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Sail the San Juans

Make a Reservation (800) 729-3207

Relaxing 6 and 12 day sailing adventures aboard Northwind!

Humpback whale encounter...

Afternoon nap...

Northwind's elegant salon.

Sailing with a pod of resident orcas.

Gourmet cuisine by Chef Jette.

San Juan Islands Sailing Charters and Cruises

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.

Request our 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

Yacht Charter Adventures

Explore the scenic San Juan Islands, Gulf Islands and Desolation Sound aboard your own private charter yacht.

Select from our fleet of power and sail yachts from 27’ to 70’ – options to suit any boater from beginner to ol’ salt.

Bareboat charters are perfect for self-guided, hands-on adventures to enjoy quiet coves, view abundant wildlife, and explore remote landmarks – right in your own backyard.

We’ve made it easy to charter…

• We have the largest charter fleet in the Northwest which gives you oodles of options to pick the vessel that’s best for your trip.
• Our sample Cruise Adventures help you plan your trip.
• Our Boating Classes teach you new skills or refresh past ones to give you the confidence to safely and comfortably skipper your yacht.
• Our Cruising Guarantee means help is available for mechanical issues.
• Our Seasonal Rates and Special Offers give options for any holiday budget.

To get started…

• Check out our How To Charter page for a brief introduction or
• Contact our Reservations team for any questions, check availability of your favorite boats, or get a quote for your cruise of a lifetime.

Special offer for readers of

on Boating Classes and 2024 Yacht Charters.

Ask for Promo Code: ANW.

Offer available through May 31 on any New Boating Class sign up and New Charter Booking for the 2024 season. 
Check out our Boating Classes and Reservation Information then give us a call at 1-800-233-3004
. Cannot be combined with any other offer or discount. 6-night charter minimum.

Toll Free: (800) 233-3004 | (360) 293-4555 | [email protected]

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