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Key West Schooner Sail with Wine

Sail into the sunset on a historic schooner in Key West, enjoying boutique wines and breathtaking views. Join a small group for an intimate, memorable voyage.

Key West
2 hrs 30 min
4.67Rating:
Last updated: August 28, 2025

Provider Score Distribution

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

Platform Scores

GYG logo
5.00
1214 reviews
Viator logo
4.66
141 reviews

Important Information

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

Experience the charm of Key West with a sailing adventure on the historic schooner 'When and If'. Built for General Patton, this yacht offers a unique blend of history and leisure. As you sail into the sunset, enjoy the unspoiled views and blue waters of the Keys' Atlantic coast. Whether you choose to help raise the sails or simply relax with a glass of boutique wine, this intimate voyage promises unforgettable memories. With a professional captain and crew, you'll be part of a small group, ensuring a personalized experience. Don't miss this chance to sail on a piece of history and enjoy the beauty of Key West. Book your spot today for an evening of adventure and relaxation.

Pros

  • Sail into the sunset on a historic schooner
  • Help raise the sails or relax and enjoy the view
  • Sip boutique wines and select beers
  • Experience blue water sailing off the Keys
  • Join a small group for an intimate voyage

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, boutique wines, champagne upgrade available
  • Use of snorkeling equipment

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, there is a restroom down a steep 7' ladder with firm handholds.

  • Can I Bring My Camera?

    Yes, cameras are welcome to capture the scenic views.

  • Is Smoking Allowed?

    No, smoking is not allowed on the schooner.

  • What Is the Maximum Weight Limit?

    The tour is not suitable for individuals over 350 lbs (159 kg).

$69.95-$71.32
4.67Rating:

Tour Highlights

  • Sail into the sunset on a historic schooner
  • Help raise the sails or relax and enjoy the view
  • Sip boutique wines and select beers
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