Stock Island Wind & Wine Sunset Sail aboard classic Schooner

A Sunset Sail That Combines Elegance and Authenticity in Key West

Imagine gliding into the Floribbean sunset aboard a beautifully maintained classic schooner, with a glass of fine wine in hand, the sea breeze gently ruffling your hair, and the world slowing down. This is exactly the kind of memorable experience you get with the Stock Island Wind & Wine Sunset Sail. For just $134 per person, this 2-hour journey departs from the Perry Hotel & Marina on Stock Island and offers a blend of relaxation, sophistication, and scenic beauty.

What makes this cruise stand out? First, the upscale selection of wines and beers—eight varieties including Champagne, along with gourmet hors-d’oeuvres—sets a luxurious tone. Second, the friendly, attentive crew helps create a relaxed, intimate atmosphere that feels more like a gathering with friends than a typical tour. While some might see the 2-hour duration as short, it’s enough time to unwind and truly enjoy the sunset views without feeling rushed.

On the downside, travelers looking for a full dinner or more extensive food options might be disappointed—this sail focuses more on light hors-d’oeuvres and drinks. Also, the cost of $134 could seem steep for some, but the quality of drinks and the intimacy of the setting generally justify the price.

This experience is particularly well-suited for couples seeking a romantic evening, small groups of friends, or anyone wanting a relaxed, upscale escape on the water. If you’re after spectacular sunset views with a touch of elegance, this cruise is likely to satisfy.

Key Points

• Upscale Experience: Premium wines, craft beers, and gourmet appetizers create a refined sailing ambiance.
• Scenic Views: Sail into the Floribbean sunset with stunning vistas over Key West.
• Intimate Atmosphere: Small groups and attentive crew make it feel special and personalized.
• Authentic Sailing: Watch the crew hoist the sails and get involved in the traditional process.
• Value for the Experience: High-quality drinks and gourmet snacks justify the price for many.
• Ideal for Romance and Relaxation: Perfect for couples or those wanting a peaceful, scenic escape.

You can check availability for your dates here:

Exploring the Details of the Wind & Wine Sunset Sail

When we think about a sailing experience, it’s not just about reaching a destination—it’s about how you get there and what you savor along the way. This cruise begins at the Perry Hotel & Marina, where you’ll check in about 30 minutes prior. Meeting at Bad Boy Taqueria & Tequila, you’ll be escorted through the marina to the schooner, which is neatly moored in slip J5. This ensures a relaxed start, with no long waits or complicated logistics.

Once on deck, you’ll be greeted by a friendly crew eager to share their knowledge and enthusiasm. Watching them hoist the sails is a small but charming highlight—this is real sailing, not just a motorized cruise. The classic schooner itself adds to the sense of history and authenticity, giving you a taste of traditional maritime craftsmanship.

What to Expect During the Sail

The two-hour voyage usually takes place during afternoon or evening hours, allowing you to enjoy breathtaking sunset views. As the boat gently rocks on the waves, you’ll be offered eight varieties of wine—including red, white, and champagne—sourced from around the world. The white wines tend to be crisp and refreshing, perfect for the warm Florida evening, while the reds add depth if you prefer something richer. The Champagne provides a celebratory touch, ideal if you’re marking a special occasion.

You will also enjoy five premium beers, both imported and domestic, providing options for those who prefer beer over wine. The gourmet hors-d’oeuvres are well-curated, with meats, cheeses, crackers, fresh fruit, crudités, and some chocolates—giving you a satisfying snack that complements the drinks without overwhelming.

The Atmosphere and Views

What really elevates this experience is the setting. Sailing under the canvas of the schooner’s sails, with the sun sinking into the horizon, you’ll see Key West’s coastline in the distance—perhaps a glimpse of the lively harbor, historic houses, or the lush greenery of Stock Island. The sea breeze and the sound of waves create a peaceful, almost meditative environment.

Many guests, including those in reviews, mention how attentive the crew is. Liz commented that it was the “best night spent in the Keys,” praising the crew for keeping the wine and appetizers flowing. Tatia enjoyed the gorgeous evening, noting that the light appetizers and drinks made the experience memorable, especially the gorgeous sunset.

Practical Details

The tour includes bathrooms on board and before boarding at the marina. You should bring a light sweatshirt if visiting in cooler months, as the evening breeze can be brisk. Sunglasses and a camera are also recommended to capture the stunning scenery. The tour is not suitable for children under a certain age—it’s more of an adult-oriented, relaxed cruise.

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Who Will Love This Cruise?

This sail is best suited for romantic couples looking for a special evening, small groups of friends wanting a relaxed social outing, or anyone interested in authentic sailing combined with excellent drinks and scenic beauty. Since the cruise offers a more refined, yet casual experience, it’s ideal for those who prefer a less commercialized, more intimate outing compared to larger, more crowded sunset cruises.

The Sum Up

The Stock Island Wind & Wine Sunset Sail offers a distinctive way to experience Key West’s legendary sunsets. With premium wines, gourmet snacks, friendly service, and beautiful views, it’s a memorable choice for anyone wanting to add a touch of elegance to their evening on the water. It’s especially appealing for travelers who value authentic sailing moments and upscale comfort in a relaxed environment.

While it might not be the most budget-friendly option, the quality of the drinks, the ambiance, and the beautiful setting make it worthwhile for those who want a special occasion or quiet escape. Whether you’re celebrating a milestone or just seeking a peaceful evening with stunning scenery, this cruise delivers a refined, intimate experience that truly captures the magic of a Key West sunset.

Frequently Asked Questions

Is this tour suitable for children?
This experience is primarily designed for adults. Since it’s a relaxed, upscale cruise with alcohol service, it’s best suited for grown-ups. Check with the provider if you’re unsure about specific age restrictions.

What should I bring on the cruise?
A sweatshirt for cooler evenings, sunglasses for daytime or sunny windows, and a camera to capture the stunning views. Bringing a photo ID is also recommended, though not explicitly required.

How long is the tour?
The exact sailing time is 2 hours, making it a perfect short escape that fits comfortably into an afternoon or evening plan.

What drinks are included?
You’ll enjoy eight varieties of wine, including red, white, and Champagne, as well as five premium beers. Soft drinks and bottled water are also provided.

What kind of food is served?
Light gourmet hors-d’oeuvres—meats, cheeses, crackers, fruit, crudités, and chocolates—designed to complement the drinks without being a full meal.

Where does the tour depart from?
From the Perry Hotel & Marina on Stock Island, with check-in at Bad Boy Taqueria & Tequila. The crew will escort you through the marina to the schooner.

Can I cancel if my plans change?
Yes, cancellations are accepted up to 24 hours in advance for a full refund, offering some flexibility in your planning.

Whether you’re after a romantic sunset, a peaceful escape from the crowds, or just want to experience sailing with a touch of class, this cruise offers a genuinely enjoyable slice of Key West life.

You can check availability for your dates here: