Key West Day Sail on Schooner America 2.0 with 2 Drinks

Sailing in Key West often conjures images of vibrant sunsets, historic forts, and colorful waterfronts. But experiencing it from the deck of a beautifully restored schooner offers a different perspective—one that’s peaceful, picturesque, and a touch luxurious. For about $73, you get roughly an hour and a half aboard the America 2.0, a replica of the schooner that won the very first America’s Cup. The tour departs from 202 William St., and from start to finish, it’s designed to make you feel like you’ve stepped back into sailing history while enjoying modern comforts.

What makes this cruise shine? First, sailing on a vessel modeled after the America—a true piece of yachting legend—adds a special touch of authenticity and intrigue. Second, the cruise offers a chance to see some of Key West’s most iconic landmarks, from Fort Zachary Taylor to Sand Key Light Tower, all from the water. Plus, with two included drinks, it’s a laid-back way to toast to a day well spent in the Florida Keys.

However, there are a few considerations. The cruise operates in all weather conditions unless safety demands cancellation, so if you’re hoping for perfectly sunny skies, it’s worth checking the forecast. Also, since it’s a small group experience—max 68 travelers—you’ll want to book well in advance, especially during peak seasons. It’s ideal for those who love sailing, scenic views, wildlife, and a leisurely pace.

Who should love this tour? If you’re after a calm, scenic adventure with friendly crew and appreciate historical vessels, this is perfect. It suits couples, small groups, and families with kids (who sail free in the afternoon). It’s especially recommended for travelers wanting a relaxing, intimate experience with lots of opportunities for photos and wildlife spotting.

Key Points

• Authentic Sailing Experience: Sail aboard the America 2.0, a detailed replica of the schooner that won the first America’s Cup, adding a sense of sailing history.
• Stunning Coastal Views: Pass landmarks like Fort Zachary Taylor, Sunset Pier, and Sand Key Light Tower, with the chance to see dolphins, sea turtles, and waterbirds.
• Inclusive Drinks: Enjoy two alcoholic drinks included in the ticket, with additional beverages available for purchase, plus complimentary soda and water.
• Small Group Atmosphere: Limited to 68 travelers, making it a personal and relaxed outing.
• Flexible and Weather-Ready: Operates in most weather but can be canceled if conditions are unsafe—good to keep an eye on the forecast.
• Great for All Ages: Kids sail free in the afternoon, making it family-friendly, while adults can indulge in drinks and scenic serenity.

A Closer Look at the Key West Day Sail Experience

When we step onto the America 2.0, it’s impossible not to admire the craftsmanship of this schooner. Its classic lines, gleaming wood, and traditional rigging evoke a sense of yachting elegance. The detailed replica of the vessel that secured America’s Cup victory breathes authenticity into the cruise, appealing especially to anyone interested in sailing history or classic boat design.

Duration & Departure Points: The tour lasts approximately 1 hour and 30 minutes. Starting at the central location on William Street, the meeting process is straightforward—arrive 15-30 minutes early to check in and receive your boarding passes. This is crucial, particularly in busy seasons or if you’re traveling with kids, who sail free but still need a ticket.

Itinerary Breakdown: The cruise is primarily coastal and focuses on the island coastline, offering views of famous landmarks like Mallory Square, Fort Zachary Taylor, and Sunset Pier. The captain will steer the schooner close to these sites, giving you memorable water-level perspectives you can’t get from land. The route hugs the coast, hugging the shoreline past Sand Key Light Tower—a scenic lighthouse—and provides a good chance to spot wildlife like dolphins, which numerous reviews highlight as a delightful surprise.

Wildlife and Scenic Highlights: Numerous reviewers mention dolphin sightings, waterbirds, and even a shark, making it an engaging experience for nature lovers. The calm waters and the slow pace of the sail allow for wildlife watching and taking in the scenery without feeling rushed.

Crew and Atmosphere: The crew, often praised for their professionalism, friendliness, and knowledge, enhances the experience. For example, one review notes that “Dan, Lexi, and Chelsie were all very friendly and very knowledgeable,” adding a layer of storytelling and local insights to the voyage. Many guests appreciate the small group vibe—just around 8 to 10 people sometimes—which fosters a cozy, personal interaction with crew members and fellow travelers.

