Europe over the holidays with sons?

The first thing I would say is that New York is at its best during the holidays. Yes, there's a possibility of awful weather, but New York isn't necessarily a place that should be visited during warmer weather. Most of the things you will do in New York are indoor activities, and some of the ones that aren't can be very special at Christmastime.

If you are rejecting New York, though, on the basis of cold weather, then most of Europe is off the table as well. I've never gone to Europe in the wintertime, but I hear there are many places in Europe that shine in winter, just as New York does.

What you probably don't want to do is plan an itinerary that involves a lot of travel from place to place.

If you prefer a warm-weather location but aren't interested in a beach vacation, how about Costa Rica or elsewhere in Central America?

Does the 5k budget include airfare for 4 people? That will limit your options of going to Europe in the winter primarily because the fares will be higher around the holidays. Looking on skyscanner.com from Chicago I only saw airfares < $1000 pp going to London or Madrid for some random December and January dates I plugged in. If you did fly to London you could easily tack on Paris via the Eurostar. There could be sales so it pays to keep looking.

$5000 is enough to pay airfare to Europe for 4 people with a bit left over for meals and some fun but not enough for hotels. Sorry. New York is an excellent idea. So what if it's cold? Wear warm clothes and stop often for coffee.

If Europe doesn't work for those prices (we are in the middle of planning and airfares are really high over the holidays and it might eat up your whole budget), how about Key West? It's not a beach vacation, in my opinion, because the beaches aren't great, but there's quite a bit to see: Hemingway House, Lighthouse, Mel Fisher's Museum, Truman White house, a day trip to the Dry Tortugas and Fort Jefferson. Opportunities for more adventurous activities like kayaking and snorkeling. Plus, plenty of opportunities for fun meals and downtime. My young adult kids would LOVE to go back, and we are not big drinkers or partiers. It's just a lot of fun even without any of that.

You might be able to get bargains in January but not in December, and certainly not over the holidays - that's high season.

Thanks everyone..Europe is out. I will mention NY.

How about Canada? Montreal and Quebec, or Vancouver and Victoria. The exchange rate is pretty favorable.

You might be able to afford to do it for around $5K if you are willing to home exchange. We have done this many times and only pay the cost of the airfare and whatever meals and entertainment we choose to partake in! There are hundreds of people in Paris who want to come to the US via home exchange. I don't know where you live but we get offers all the time for France.
Let me know if you want more info!
www.homeexchange.com

Costa ica is a great spot, even joining up with a tour like caravan tours.

Anita - Lulu's from Indiana. I doubt many Parisians are looking to home-exchange there over the holidays.

What about Santa Fe? It's supposed to be beautiful over the holidays with all of the farolitos, and there are lots of cultural events going on. It's one of my favorite little U.S. cities, with all of it's color and indigenous/Spanish influences, and one we plan to spend a Christmas holiday at ourselves one day.

Not 'advertising' a website here but to give you an idea:

http://santafe.org/Visiting_Santa_Fe/Winter_Events/

It won't be warm but averages aren't usually completely frigid in December either:

http://www.accuweather.com/en/us/santa-fe-nm/87501/december-weather/329558