Best results for Sailing

Build team racing skills and strategy on Long Island Sound

Charter the Wind Dancer schooner for your group of up to 18

Private moonlight sail past the Manhattan skyline and Statue of Liberty

Sail Charleston Harbor at sunset with a fully crewed catamaran

Sail into sunset on a 2-hour Big Island catamaran cruise with drinks and snacks

Sip included drinks on a 2-hour sunset sail with a small 21+ group

Sail for 2 hours and watch fireworks from the water

Choose a morning or afternoon private sail for up to 5

Enjoy a private golden-hour voyage on a 69-foot luxury yacht with attentive crew and ocean views.

Spend 7 hours sailing, swimming, and grilling on a private trip for up to 6

Private 8-hour sailing expedition with hands-on instruction and a sunset return

Enjoy sailing and dolphin sightseeing in paradise

Snorkel pristine Kona-Kohala reefs on a sailing catamaran

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

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.

Sail longer and see more of Saco Bay on a half-day trip

Sail into the Key West sunset with drinks and hors d'oeuvres included

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