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Flotillas

Explore new cruising grounds with the confidence of an expert flotilla leader and the camaraderie of fellow sailors.  Or share popular cruising grounds with the companionship of new faces! Our flotillas give you as much privacy or community as you like.

Each day you can cruise together with the flotilla or separately. You are welcome to raft to other boats in the group, or seek solitude in your own corner of an anchorage. You can join your cruise mates for evening appetizers, beverages and meals after exploring island trails, poking your paddle board into tiny inlets, or enjoy a relaxing evening watching the sun fade over the horizon as your boat gently rocks to the rhythms of the sea. 



What are the benefits of flotilla cruising?

Flotillas are an ideal setting to gain confidence and familiarize yourself with new cruising grounds, while enjoying the camaraderie of fellow cruisers. Your flotilla leader serves as a knowledgeable guide, providing skills “coaching” and docking or anchoring assistance as needed. Have a question? Assistance is always there.

In addition to safety and guidance, your flotilla captain offers insights and history on each cruising area. They’ll organize the weather and chart briefing and review the day’s travel itinerary with all flotilla members. The flotilla leader will highlight both hazards and special natural scenes en route. 

Joining a flotilla is really the best of both worlds as everyone helps and contributes whether it’s mooring, spotting wildlife, avoiding rocks and reefs and sharing great moments while rafted together or secured to a dock. Our flotillas represent some of what’s best about being a member in Windworks. We love to share our passion with fellow adventurous souls.



Flotilla Options

We offer four-day flotillas and two-day excursions:

  • Spring Tides - a four-day odyssey that ventures to the San Juan Islands during late April or early May when the Earth, Moon and Sun are aligned. This combined gravitational pull of the Sun and the Moon creates the greatest difference between high and low tides. The name refers to the concept of the water “springing forth.”

  • Southern Crossing - A four-day journey that explores the islands, coves and inlets of South Puget Sound that takes place in mid-September. Recent trips have included circumnavigation of Vashon Island and port visits to Bremerton or exciting trips under the Tacoma Narrows Bridge and finding quiet anchorages in Case Inlet or near Raft Island. The South Puget Sound is some of the most underrated cruising grounds in the region.

  • Mini-Flotillas - These are one or two-night mini trips to closer destinations such as Langely, Poulsbo, Blake Island, Gig Harbor, Kingston, Port Ludlow and Everett. These events usually include a theme and are a great way to explore what’s in your own backyard while gaining experience and confidence cruising with others.