Key West Day Sail on Schooner America 2.0 with 2 Drinks

Imagine drifting along the sparkling waters of Key West aboard a beautifully restored schooner, feeling the ocean breeze and soaking up iconic sights. This Key West Day Sail on Schooner America 2.0 promises a delightful blend of scenic views, history, and relaxation—without breaking the bank. With a perfect rating of 5.0 from hundreds of reviews, it’s clear that many travelers find this cruise a highlight of their trip.

What makes this experience so appealing? First, the chance to sail on a replica of the schooner that won the first Americas Cup adds a touch of maritime history you can see and feel. Second, the views of landmarks like Fort Zachary Taylor, Mallory Square, and Sand Key Light Tower are truly picture-worthy. Third, the inclusion of two drinks—plus complimentary soda and water—means you can toast to a perfect afternoon without extra expense.

One consideration is the duration; at just 1 hour 30 minutes, it’s a relatively short trip. While this means it’s great for fitting into a busy schedule, those seeking a longer sailing adventure might want to look at other options. This tour suits travelers who appreciate scenic, laid-back outings, love wildlife spotting, and enjoy a good drink in good company.

Key Points

• Historic Sailing: Sail on a detailed replica of the schooner from the first Americas Cup.
• Iconic Landmarks: Get up close views of Fort Zachary Taylor, Mallory Square, and Sunset Pier.
• Wildlife Viewing: Keep your eyes open for dolphins, sea turtles, and seabirds.
• Inclusive Drinks: Two alcoholic drinks are included, with additional beverages for purchase.
• Short & Sweet: A 1.5-hour cruise offers relaxed sightseeing with a focus on comfort.
• Small Group Feel: Many reviews mention a cozy, intimate atmosphere with friendly crews.

Introduction to the Experience

Starting with a quick overview, this Key West Day Sail aboard the America 2.0 offers a unique way to see the island from the water. Unlike typical boat tours, this one emphasizes sailing on a vessel modeled after the historic schooner that won the first America’s Cup—adding a dash of maritime heritage to your trip.

What we love most about this cruise is the combination of beautiful scenery, knowledgeable crew, and the chance to unwind with a couple of drinks. Whether you’re a history buff, wildlife enthusiast, or simply craving a relaxing escape, this sail ticks many boxes. Plus, reviews highlight how professional and friendly the crew are, making the experience even more enjoyable.

That said, it’s worth noting that the cruise is relatively short, so if you’re after a lengthy day at sea, you might prefer a sunset or longer sailing tour. But for those who want a taste of sailing with plenty of picturesque moments, this is a solid pick. It’s especially perfect for travelers who value good value, friendly service, and authentic maritime experiences.

The Itinerary and What to Expect

The tour kicks off at 202 William St, Key West, with guests arriving 15-30 minutes early to check in and secure their boarding passes. It’s a straightforward process, and with most travelers booking roughly three weeks in advance, it’s recommended to reserve early if you’re keen.

What does the cruise include?

• A 1.5-hour coastal sail along Key West’s coastline
• Soda and water—complimentary for all guests
• Two alcoholic beverages included (for guests 21+), with options for purchase onboard

The Stops & Highlights

First stop: As the schooner departs the dock, you’ll enjoy an expansive view of Mallory Square, famous for its sunset celebrations but just as stunning during the day from the water. The crew often shares insightful commentary about the sights, making this part both scenic and educational.

Second stop: The cruise glides past Fort Zachary Taylor, offering a unique perspective that you can’t get from land. Many reviews, like Patti W’s, mention dolphin sightings and the chance to see sharks or sea turtles swimming nearby—though wildlife encounters can vary, most guests report dolphin sightings on their trip.

Third stop: The captain hugs the coast, providing excellent views of Sunset Pier and other landmarks. This part of the cruise is particularly appreciated by those wanting that “postcard shot” of Key West’s waterfront.

What makes this sailing special?

The crew, often praised for their friendliness and professionalism, will sometimes involve guests in the sailing process—helping hoist sails or sharing local stories. As Glenna B remarks, “It was a small group of people, which was nice and fun and informative.” The intimate setting, with most reviews mentioning a group size around 8 to 10, enhances the personal feel.

