing?
The boat comes equipped with restrooms for guests to use during the sailing adventure. Guests can comfortably refresh themselves mid-voyage, allowing them to fully immerse in the scenic sunset cruise experience.
Do I Need to Bring My Own Wine Glasses?
No need to bring your own wine glasses – the schooner’s well-stocked bar has all the glassware you’ll need to enjoy the sunset and savor the provided premium wines and beers during the sail.
Can I Bring My Own Food and Drinks on the Boat?
No, guests are not permitted to bring their own food or drinks on board. The experience provides a wide selection of premium wine, beer, and gourmet appetizers for guests to savor as they sail into the Florida sunset.
Is the Sailing Experience Suitable for Children?
The sailing experience is generally better suited for adults, as the focus is on enjoying fine wine, gourmet appetizers, and the serene sunset atmosphere. However, well-behaved children may still find the journey captivating if accompanied by attentive parents or guardians.
Is There a Dress Code for the Sunset Sail?
The sunset sail has a casual, relaxed dress code, allowing guests to comfortably enjoy the experience. Comfortable, weather-appropriate attire is recommended, as the gentle sea breeze and stunning vistas are the true focus of the journey.
Recap
Sail into the vibrant ‘Floribbean’ sunset aboard a classic schooner, sipping premium wines and savoring gourmet appetizers.
This enchanting Stock Island Wind & Wine Sunset Sail promises an unforgettable evening of breathtaking views and local insights, making it a top-rated experience in North America.
Indulge in this unique excursion for an unparalleled taste of the Keys’ captivating natural beauty.
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