Join a flotilla in the San Juan Islands and take along a qualified training captain to learn while you cruise.
The San Juan Islands and Inside Passage of the Pacific Northwest are some of the most incredible cruising areas in North America. Mountains, islands, forests, and, if you go far enough north, glaciers, line both sides of your cruising path, giving you endless opportunities for exploring. Whether you overnight at marinas or choose a mooring ball or anchorage, there’s plenty to see and do along the way.
If the area is new to you, one of the best ways to explore by boat is to join a flotilla — a group of boats traveling together. That’s what I did in autumn 2024 when I returned from my Great Loop trip. I signed up for an early autumn flotilla with San Juan Sailing & Yachting to Desolation Sound. I did it in my own boat — after all, I had a boat — but other flotilla participants were chartering the boats they were on. The flotilla was led by an experienced captain and his wife who handled trip planning, navigation, and daily briefings along the way. We spent 14 days cruising in a group, making friends while enjoying the adventure of seeing new places.
Here’s a drone shot of our flotilla rafted at anchor up on the Inside Passage. The scenery was awesome!
If you’ve been wanting to do a trip like this, what are you waiting for? Yes, the company offering the flotilla can charter a boat to you. And yes, they’ll require some assurance that you know what you’re doing before they hand over the keys.
But if you don’t know what you’re doing, that’s where someone like me can help. I’m an experienced single and twin engine power boat captain and instructor. Listing me among your crew will enable you to charter the boat without being required to take a costly training class. Instead, I’ll provide the training as we cruise.
Although you might not be comfortable captaining a cruising boat on Day One, before the end of the trip, you’ll have the skills and knowledge you need to charter a similar boat there or elsewhere — without a captain on board.
Here are two Bellingham WA-based companies I recommend for flotillas:
But I can join you on a flotilla with another company — or even in another place! Let me know what you have in mind.