My favorite "regular" vacation is ski trip. We try to go every year. We go to Snowshoe, WV, rent a big house and have a blast. It is so much fun and in many cases, that trip is the only time I see some of those friends all year.
Wow, this is a hard one. I have several cities that I love for different reasons and I can't pick just one...so I will list several :)
Nashville, TN: What can I say, I love my "home town". I absolutely love living in Nashville. It is southern, home of country music, and almost like mini-Hollywood in a good way--not the stuck up, snob way. :) It isn't unusual for people to see Keith Urban & Nicole Kidman at Starbucks. My mom goes to the same dentist as Sheryl Crow and we saw her at the movies. And no one bothers them. I guess that's why they love living here too.
(image courtesy of Google)
Charleston, SC: For me, this is the ultimate in Southern charm. There is so much to do in the city, lots of sightseeing, great places to eat, and the beach all in one. I just love it and was so excited when Southwest recently announced they will be flying direct from Nashville to Charleston starting in March. Yay for a cheaper vacay!
NYC: I just love NYC. There are SO many things to do and see and fabulous shopping! I think it would be so much fun to date in NYC. You could do something different all the time. Central Park is my favorite. I just love it.