Key West: Classic Schooner Sail With Boutique Wines

The classic schooner sail in Key West offers a unique opportunity to step back in time and experience the maritime history of the region. Aboard the historic yacht When and If, guests can enjoy the stunning Atlantic views while enjoying boutique wines and even lending a hand to raise the sails. This 2-hour adventure provides a captivating blend of scenic beauty, nautical traditions, and a chance to connect with the yacht’s storied past. Whether you’re a seasoned sailor or simply seeking a memorable outing, this sailing excursion promises to leave a lasting impression.

Key Points

• Set out on a 2-hour classic schooner sail aboard the historic yacht When and If, offering opportunities to assist in sailing activities and take in scenic coastal views.
• The sailing experience is part of a fundraising effort to preserve the yacht’s legacy, departing from Key West’s Perry Marina.
• Prices start from $80.62 per person, with no upfront payment required and free cancellation available up to 24 hours in advance.
• Guests can actively participate in sailing maneuvers under the guidance of knowledgeable crew, allowing for both active involvement and relaxation.
• The sailing activity is not suitable for wheelchair users or individuals over 350 lbs, and comfortable, weather-appropriate clothing and non-marking shoes are recommended.

You can check availability for your dates here:

Experience Overview

Offering a unique opportunity to experience the Keys’ maritime heritage, this classic schooner sail provides guests with a 2-hour journey aboard the historic yacht When and If.

Accommodating up to 28 guests, the intimate experience allows participants to assist in raising the sails, take a turn at the helm, or simply relax and enjoy the unspoiled views of the Atlantic coast.

Built for General George S. Patton, the schooner is part of a fundraising effort to preserve its legacy.

Departing from Key West’s Perry Marina, the sail showcases the area’s natural beauty and rich nautical history.

Booking Information

The experience can be booked for prices starting from $80.62 per person.

Prices for the experience start from $80.62 per person.

No upfront payment is required, as guests can reserve their spot and pay later.

Plus, free cancellation is available up to 24 hours in advance for a full refund.

The meeting point for the sail is the dockside at Perry Marina dock H16, in front of Bad Boy Taqueria.

Guests are advised to arrive 15 minutes before the scheduled departure time.

While crew gratuity isn’t included, it’s appreciated.

• Reservation: Reserve now & pay later

• Cancellation: Free cancellation up to 24 hours in advance

• Meeting Point: Perry Marina dock H16, in front of Bad Boy Taqueria

• Arrival: 15 minutes before scheduled departure

Sailing Activities

As guests set sail on the historic schooner yacht, they’ll have the opportunity to actively participate in the sailing experience.

Guests can help raise the sails, take a turn at the helm, and enjoy the maritime heritage. The knowledgeable crew will guide them through the sailing maneuvers, allowing for an interactive and educational adventure.

Whether seeking an active role or a more relaxed experience, guests can soak in the unspoiled views and blue water sailing off the Keys’ Atlantic coast.

This intimate sailing trip offers a chance to connect with the yacht’s fascinating history.

Picturesque Views

Guests aboard the historic schooner yacht When and If can enjoy the breathtaking vistas of Key West’s Atlantic coast.

The 2-hour sailing experience offers:

• Unspoiled, panoramic views of the blue, open waters

• A chance to spot native wildlife like dolphins, sea turtles, and seabirds

• Unparalleled views of the sun setting over the horizon

• The opportunity to sail along the island’s picturesque shoreline

With the keys’ natural beauty as the backdrop, this sailing excursion provides a truly memorable way to experience the region’s stunning coastal scenery.

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Historical Significance

Though built in 1936, the historic schooner yacht When and If has an intriguing backstory. It was originally commissioned by General George S. Patton, who was fascinated by sailing.

The yacht was later used as a fundraising tool to preserve the vessel and its legacy. Guests aboard the classic schooner can appreciate its historical significance, having been part of Patton’s life and now serving as a symbol of Key West’s maritime heritage.

This unique sailing experience allows visitors to connect with the yacht’s storied past while enjoying the scenic views off the Keys’ Atlantic coast.

Onboard Amenities

The schooner yacht offers a variety of onboard amenities to enhance the sailing experience. Complimentary beverages include a selection of beer, boutique wines, and soft drinks, ensuring guests can unwind and enjoy the journey.

Comfortable seating is available throughout the vessel, with cushioned benches, cabin houses, and a roomy cockpit, allowing visitors to relax and take in the stunning views. Onboard restrooms are accessible via a steep ladder, providing necessary facilities during the excursion.

Plus, the professional crew is on hand to ensure a safe and memorable experience for all guests.

Important Considerations

While the classic schooner sail offers a unique and enjoyable experience, there are a few important considerations guests should be aware of.

The activity isn’t suitable for wheelchair users or individuals over 350 lbs. Guests should wear comfortable, weather-appropriate clothing and non-marking shoes, as smoking and high heels are prohibited.

It’s essential to check weather conditions and arrive 15 minutes before departure. Although crew gratuity isn’t included, it’s appreciated.

Finally, guests should be prepared to access the restrooms via a steep ladder onboard.

Meeting Point and Directions

Guests can find the meeting point at the Perry Marina dock H16, in front of Bad Boy Taqueria. This convenient location provides easy access to the historic schooner yacht, When and If.

To arrive at the meeting point:

• Head to the Perry Marina on Key West’s Atlantic side

• Look for dock H16, which is clearly marked

• The yacht will be docked directly in front of the Bad Boy Taqueria

• Arrive approximately 15 minutes prior to the scheduled departure time

Remember to wear comfortable, weather-appropriate attire and non-marking shoes for the classic schooner sailing experience.

Frequently Asked Questions

Are Children Allowed on the Schooner Sail?

Yes, children are allowed on the schooner sail. The activity has a capacity of up to 28 guests, and there are no age restrictions mentioned in the details provided.

Can I Bring My Own Alcoholic Beverages Onboard?

No, guests cannot bring their own alcoholic beverages onboard. The tour provides complimentary beer, boutique wines, and soft drinks as part of the experience. Bringing outside alcohol is not allowed.

Is There a Dress Code for the Sailing Experience?

The sailing experience doesn’t have a strict dress code, but passengers should wear comfortable, weather-appropriate clothing and avoid high heels. Non-marking shoes are required to protect the yacht’s surfaces.

Can I Disembark at Any Point During the Cruise?

No, guests can’t disembark at any point during the cruise. The sailing experience lasts 2 hours, and passengers are expected to remain onboard for the full duration of the tour.

How Much Gratuity Should I Tip the Crew?

The crew gratuity is not included, but it’s customary to tip 15-20% of the total tour cost to show appreciation for their service and expertise in providing a memorable sailing experience.

The Sum Up

This classic schooner sail in Key West offers a unique opportunity to experience the area’s maritime history and stunning coastal views. Guests can assist in raising the sails or simply relax with a glass of boutique wine. Departing from Perry Marina, this 2-hour journey aboard the historic yacht When and If provides an intimate and memorable way to connect with the yacht’s legacy.

You can check availability for your dates here: