Best results for Sailing

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 beach-boarded sail with Diamond Head Lighthouse views

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

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

Sail Boston Harbor with stories, skyline views, and complimentary pastries

Cruise Boston Harbor for views of the tall ships on a classic schooner

Sail Boston Harbor at sunset for views of the tall ships and skyline lights

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

Help your toddler build confidence on the water with an instructor-led sailing introduction

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

Two-hour quiet morning sail with coffee, tea, and a welcome cocktail or mocktail

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

Sip wine on a 90-minute Kennebunkport sail with a sommelier-led tasting

Sail Kennebunkport with options to relax or take the helm

Build practical keelboat sailing skills in a small-group course

Build coastal cruising skills through hands-on sailing and ASA certification testing

Practice coastal navigation skills on the water in Monterey

Celebrate your birthday with a private sail on San Diego Bay