outside of the U.S: Barcelona (I have such an attachment to this city since i studied there for a summer), Amsterdam (because i used to practically live on a houseboat there with my ex), and Thailand (amazing prices, incredible beaches, and awesome food)
within the U.S. - I go to New York and Vegas at least twice a year (gambling, food, shopping cant beat it!), and Big Sur or anywhere on the Pacific highway coast 1!
Dominican Republic. I go to the Puerto Plata region or Santo Domingo quite often. I've also been to the rest (Punta Cana, Higuey, Constanza, Santiago) but those are my favorit areas. I just can relate to the mentality, the weather is nice, they produce great rum and the people are nice. Did I mention the music? God how I love Bachata and Merengue.
Last year I've been 3 times for vacation, summing up to appr. 7 or 8 weeks. Next trip is beginning of February for 2 weeks but unfortunately it looks like I have to play it a bit slow this year cuz I have to save money for other things and will be quite busy with business trips.
I guess I'm kind of biased because I live in Canada, but British Columbia is the most beautiful province. The mountains are beautiful and the Okanagan where all the wineries are the orchards, etc. And then out on the coast (Victoria, Nanaimo, Tofino, etc) is beautiful. I live in Alberta, which is nice in the mountains.
Outside of Canada.. I loved Cozumel for some reason. I loved Cabo.. it's beautiful there. I have been on about 5 cruises with my family mostly to the Caribbean and there are some places I loved and some that I would never go back to.
In the States, I love Florida (Orlando for Disneyworld) and California (my dad owns a condo outside of Palm Springs) and Vegas. I love driving through Vegas at night with all the lights. I was in Denver this past summer for a conference and loved it there too. The airport was huge though!