Best results for Sailing

Enjoy sailing and dolphin sightseeing in paradise

Explore Kailua's reefs on a 3-hour traditional Hawaiian sailing canoe and hear local stories from expert watermen

Enjoy a two-hour self-guided sail aboard a stable Rhodes 19 from Jetties Sailing Center

Experience an unforgettable whale watching journey aboard the Ocean Spirit, Maui’s premier eco-friendly sailing catamaran.

Glide across Grapevine Lake on a guided 1-hour Hobie Cat sail with captain included.

Customize your private Waikiki charter for groups up to 40

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

Private Key West schooner charter with snorkeling, kayaking, drinks, and snacks

Sail the Nights of Lights with dessert and a festive drink

Sail into the sunset on an adults-only catamaran cruise with pupus and island-style music

Sail a Catalina 34 and build practical skills in 2.5 hours

Sail a restored 1925 schooner at sunset with drinks and charcuterie

Sail the historic Cutter Bloodhound during the Sail Boston 2026 Festival

Sail for 3 hours with up to 6 guests and a welcome cocktail or mocktail

Practice coastal navigation theory in a four-day ASA course

Train to skipper a 30–50 ft sailboat on a 4-day ASA 106 course

Sail Grand Traverse Bay and enjoy Moomers ice cream on a 2-hour fall cruise

Sip fine wines and craft beers on an intimate schooner sail as the sun sets off Key West’s coastline

Charter a private NYC sail for FIFA World Cup match day

Sail a private catamaran whale watch from Ma‘alaea Harbor with hydrophone listening

Sail at sunset with whale watching and pupu appetizers from Maʻalaea Harbor

Rent a kayak by the hour and paddle Hilton Head waterways

Paddle Skull Creek marshes and learn about Lowcountry tides and wildlife

Experience Acadia’s wildlife and scenery with an expert captain and a trip tailored to you