In MD, Annapolis
specifically, we raced year round. Though admittedly winter was called frostbite season for obvious reasons. But with a heating
system on the boat & a good dodger/hard dodger
, especially with rear curtains, I'd have zero issues with sailing there 10-12 months of the year, & living onboard... Actually I'd love it.
AC would be really nice to have for a few of the summer months, but you can get by without. Especially when you're out sailing vs. being anchored in an estuary somewhere out of the wind
Winds in July & August tend to be really light, even for boats with big sail plans, but it's possible to sail everywhere. Also, it's really, really rare for named storms to head
your way in the Chesapeake. And in spring you have great winds, with them fading about the time which folks that can, head
north. Call it May+/-
The cruising's exceptional. As are cultural activities, given the location. And you can't want for sailing services or opportunities. Plus should you choose to head north or south, you can do so via ocean, or more protected routes for much of the journey.
On SF, no one's mentioned it yet, but there are lots of spots to sail & explore in addition to the bay proper. So that you won't lack for that, though a good bit of it's estuarys which require motoring, & or, a shallower draft
I'm not sure if there's 5yrs worth of exploring to do there or not. Others can chime in, & there's a good bit mentioned about the Delta
here on the forums
. And also some in www.latitude38.com
Up in the NW you'll never run out of places to explore, or things to do, & it's a fav of many folks for a reason. You'll want a heater onboard (but where don't you) due to water
temps, & cooler temps. And some warm gear
in lieu of sun screen
. But the food's good, if a bit tame, & there's also lots to do & see in Canada
. Plus if you like beach combing, or collecting your own seafood, opportunities abound.
I haven't spent enough time in the other spots to contrast them, so... it's up to you. With some of it being, in order of priority, what do you want? Plus, given the stakes, it makes sense to visit several areas for a long weekend. Especially with flights being cheap
. That way you have a sense for yourself of how well each of your top picks "fit".
Ah, & this may sound silly, but look at what type of festivals each area has that call to you. Do you like street fairs with music
? Boat related ones? Film fest's, etc. As for me, such events
do tend to color the flavor of somewhere a lot, & definitely play to the quality of life factor. And there are loads of online resources to look up such things, as well as the literal quality of life in places.
PS: I love San Diego
too, there's just much less to do in the area cruising wise. Especially in terms of places to explore or anchor
. You have to head out to the Channel Islands basically. But the food
& culture are great, even if slips are tough to come by. Sailing weather
is year round, with drifting strength winds in summer. And super mild winters.