Best results for Sailing

Learn boat handling and docking in a 3–6 hour lesson for 1–2 people

Learn boat handling on your own boat with an instructor who comes to you

Sail Boston Harbor and enjoy freshly shucked oysters onboard

Sail into the Cocoa Beach sunset on a private 2-hour catamaran cruise

Sail a Cocoa Beach sunset cruise with chances to spot dolphins and manatees

Sail the Indian River Lagoon on a private catamaran and watch for dolphins

Private 3-hour catamaran sail with a spoil island swim stop

A private sail for proposals, photos, and a champagne toast

A quiet private weeknight sail with Chicago skyline views

Charter a private historic schooner sail with drinks and snacks included

Sail a historic schooner, snorkel and kayak, then cruise into the Key West sunset

Private 2-hour sunset sail for up to 30, with wine, beer, and hors d'oeuvres included

Sail to a Key West sandbar with snorkeling, snacks, and sunset views

Sail with a licensed captain for a proposal or anniversary cruise

Sail Frenchman Bay for sea views of Acadia National Park

Sail at sunset with live folk music on the Margaret Todd

Sail into Destin Harbor for a private sunset and fireworks view

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

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

Cruise Waikiki toward Diamond Head with drinks and snacks included

Sail Ko Olina at sunset with live Hawaiian music and an open bar

Sail Ko Olina at sunset, then head ashore for a Kaula Luau

Sail Cape Cod Bay on the historic Schooner Hindu

Charter a private sail in Provincetown for up to 34 guests