Key West: Schooner Day Sail with Onboard Bar

Sailing in Key West offers a unique way to soak in the island’s iconic views, and the Schooner Day Sail aboard America 2.0 promises an experience that balances elegance, fun, and genuine local charm. This 1.5-hour cruise is perfect for those eager to see Key West from the water, with highlights including views of Fort Zachary Taylor, Mallory Square, and Sunset Pier, all while enjoying a well-maintained schooner with a knowledgeable crew.

What makes this tour stand out? We love how it combines classic sailing with casual luxury—comfortably padded benches, teak decks, and mahogany trimmings create a genuinely inviting atmosphere. Plus, the inclusion of two complimentary drinks for guests over 21 elevates the experience without adding extra cost. But it’s worth noting that at just 1.5 hours, this isn’t a long cruise, so those seeking a more extensive adventure might want to explore other options. Still, it’s a wonderful choice for families, couples, or anyone wanting a taste of the keys’ maritime charm in style.

This sail is best suited for those who appreciate scenic views, a relaxed vibe, and the chance to learn a bit about sailing from friendly, professional crew members. It’s also an excellent option for travelers looking for a reasonably priced activity that combines sightseeing and light refreshment, all aboard a beautiful vessel. Now let’s get into the details and see what makes this trip worth considering.

Key Points

• Elegant vessel: The America 2.0, built in 2011, offers a stunning, well-maintained setting with teak decks and mahogany accents.
• Ideal length: 1.5 hours is perfect for a quick yet memorable sail, with numerous photo opportunities.
• Scenic stops: You’ll pass iconic sights like Fort Zachary Taylor, Mallory Square, and Sunset Pier, with chances of spotting dolphins, sea turtles, and water birds.
• Inclusive drinks: Two free alcoholic drinks for guests 21+ enhance the relaxing vibe, along with soft drinks and water.
• Kids sail free: Children under 12 can join for free on all afternoon departures, making it family-friendly.
• Professional crew: The reviews highlight knowledgeable, friendly crew members—adding value to the experience.

An In-Depth Look at the Key West Schooner Experience

Setting Sail on the America 2.0

The America 2.0 is a gorgeous vessel, meticulously maintained and built in 2011. Its teak decks and mahogany trims give it a timeless, nautical feel that travelers will appreciate. With 3,600 square feet of sail, this schooner glides smoothly through the waters, offering stability and comfort—something sailors and casual cruisers alike will enjoy.

The boat’s size is ideal for a relaxed group, not overly crowded, but still lively enough that you can chat with fellow passengers or focus on the spectacular scenery. The padded bench seating invites you to relax and take in the views at your own pace, making it a good choice for families, couples, or solo travelers.

The Itinerary and Sights

The cruise begins at 202 William Street, right behind the Schooner Wharf Bar, a lively spot in the heart of Key West. After setting sail, the crew guides you past some of the most recognizable landmarks. You’ll see Fort Zachary Taylor, a historic military site with impressive coastal defenses, and the waters surrounding Sand Key Reef, known for its vibrant marine life.

As the schooner glides past Mallory Square and Sunset Pier, you’ll get a different perspective of these popular spots—more serene and scenic than bustling. The crew encourages guests to keep a lookout for dolphins, which are quite common in these waters, as well as sea turtles and various water birds.

The Crew and Service

One of the highlights, according to reviews, is the knowledgeable and courteous crew. Guests have praised the staff for answering questions and sharing sailing insights, making the trip both educational and enjoyable. Rae, Tom, and Jay—mentioned explicitly in reviews—are noted for their professionalism and friendly attitude.

Drinks and Refreshments

The included beverage package, featuring two alcoholic drinks for guests 21 and older, is a welcome addition. You might opt for a cold beer, a refreshing cocktail, or a wine, depending on your preference. Soft drinks and water are also available throughout the cruise, keeping everyone hydrated under the sun. Travelers are encouraged to bring their own picnic lunch if they wish, adding to the relaxed, picnic-style atmosphere.

