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Key West Schooner Sail with Boutique Wines 2 hr

Sail Key West's waters on a historic schooner with boutique wines and breathtaking views. Enjoy a 2-hour sunset cruise with a professional crew.

Key West
2 hrs 30 min
4.19Rating:
2 providers combinedLast updated: March 29, 2026

Provider Score Distribution

Cumulative distribution showing how many tours score at or below each rating on each provider platform in Key West.

Provider Scores

Viator logo
4.67
150 reviews
GYG logo
1.00
1 review

Important Information

  • Check weather conditions before your trip
  • Arrive 15 minutes before departure time
  • Wear non-marking shoes or be prepared to take them off
  • Minimum drinking age is 21 years
  • Children must be accompanied by an adult

Embark on a captivating 2-hour schooner sail in Key West aboard the historic yacht 'When and If'. This intimate experience allows you to help raise the sails, take the helm, or simply relax as you glide across the blue waters of the Keys' Atlantic coast. With a professional captain and crew, you'll enjoy boutique wines and select beers while taking in the unspoiled views. The schooner, originally built for General Patton, offers a unique glimpse into maritime history. Join us for an unforgettable sunset sail and be part of the story of this legendary vessel. Book now to secure your spot on this enchanting journey.

Pros

  • Sail into the sunset on a historic schooner
  • Help raise the sails or relax and enjoy the view
  • Admire unspoiled views off the Keys' coast
  • Sip boutique wines and select beers
  • Experience a piece of maritime history

Includes

  • Sailing experience on the historic yacht 'When and If'
  • Opportunity to help raise sail and take a turn at the helm
  • Professional captain and crew
  • Select beers and boutique wines
  • Champagne upgrade available

Excludes

  • Crew gratuity
  • Ship's merchandise

FAQ

  • What Should I Wear?

    Wear comfortable, weather-appropriate clothing and non-marking shoes.

  • Is There a Restroom Onboard?

    Yes, restrooms are available down a steep ladder with handholds.

  • Can I Bring My Camera?

    Yes, cameras are welcome for capturing the beautiful scenery.

  • Is Smoking Allowed?

    No, smoking is not permitted on the schooner.

  • Are Wheelchairs Accessible?

    Unfortunately, the schooner is not wheelchair accessible.

$59.45-$80.62
4.19Rating:

Tour Highlights

  • Sail into the sunset on a historic schooner
  • Help raise the sails or relax and enjoy the view
  • Admire unspoiled views off the Keys' coast
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