Best results for Sailing

Sail Waikīkī’s Gold Coast at sunset with optional swim time

Reserve a private 2-hour sunset sail for up to 6 guests

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 Lake Michigan on a private weeknight cruise with sunset and skyline views

Learn basic coastal cruising skills in a 2-day sailing class

Review and refresh your ASA 111 sailing skills in a 3-hour class

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 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

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

Private Waikiki afternoon catamaran sail with Diamond Head views and beach boarding

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

Sail to see the Blue Angels practice from the water (up to 6 guests)

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

Sail the Delaware River and hear Philadelphia waterfront history from your guide

Sail past NYC’s lit-up skyline on the Clipper City at night

Introduce your toddler to sailing with a 1-hour instructor-led lesson

Private sunset sail for up to 4 on Narragansett Bay

Sail at sunset on a classic schooner with cocktails or mocktails

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

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