Family-Friendly and Value

Kids under 12 sail free on all afternoon departures, which makes this experience even more appealing for families. You can select the appropriate tickets when booking, ensuring everyone in your party can enjoy the scenery together.

Priced at $73 per person, the cost is quite reasonable given the quality of the vessel, the scenic value, and the inclusive drinks. While this isn’t a full-day cruise, the 1.5-hour sail is a perfect snapshot of Key West’s maritime charm—ideal for those with limited time or a desire for a relaxed activity.

What to Bring and What Not to Expect

Guests should bring essentials like sunscreen, a hat, sunglasses, and a valid ID or passport. Since smoking isn’t allowed onboard, plan accordingly. The tour isn’t wheelchair accessible, so visitors with mobility concerns should consider this before booking.

The Overall Experience

From the consistent praise in reviews—highlighting the professional crew, beautiful boat, and value for money—it’s clear this sail strikes a good balance between quality and affordability. Comments from travelers like Hope, Marina, and Lynn emphasize how much they appreciated the crew’s expertise and the chance to learn about sailing firsthand.

Who Should Consider This Tour?

This sail is perfect for travelers who want a relaxing, scenic experience without committing to a lengthy cruise. It’s well-suited for families, couples, or solo visitors eager for a taste of maritime life in Key West. If you’re looking for a beautiful boat, knowledgeable crew, and good value, this tour offers all that in a compact, enjoyable package.

It’s also an excellent option for those who like a laid-back vibe, light drinks, and stunning water views. However, if you prefer more active water adventures like snorkeling or longer sailing trips, you might want to explore other options. This sail is about appreciating the scenery, enjoying the moment, and maybe catching a glimpse of dolphins.

Frequently Asked Questions

How long is the schooner sail?
The cruise lasts about 1.5 hours, making it a quick but memorable way to see Key West from the water.

What sights will I see during the cruise?
You’ll pass landmarks like Fort Zachary Taylor, Mallory Square, Sunset Pier, and Sand Key reef. The crew encourages guests to look out for marine life such as dolphins, sea turtles, and water birds.

Is there a drink package included?
Yes, for guests 21 and older, your ticket includes two alcoholic drinks. Soft drinks and water are also available on board.

Can children join the cruise?
Absolutely. Kids under 12 always sail free on all afternoon departures, so families can enjoy this scenic adventure together.

What should I bring?
Bring sunscreen, a hat, sunglasses, and your ID or passport. If you want to bring snacks, you can do so, but keep in mind that food isn’t included in the ticket price.

Is the tour accessible for everyone?
No, this tour is not wheelchair accessible. Be sure to plan accordingly if you have mobility concerns.

Where does the tour start and end?
The meeting point is at 202 William Street, Key West, directly behind the Schooner Wharf Bar. The activity ends at the same location.

Is gratuity included?
No, gratuity is not included and is at your discretion.

Final Thoughts

The Key West Schooner Day Sail aboard America 2.0 offers an attractive blend of style, comfort, and scenic beauty for a reasonable price. The beautiful vessel, professional crew, and stunning waterway views combine to create a memorable experience that captures the essence of sailing in the Florida Keys.

This tour excels at providing a relaxed, family-friendly atmosphere, with the bonus of complimentary drinks and light educational insights about sailing. If you’re seeking a quick, picturesque escape on the water, this cruise delivers genuine value and a taste of maritime elegance.

For travelers who prioritize authentic experiences and good service without a hefty price tag, this schooner sail ticks all the boxes. It’s best suited for those who want to enjoy Key West’s natural beauty from a comfortable, well-appointed boat, with plenty of opportunities for photos, dolphin sightings, and relaxing conversation with a friendly crew.

Whether you’re celebrating a special occasion or simply want a peaceful break from the busy streets of Key West, this cruise is a charming way to add a splash of nautical magic to your trip.

End of review.