signature windjammer classic sunset sail
Key West Sunset Sailing Aboard the Windjammer
Now Starting At
$79.95
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.
the ultimate Key West windjammer sailing experience
Start your evening with our signature windjammer classic sunset sail aboard a magnificent historic schooner! This amazing 2-hour windjammer sailing adventure combines authentic traditional sailing with breathtaking sunset views. Enjoy windjammer sunset sail aboard our classic vessel as you glide across pristine waters, then savor premium cocktails and light bites while watching the sun dip below the horizon in spectacular fashion.
Our sailing cruises offer an incomparably romantic experience aboard a beautifully restored schooner. Tall masts and billowing sails provide the perfect backdrop for Key West’s legendary sunsets. Whether you’re celebrating a special occasion or simply seeking an authentic adventure, our sailing cruises offer timeless charm and unforgettable memories.
What to Expect
Check In & Boarding
Arrive at the dock 30 minutes before departure to board our historic schooner. Enjoy a welcome cocktail as the crew prepares for departure.
Sunset Sail
Set sail into the Gulf of Mexico aboard our historic sailboat. Relax as the crew raises the sails and enjoy the peaceful experience of wind-powered cruising.
Premium Drinks & Refreshments
Sip unlimited cocktails, wine, beer, and other premium beverages throughout the sail while enjoying a selection of light refreshments.
Golden Hour Views
Take in panoramic views of Key West as the sun sets over the Gulf of Mexico. Your captain and crew will position the schooner for the best possible sunset viewing and photo opportunities.
Evening Return
As twilight settles over the water, enjoy a tranquil sail back to Key West under the evening sky before returning to the Key West port.
*Itineraries, destinations, and inclusions are subject to seasonal and weather-dependent availability.
What’s Included
Ultimate Sunset Experience – Sail to the best sunset viewing locations with unobstructed horizon views
Historic Windjammer Schooner – Cruise aboard an authentic traditional sailing vessel with classic charm
Premium Beverage Service – Unlimited cocktails, wine, beer, and soft drinks throughout the sail
Light Refreshments – Carefully selected appetizers and snacks to complement your evening cruise
Professional Crew – Expert captain and sailors sharing maritime knowledge and hospitality
- Light jacket or sweater for evening breezes
- Camera for sunset and sailing photos
- Swimsuit (optional)
- Sunglasses
- Comfortable non-slip shoes
- Valid, government-issued photo ID (for alcoholic beverages)
- Boarding starts 30 minutes before departure time
- Please bring a valid, government-issued photo ID
- All prices do not include Florida sales tax
- Weather conditions may affect departure times
- Departure location: Key West Harbor
Now Starting At
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