Drinks and Refreshments: The included two alcoholic drinks are a real perk, especially since the beers are ice-cold, and the crew often offers a variety of options. Soda and water are free, making it easy to stay refreshed. Additional beverages like cocktails, wine, or mimosas are available for purchase, typically via credit card onboard, offering a bit of indulgence without breaking the bank.

Weather and Comfort: The tour is operated in all weather conditions unless safety is a concern. While rain might dampen the experience, many reviews mention that crews are adept at adjusting, such as moving into sheltered areas or minimizing discomfort. Dressing appropriately for the weather—hat, sunscreen, and layers—is recommended, especially since the boat is open-air.

Value for Money: At $73.10 per person, the tour offers good value—especially considering the historic significance of the vessel, the scenic beauty, wildlife sightings, and drinks included. Small-group sailing is a step above typical boat rides, offering a more intimate and relaxing experience.

Authenticity and Experience Beyond the Basics

Beyond the basic facts, what truly makes this cruise stand out is the sense of connection to sailing tradition. Several reviews mention how watching the crew hoist the sails or helping with the rigging adds a tangible depth to the trip. One guest remarked, “Being on a real sailboat and watching—and helping—the hoisting of the sails really added to the experience.”

The landscape around Key West is stunning, and from the water, you see it in a new light—waves gently lapping against the hull, waterbirds circling overhead, and the sun casting shimmering reflections. Many reviewers compared the sail to a peaceful, almost meditative experience—“Very relaxing and peaceful,” one said—and that’s a common theme.

Some travelers also mention the crew’s storytelling as a highlight—sharing local lore, the history of the schooner, or ecological insights. This adds an educational layer that elevates the trip from merely scenic to engaging.

Who Will Love This Tour?

If you’re seeking a calm, scenic outing with a touch of history and wildlife, this cruise hits the mark. It’s perfect for couples, small groups, families, and anyone who wants to unwind on the water without the crowds or loud music. Kids, in particular, appreciate sailing free in the afternoon, and many reviews mention how much they enjoyed spotting dolphins or helping with sails.

For those interested in sailing vessels or historic ships, the replica America schooner offers both a visual treat and a story to tell. It’s also suitable for travelers looking for a value-packed experience—a good mix of scenery, wildlife, drinks, and expert crew service.

The Sum Up

This Key West day sail offers a splendid mix of history, scenery, and relaxation. With its beautifully crafted replica schooner, knowledgeable crew, and scenic landmarks, it provides a calming yet engaging water adventure. The inclusion of two drinks, small group setting, and opportunities for wildlife sightings make it a well-rounded experience that stands above typical boat rides.

If you love being on the water, enjoy picturesque coastlines, or want to learn a bit about sailing history, this tour will serve you well. It’s especially suited for those who appreciate a laid-back atmosphere and authentic sailing charm. Whether celebrating a special occasion or simply seeking a peaceful escape, this cruise delivers a memorable Key West moment.

Frequently Asked Questions

How long is the tour?
The cruise lasts approximately 1 hour and 30 minutes, providing ample time to relax, take photos, and enjoy the scenery without feeling rushed.

Where does the tour start?
It departs from 202 William St., Key West, FL, with check-in recommended 15-30 minutes before the scheduled departure.

Are kids allowed?
Yes, kids sail free on the afternoon departures, but every attendee must have a ticket, so plan accordingly.

What’s included in the ticket price?
Your ticket includes a 1.5-hour coastal sailing, two alcoholic drinks (for those 21 and over), and complimentary soda and water.

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

What if the weather is bad?
The tour operates in most weather conditions, but if safety is a concern, it may be canceled or rescheduled. You’ll be notified and offered a different date or a full refund.

Do I need to bring anything special?
Dressing in weather-appropriate clothing, sun protection, and sunglasses is advised. The boat is open-air, which makes the weather a key consideration.

Whether you’re a sailing enthusiast or just want a peaceful way to see Key West from the water, this America 2.0 cruise combines history, scenery, and relaxation into one charming outing. We found it to be a memorable highlight of any trip to the Keys—an experience that feels authentic, enjoyable, and beautifully simple.