Best results for Sailing

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

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

Savor island pupu dishes and open-bar drinks while cruising past Oahu’s coast on an intimate six-guest sunset sail.

Customize a 7-hour private sail in Maalaea Bay with guided snorkeling and flexible stops for your group of up to six

Sail at sunset with appetizers and beverages while spotting humpback whales