Best results for Sailing

Savor Gulf Coast views on a quiet private sail with licensed crew and complimentary water and sodas

Build a custom itinerary with a USCG licensed captain for up to six guests

Sail a private 2-hour charter past St. Augustine's historic waterfront with USCG-licensed captains

Glide along the Kona Coast on a 1.5-hour sailing catamaran with drinks and coastal views

Learn essential sailing skills in a personalized session guided by a USCG-certified captain.

Set your own Ko Olina itinerary with snorkeling, sailing, and hosted bar, guided by a certified crew

Savor a curated tasting menu and drinks while sailing past Diamond Head at sunset.

Sail Key West's clear waters, kayak mangrove islands, snorkel vibrant reefs, and refuel with a buffet lunch—all in one day.

Sail past Key West landmarks on a 105-ft schooner while enjoying complimentary soft drinks and expert crew narration.

Watch Hilton Head's vibrant sunset while relaxing or helping crew aboard the historic Stars & Stripes

Sail the serene Lowcountry waterways aboard a 35' catamaran with champagne and space for up to six guests.

Enjoy a swim-optional sunset sail along the Waikiki coastline with inside and outside seating

See Oahu’s top sights by van, then sail at sunset on a Polynesian canoe

See wild dolphins, snorkel with turtles, and enjoy lunch on a 3-hour West Oahu sail

Sail a catamaran off Diamond Head and snorkel with tropical marine life

Sail Waikiki’s coast on a 1-hour BYOB cruise with Diamond Head views

Sail Maalaea Bay with snorkel stops, guided in-water tour, and meals included

Sail a well-equipped 30-foot cruiser and explore the bay at your own pace

Watch Waikiki's fireworks from a 55ft catamaran with inside seating and ocean views

See the Statue of Liberty and skyline under sail from Chelsea Piers, with one complimentary drink

Sail past NYC icons at sunset aboard an 80-foot schooner with a complimentary drink

Sail Margaritaville Bay with an experienced Hobie Cat captain—learn to sail or relax on a 30–60 minute ride

Sail calm waters to spot dolphins and catch a Gulf sunset

Choose where to explore on a private, captain-led sail for up to 6 guests