Well, I LOVE to talk about traveling.
My dream vacations include (realistically) NoLa, Quebec, and more of California (maybe San Diego or San Jose), and (idealistically) Borneo, Paris, and Argentina.
Places I've been, divided by category:
CITIES:
New York - if you've never been here, come here. It IS expensive...but you can find lots of ways to save and there's a zillion free or low-cost things to do. It's definitely only fun if you want a city vacation, but past the fact that it's not a relaxing beach vacation, there's stuff for everyone...really cool historical sites, great art and science museums, fantastic shopping, shows, amazing food, botanical gardens/parks, nightlife, etc. Very dog friendly - most stores that don't sell food allow dogs, many hotels allow dog, there's very little breed/size restriction.
Boston - lots and lots of history, which is really cool, beautiful old buildings, they also have some impressive art museums, and some cool shopping. It's kind of hard for me to compare the restaurants/nightlife/etc. to New York, but it seems like there are some good places. The downsides are public transportation is slow and terrible and if you drive, good luck figuring out how the roads work.
Los Angeles - Also fun and kind of caters to lots of people...obviously there's less historical stuff and old architecture there. It might be *slightly* geared towards the younger, more night-lifey crowd, or families. On the plus side it's close to both the beach and mountains, and there's tons of hiking/swimming/etc...within VERY close distance to the city, you can walk to whichever you're closer to. The flowers are gorgeous. The weather is gorgeous. There's lots of neat art museums and shows, and the shopping is so great you need an extra suitcase for all the cool stuff you'll want to buy.
Washington DC - I've only been here for short weekend/overnight trips and it never seems like enough time. Lots of history/politics/and tons of fabulous museums (even better than New York!)...but not a whole lot of shopping, nightlife, etc. You can get to things like hiking/canoeing/kayaking/outdoorsy stuff, but it's not that convenient to someone staying in the city (especially without a car). Public transportation is easy/safe/good.
BEACHES:
Cape Cod - Cape Cod is ADORABLE. I've actually only been there off-season, and the stores/restaurants/bed and breakfasts/etc. are all really fun and cute then. I'm not sure if in summertime it gets horribly overcrowded or something, but I don't think so. The landscape is beautiful, there isn't really any crazy nightlife but there is a small bar scene and stuff like local cover bands/small outdoor concerts. There's lots of whale watching. And fishing/kayaking/beaches.
Ok I'll write more later! I'll tell you all about The Hamptons, various beach areas in Florida, and all the camping/mountainy/lake vacations I've done.