Key West Wind and Wine Sunset Sail aboard classic Schooner

Key West Wind and Wine Sunset Sail aboard Classic Schooner

Imagine slipping away from the busy streets of Old Town Key West onto a beautifully maintained historic schooner. For two hours, you’ll glide into the Floribbean sunset with a cocktail in hand, surrounded by gentle sea breezes and the warm glow of the setting sun. The $134 per person price includes a curated selection of eight fine wines, premium beers, and gourmet hors-d’oeuvres — a real treat for those who appreciate a sophisticated yet relaxed experience on the water.

What we love about this cruise? First, the upscale wine selection from around the world, which is quite rare for a sailing excursion in the U.S. Second, the friendly crew patiently hoisting sails and making everyone feel comfortable, whether you’re a seasoned sailor or a first-timer. A possible consideration: since it’s a 2-hour sail, it’s a relatively short experience, so if you’re craving a lengthy adventure, this might feel a bit brisk. However, for those seeking an intimate, luxurious sunset viewing with excellent drinks and snacks, this cruise hits the mark.

This experience suits couples, friends, or anyone wanting a romantic, upscale evening in Key West. It’s perfect if you want to combine spectacular scenery with quality beverages and a laid-back atmosphere. The reviews consistently highlight how special it is — many plan to return every time they visit, which speaks volumes about its charm.

You can check availability for your dates here:

Key Points

• Elegant Atmosphere: An upscale, intimate sailing experience with premium wines and gourmet hors-d’oeuvres.
• Beautiful Setting: Sail into the sunset aboard a classic schooner, offering memorable views and potential dolphin sightings.
• Experienced Crew: Friendly guides who handle the sails and create a welcoming environment.
• Convenient Location: Depart from and return to the Opal Key Resort & Marina, with bathrooms and easy check-in.
• Flexible Booking: Reserve now, pay later, with free cancellation up to 24 hours in advance.
• Limited Duration: At 2 hours, it’s a perfect escape without taking too much of your evening, ideal for those with a packed itinerary.

In-Depth Review of the Key West Wind and Wine Sunset Sail

Setting the Scene: The Classic Schooner and Departure Point

As you arrive at the Opal Key Resort & Marina (specifically the Danger Chandlery Store), you’ll find yourself in the heart of Key West’s Old Town. The departure is straightforward — just check in 30 minutes early, use the bathrooms, and get ready to step aboard a beautifully maintained historic schooner. The boat itself is elegant, with tall sails ready to catch the wind, evoking the golden age of maritime adventure.

From the moment you step on deck, the atmosphere leans toward relaxed sophistication. You notice the friendly crew — eager to make sure everyone feels comfortable, whether it’s hoisting sails or pouring wine. This is not a crowded party boat but a more upscale experience meant to blend scenic beauty with refined indulgence.

The Sail: Nature’s Show and the Experience

Once underway, you’ll start to feel that gentle motion of the sea as the schooner glides smoothly into the sunset. The ship’s design allows for great views from all angles, so whether you’re on the bow or the shaded side, you’ll have plenty of photo opportunities.

The highlight: watching the crew hoist the sails — it’s surprisingly lively and offers a behind-the-scenes glimpse into traditional sailing methods. Many reviews mention how the staff’s knowledge and skill add a layer of authenticity and comfort to the cruise.

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The Wines, Beers, and Hors-d’Oeuvres

What sets this cruise apart? The wine selection — eight different varieties, including reds, whites, and a Champagne-like Champagne — served in generous pours. It’s rare to find such an extensive wine list on a short cruise, especially with real wine rather than cheap alternatives.

Alongside, you’ll enjoy premium beers — both imported and domestic — perfect for pairing with the gourmet hors-d’oeuvres. The charcuterie boards are thoughtfully assembled, with meats, cheeses, crackers, fresh fruit, crudités, and even chocolates, catering to a variety of tastes. Several reviews mention the delicious snacks and wine, which elevate this experience from a simple cruise to a culinary escape.

