Wondering if anyone has insight for a short trip from NYC to celebrate turning 50th with a friend doing the same. Maybe Montreal? Specifics?

Having done it several times, I can't recommend Montreal in January. It's too cold. When I want to celebrate, I want to go someplace warm like Miami or New Orleans. But by all means pick a destination that makes sense based on you and your friends' interests. If food, New Orleans is a great place. If nightlife, then Miami. San Francisco is a great destination for anyone interested in food and wine (or Napa, a couple of hours to the north). Las Vegas is great for gamblers. But if you like the cold, maybe even Quebec City. If you really want warmth, look at the Caribbean: San Juan, Montego Bay, and St. Thomas are all nonstop flights from NYC, as is Providenciales in the Turks & Caicos and Nassau in the Bahamas. The latter two are not reliably tropical in the winter, but they are a lot warmer than NYC.

I can do a long weekend if I have to travel 4 or 5 hours by plane. But I'd push it to go to a place like San Francisco or Las Vegas.

I was in Montreal once in late December. It was seriously cold and snowed every day. If that was unusual, please ignore me, but I don't think it was.

I love Montreal, so if that kind of weather doesn't deter you, I highly recommend it.

If you like cold, go for it. I would go to San Juan for a birthday in Jan, if I could.

Montreal is lovely and has a ton to do in the winter - as long as you are prepared for bitter cold. Seriously colder then NYC and gets a lot more snow. But they are set up with a lot to do indoors.

http://www.findfestival.com/quebec/montreal/january/

Mont Tremblant in Quebec is wonderful. Even if you don't ski, the village is so pretty. Also, Ottawa hosts a really fun Winter Festival, usually at the end of Jan/early Feb.

However, I would also opt to go somewhere warmer to celebrate the milestone - some ideas for a short trip: New Orleans, Charleston, Bermuda, Miami.

Happy bday.

Montreal is really good place but January may be cold, but with lots of post-holiday sales, bargains and few crowds, it can be a good time to visit Montreal. In case you are looking for a warm place then I recommend Las Vegas, 24-hour casinos and endless entertainment options. Its focal point is the Strip, just over 4 miles long and lined with elaborate theme hotels such as the pyramid-shaped Luxor and the Venetian, complete with Grand Canal.

South Beach Miami or Key West...