Best results for Sailing

Book two separate trips: an Alcatraz visit plus a Bay sail on Adventure Cat

Customize a private sail with a USCG-licensed captain for up to 6 guests

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

Sail Casco Bay at sunset with live music and a BYOB vibe

Sail Cape Cod Bay on a family-friendly cruise where you can help raise sails and bring a picnic aboard

Spend two days exploring charming North Shore towns with a private sunset sail and landmark stops

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

Cruise Lake Tahoe at sunset with live local music

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

Build advanced sailing skills in a 5-day Flying Scot course for ages 8–15

Sail a Catalina 34 and build practical skills in 2.5 hours

Get hands-on sailing practice in New York Harbor on a Catalina 34

Sail Boston Harbor and enjoy freshly shucked oysters onboard

Sail Boston Harbor on a 1.5-hour schooner cruise from Rowes Wharf

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

Sail Cape Cod Bay at sunset on a bring your own food and drinks cruise

Sail a restored 1925 schooner at sunset with drinks and charcuterie

Charter a private sail in Provincetown for up to 34 guests

Charter a sailboat in Key West for up to 42 guests

Sail the historic Cutter Bloodhound during the Sail Boston 2026 Festival

Sail Boston during Sail Boston 2026 on the restored Schooner Hindu

Taste Truro Vineyards pours on a 2-hour schooner sail in Provincetown

1.5-hour private sunset sail with wine, beer, and non-alcoholic drinks

Watch Honolulu’s Friday-night fireworks from a private sail