We strive to make these trips the ultimate experience; an opportunity to let go of the hustle and bustle of the daily grind and reconnect. Whether you just want to spend some quiet quality time with your family, have a special occasion planned like a family renunion or a wedding, or you want to head out on your own personal adventure, we can help you plan an unforgettable private voyage.

Call or email us today and the Captain will work with you to design the perfect charter that’s just right for you. 


Full Day - Multi Day - Sunset Sail

After sailing down the coast to Baja, we discovered a seascape so incredible, we just have to go back. This time you're invited.


We will be offering trips between La Paz and Loreto, as well as other destinations, for 10 to 14 days regularly scheduled departures, as well as longer voyages and Private Charters. These trips will be open to groups of 4-6 people and specifically created for adventurous, outdoor, fun loving and hearty individuals. 

Please stay tuned for trip dates, but in the mean time feel free to contact us now with questions or to get your name on the roster.

What can I say, I have a thing for wooden boats and sailing, so my review may be a bit biased, but I don't think so. San Juan Classic Day Sailing offered an amazing sail that would be appreciated by anyone who has an affinity for relaxing, peaceful, and exhilarating experiences. We sailed as two of four clients, and the intimate experience of sailing with so few offered a unique ability to participate in both trimming sails and steering the helm. I like to do that sort of thing, so I was an eager volunteer; others simply sat and enjoyed being carried by the wind. After a bit of instruction and playing with sails, we all then kicked back with wine and nibbles while the captain took charge of the helm and sailed us back to harbor, under sunset. It was indeed a very nice way to end the day.

“sunsets, sails and good humor...what a winning combination!”

Rachel M. - Corvallis, Or.

Holidaying from Australia, we had read much about the San Juan Islands and were keen to spend a day of our vacation sailing around them. Not being a sailor, we found the notion of sailing in an classic old schooner very appealing and great way for the kids to pick up a few pointers on the art of sailing. With this criteria in mind, we quickly settled on San Juan Classic Day Sailing and the beautiful “Dirigo II”. 
To say our day was picture perfect is an understatement. Art and his family were the perfect hosts – not only were we well looked after and well feed, but we thoroughly enjoyed just sitting, relaxing and having a wonderful conversation. The kids (9,6) had a wonderful time and Art was the perfect teacher – patient and with lots of knowledge which he was very gracious in sharing.
The sailing itself was just beautiful. There is always something to see and marvel over – on our trip we not only got to take an up close look at some of the beautiful islands (the Dirigo II has a zodiac which can get you into any cove or small island), but we joined by many seals and propoises.
This was a day that my family and I will never forget. I cannot recommend San Juan Classic Day Sailing enough !!!!

“A picture perfect day of sailing”

rforte Melbourne, Austraila

We wanted to celebrate our 45th wedding anniversary with something special and we found it. Captain Art and his crew made our day on the Dirigo II an absolute delight. They are very seasoned sailors with expert knowledge of the area, of this exquisite vessel, and of how to meet the needs of their guests. There is no way to describe the experience as wonderful as this was, spending the day on a beautiful classic craft with this group of skilled sailors which gave us great confidence and pleasure. The day was totally relaxing and often educational. The thrill of silently slicing through the waters is like no other experience. This has to be the best way to enjoy the scenery of the San Juan islands. Simply put - it just doesn't get any better than this!!!

“Best vacation in 45 years”

mauibird -Vacaville, CA

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dirigo2sailing@gmail.com  |  Captain: 360-298-4007  |  Office: 360-378-6700