Wildlife & Nature

Many reviewers mention dolphins swimming alongside the schooner, a highlight that adds a magical touch. Waterbirds and other marine life are also common sights, creating a peaceful, natural backdrop. This is a trip where patience pays off and simply enjoying the moment counts.

The Crew & Service

From the reviews, it’s clear the crew makes a significant difference in the experience. Multiple reviewers comment on their knowledgeable, friendly, and professional approach. For instance, Dan, Lexi, and Chelsie received praise for their friendliness and knowledgeability, making the trip informative and fun.

Some guests appreciated the crew’s efforts to get photos, especially Anthony C, who mentioned they took pictures so guests could relax without worrying about selfies. The crew’s attentiveness, especially during unexpected weather (like Brian C’s experience with rain), shows they prioritize guest comfort.

Drinks, Food, and Amenities

The included two alcoholic drinks are a nice touch, offering good value and a chance to toast while enjoying the scenery. Many guests noted the beverages were ice cold and poured generously, especially beers. Additional drinks like wine, cocktails, or mimosas are available for purchase with a credit card onboard, giving options for those who want more than the included beverages.

Soda and water are always complimentary, perfect for staying hydrated on a sunny day. One review mentions a surprise charcuterie plate—though not advertised—indicating that some trips might include extra touches.

Pricing & Value

Priced at $73.10 per person, this tour presents a good value when you consider its inclusions: a scenic, historical sail, wildlife sightings, and drinks—all in a small, intimate group. The reviews consistently praise the trip’s relaxing atmosphere and beautiful vessel, with many saying they would do it again.

Compared to longer or sunset cruises, this short but sweet sail offers an excellent way to enjoy Key West from the water without spending a fortune. It’s also flexible enough to fit into a busy itinerary, especially since most book about three weeks in advance.

Who Is This Tour Best For?

This experience is perfect for travelers looking for a relaxing, scenic cruise with a touch of sailing history. It’s well-suited for honeymooners, small groups, wildlife lovers, or anyone wanting a peaceful break from busy streets. Kids sail free on the afternoon departures, making it family-friendly, as long as everyone has a ticket.

If you enjoy authentic sailing experiences, gorgeous views, and a friendly crew, you’ll likely find this tour a highlight. Those seeking a longer or more adventurous trip might prefer other options, but for a quick, charming sail, this one hits all the right notes.

Frequently Asked Questions

Is there hotel pickup or parking available?
No, the tour starts at a designated meeting point at 202 William St. in Key West. Guests should plan to arrive 15-30 minutes early.

What is the duration of the tour?
The cruise lasts approximately 1 hour 30 minutes, making it a convenient option for fitting into your day.

Are children allowed?
Yes, kids sail free on the afternoon departures, but all travelers need to hold a ticket.

What should I wear?
Dress comfortably for weather conditions. Since the tour operates in all weather unless unsafe, bring sun protection or rain gear as needed.

Can I buy additional drinks onboard?
Yes, additional wine, beer, cocktails, and mimosas are available for purchase with credit card.

Is the experience suitable for people with mobility issues?
Most travelers can participate, but it’s best to check with the provider for specific accessibility concerns.

What does the tour include?
A 1.5-hour sailing, two included alcoholic drinks (for 21+), and complimentary soda and water.

Will I see wildlife?
Dolphins, sea turtles, and seabirds are common sightings, but as with all wildlife, sightings can vary.

What if the weather is bad?
Tours operate in all weather unless unsafe. If canceled due to poor weather, you’ll be offered an alternative date or full refund.

Can I cancel the tour?
Yes, cancellations are free if done at least 24 hours in advance for a full refund.

Final Thoughts

This Key West Day Sail aboard America 2.0 offers a wonderfully authentic sailing experience that emphasizes scenic beauty, wildlife encounters, and easy relaxation. Its small group size, friendly crew, and beautiful vessel make it stand out among water-based tours.

While short, the trip packs enough charm, history, and gorgeous views to leave a lasting impression—especially with included drinks and the chance to see dolphins up close. It’s an ideal option for travelers seeking a laid-back, scenic adventure that’s both fun and educational.

If you’re after a memorable, reasonably priced way to experience Key West from the water, this cruise delivers in spades. Perfect for couples, small groups, or families with kids, it’s an experience to savor and remember long after you’ve returned to dry land.