Day Sails, Whale & Nature Sails, Sunset Sails, Private Charters and Schooner Adventures out of Friday Harbor – San Juan Island, the heart of the Salish Sea and beyond!


 With sailing options ranging from a multi-day adventure aboard the 1939 schooner “Dirigo II”, to a two-hour sail aboard the 1934 cutter “Iris”, we have a sailing experience for everyone!


Coming to the islands this spring? Join us for a sail!

We are open for business early this year and currently offering our 2 hr Afternoon Sail, the Sunset Sail and our Half Day Private Charter aboard the “Iris” out of downtown Friday Harbor, San Juan Island. 


San Juan Classic Daysailing

2015 – Friday Harbor

Embark aboard the lovely “Iris”, our 42′ Alden cutter, on a 2 Hour Sail, a Half or Full Day Private Charter or how to buy Facebook stocks in the Philippines a SunSet Sail.

We sail Spring, Summer and Fall from our home port in Friday Harbor, on beautiful San Juan Island.

Contact Captain Morgan today to find out about our 2015 Sailing Schedule out of Friday Harbor or to make reservation.



Dirigo Sailing – 2015 Sailing Season

Spring – Summer – Fall

From the Facebook stocks Sea Of Cortez & Baja, and Southern California, to the San Juan Islands…

Schooner at sea

Join the Schooner Dirigo II as she continues her adventure!

Chart the Dirigo’s course in real time, as she makes her way back up the West Coast, from port to secret cove, relaying her daily position and news en route!

Want to get your name on the crew roster? There will be openings on certain legs of the journey for a few passengers!

ANNT: Passage aboard the Points South Voyage is open to anyone with blue water or other considerable sailing experience, or those with a sturdy constitution and a hunger for adventure. This is real ocean sailing and not for the faint of heart. This is a real life authentic adventure!

Stay tuned for charter availability for the southern California area for the spring sailing season!

Contact Captain Morgan @ (360)378-6700 or via email at for information and reservations.

Click here to find the Dirigo II!

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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 out of Friday Harbor, on beautiful San Juan Island, Washington, and 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 out of Friday Harbor are open to sailors of any experience level and are limited to a maximum of 6 guests! First time sailors welcome!

Or catch us en route aboard the schooner Dirigo II on her Points South Voyage at one of the many exciting and fun ports of call!

Feel the fresh sea breeze and the power of the ocean, as we set the sails and the boat comes alive under your feet!


Coming to the San Juan’s to see the whales?

Reserve your sailing for the 2015 summer season with us on our

West Side Whale & Nature Sail

A truly unique whale watching experience from the deck of a beautiful classic sailboat!

Hurry, there will be limited sailings!

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



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.

A time to rejuvenate and appreciate the moment. Experiences to savor and remember.


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


For questions, information or reservations on any of our trips, contact us at

(360)378-6700 or email.