Sip wine as Key West’s skyline dissolves into color on this relaxed two-hour schooner cruise from Stock Island. Expect small-group service, hors d’oeuvres, and close-up views of mangroves, seabirds and evening dolphins.
More ways to explore the area's outdoor wonders
The schooner slows as the sun slides toward the Gulf horizon, varnished timbers humming underfoot and a warm breeze cutting across the deck. Guests lean on the rail with a glass in hand while Key West’s skyline softens to silhouette; the water seems to urge you westward, carrying the day with it.
Difficulty
easy
Duration
2 hours
Fitness Level
Suitable for most fitness levels; requires basic mobility for boarding and moving around a small schooner.
Wildlife
History
Key West and Stock Island grew from coral-cay geology and a maritime economy of wrecking, salvage and fisheries; the area blends Bahamian and Cuban cultural influences that shaped local music, food and boatbuilding.
Conservation
The Florida Keys’ shallow reefs and seagrass beds are fragile—avoid touching marine life, dispose of trash properly and choose tours that follow local reef-friendly practices.
Reserve your spot on the 2-Hour Sunset Sailing With Wine In Stock Island today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Arrive early for boarding
Check in 30 minutes before departure at Perry Hotel & Marina; arriving early eases parking and boarding logistics.
Bring motion-sickness meds if needed
Conditions are usually calm but the bays can roll; take prevention an hour before departure if you’re sensitive.
Wear non-marking, closed-toe shoes
Decks can be slippery; flat-soled, non-marking shoes improve stability and protect feet.
Carry photo ID for alcohol service
The cruise serves wine and beer and enforces an age minimum of 13 or older — bring ID for any drinking passengers.
Light windbreaker
Evenings on the water can be cool and breezy—layering keeps you comfortable.
spring
Sunscreen & sunglasses
Sun reflects off the water; high-SPF sunscreen and polarized sunglasses protect skin and eyes.
summer
Non-marking deck shoes
Provide traction on wet surfaces and protect the vessel’s finish.
Motion-sickness remedy
Helpful for anyone prone to seasickness, even on usually calm Gulf waters.