Key West Wind and Wine Sunset Sail aboard classic Schooner

Introducing the Key West Wind and Wine Sunset Sail

If you’re dreaming of a relaxing, upscale way to end your day in Key West, the Wind and Wine Sunset Sail aboard a classic schooner might just be the perfect choice. Based on the glowing reviews and detailed descriptions, this tour offers a refined experience that combines the beauty of a sunset with excellent drinks and good company—whether you’re in a romantic mood or just want to unwind with friends.

What really appeals to us about this cruise is the focus on quality. From eight varieties of wine from around the globe to premium beers and gourmet hors-d’oeuvres, the attention to detail is clear. Plus, the opportunity to watch the crew hoist the sails adds a touch of charm and authenticity that’s hard to match. However, one thing to consider is that this cruise leans towards a more upscale, relaxed vibe — so if you’re after a party atmosphere or a high-energy experience, this might not be your best fit.

This sail is ideal for those who appreciate good wine, beautiful scenery, and a quieter, more intimate atmosphere. Perfect for couples, friends, or anyone looking to enjoy a special sunset on the water with a touch of class.

You can check availability for your dates here:

Key Points

• Upscale Experience: A refined sunset cruise with premium wines and gourmet hors-d’oeuvres.
• Beautiful Setting: Sail on a classic schooner into the Floribbean sunset with breathtaking views.
• Authentic Atmosphere: Watch the crew hoist the sails and join in the relaxed, intimate vibe.
• Wine Selection: Eight varieties of wine, including reds, whites, and Champagne, served during the cruise.
• Inclusive Refreshments: Cold beers, sodas, and bottled water are also available, making it well-rounded.
• Ideal for Romance & Relaxation: An elegant way to wind down and enjoy the scenery.

What to Expect on the Wind and Wine Sunset Sail

When you book this tour, you’re signing up for a two-hour journey into the sunset aboard a historic Key West schooner. The experience kicks off at the Opal Key Resort & Marina, a central spot in Old Town, with check-in about 30 minutes prior. The crew will greet you as they prepare to set sail, and you can expect a friendly, knowledgeable team that’s eager to make your evening special.

The Sailing Itself

Once onboard, you’ll get a chance to watch the crew hoisting the sails, which is quite a sight if you’re into traditional sailing. As the schooner slips away from the marina, you’ll be treated to sweeping views of the horizon, with the sun gradually dipping below the horizon, casting warm hues across the sky.

The Wine & Beverages

One of the tour’s highlights is its wine selection. You’ll enjoy eight different varieties, usually including four reds, three whites, and a Champagne, served from around the world. If you’re a wine lover, this is a rare U.S. opportunity to sip real wine on a sailing cruise. Alongside wine, there’s also a good selection of premium imported and domestic beers.

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The Hors-d’Oeuvres

The onboard gourmet appetizers are designed to complement the drinks and enhance the experience. Expect a thoughtfully curated charcuterie board, featuring meats, cheeses, crackers, fresh fruit, crudités, and even chocolates. Many reviews mention how tasty and plentiful the snacks are, making this a true culinary treat.

The Atmosphere

The overall vibe is relaxed yet refined. Many reviewers have highlighted the knowledgeable and friendly crew who create a welcoming environment. The combination of the classic schooner setting, the gentle sway of the boat, and the stunning sunset makes for a very memorable, almost romantic experience—though certainly suitable for groups and couples alike.

The Details That Matter

Duration & Timing

At just two hours, this cruise is a perfect length—long enough to unwind and enjoy the scenery without feeling rushed. It’s usually available both in the afternoon and evening, so you can choose the time that best fits your schedule.

Accessibility & Comfort

Bathrooms are available before boarding and onboard the schooner—important for comfort during the cruise. The check-in process is straightforward, and the meeting point is the Danger Chandlery Store at the Opal Key Resort & Marina, right in Old Town Key West.

Price & Value

At $134 per person, this experience might seem a bit lofty, but considering the quality of wines, the gourmet hors-d’oeuvres, and the caliber of the sailing experience, it’s quite a fair value. Many reviews note how well the price matches the overall experience, especially given how often guests say they’d happily do it again.

Group Size & Experience

While the exact size of the group isn’t specified, classic schooners tend to be intimate, ensuring you won’t feel crowded. The focus on personalized service and the opportunity to mingle with the crew enhances the overall quality.

What We Love & What to Keep in Mind

From the reviews, it’s clear that knowledgeable guides and excellent wine are the core strengths of this tour. Guests frequently mention the great food and the friendly crew going above and beyond. One reviewer even appreciated that the crew waited when they were running late, showing genuine attentiveness.

On the flip side, this cruise isn’t designed as a wild party. If you’re seeking loud music or dancing, you’ll want to look elsewhere. It’s more about enjoying the sunset, the scenery, and the fine drinks in a refined, peaceful setting.

Who Is This Experience Best For?

This sail is perfect for couples seeking a romantic evening, wine enthusiasts wanting to sample different varieties, or anyone who appreciates a quieter, more elegant way to enjoy Key West’s sunsets. It’s also suitable for small groups or friends looking for a memorable, intimate outing. If budget isn’t a concern and you’re after a classy, scenic cruise with high-quality drinks and snacks, this tour hits the mark.

Final Thoughts

The Key West Wind and Wine Sunset Sail offers a delightful blend of tradition, comfort, and sophistication. It’s especially appealing for those who value quality drinks, gourmet bites, and stunning vistas in a relaxed, intimate setting. The knowledgeable crew, excellent wine selection, and gorgeous sunset views make this a memorable addition to any Key West itinerary.

If you’re someone who loves a quiet, elegant evening on the water with a glass of wine in hand, this cruise is likely to be one of your highlights. Just remember, it’s more about savoring the moment than partying into the night—making it ideal for a peaceful, memorable sunset experience.

FAQ

Is this tour suitable for children?
This cruise is geared more towards adults looking for an upscale, relaxing experience, so it’s not specifically designed for children. The focus on wine and gourmet food makes it a better fit for adults.

What should I bring?
You should bring a photo ID, and depending on the season, a sweatshirt might be helpful. Sunglasses and a camera are also good ideas to capture the sunset.

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

How long is the cruise?
The cruise lasts approximately 2 hours, making it a manageable yet fulfilling experience.

Are drinks included?
Yes, the cruise includes eight varieties of wine, premium beers, sodas, and bottled water.

Can I cancel if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund.

Is there a dress code?
While not strictly enforced, casual and comfortable clothing is recommended, especially if you plan to stay for the sunset.

What is the crew like?
Guests consistently rave about the crew’s friendliness and professionalism, noting they go above and beyond to make the experience special.

Are the hors-d’oeuvres filling?
Yes, many reviews mention that the gourmet snacks are plentiful and delicious, complementing the drinks well.

Can I go more than once?
Absolutely—many guests consider it a recurring favorite, with some planning to do it every time they visit Key West.

If you’re after a refined, scenic, and memorable way to enjoy a Key West sunset, the Wind and Wine Sunset Sail definitely deserves a spot on your list. Just prepare to sip, savor, and soak in the views in relaxed, elegant style.

You can check availability for your dates here: