Best results for Sailing

Sail close to the water on an interactive harbor charter

Caribbean sunset catamaran sail with a full open bar

Sail into the evening with live saxophone and an open bar

Set sail privately with your group on Pleasant Bay

Take the helm of a forgiving catamaran for easy bay sailing

Sail Banderas Bay at sunset with snacks and an open bar

Unwind on an evening sail with drinks and skyline views

Learn sailing basics and take the helm on the Hudson River

Build your sailing skills with instruction tailored to your goals

Tailor a private sunset sail for your special occasion

See visiting schooners up close during Gloucester's Heritage Day celebration

Photograph visiting schooners as they arrive for Gloucester’s festival weekend

Sail the North Shore with a naturalist and seasonal whale listening

Private clothing-optional sailing with a licensed captain and crew

Private sailing with a captain, crew, paddle gear, and refreshments

Sail quiet Lowcountry waterways while looking for dolphins and Morgan Island monkeys

Take the helm with a private, customizable keelboat sailing lesson

Sail past Old San Juan landmarks with drinks and appetizers at sunset

Private river sailing with a waterfront tasting-room lunch stop

Sail, navigate, and anchor beside Cedar Island's sandy beach

Private sailing with room to relax or take the helm

A relaxed evening sail with sunset views on the Rappahannock River

Learn hands-on sailing skills aboard a private Chesapeake Bay charter

Sail Door County aboard a registered tall ship