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San Juan Islands Sailing Charters and Cruises
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We provide yacht and crew. You relax and enjoy.
The Art of Slow Travel
Something special happens when we cast off the dock lines and head out into the San Juan Islands on a sailing charter. We become aware of the rhythm of the tides, the wind filling the sails, the salty sea air, and the porpoise following in our wake. The hidden coves and diverse marine life of the San Juans beckon us to make discoveries and submerge ourselves in its delightfully relaxed pace.
So much of the world passes by without our being able to see, touch, or feel it. A sailing charter through the San Juan islands allows us to take a moment to slow down and experience it for ourselves.
We have been perfecting the art of “slow travel” for over 25 years. Our new 55′ sailboat Northwind, offers a luxury yacht charter experience for up to six guests in private staterooms with ensuite baths. Each one of our San Juan Sailing Charters and Inside Passage cruises are one of a kind, designed for your group from the ground up. From your preferences on food and drink, to where we go and what we see and do, the result is a perfect blending of islands, yacht, crew, and cuisine. It’s your perfect vacation, Sailing the San Juan Islands in style.
This is what a carefree sailing vacation is all about
Sailing the San Juan Islands
Captains Jette & Jon Baker, with TailR
A fully crewed sailing charter with Sail the San Juans is a world away from any vacation experience you probably have ever had. A sailboat charter aboard Northwind will open a door to see and experience the more remote islands and coves that are not easily accessible to most people.
At the same time, sailing yachts are in a unique position to be less intrusive to marine mammals which helps encourage encounters with Orca, seals and porpoise.
A sailboat charter with Sail the San Juans is a first class experience, from our impeccable yacht and crew to your private chef’s menu built around your preferences.
Join us to explore over 200 forested islands, help trim the sails on Northwind, or just relax while you savor gourmet fare, and great hiking and kayaking through protected bays and inlets.
This is the art of slow travel.
16 Page Full-Color Brochure
Two booking options
Private Charters: Groups of up to six people receive exclusive use of the sailboat for their group.
Join A Cruise: Reserve a stateroom for two, and let us take care of filling the other cabins.
Learn more about
Booking Options and Rates
Two unique island cruises
San Juan Islands: These six day sailing trips cruise through the San Juan Islands, an enchanting archipelago of hidden coves, abundant wildlife, and forested islands located in the sheltered inland waters of Washington State.
Learn more about
San Juan Islands Sailing Charters
The Inside Passage: These twelve day wilderness sailing trips cruise through the southern portion of the Inside Passage, an area rich with native culture, mountain vistas, fjords and waterfalls located in British Columbia.
Learn more about
Inside Passage Sailing Charters