Key West: Classic Schooner Sail With Boutique Wines

Discover the Charm of the Key West Schooner Experience

The Key West: Classic Schooner Sail With Boutique Wines offers a distinctive way to enjoy the island’s Atlantic coast. Priced at $81 per person for a 2-hour voyage, this tour stands out for its intimate setting aboard the historic schooner ‘When and If’, built for General George S. Patton. The tour departs from Dock H16 at Perry Marina, providing a peaceful escape with cushioned seating, onboard restrooms, and a friendly crew. Its small group size—up to 28 guests—ensures personalized attention and plenty of opportunities to participate in sailing activities or simply relax.

This experience is ideal for those seeking a relaxed, scenic water adventure that combines sailing, history, and wine. The uncrowded nature of the tour means guests can enjoy a peaceful sunset without large crowds, making it a perfect choice for couples or small groups. Its interactive elements, like helping raise the sail or taking a turn at the helm, add a fun, hands-on touch to the experience. Keep in mind that the tour is not suitable for wheelchair users or individuals over 350 lbs, and no smoking is allowed onboard.

You can check availability for your dates here:

Key Points

• Duration: 2 hours, with boarding starting 15 minutes prior to departure
• Location: Dock H16 at Perry Marina, in front of Bad Boy Taqueria
• Price: $81 per person, includes boutique wine, beer, or soft drinks
• Activities: Help raise the sail, take a turn at the helm, or relax on cushioned benches
• Highlights: Historic schooner ‘When and If’, blue water sailing off the Atlantic coast, intimate group size, excellent photo opportunities
• Additional info: Restrooms onboard, free parking, and a chance to be part of preserving a famous vessel

The Historic ‘When and If’ Schooner and Its Unique Story

The ‘When and If’ schooner is more than just a vessel; it’s a piece of history. Built as General Patton’s personal yacht, it represents a peacetime dream of a renowned American military leader. Now open to the public, this yacht is maintained in excellent condition through ongoing fundraising efforts. Being onboard offers a chance to connect with maritime history while enjoying a blue water sailing experience.

The schooner’s 80-foot length and custom design contribute to a stable, comfortable ride. Its two masts, traditional rigging, and classic schooner features create an authentic sailing environment. The crew’s professional guidance makes it easy for guests to participate actively or to sit back and soak in the scenery.

Practical Details for a Smooth Sailing Experience

The meeting point at Perry Marina dock H16 is easy to find, with parking available free of charge on-site. Guests are advised to arrive 15 minutes before departure to allow for check-in and boarding. It’s recommended to wear comfortable, weather-appropriate clothing and non-marking shoes—high heels are discouraged—to protect the deck surface. Bringing a camera is encouraged for capturing the stunning sunset views.

The tour operates primarily in the afternoon and evening hours, with flexible booking options that allow for free cancellation up to 24 hours before the scheduled trip. Payment is done later, offering the flexibility to secure a spot without immediate commitment.

The Sailing Experience on the ‘When and If’

Sailing on the ‘When and If’ schooner is a chance to feel the wind and harness the power of nature. The crew actively involves guests in raising the sails and offers turns at the helm—an engaging way to learn about traditional sailing techniques. Many enjoy the serene atmosphere and unspoiled water views as the boat drifts along the Atlantic coast of the Keys.

The 2-hour duration balances enough time to relax and enjoy the scenery without feeling rushed. The interactivity enhances the experience, making it suitable for those interested in learning about sailing or simply unwinding in a peaceful environment.

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Wine, Beer, and Soft Drinks to Enjoy Aboard

A key feature of this tour is the opportunity to sip boutique wines, beers, or soft drinks while watching the sunset. The complimentary beverages are served onboard, and an upgraded champagne option is also available. These drinks complement the beautiful water views and create a relaxed, celebratory vibe.

Guests should note that crew gratuity and merchandise are not included but are appreciated. The onboard schooner apparel may be available for purchase, adding a souvenir to remember the trip.

What Makes This Tour Stand Out Among Water Cruises?

Unlike typical large cruise options, this private-style sailing offers an uncrowded environment with personalized interaction. The small vessel size ensures guests are close to the action, whether helping with the sails or simply enjoying the scenic panoramas.

This tour’s focus on history, sailing, and relaxation sets it apart from other water activities around Key West. The professional captain and crew provide expert guidance, ensuring a safe and informative journey. It’s especially appealing for history enthusiasts or anyone wanting a peaceful sunset cruise with a touch of tradition.

Accessibility and Practical Considerations

While the tour is suitable for most, it is not accessible for wheelchair users or individuals over 350 pounds. The restrooms onboard are accessible but require navigating a 7-foot steep ladder with firm handholds—guests should be prepared for this aspect of the vessel’s design. Weather conditions can influence the trip, so checking the forecast before booking is advisable.

Guests are encouraged to bring comfortable clothes and weather-appropriate attire. Since smoking is not allowed onboard, those who wish to relax with a drink can do so in a responsible manner—the beverages included enhance the enjoyment without excess.

Who Will Love This Sunset Sail?

This intimate sailing experience appeals most to those interested in history, traditional sailing, and serene water views. It’s perfect for couples seeking a romantic sunset, small groups of friends, or solo travelers wanting a peaceful escape. The participatory elements make it ideal for those curious about sailing techniques or simply looking to relax in a beautiful setting.

It’s less suitable for travelers requiring full wheelchair access or with significant mobility restrictions, but the beautiful, quiet waters and historic vessel make it a memorable experience for most.

Key Benefits and Considerations for Booking

The value of this tour lies in its combination of history, sailing, and scenic views, all in an intimate group setting. The included boutique wines, beers, and soft drinks add a special touch, making it a relaxing, enjoyable outing. The lack of large crowds and personalized experience are significant advantages.

However, guests should remember that crew gratuity and merchandise are not included. The timing in the afternoon or evening provides flexibility for different schedules, but weather conditions can influence the trip, so staying flexible is wise.

Frequently Asked Questions

Is this tour suitable for children?
The tour requires climbing a 7-foot ladder to access the restrooms, and physical activity is involved. It’s best suited for adults and older children comfortable with these aspects.

Can I help raise the sails during the cruise?
Yes, the crew invites guests to help raise the sails and offers turns at the helm for those interested in participating.

What beverages are included?
Guests receive complimentary boutique wines, beers, or soft drinks. An upgrade to champagne is available for purchase.

Where exactly do we meet for boarding?
The meeting point is at Dock H16 at Perry Marina, in front of the Bad Boy Taqueria. Look for the large black schooner with two wooden masts.

How long is the tour and what is the pacing?
The 2-hour cruise typically runs in the afternoon or evening with a relaxed pace, allowing plenty of time to enjoy the sunset and water views.

Is parking easy to find near Perry Marina?
Yes, free parking is available on-site at Perry Marina, making access simple and straightforward.

Can I cancel the booking?
Yes, full refunds are available for cancellations made up to 24 hours before the scheduled trip, offering flexibility in planning.

Does the tour operate in bad weather?
The tour depends on weather conditions; if the weather is unsuitable, the trip may be canceled or rescheduled for safety.

Are there any additional costs I should be aware of?
Beyond the ticket price, crew gratuity and merchandise are not included but are appreciated.

Is this tour good for history enthusiasts?
Absolutely. The schooner ‘When and If’ has a rich history connected to General Patton, enriching the sailing experience with historical significance.

You can check availability for your dates here: More Great Tours Nearby