I've decided to take a four day weekend in the middle of May, but am having trouble deciding where to go. I'd like to visit a location outside of California, and aim to spend less than $1200/person. Both beach, city, and ski destinations are options. I'm playing around with:
1. NYC
2. Hawaii
3. Montreal (not sure about the weather in mid May)
4. London (manic weekend in Europe - should do it once before having kids)
5. Park City/Jackson Hole/Other ski destination

What would you do???

Since I live in L.A. county, this is a question I am always contemplating.

I think Europe is too long a flight for only 4 days. I would save that when you have more time to spend. Same with Hawaii. We once did a Maui trip for only 5 days, and it was torture to not stay longer.

Park City ski resorts generally close down in early April. I'm not sure about Jackson Hole, etc.

I love both Montreal and New York. Either would be great for a city vacation.

Costa Rica would be great if you can get a direct flight and stay in one location. I would also consider Belize or the Caribbean. Hurricane season doesn't start until June, and the prices are usually reasonable in May.

Have fun and let us know what you choose.

For (4) days - I would pick a short flight - like to Puerto Vallarta (or some other Mexican destination - Acapulco?) . It would definitely be within your budget and PV is such a fun, relaxing and pretty spot. You can do lots of stuff or do nothing -- and there are plenty of great restaurants and shopping (love the silver).

Pick where YOU want to go and in my opinion don't base it on 'you need to do it before having kids' -
keep thinking.... I will travel with my kids, I will travel with my kids....many of us did and do -
so choose what you need for this time in your life and I'd keep, for 4 days, the getting there and back as easy and quick as possible so you get more time enjoying your destination.

I'd pick a west coast destination: Seattle, Portland, Phoenix or Tuscon. I think with one of those it would be easy to stay within your dollar amount. I also liked the Puerto Vallarta suggestion. there's a lot of good posts on PV.