I admire Anna's impressive list very much, and can't top that, but I've been to:
USA-
all over the east coast- New England, New York, Pennsylvania, New Jersey, Delaware, Maryland, Virginia, North Carolina (many times to the Outer Banks- just love Cape Hatteras), Florida (especially love the keys)
New Orleans probably 8 or 9 times, one of my favorite cities, for Jazzfest,
New Mexico, Arizona (Tucson at least a dozen times).
Then, Mexico-
over the AZ border about a dozen times as well, and Puerto Vallarta, Punta de Mita, Mazatlan and- inland a couple of hours to my aunt's little town of Cosala, where by the way I attended the most memorable wedding EVER (my cousin's), other than my own, of course
, and PDC a couple of times (with day trips to Cozumel)...
Canada-
Montreal, Quebec City, all over Nova Scotia
Caribbean-
Jamaica maybe 9 times- we were married there..., Puerto Rico, St. Thomas, St. John, Tortola, St. Martin/Maarten, Anguilla- think that's about it.
Brian's been with me most of these places- basic difference is I've been out west more often and used to spend lots of time in NYC, and he's been through many more states in his old Grateful Dead touring days
