Sailing

Sail past Manhattan’s night skyline on a private 1.5-hour charter

Pair a private sail with relaxed dining on the bay

Step ashore on quiet harbor islands while your captain waits

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

Sail into the evening with pupus, island-style music, and sunset views

Sail the Straits on a catamaran with time to relax, swim, and try stand-up paddleboarding

Sail into sunset views of Mackinac Island and the Mighty Mackinac Bridge

Take the helm of a Hobie sailboat on Pensacola Beach

Private captained sail on Calibogue Sound with room for your snacks and drinks

Sail Lake Erie in the evening and watch the sunset from the water

Sail Margaritaville Bay with a Hobie Cat captain in 30 or 60 minutes

Sail Lake Erie’s shores and islands, with time to anchor for a swim

Private sailing with onboard lunch, sunbathing space, and a covered bar area

Sail Boothbay Harbor aboard the Friendship Sloop Bay Lady on a 1.5-hour trip

Catch the bay breeze past New Bedford's working waterfront

Sail New Bedford Harbor and Buzzards Bay on a private charter

Sail close to the water on an interactive harbor charter

Tailor a hands-on sail to the skills you want to sharpen

Tailored one-on-one instruction for first sails, returning sailors, and J/22 certification prep

Sail Bahia Banderas with a private captain and coastal views

Sail Roanoke Sound aboard a 41-foot ketch with daytime and sunset departures

Sail Lake Michigan for sweeping views of Chicago’s skyline

See Chicago’s skyline from Lake Michigan on an evening sail

Watch Navy Pier fireworks from the water with Chicago skyline views