You don't mention how much time you have but if it's less than 2 or 3 weeks, and you want to make a stop in the San Juans, I would not try to include Desolation Sound in your plans, it just takes too much time to get up there. I spent 3 weeks last summer in the San Juans and Gulf Islands but coming from Seattle
I didn't really think there was enough time to get to Desolation Sound unless we spent a few really long days just motoring up there. I really want to get up there though, I just have to find the time...
It's not much hassle to check in to the US or in to Canada
for all US citizens (though I've never brought a boat chartered in Canada
in to the US.) Coming in to the San Juans you check in at Roche Harbor or Friday Harbor, they do the usual check your passports and look through the boat for contraband (ours was garlic that was imported from China) and then you're on your way. Make sure no one has a DUI on their record
because they will probably be denied entry in to Canada. Sidney and Victoria are the easiest places to check in to Canada from the San Juans.
As far as favorite places...
1. Sucia Island in the San Juans, there's a small cove called Ewing Cove on the north east side of the island, if you can get a mooring
ball in there (there are 4 I think) it's an awesome place to dinghy
around to the little islands and just to relax. No facilities (well maybe there's an outhouse, can't remember.)
2. Rosario Resort on Orcas Island (small-ish) marina but you can anchor
outside the breakwater and dinghy
in to use the facilities at the hotel
for a fee.
3. Sidney Spit in the Gulf Islands is really pretty but no facilities. We anchored at the north end of the spit but watch the depth
4. Otter Bay on North Pender Island - they have two pools (one is adults only which was nice) and a little shop.
5. Russel Island (south east end of Saltspring Island) - this was probably my favorite place overall, quiet (I hear it gets busy but we were one of 4 or 5 boats), beautiful trails around the island. No facilities.
One thing to watch out for in the Gulf Islands is there are very few pump-out stations, so keep an eye on the holding tank
Make sure you get the current
prediction book, you can get a good boost or it can make your trip much longer if you're not aware.
And now for the most important point, beer
is much more expensive in Canada and there aren't nearly as many small breweries, so stock up before you leave the San Juans!
Here's a link to the photos
I took up there last year...
Maybe we'll see you up there!