Day Sails, Whale & Nature Sails, Sunset Sails, Private Charters and Schooner Adventures on the Salish Sea and beyond!

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 With sailing options ranging from a multi day adventure aboard the schooner “Dirigo II”, to a 2 hour tour out of Friday Harbor on a beautiful vintage sloop, we have a sailing experience for everyone.

Book Now to let your adventure begin!

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Sailing with the Orca Whales in the San Juan Islands!

Join us on our

West Side Whale & Nature Sail

A truly unique whale watching experience from the deck of a beautiful 74′” schooner!!

Sailing with the Orca Whales in the San Juan Islands! Photo by Captain Alan NIles of San Juan Classic Day Sailing.

Sailing with the Orca Whales in the San Juan Islands! Photo by Captain Alan NIles of San Juan Classic Day Sailing.

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2014 Sailing Season

This is an exciting year for San Juan Classic Day Sailing!

We will be sailing our fleet of beautiful classics throughout the San Juan Islands, basing out of two of the most outstanding and unique ports of call in the Salish Sea.

The Schooner Dirigo II will be sailing throughout the Salish Sea and the San Juan Islands this summer, offering trips that depart from both Friday Harbor and Roche Harbor. Both ports of call are unique and offer access some of the greatest sailing in the world!

Dirigo Sailing

Follow the Dirigo II in real time, as she makes her way from port to secret cove, relaying her daily position and news from her new Spot device! Plan your trip in advance or jump aboard mid-adventure!

Click here to find the Dirigo II!

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San Juan Classic Daysailing

Friday Harbor

The lovely sloops “Tempest” and “Isabella” will continue to offer 2 Hour Sails, Half and Full Day Private Charters and SunSet Sails all summer from our home port in Friday Harbor.

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Schooner Dirigo II under full sail! View from aloft!

Escape the crowds and connect with nature; Your journey beckons!

Step aboard and cast off with us from one of our two locations on San Juan Island, Friday Harbor and Roche Harbor! Feel the breeze as we set the sails and the boat comes alive under your feet. Venture out into the pristine waters and awe inspiring environment of the Salish Sea, one of the most beautiful places on Earth.

All of our sailing trips are open to sailors of any experience level and are limited to a maximum of 6 guests! First time sailors welcome!

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2014 Sailing Season This is an exciting year for San Juan Classic Day Sailing! We will be sailing from two of the most outstanding and unique ports of call in the Salish Sea. The Tempest and Isabella will sail from our home port in Friday Harbor and the Schooner Dirigo II  will be sailing from historic Roche Harbor. Both locations are unique and beautiful and access some of the greatest sailing in the area!  It’s going to be a good summer for sailing, relaxing, adventuring, and just “messing about in boats”.

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Fun in the sun aboard the schooner Dirigo!

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History comes alive when you step foot aboard this 1939 beauty!

Come sail with us on an exciting Afternoon Daysail, a romantic Sunset Sail or reserve your own Private Charter for your family vacation or small group event. Take your “moment away” and answer the call of the sea. Our friendly, capable, and experienced crew await aboard “your yacht in the Islands”.

An afternoon or a weekend, the choice is yours. Welcome aboard.

blue-nautical-starA time to rejuvenate and appreciate the moment. Experiences to savor and remember.

We love our boats, we love sailing, we love our Salish Sea between the mountains and we would love to share it all with you. Come join us.

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Sailing at sunset with the Orca Whales under snow capped mountains in the Puget Sound. Does it get any better than this?

blue-nautical-starFor questions, information or reservations, contact us at (360)378-6700 or email.