Set sail from Key West’s Historic Seaport for an intimate 2.5-hour catamaran cruise that pairs dolphin viewing with premium wines and tapas. Expect close dolphin encounters, skyline views of Sunset Key and Fort Zachary Taylor, and a curated culinary pairing while the sun drops into the Gulf.
More ways to explore the area's outdoor wonders
The afternoon light slants low over Key West’s Historic Seaport as you step aboard a luxury catamaran and the harbor breathes out behind you.
Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for most fitness levels; short standing or stair access during boarding and moving about the boat.
Wildlife
History
Key West’s seafaring past—wreck salvaging, sponging, and Cuban trade—shaped its harbor culture; Mallory Square’s sunset celebrations grew from that maritime energy.
Conservation
Operators follow guidelines to avoid harassing marine life—do not feed or approach dolphins, and support operators that report sightings and respect protected reef zones.
Reserve your spot on the Key West Sunset Sail: Dolphin Watching, Wine, and Tapas today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Arrive Early for Boarding
Check in at the Sebago office on Lazy Way Lane and arrive 30 minutes before departure to secure seating and complete check-in.
Bring ID for Alcohol
Premium wine, beer and champagne are included—bring government ID if you plan to drink.
Sun Protection and Layers
Late afternoons on the water are sunny yet breezy—sunscreen, sunglasses and a light windbreaker keep you comfortable.
Prepare for Motion
If you’re prone to seasickness, take medication beforehand and sit midship where motion is least noticeable.
Sunscreen (SPF 30+)
Protects against prolonged sun exposure on reflective water.
summer
Non-slip shoes
Stable footing on wet decks makes boarding and moving around safer.
Light windbreaker or sweater
Even warm evenings can be breezy on open water; layers trap heat without bulk.
spring
Motion-sickness medication or wristbands
Useful if you’re sensitive to boat motion during open-water portions.