San Juan Islands, Pacific Northwest, USA & Canada hosted by San Juan Sailing June 23rd - 30th 2023 starting from $1,299

Contact Us

Danelle Carnahan
  • This San Juan Islands flotilla is always very popular so sign up today!

Dear Sailor,

Our upcoming 2023 flotilla to the San Juan Islands will fill up fast, so sign up now. Our cruise is June 23 – 30, 2023, departing and returning from Bellingham, WA. Whether you are a qualified captain or interested in being crew, we have boats looking for both. These trips are designed to accommodate beginners and experienced sailors alike.

The San Juan Islands, located in the sheltered waters of Puget Sound in Washington State, offer a unique and incredibly scenic sailing experience.  Many sailors prefer the San Juans to more traveled bareboat waters such as the British Virgin Islands or other tropical destinations.

Our planned destinations include quiet anchorages, resort visits, beach barbecues and fleet raftups. Also included will be a welcome gathering, group dinners, and an informal regatta.

To find out more about this event and how to charter a boat, click the green button to the right or please contact San Juan Sailing at 1-360-671-4300. To enter with your own boat, or to find a crew opportunity, contact flotilla leader and ASA Instructor Capt. Roger Philips at or 1-602-300-7079.  Each flotilla is limited to ten boats.

 We look forward to seeing you next June in the San Juans!

Sunset in the Islands

Downwind off San Juan Island

Rosario Resort, Orcas Is.


Your Flotilla Leader

Roger Philips, an ASA instructor and U.S. Coast Guard Captain, is a veteran of the local Salish Sea waters and has been leading this summer guided flotilla since 2008.