Key West Sunset Sail Aboard Legendary Schooner Appledore

A Relaxing Sunset Escape on the Schooner Appledore in Key West

If you’re dreaming of watching a sunset over the water with a cold drink in hand, the Key West Sunset Sail aboard the legendary Schooner Appledore might just be what you’re looking for. This 2-hour evening cruise offers a chance to enjoy the iconic Key West skyline from a unique perspective — all aboard a beautifully maintained, historic wooden schooner.

What we really like about this experience is how it combines a classic sailing vibe with modern comforts. The friendly crew makes you feel right at home, and the included beers, wines, and cocktails elevate the whole mood. Plus, the opportunity to help raise the sails adds a bit of a hands-on element that makes it feel authentic. On the flip side, it’s worth noting that this tour is quite popular — so booking a bit in advance is advisable to secure your spot.

This cruise is ideal for travelers seeking a more relaxed, intimate evening out — especially if you love boats, beautiful scenery, and a bit of local charm. While it’s not overly family-focused, it’s a fantastic choice for couples, groups of friends, or anyone wanting a peaceful, scenic end to a day in Key West.

Key Points

• Beautiful Sunset Views: Imagine orange, gold, and pink skies framing the Gulf of Mexico, with Key West’s skyline as your backdrop.
• Historic Schooner: Sail aboard a vessel that has circumnavigated the globe, offering a genuine maritime experience.
• Inclusive Drinks and Snacks: Premium beers, boutique wines, champagne, cocktails, plus tasty hors d’oeuvres make the two hours feel special.
• Engaging Sailing Experience: You can take part in raising the sails, adding an interactive touch to your evening.
• Prime Locations: Sail past the historic seaport, Navy Mole, and Mallory Square, with a view of Sunset Key just off the coast.
• Limited Group Size: With a maximum of 36 travelers, you’ll enjoy a more personal atmosphere and attentive service.

The Experience in Detail

Starting Point and Setting Off

Your evening begins at the Key West Historic Seaport, a lively waterfront with colorful shops, restaurants, and the charm of old Florida. It’s a great place to soak in the local vibe before setting sail. The schooner, Appledore, is a classic wooden vessel, with a history of circumnavigation that adds a touch of adventure to your sunset cruise.

The Voyage and Sights

Once onboard, you’ll get the chance to participate in raising the sails, just like sailors of old. This hands-on element is a highlight for many guests, giving you a real sense of connection to the vessel. The crew, as numerous reviews point out, are friendly, entertaining, and knowledgeable. They’ll share insights into the boat’s history, local stories, and point out landmarks as you glide past Key West’s skyline.

The route includes views of the historic seaport area, famous for its vibrant activity and nautical history. As you cruise past the Navy Mole and toward Sunset Key, you’ll be treated to picturesque vistas. The boat glides smoothly over the water, so expect a calming, almost meditative experience — perfect for unwinding after a busy day.

Sunset and Photos

The highlight, of course, is the sunset. Guests consistently praise the breathtaking views as the sky transforms into shades of orange, pink, and gold. Several reviews mention how impressive the sunset is, with some describing it as “spectacular.” It’s a moment that’s perfect for photos or simply soaking in the scene.

Refreshments and Snacks

Included in the tour are premium beers, boutique wines, champagne, and cocktails for guests over 21, along with soda and a chef’s selection of hors d’oeuvres, including cocktail shrimp. Reviewers have appreciated the quality of the drinks and snacks, mentioning that the hors d’oeuvres added a nice touch to the cruise.

Atmosphere and Crew

The crew’s friendliness and professionalism come through strongly in reviews. They’re attentive to guests, entertaining, and willing to share information — making the experience more than just a sightseeing trip. Many mention the crew’s efforts to make everyone feel comfortable and included, especially when helping with the sails or serving drinks.

Duration and Group Size

At just about two hours, the cruise fits well into most travelers’ schedules. The group size, capped at 36 people, ensures a cozy feeling and personalized service. Guests have noted that the small group setting improves the overall experience, avoiding the noise and crowds that some larger tours attract.

What Could Be Better?

While the cruise receives near-perfect reviews, there are a couple of minor points to keep in mind. Some reviewers found the drinks to be of average quality — not necessarily a deal-breaker, but worth noting if you’re particular about your beverages. Plus, the tickets tend to book out about 12 days in advance, so planning ahead is wise to secure your preferred date.

Weather can also be a factor. Since this is an outdoor activity, cancellations due to poor weather are possible, but the company offers full refunds or rescheduling options. If you’re visiting during hurricane season or unpredictable weather periods, it’s good to keep an eye on the forecast.

Pricing and Value

At $89 per person, this cruise isn’t the cheapest activity in Key West, but it offers a lot for the price. The combination of historical sailing, stunning scenery, included drinks, and snacks makes it feel like a reasonable deal — especially considering how many reviews highlight the quality of the experience and the crew’s attentiveness.

Who Should Book This?

This sunset sail is best suited for those wanting a relaxed, scenic, and somewhat interactive experience. It’s perfect for couples, small groups, or anyone craving an authentic sailing vibe without the crowds or loud music often found on larger tour boats.

If you love boats, beautiful views, and a peaceful end to your day in Key West, this cruise checks all the boxes. Families with older children or teenagers might enjoy it too, especially if they appreciate sailing or want a more laid-back activity.

Frequently Asked Questions (FAQs)

Is this tour suitable for kids?
Most reviews don’t specify age restrictions, but given the tranquil and scenic nature of the cruise, it’s suitable for older children or teenagers who can sit quietly and enjoy the views. The focus on relaxing sailing and adult beverages suggests it’s not specifically geared toward very young kids.

What’s included in the price?
Your ticket covers a 2-hour sunset sail on a historic schooner, with premium beers, boutique wines, champagne, cocktails, soda, and a selection of hors d’oeuvres and cocktail shrimp.

Are drinks and snacks really included?
Yes, the tour includes a variety of alcoholic beverages and snacks. Reviewers have praised the quality, mentioning that the drinks and hors d’oeuvres add to the enjoyment of the cruise.

How far in advance should I book?
Most bookings are made about 12 days in advance, and given the popularity and fixed capacity, it’s wise to reserve early to secure your preferred date.

What if the weather is bad?
The tour requires good weather. If canceled because of weather conditions, you’ll be offered a different date or a full refund.

Where does the cruise start and end?
It departs from 200 William St, Key West, and returns to the same location at the end of the cruise.

Final Thoughts

The Key West Sunset Sail aboard the Appledore is a gentle yet memorable way to experience the beauty of Key West from the water. The combination of a historic schooner, friendly crew, stunning sunset views, and included drinks and snacks makes it a solid choice for anyone looking to unwind and soak in the scenery.

It’s especially suitable for those who enjoy sailing, historic vessels, and a relaxed atmosphere without the loud music or crowded boats. If you’re hoping for a peaceful, picturesque, and well-organized evening, this cruise could very well become a highlight of your trip.

Remember to book early, dress comfortably, and bring your camera — those sunsets are truly worth capturing. Whether you’re celebrating a special occasion or simply want a different perspective on Key West, this cruise offers a lovely blend of tradition, scenery, and serenity.