Schooner Appledore Day Sail with Full Bar in Key West

Imagine gliding over the calm waters of Key West aboard a beautifully restored 19th-century-style schooner. The Schooner Appledore Day Sail offers a peaceful escape into the Gulf of Mexico, with the added bonus of a full open bar and hands-on sailing opportunities. Whether you’re a seasoned sailor or just looking to enjoy a scenic cruise, this tour has a bit of everything—history, beauty, and fun.

What we really love about this experience is how accessible it is. The crew’s friendliness and knowledge make the trip feel welcoming rather than stuffy, and the open bar is a delightful perk for those looking to unwind. Plus, the chance to help hoist the sails and take the wheel adds a tangible sense of adventure.

However, if you’re expecting a long or highly structured itinerary, you’ll need to set your expectations accordingly. This is a 2-hour sail without stops, focused on relaxation, scenery, and participation—perfect if you’re after a laid-back, authentic experience.

This tour is ideal for travelers who enjoy the ocean, want an interactive experience, and appreciate a good drink with a view. It suits couples, families, or solo explorers seeking a memorable, engaging way to experience Key West’s maritime charm.

Key Points

• Duration: About 2 hours, with no stops, making it easy to fit into a busy day.
• Price: Free per person—value is in the experience, scenery, and included beverages.
• Activities: Sailing, helping raise the sails, taking the wheel, and enjoying the view.
• Highlights: Historic schooner, knowledgeable crew, full open bar, gorgeous waterfront scenery.
• Group Size: Limited to 49 travelers, ensuring a more intimate experience.
• Best for: Those who enjoy hands-on activities, scenic relaxation, and socializing over drinks.

A Closer Look at the Key West Schooner Experience

The Setting and Meeting Point

The tour starts at 200 William St in Key West, a convenient location close to the waterfront. The meeting process is straightforward, and most travelers will find it easy to arrive on time—especially since the tour confirms immediately at booking and offers flexibility with cancellation up to 24 hours in advance. This is a smart feature, as weather-dependent sailing can sometimes be canceled, but you’ll be offered an alternate date or full refund if that happens.

Once aboard, you’ll be introduced to the schooner, a vessel that beautifully balances modern comfort with traditional style. Her decks are spacious enough to relax comfortably—an important detail, considering the sometimes lively or windy conditions at sea.

What to Expect on the Itinerary

The tour involves a single stop at Mallory Square and the Key West Historic Seaport. Mallory Square is famous for its sunset celebrations, street performers, artists, and lively crowds. While the sail itself doesn’t stop here, it’s a scenic vantage point to start or end your trip, offering excellent photo opportunities of the lively waterfront.

The Key West Historic Seaport is a charming harbor lined with colorful boats, old warehouses, and restaurants—perfect for a post-sail walk or a quick snack before or after your trip. This location emphasizes the maritime history that makes sailing here so special.

The Sailing Experience

The real highlight is the 2-hour sail on a two-masted schooner. The crew provides historical context about the vessel and the tradition of sailing, which many reviews praise as both informative and engaging. As one reviewer notes, the captain offers “great historical information” and makes the experience accessible for everyone.

Feel the wind in your hair as the crew hoists the sails, a process that is surprisingly participatory. Guests are encouraged to help, with opportunities to take the helm or assist with the sails—adding a tangible feeling of involvement that many travelers find rewarding. This is not just a passive cruise; it’s about experiencing the ship and the sea.

The Full Bar and Refreshments

The full open bar is a standout feature, especially for those who enjoy a relaxing drink while taking in the scenery. Most travelers over 21 are entitled to enjoy a variety of alcoholic beverages, with additional options like soda and bottled water also available. Guests consistently mention the open bar as a nice touch that adds to the leisurely atmosphere without feeling excessive or overindulgent.

The Crew and Atmosphere

Guests overwhelmingly praise the crew’s friendliness, attentiveness, and passion for sailing. Multiple reviews highlight how knowledgeable and engaging the crew are, making the journey not just scenic but also educational and personable. This crew-guest interaction is what elevates the experience beyond a simple boat ride.

The Overall Value

Though the tour is free, the value lies in the overall experience—scenic beauty, engaging activities, and included beverages—rather than cost. The small size of the group (up to 49 guests) ensures everyone feels included, making it a social but relaxed outing.

Weather and Cancellation Policy

Since sailing is weather-dependent, the tour can be canceled if conditions aren’t suitable. Luckily, the policy is straightforward: full refunds or rescheduling options are available if bad weather strikes. This flexibility is reassuring for travelers concerned about the unpredictability of outdoor activities.

Who Is This Tour Best For?

This sail is most suited for those seeking a laid-back, participatory maritime experience in Key West. If you enjoy hands-on activities, beautiful waterfront views, and conversations with friendly crew, you’ll find this trip rewarding. It’s also a good option for travelers who want an authentic glimpse into the sailing tradition without the expense of a private charter.

It’s less ideal for those looking for a long cruise, a guided tour of specific sites, or a formal dinner experience. Also, since the tour is only two hours, it fits well into a day packed with other activities but shouldn’t be the sole focus if you’re after a full day of sightseeing.

The Sum Up: Is This the Right Choice for You?

If you value relaxing on the water, enjoying stunning views of Key West’s waterfront, and having the chance to participate actively in sailing a traditional schooner, then this tour hits the mark. The knowledgeable crew makes the experience approachable and educational, adding depth beyond just a scenic ride.

The full bar is a significant perk, allowing you to unwind with a drink in hand as you soak in the scenery. The small group size and informative narration elevate this from a simple boat trip to a memorable experience that leaves many wanting to do it again.

This cruise is perfect for couples looking for a romantic outing, families seeking a fun, interactive activity, or solo travelers eager to meet others in a relaxed setting. If you’re after authentic maritime charm combined with good company and great views, this sail on the Appledore is sure to satisfy.

FAQ

Is the tour suitable for children?
Most travelers can participate, and the experience is generally family-friendly. However, it’s best to consider the age of children, as the sailing and participation might be more enjoyable for older kids who can help hoist sails and take turns at the wheel.

How long is the sailing trip?
The tour lasts approximately 2 hours with no stops, focusing on sailing and enjoying the scenery.

Do I need any sailing experience?
No prior experience is necessary. The crew provides guidance, and participation is encouraged but optional.

Where do I meet for the tour?
The meeting point is 200 William St, Key West, FL 33040, conveniently located near the waterfront.

What should I bring?
Bring sunscreen, sunglasses, a hat, and perhaps a light jacket if it’s breezy. Comfortable clothing suitable for being outdoors is recommended.

Can I cancel if the weather is bad?
Yes, the tour has a full refund policy if canceled due to poor weather, provided you cancel at least 24 hours in advance.

In essence, the Schooner Appledore Day Sail offers a beautifully balanced experience—combining history, hands-on sailing, scenic views, and drinks—making it a memorable way to enjoy Key West’s maritime heritage without breaking the bank. Whether you’re celebrating a special occasion or simply craving a peaceful day on the water, this trip offers genuine value and authentic fun.