Best results for Sailing

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

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)

Sail out for close-up views of Honolulu’s Friday night fireworks

Sail Provincetown Harbor and Cape Cod Bay on a private 6-hour charter

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

Sail the Nauti-Cat on a 1.5-hour kids cruise in Traverse City

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

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

Train to sail a 30-foot keelboat in a 3–4 day course (max 4 students)

Learn coastal cruising skills in a 3-day ASA 103 course, capped at 4 students

Learn the basics of keelboat sailing in a 2-day ASA course on San Diego Bay

Build catamaran handling skills in a 2-day ASA 114 course

Practice sailing skills on Capri 22s with a certified captain (2 hours)

Sail St. Augustine and swap book club notes over tea

Practice coastal navigation theory in a four-day ASA course

Train to skipper a 30–50 ft sailboat on a 4-day ASA 106 course

Join a women’s sailing race team and practice on Zephyr

Charter the 60-foot Oyster Sloop CHRISTEEN for a private cruise

Sail Grand Traverse Bay and enjoy Moomers ice cream on a 2-hour fall cruise