Stock Island Wind & Wine Sunset Sail aboard classic Schooner

If you’re dreaming of unwinding on the water with a glass of wine in hand, this Stock Island Wind & Wine Sunset Sail offers a lovely blend of serenity and sophistication. Set aboard a historic Key West schooner, this two-hour cruise promises an intimate setting where you can sip premium wines, enjoy gourmet hors-d’oeuvres, and take in spectacular sunset views. It’s a go-to choice if you’re looking for a refined yet laid-back way to kick off your evening in the Keys.

What really makes this experience special are the quality wines from around the world and the friendly, attentive crew who keep drinks and snacks flowing. Plus, the peaceful setting aboard a classic sailing vessel makes for a memorable, romantic outing or a mellow gathering with friends. However, since this is an upscale cruise with limited amenities beyond the wine and snacks, it might not satisfy those seeking a lively party scene or a more active adventure.

This cruise is best suited for travelers who want a quiet, elegant way to enjoy the sunset—whether that’s with a loved one or a small group of friends. If you’re a wine enthusiast or simply love the idea of sailing under the sun-dappled sky with a glass in hand, you’ll likely find this tour just right. It’s less about adrenaline and more about savoring the moment on the water.

• Upscale yet relaxed: Perfect for those wanting a sophisticated, calm environment to enjoy sunset.
• Premium wine selection: Features 8 varieties, including reds, whites, and Champagne, served from around the world.
• Delicious hors-d’oeuvres: Gourmet meats, cheeses, fruits, and chocolates complement the drinks.
• Intimate atmosphere: Small groups on a classic schooner provide a personalized experience.
• Great reviews: Consistently praised for the attentive crew and beautiful setting.
• Accessible location: Departs from and returns to the Perry Hotel & Marina on Stock Island.

The Wind and Wine sunset sail starts with check-in at Bad Boy Taqueria & Tequila, about 30 minutes before departure. From there, your captain will escort you through the marina to the schooner, a vessel that exudes charm and history. Once aboard, you’re invited to settle into the relaxed ambiance while the crew hoists the sails, setting the stage for a peaceful ride into the Floribbean sunset.

As the boat gently rocks, you’ll be served a carefully curated selection of eight different wines—usually a mix of reds, whites, and a sparkling Champagne. This variety is a highlight for wine lovers; it’s one of the few sailing excursions in the U.S. that serve real wine, making it feel like a special occasion. Alongside, you’ll enjoy upscale beers, with both imported and domestic options, as well as gourmet hors-d’oeuvres that include meats, cheeses, crackers, fruits, crudités, and chocolates.

The two-hour duration means plenty of time to relax, chat, and take in the scenery. The views of the sunset casting warm hues over the water are truly unforgettable, and the entire experience is designed to be both elegant and intimate. It’s easy to see why Coastal Living Magazine ranked it among the top two sunset sails in North America.

The crew and atmosphere

Guests frequently mention the knowledgeable and attentive crew, who are genuinely friendly and keep the drinks and snacks flowing without being intrusive. According to one review, “The Captain and crew are very attentive and kept the wine/appetizers flowing. Great boat, great experience.” Their professionalism adds a lot to the overall enjoyment, making the experience feel special without feeling overly formal.

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The food and drinks

The hors-d’oeuvres are described as “light but good,” and the wine selection is appreciated for its quality. One guest noted that the apps were satisfying and that they enjoyed a “gorgeous evening,” underscoring the experience’s ability to shape a memorable evening. The availability of sodas and bottled water ensures everyone stays refreshed.

The setting and views

Sailing aboard a classic schooner under a canvas of sails allows you to truly feel like you’re in a timeless part of the Keys. The vantage point from the water provides ideal views of the sunset, turning the sky into a palette of oranges and pinks. It’s a calm environment perfect for romantic evenings or peaceful gatherings.

Price and value

At $134 per person, this cruise is priced for those seeking an upscale experience. When you consider the premium wines, gourmet snacks, and the boat ride itself, it offers good value. It’s not a cheap outing, but for the quality of drinks, the setting, and the intimate vibe, many guests feel it’s worth the splurge.

This sailing cruise appeals most to travelers who appreciate fine wine, a peaceful setting, and a more refined approach to sunset viewing. It’s ideal for couples celebrating an anniversary, special dates, or simply those wanting a quiet escape from the busier, more commercial water tours. It’s also suitable for small groups of friends who want to share a special moment together.

If you’re looking for a lively party or a high-energy adventure, this cruise might not be the right fit. But if you’re after relaxing, quality time on the water with excellent drinks and beautiful scenery, this is a great pick.

The Stock Island Wind & Wine Sunset Sail offers a charming, relaxed way to enjoy a Key West sunset. The combination of premium wines, gourmet bites, and a beautifully maintained classic schooner makes it a memorable experience for those seeking elegance with a touch of local character. It’s a cruise that prioritizes comfort, quality, and intimate scenery, making it well-suited for romantic outings or laid-back evenings with friends.

While it’s priced on the higher side, most guests agree that the experience delivers good value for the quality and ambiance. The knowledgeable crew, serene environment, and stunning sunset views create a peaceful escape into the Keys’ waters that’s worth considering if you want something a little more refined during your visit.

If you love wine and sailing, or simply want a peaceful way to witness the sunset in Key West, this cruise could be just what you’re looking for. It’s an experience that invites you to slow down, savor the moment, and enjoy the beauty of the coast in style.

Is this cruise suitable for children?
The tour is geared toward adults who appreciate fine wine and a relaxed atmosphere. While children are technically allowed, the focus on alcohol and the upscale environment might make it less ideal for young kids.

What should I bring with me?
You might want to bring a sweatshirt for cooler evenings, sunglasses to shade your eyes, a camera for photos, and your Photo ID since alcohol is served.

Where does the cruise depart from?
All excursions depart from and return to the Perry Hotel & Marina on Stock Island. Check-in is at Bad Boy Taqueria & Tequila, and you’ll be escorted to the boat about 30 minutes before departure.

How long is the cruise?
The cruise lasts approximately 2 hours, generally available in the afternoon and evening, providing plenty of time to relax and enjoy the scenery.

What’s included in the price?
Your ticket covers premium wines, upscale beers, gourmet hors-d’oeuvres, sodas, and bottled water. Bathrooms are available before boarding and during the trip.

Are gratuities included?
No, gratuities are not included in the price, so you’ll want to tip the crew if you feel they provided excellent service.

This sail offers a wonderful way to enjoy the natural beauty of Key West in a refined setting. Whether you’re celebrating a special occasion or just want a peaceful way to end your day, it’s a memorable experience that balances elegance with the simple pleasure of being on the water.