Heads up! Course change!!

We have just proudly launched into two new websites!

 NEW! San Juan Classic Day Sailing website!

Follow this link to see our new website, all of our sailing options and online booking!

And introducing the Dirigo Sailing website!

Please take a look for information about sails, charters and adventures aboard the schooner Dirigo II!

Feel free to use our existing site while it’s still up, or browse either of our new sites, as we continue to offer your the same great sailing experiences with improved customer service!


Day Sails – Whale & Nature Sails – Sunset Sails

Private Charters and Schooner Adventures

Friday Harbor – San Juan Island

The heart of the Salish Sea!


 With sailing options ranging from a Multi-Day Schooner Adventure aboard the 74′, 1939 “Dirigo II”, to a 2-hour sail aboard the 42′, 1934 cutter “Iris”, we have a sailing experience for everyone!


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


San Juan Classic Daysailing – 2015

IMG_4539 10428541_726590624077535_6142814493286459220_n (1) sunsetondeck


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 more about our 2015 Sailing Schedule out of Friday Harbor or to make a reservation.



Dirigo Sailing – 2015 Sailing Season

Spring – Summer – Fall

From the 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 through the Salish Sea, from port to secret cove, relaying her daily position and news en route!

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

Click here to find the Dirigo II!

Screen Shot 2014-07-16 at 2.07.46 PM




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.