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” on the high seas, to a two-hour tour on the 1934 cutter “Iris” out of beautiful Friday Harbor, we have a sailing experience for everyone!

Contact Captain Morgan today for information on our sails, availability and reservations. 


Dirigo Sailing 2014 Sailing Season

Fall – Winter – Spring

Southern California – Baja – Channel Islands – Sea of Cortez

Schooner at sea

Join the Schooner Dirigo II as she embarks on her adventure South!

Chart the Dirigo’s course in real time, as she makes her way down 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!

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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San Juan Classic Daysailing

Friday Harbor

The lovely “Iris”, our 42′ Alden cutter, will continue to offer 2 Hour Sails, Half and Full Day Private Charters and SunSet Sails through the Fall, from our home port in Friday Harbor.

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




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 aboard the Schooner Dirigo II on our

West Side Whale & Nature Sail

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

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.