most romantic sailing experience in the Florida Keys

Schooner Champagne Sunset Sailโ€”Key West’s Premier Cruise

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Now Starting At

$109.95

If It’s Not Unforgettable, It’s On Us. Backed by the Sebago Satisfaction Guarantee. If It’s Not Unforgettable, It’s On Us.

Your time in Key West should be nothing short of incredible, and we’re committed to making sure it is. If your overall experience doesn’t meet your expectations, we’ll make it right by refunding up to 100% of your ticket price or rebooking you on another Sebago Watersports adventure at no additional cost.

Because every day on the water is unique, experiences may vary slightly due to weather conditions, seasonal menu updates, marine life sightings, or other factors that help us prioritize guest safety and comfort. These natural variations are part of the adventure and may not qualify for reimbursement.

When you sail with Sebago Watersports, you can book with confidence knowing your experience is backed by a team that stands behind every trip.

Please note that minor variations may occur due to factors beyond our control, such as weather conditions, updates to food and beverage offerings, or operational considerations. These adjustments are made with your safety and comfort in mind.

genuine schooner experience unlike any other in Key West

What to Expect

Boarding

15 minutes before departure for your Key West sunset cruise

Departure

Sail from Key West harbor aboard our historic schooner

Scenic Route

Pass Mallory Squareโ€™s Sunset Celebration and local landmarks

Golden Hour

Prime sunset Key West viewing with champagne service

Hors dโ€™oeuvres Service

Chefโ€™s selection, including cocktail shrimp

Return Journey

Romantic sail back to the harbor under twilight skies

Note: Spring and fall departure times vary based on sunset schedule

What’s Included

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Historic schooner sailing aboard The Appledore Star

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Premium beverage service featuring our floating schooner bar with:
  • Champagne and boutique wines
  • Premium beer and signature cocktails
  • Sangria and soft drinks
  • Filtered water
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Gourmet hors dโ€™oeuvres, including chefโ€™s selections and cocktail shrimp

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Professional crew with expert knowledge of schooner sailing

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Scenic sunset cruise past Key Westโ€™s most famous landmarks

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Intimate atmosphere with a maximum of 22 passengers


What To Bring
  • Valid government-issued photo ID (required for alcoholic beverages)
  • Hat and sunglasses for sun protection
  • Camera to capture your sunset Key West memories
  • Light jacket for evening breeze
Important Notes
  • Non-smoking tour for all guestsโ€™ comfort
  • Boarding begins 30 minutes before departure
  • Seasonal schedules vary with sunset times
  • Age policy welcomes all ages for this family-friendly experience
  • Weather dependent โ€“ tours subject to sea conditions
  • Florida sales tax is not included in the listed prices

Now Starting At

$109.95

Check Availability

Backed by the Sebago Satisfaction Guarantee.

Now Starting At

$109.95

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Couple in hats gazes at ocean from boat, tiki surfboard decor on wall.

Hula Hank's Tiki Sunset Cruise

As the sun begins its descent, a 53-foot tiki boat carries you across calm waters. Sip on beers, wine, soda and wine-based frozen cocktails from our open bar while vibrant hues paint the evening sky. Enjoy the serene ambiance of this sunset cruise as you take in panoramic views of the glowing horizon.

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Key West Sunset Sailing Aboard the Windjammer

On a wooden schooner, watch the sun dip below the horizon. The two-masted vessel glides past historic sites as you savor hors d'oeuvres and sip champagne or premium beer. Join in hoisting the sails for an authentic sailing experience.

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Frequently Asked Questions

What makes this one of the best things to do in Key West?

Our Key West sunset cruise aboard The Appledore Star combines multiple magical elements: authentic schooner sailing, premium champagne service, gourmet food, and front-row seats to Key Westโ€™s world-famous sunset.

How does your schooner compare to other Key West excursions?

The Appledore Star is a genuine 2-masted schooner, not just a motorboat with sails. This authentic tall-ship experience sets us apart from other Key West excursions. Our schooner offers the romance and elegance of traditional sailing, combined with modern luxury amenities.

What drinks and food are available during the sunset sail in Key West?

Our floating schooner bar rivals any land-based establishment with a full selection of premium beverages. Think of our schooner bar menu as including champagne, boutique wines, craft beer, signature cocktails, sangria, and non-alcoholic options.

When is the best time to book this Key West sunset cruise?

Our Key West sunset cruise is popular year-round, but booking in advance is especially important during peak season (December-April). Departure times change seasonally to align with sunset Key West timing โ€“ weโ€™ll provide exact times upon booking.

Is schooner sailing suitable for people who get seasick?

Schooners like The Appledore Star are among the most stable sailing vessels due to their traditional design and dual-mast configuration. The gentle motion of a schooner sailing is typically much smoother than motorboats. Key Westโ€™s protected waters during sunset hours are usually calm.