Key West: Schooner Sunset Sail with Food & Drinks

Imagine gliding over calm waters, feeling the wind in your hair, and watching the sun paint the sky in shades of orange and pink. That’s essentially what you get with the Key West Schooner Sunset Sail—a two-hour journey that’s as much about the scenery as it is about relaxing in style. Whether you’re celebrating a special occasion or just want a laid-back evening with beautiful views, this cruise provides a memorable way to end your day in the Keys.

What makes this experience stand out? For starters, the luxurious schooner—America 2.0—is a beautifully maintained vessel with teak decks and mahogany trimmings that make you feel like you’re on a private yacht. Plus, the afternoon/evening timing lets you enjoy a peaceful, uncrowded environment with stunning visual effects. On the downside, some travelers mention that space between seats can be tight, which might matter if you’re seeking more room or are traveling with larger groups.

This experience suits those who are looking for a relaxed, adult-oriented activity with quality drinks and good company. If you love nature, beautiful water views, and a touch of elegance, this sail could really be a highlight of your trip.

Key Points

• Elegant vessel enhances the sense of occasion and comfort.
• Wildlife sightings like dolphins and sea turtles add a special touch.
• Quality drinks and hors d’oeuvres make it feel like a floating happy hour.
• Sunset and Green Flash experience makes for unforgettable photos.
• Professional crew ensures a smooth, friendly experience.
• Limited space between seats may be a consideration for some.

You can check availability for your dates here:

What You Can Expect from the Sunset Sail

The sailing adventure takes place aboard the America 2.0, a stunning schooner with teak decks, mahogany details, and a huge canvas area that’s perfect for catching the breeze and the sunset. The tour usually runs for about two hours, often in the late afternoon or early evening, depending on the schedule. It’s designed to be a relaxing, scenic experience rather than a high-energy party—though drinks and hors d’oeuvres are included, so there’s plenty of opportunity to unwind and chat.

The Itinerary and Sights

The cruise kicks off from the meeting point at 202 William Street—directly behind the Schooner Wharf Bar—making it accessible and central. Once onboard, the crew sets sail toward some iconic sights like Fort Zachary Taylor, visible from the water, and Sand Key Reef, a famous spot for snorkeling and marine life. You’ll also get scenic views of Mallory Square and Sunset Pier, which are key locations in Key West’s sunset culture.

As the boat cruises, you’ll want to keep your eyes open for wildlife. Guests frequently mention dolphin sightings, which feel like a real bonus, especially when they jump and play near the boat. Water birds and perhaps even a sea turtle or two might cross your path, adding to the natural spectacle. The highlight, of course, is watching the sunset—an event that often includes the rare and atmospheric Green Flash, a brief flash of green at the horizon’s edge right as the sun dips below the water.

The Atmosphere Onboard

The America 2.0 is a vessel that combines style and comfort, with enough space for passengers to spread out. Many reviews note that the crew is courteous, attentive, and professional, creating a welcoming environment. Guests are encouraged to relax, nibble on hors d’oeuvres, and sip their favorite drinks—complimentary alcoholic and non-alcoholic options are provided, with the option to upgrade to champagne or special holiday treats during certain occasions.

Some reviews mention that the experience feels like a peaceful escape—not a boisterous party cruise. This is perfect if you’re looking for a more refined and scenic experience rather than a loud, crowded boat.

Is It Worth the Price?

At $116 per person, this cruise is competitively priced considering what’s included: a 2-hour sail, drinks, hors d’oeuvres, and the chance to see dolphins and a stunning sunset. The reviews consistently praise the value for money, especially noting the quality of service, the beautiful vessel, and the overall ambiance.

Many guests comment that the experience exceeds expectations and feels like a special occasion, especially with the added touches like holiday champagne toasts or taking photos at the helm during key departures. The caliber of the crew and the vessel’s condition make it clear that this isn’t a “cheap cruise,” but rather a quality, memorable outing.

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The Experience for Different Travelers

This cruise is particularly suited to adults who appreciate the finer things in life—good drinks, graceful sailing, and scenic beauty. It’s perfect for romantic outings, celebrating anniversaries, or simply enjoying a peaceful evening in Key West. While it isn’t specifically designed as a family adventure, older children who enjoy boats and wildlife would also likely appreciate the experience.

If you’re visiting during the holiday season, you’ll appreciate the special Christmas or New Year’s offerings, including holiday treats and champagne toasts, which add a festive touch.

The Pros and Cons

Pros

• The stunning sunset views are the main highlight, especially with the possibility of seeing the Green Flash.
• The professional, friendly crew ensures a smooth, enjoyable experience.
• Quality drinks and hors d’oeuvres make the cruise feel like a floating cocktail party.
• Frequent wildlife sightings, including playful dolphins, add a magical element.
• The vessel’s elegant design enhances the overall atmosphere and comfort.

Cons

• Seating space can be tight, which might be uncomfortable if you’re taller or prefer more legroom.
• It’s a two-hour experience, so if you want something more extensive or active, you might look elsewhere.
• If you’re sensitive to sea sickness, brief info isn’t provided, though many find the waters off Key West relatively calm.

Final Thoughts

The Key West Schooner Sunset Sail offers a beautifully curated experience that balances scenic beauty, comfort, and a touch of luxury. It’s especially well-suited for those who want to enjoy the sunset in style, with excellent drinks and the chance to see local wildlife. The professional crew and the vessel’s elegance elevate this from a typical boat ride to a memorable evening in the Keys.

While it’s not a party cruise or a family activity (unless your kids are older and enjoy boats), it’s perfect for couples, friends, or anyone looking to unwind and soak in a truly breathtaking sunset. The price reflects the quality, and based on rave reviews, it’s a worthwhile splurge for a special evening.

FAQ

Is this tour suitable for children?
While the tour is primarily geared toward adults, older children who enjoy boats and wildlife might find it enjoyable. It’s not specifically marketed as a family activity.

What’s included in the price?
You get a sailboat tour, complimentary drinks (both alcoholic and non-alcoholic), and personal hors d’oeuvres. Champagne is available if you select that option.

How long is the cruise?
The experience lasts about 2 hours, usually scheduled in the late afternoon or evening.

Where do I meet for the cruise?
The meeting point is 202 William Street, Key West, right behind the Schooner Wharf Bar.

Are drinks and snacks plentiful?
Yes, guests typically find the drinks to be generous, with many reviews praising the quality. Snacks are also well-received, although one review wished for just a bit more food.

Is this a romantic activity?
Absolutely. The combination of a beautiful vessel, sunset views, and drinks makes it ideal for couples celebrating special occasions.

Are there holiday-specific options?
Yes. During Christmas and New Year’s, there are special departures with holiday treats, champagne toasts, and photos at the helm.

What are the main sights?
You can expect to see Fort Zachary Taylor from the water, Sand Key Reef, Mallory Square, and Sunset Pier, plus wildlife like dolphins and sea turtles.

Is it a crowded experience?
Most reviews mention a comfortable number of passengers, though space between seats can be tight. It’s not a “party boat,” so it’s more intimate and calm.

In the end, if you’re after a beautiful, relaxing, and well-organized sunset cruise in Key West, this schooner sail offers a delightful blend of scenery, comfort, and good company. Whether celebrating a special occasion or just wanting a peaceful evening, it’s a cruise that many guests remember fondly—and, judging by the reviews, it’s clear this experience lives up to its reputation.

You can check availability for your dates here: