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Old 11-15-2013, 11:33 AM
 
387 posts, read 732,854 times
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If I were in your shoes, I'd pick the Caribbean, no question. You and your daughter will be hard-pressed not to enjoy the beauty and relaxation there, but your wife would likely be miserable in Boston since she hates the cold.

Mid-October is a great time of year to come to Boston -- beautiful foliage, attractions are open but not too cold to enjoy, and you can even catch the Head of the Charles race if you time your visit right.
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Old 11-15-2013, 04:21 PM
 
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I too would visit Boston another time of year, either May-June or Sept-Oct, especially if your family doesn't like cold weather.

My only piece of advice is to be prepared to stay 2-4 extra days if there is a snowstorm that cancels flights. Flying over the holidays is crowded and any disruption means that there is no extra capacity in which to rebook travelers. Big snowstorms are rare in December but not unheard of - it happened 2 years ago and I spent an extra 4 days with my family before I could get a ticket back to Boston. There are worse thing than being stuck in snowy Boston, but it is something to think about if you need to be home by a specific date.
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Old 11-17-2013, 06:14 AM
 
Location: Boston, MA
10,923 posts, read 7,722,587 times
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Quote:
Originally Posted by Joansperspective View Post
You might want to consider going to Jackson, NH for part of your trip. It us the quintessential New England town, the Wentworth Inn is very festive, you can try cross country skiing at one of the best places in the world, take a sleigh ride at Nestlenook, and shop in North Conway. Lots to do!
I second that.

It's about a two and a half hour drive from Boston but it's worth it.
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Old 11-17-2013, 06:47 AM
 
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We traveled to Boston for Christmas via plane for years before we moved back here and we found everything from mild sweater-weather to 15" of heavy snow. Be prepared and make sure your rental car has an ice scraper. Also, the Boston area shuts up like a drum from around 4 pm Christmas Eve through December 26th. Boston is still primarily very Christian and you'll be hard pressed to find a restaurant open except for the big hotels. I know the Hawthorne Inn in Salem, MA does a nice Christmas Eve dinner and Christmas Day buffet but you need to make reservations early for this so think ahead.
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Old 11-17-2013, 05:24 PM
 
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Quote:
Originally Posted by ipoetry View Post
Also, the Boston area shuts up like a drum from around 4 pm Christmas Eve through December 26th. Boston is still primarily very Christian and you'll be hard pressed to find a restaurant open except for the big hotels.
Almost every Chinese restaurant is open on Christmas...
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Old 11-20-2013, 08:47 AM
 
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1) Will it be too cold? Weather.com says 20s and 30s, which makes me wonder if "hot climate" people like us will in fact be miserable, stuck indoors at hotel, which would be dumb. My wife wants to rule it out after I looked up the expected temps. None of us have warm shoes or anything, though we are willing to outfit ourselves with proper outerwear.
Weather around here is VERY variable. The last couple weeks the temperature has varied from the 20s (at night) to the 60s. Daytime temperatures in the 20s are rare...you could be dealing with anything from the 30s to the 40s in December. Warm shoes are seldom necessary. Nearly any temperature is comfortable if you dress properly. A warm winter coat and a wool sweater or flannel shirt should be fine. If you want to be thorough you can throw in wool socks, but I rarely need them. The people who are miserable are the people who don't plan, or women and teens who put fashion ahead of practicality.

The real problem is snow. Now, we usually only get a handful of big snow storms in the winter (contrary to what you may have heard). The worst is if it snows and the weather flutters around 32F...snow melts and refreezes, creating a layer of ice.

Quote:
2) Are many of the "things to do in Boston" that I see online shut down and/or unenjoyable during cold weather, or is it pretty much business as usual no matter? Do people just bundle up and walk about like normal?
What things were you thinking of? Anyway, most things are open. Museums are, bars are, and the Freedom Trail is. (But that last is cold.)

Quote:
Is Boston a festive place during this season? I know it's a (possibly stupid) subjective question, but will Boston abound with Christmas cheer and activities aplenty? Is it a "special" place to be, or just "AnywhereUSA" during Christmas, with mostly commercialism and shopping as the focus?
Yes. Faneuil Hall is always decorated. The Stone Zoo is covered in lights. Various mansions are decorated so you can get a taste of a "Victorian Christmeas". They are out of the way, but Sturbridge Village has displays on old timey Christmas customs, the Newport Mansions give you a taste of a Victorian Christmas, and La Salette Shrine in Attleboro is covered with lights.

Yes, there will be lots of commercialism and shopping.
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Old 11-21-2013, 01:31 PM
 
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Although I think Boston is a great vacation spot, I am concerned that if you are not used to the cold then you will not fully enjoy your trip. Or at least your wife will not. Let's face it, the end of December time frame is really cold and it would be difficult to enjoy the best of Boston that is best discovered walking on foot for substantial periods of time - that's the type of town it is. With the exception of winter, Boston would be great in the summer, spring or fall but I'm not sure about the dead of winter for folks that aren't used to it or detest the cold.
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Old 11-21-2013, 01:35 PM
 
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Originally Posted by Dm84 View Post
Almost every Chinese restaurant is open on Christmas...

The Golden Temple is a Christmas staple of mine.
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Old 11-21-2013, 01:54 PM
 
Location: Massachusetts
7,074 posts, read 10,820,593 times
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Originally Posted by johnathanc View Post
Although I think Boston is a great vacation spot, I am concerned that if you are not used to the cold then you will not fully enjoy your trip. Or at least your wife will not. Let's face it, the end of December time frame is really cold and it would be difficult to enjoy the best of Boston that is best discovered walking on foot for substantial periods of time - that's the type of town it is. With the exception of winter, Boston would be great in the summer, spring or fall but I'm not sure about the dead of winter for folks that aren't used to it or detest the cold.
Agree with this. If your wife doesn't like the cold, she won't like it.

Come in the spring.
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Old 11-22-2013, 03:49 PM
 
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Quote:
Originally Posted by Dm84 View Post
Almost every Chinese restaurant is open on Christmas...
Not quite as bad as London during Christmas week.
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