Originally Posted by sparrowe
Eric, a few quick thoughts about the San Juans. We chartered for two weeks in June of 2012 out of Bellingham. Overall, it was a terrific experience. Next time we go, we will charter from San Juan Sailing - probably one of their Tartans (they offer a 34, a 35 and a 37). We were in a slip next to their Jeanneau 34 at the Rosario Resort and it was in much nicer condition than the Islander 32 we had chartered from the competition. (I haven't enough posts to include a link; google San Juan Sailing and they will come up.)
If you haven't sailed the San Juans, be prepared for some interesting challenges. The tides and currents are not to be treated lightly - they determine where, when and what direction you can travel. A copy of the "Canadian Current Atlas" of currents and tides for the area is essential, as is the concordance that tells you which chart to consult given the time and date. Ask if copies are on the boat when you arrange you charter. Also necessary are up-to-date charts, in detail, as there are numerous rocks that lurk just under the surface. Although I expect the charter boats have chartplotters, you need paper as a backup. Finally, I found Active Captain, mapping on to the Navimatics U.S. West Charts and Tides app to be really useful.
(To see what the currents can be like, go to YouTube and search for "Sailboat struggling Deception Pass" then watch as the boat goes against the flow, gives up, and sleds back the other way.)
One of the great things about sailing in the San Juans is that you can alternate between harbors and anchoring or mooring. In one week, for example, we moored at Sucia Island, had a slip at Roche Island, anchored in English Bay, rafted to another boat at Jones Island (where raccoons snuck into our boat while we were sleeping!), had a slip at Friday Harbor, and anchored at Inati Cove. I suppose the BVIs are similar; but, for us, it was a novel and very enjoyable experience after sailing day after day from the same slip in Belmont Harbor in Chicago.
You can fly in to Seattle and arrange a bus to Bellingham (or, you can take a short flight into Bellingham from Seattle). Rather than a taxi, we arranged with Evergreen Town Car Service to meet us at the Bellingham airport (that's where the shuttle bus from SEA-TAC stops). They schlepped us over to Fred Meyers grocery to provision, and then down to the marina. Same service on the return leg - and reasonably priced.
Let me know if you want more details - or, post a general request on Sailnet. I think there are a number of folks based in the area.