The Sunset and Scenery

As the sun begins its descent, the sky transforms into a canvas of oranges, pinks, and purples. The views of Key West’s shoreline are stunning, and many guests find themselves snapping dozens of photos. The reviews emphasize how beautiful and peaceful the experience feels, with some lucky enough to spot dolphins — one reviewer even said, “We even saw dolphins,” describing the added bonus of wildlife viewing.

Who It’s Perfect For

This tour is ideal for those craving a refined yet relaxed experience. It’s especially well-suited for romantic couples, wine lovers, and small groups seeking a more intimate setting. If you’re looking for a casual party vibe or a lengthy excursion, this might not be your best fit. But if you value quality drinks, beautiful scenery, and friendly service, this cruise delivers.

The Drawbacks

While short and sweet, some might wish for a longer sail or more interactive elements. Also, since it’s an outdoor-only experience, weather can impact the trip — a cloudy or windy evening might slightly alter the ambiance or comfort level. Finally, the cost is higher than some basic sunset cruises, but the quality of drinks and the setting make it a good value for those who appreciate finer details.

Who Will Enjoy This Cruise?

If you’re a couple celebrating an anniversary, or a small group of friends seeking a luxurious evening, you’ll love the upscale atmosphere and beautiful vistas. It’s also perfect if you enjoy wine and gourmet snacks paired with scenic views. Travelers who’ve experienced it describe it as a “fantastic time” and plan to repeat the experience on each visit, showing its enduring appeal.

This tour is best suited for those who want a more relaxed, intimate outing rather than a lively party or bulk cruise. It’s a great way to unwind with a glass of wine in hand, watching the sun melt into the Gulf.

Practical Tips and Final Thoughts

• Bring a sweatshirt if visiting in cooler months; evenings can get breezy.
• Sunglasses and a camera are must-haves for capturing the scenery.
• Arrive 30 minutes early for check-in and to settle in.
• The duration is just 2 hours, so plan your evening accordingly.
• No gratuities included, so tip the crew if you’re pleased with the service.
• The cruise departs from a convenient, central location with facilities available before sailing.

The Key West Wind and Wine Sunset Sail offers a refined, scenic, and delicious way to enjoy a Key West sunset. It’s a perfect blend of luxury and laid-back charm, ideal for those who want to indulge a little while soaking in the stunning coastal views. Whether celebrating a special moment or simply seeking a memorable way to end your day, this sail delivers an experience you’re unlikely to forget.

FAQ: Your Questions Answered

What is the price for this sunset sail?
It costs $134 per person, which includes all the wines, beers, and gourmet hors-d’oeuvres.

How long is the cruise?
The experience lasts 2 hours, making it a perfect short outing without feeling rushed.

Where does the cruise depart from?
All departures are from the Danger Chandlery Store at Opal Key Resort & Marina in Old Town Key West.

Is there a dress code?
There’s no formal dress code, but casual, neat attire with a sweatshirt in cooler months is recommended. Sunglasses and a camera are also advised.

Are drinks served on the boat?
Yes, you’ll enjoy eight varieties of wine, five premium beers, plus soft drinks and bottled water.

Are gratuities included?
No, gratuities are not included. It’s customary to tip the crew if you’re pleased with the service.

What should I bring?
Bring a photo ID, sunglasses, a camera, and possibly a sweatshirt for cooler evenings.

Can I cancel my reservation?
Yes, you can cancel up to 24 hours in advance for a full refund, offering some flexibility for your plans.

Is this experience suitable for children?
The tour is adult-oriented due to alcohol service and the nature of the experience, so it’s best suited for guests over 21.

Will I see wildlife?
While not guaranteed, many guests have reported dolphin sightings during their sail, adding a magical touch to the sunset.

To sum it up, the Key West Wind and Wine Sunset Sail offers a delightful blend of scenic beauty, high-quality drinks, and a cozy atmosphere. It’s an excellent choice for travelers wanting a more sophisticated and intimate way to experience a Key West sunset. Whether celebrating a special occasion or simply indulging in a relaxing evening, this cruise promises a memorable evening on the water that’s worth every penny.

You can check availability for your dates here: