I get a short break from a large project around the holidays, and we would like to go someplace new. Given that we'd like an excuse to escape the Florida heavenly winter in favor of ice and snow, and of course great airfare, we thought maybe Boston...

Question: Any New Years Event events that feature old time big bands, or failing that, your recommendations? Then if we have a few days to spend at the coast (figuring there might be icy/stormy weather, that's ok), where could we go?

Yes, we can drive in ice/snow and yes, we have winter clothes. And yes, we would want to use public transportation whenever possible in Boston. But I've never been to Boston, enjoy the rare winter weather (only on vacation, of course), is there anything worth the trip?

BTW - museums and the like, great. Night clubs, not so much. DH says there is nothing at all romantic or comfortable about Boston that he knows of. Your opinions? "You're nuts!" is okay but not original. Feel free though, all opinions welcome. (P.S. I'll be sure to tell you what is so wrong about coming to Orlando, anytime.)

We go into Boston for New Year when we know the temperature is going to be 40F+ and stay overnight. There's a parade, music, great ice sculptures and fireworks.
If it's just too cold we stay home!

Here's the link to events of First Night (will be updated closer to the date)
http://www.firstnightboston.org/

Thanks, sassy_cat.

There is public skating with skate rentals on the Boston Common. Walk around there after dark and see the lights, as well as those at Faneuil Hall area. The top of the Prudential observation deck is a nice place to see lights all over the city. Walk through the North End (Italian area) which will be all decorated and sip an espresso or coffee in the cold air.

Dinner out on New Years Eve can be problematic. If you just want dinner and then to do First Night, not usually a problem if you eat early. But many restaurants and hotels only seat for a fixed price New Years Eve party. However, you mentioned old time big bands and while I do not know of any place that would have that, I think there is a reasonable chance one of the Boston hotels might.

As far as wanting to see some storms on the coast, you could head up to Cape Ann (Gloucester/Rockport) either as a day trip or to stay. I love to walk along the beach in the winter - in the cold dry air every color is twice as vibrant as in the summer. If you have a little more time, Portland, ME is a nice little city less than 2 hours north of Boston with cute shops and restaurants.

While you are here, if you want a real Boston experience you are welcome to come shovel my walk. Seriously, I think you will have fun - and at the very least it will be good for a winter's worth of conversations with FL friends who will think you are insane.

gail, great advice! My walk is also available for shovelling. I will even supply some mulled wine

I love First Night in Boston, and think it qualifies as a romantic experience. Walk around in parks holding hands and seeing the ice sculptures, pop indoors to listen to the music, enjoy the fireworks. Hot chocolate and cider vendors abound.
Though the scene is lively, it nothing like the crowded/crazy scene in Times Square NYC.

mmmmm... mulled wine... gail and sassycat, we are ALMOST insane enough to consider shoveling your walk. However... although it has been years since we've had the privilege, DH is voting for the treats at First Night.

Am finding some nice hotel packages for the area where First Night takes place, with some interesting dinner options. So thanks to you all, progress there.

DH would like investigate Cape Ann and other options for the rest of the time (I can take about a week altogether, need to allow some cushion for weather flight delays I think). Any specific recommendations for a couple of nights outside Boston? Maybe B&Bs?