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Consider re-posting your inquiry under: Destinations/Pacific Northwest. You may get more replies.

Visit this site, buy the book Home | Waggoner Cruising Guide.

It will be your main cruising resource in the San Juan Islands.

If your time permits and you all have passports, consider hopping over to Canada. Two places in particular. Ganges on Saltspring Island. For a very (and then some) large splurge you could dine at the exquisite Hastings House. Or, you could have a beer and a burger at The Treehouse Cafe and take in some great music. This is a highlight of my family's summer. After that head over to Montegue Harbor. In May, the harbor may be peaceful. In the summer it's too crowded for my tastes. Instead, anchor on the north side of the peninsula by the "Shell Beach". Just ask a local in Ganges to point it out on a chart.

Get the Waggoner guide ASAP so you have time to dream and plan.

As far as charter outfits go, San Juan Sailing in Bellingham, WA would be my first recommendation. boats are maintained to the highest standards. They will also be able to suggest itineraries. Welcome to San Juan Sailing. The next is Anacortes Yacht Charters. Anacortes Yacht Charters.

A word of caution. May is "iffy" weather wise. It could be glorious. It could be wet, cold and rainy. The best Nw weather is July 5 - Sept 30.

Good luck.
 

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I doubt any difference in distance equates to more than a few hours time on the water. I own a charter sailboat in Seattle. The biggest reason I recommend SJ Sailing is that I Have talked with their charter customers and boat owners while cruising. Nothing but rave reviews. I have also talked with the folks who run SJ Sailing. They are an independent, well run outfit. That is, they don't have an affiliation with Sunsail or Morrings. I hope to buy a newer/bigger boat in the future and put it in to their program.

I can't say anything bad about the Anacortes operation. I think they are a Morrings (sp?) affiliate. I just have not had any direct contact with owners or charter customers.

If you do have a size able group make sure you start making any necessary marina reservations soon after January 1.

Also, Deer Harbor on Orcas is also a family favorite.
 
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