Is there a minimum age for this experience?

Yes, participants must be 21 or older to partake in the wine tasting during the sail.

Can I bring my own drinks or food onboard?

No outside beverages or food are allowed; all snacks and drinks are provided during the trip.

What is the dress code for this sail?

Guests are encouraged to dress comfortably and casually but may also dress up; just avoid high heels on the gangplank.

Is tipping included in the ticket price?

Tipping is not included but is customary; you can tip in cash, Venmo, or by adding it to your credit card payment.

Where exactly is the meeting point?

The meeting point is at the dock located at 0 Duval Street - Ocean Key Resort Marina (Sunset Pier), Key West.

How early should I arrive for boarding?

You should arrive at least 15 minutes before the scheduled departure time for check-in and a safety briefing.

Sunset Sail and Rosé Wine School in Key West: Sip, Learn, and Sail | Sailing | Boat Tour

Set sail into the warm Florida breeze aboard the Sunset Sail + Wine School with Cayo Provisions, an unforgettable combination of coastal adventure and refined taste located in vibrant Key West, Florida. This two-hour excursion invites travelers to experience the magic of the island’s skyline as the sun sets over the Gulf of Mexico, while diving deep into the world of rosé wine through a unique, onboard wine school.

The journey begins right at the Ocean Key Resort Marina on 0 Duval Street, a prime spot in Key West offering easy access to the best the island’s waterfront has to offer. As you board the sleek sailboat, you’ll find yourself quickly immersed in a sensory experience that balances laid-back island vibes with cultured exploration. The highlight is a dedicated hour-long wine class led by Cayo Provisions experts who guide you through five carefully curated expressions of rosé. You’ll learn both the history and science behind this increasingly popular style, gaining insights that elevate every sip.

Throughout the sail, palates remain engaged with six rounds of thoughtfully paired small bites that complement the subtle floral and fruity notes of the wines served. All tastings and snacks are covered in the ticket price, making this a seamless experience for wine lovers and novices alike. Once the wine school concludes, guests can continue to enjoy drinks available by request, mingle with fellow travelers, or simply soak in the stunning Key West seascape as the sun slips below the horizon.

What makes this sail especially unique is its effortless blend of education, relaxation, and local flavor, set against the backdrop of Key West’s renowned marine environment. Unlike typical wine tastings held in city cellar bars, this sailing creates an unparalleled sensory connection between the drink, the sea, and the skies. Whether you’re celebrating a special occasion or seeking an evening escape from the ordinary, this trip stands out as a sophisticated yet laid-back way to engage with a beloved regional drink.

Visitors are advised to arrive at least 15 minutes early for check-in and a safety briefing and to bring identification for alcohol consumption. Parking tips include using ride shares or taxis, as parking near Mallory Square can be limited. Dress comfortably with layers as temperatures may dip during the evening, though blankets are available on board. Tipping is customary and can be given via cash or Venmo.

For travelers staying in Key West, this experience offers a memorable way to combine the island’s marine beauty with its growing reputation as a wine destination—one sunset at a time.