Should I visit Boston in January?

I just booked the Hilton in downtown Albany for a similar price for around Christmas time. It’s extremely well-located, being practically across the street from the Capitol, but I also suspect that few people will be travelling on government-related business during the holidays.

Yeah, I can often get a suite at State House Inn in Springfield, Illinois for almost nothing when there’s nothing going on with the government. Great location for tourists.

I would think that would be the heart of business travel season but maybe the MLK holiday has helped plus whatever Wyndham discounts I get.

No, Boston has a ton of hotel space, that goes largely unused in winter. The tourists completely dry up by Thanksgiving/end of leaf peeping season, and conventions and the like get a lot more traction going someplace warm. So whatever leftover business travel there is doesn’t come anywhere near filling the hotels.

The Westin Waterfront gets filled up because both the New England Auto Show at the Convention Center next door and Arisia at the Hotel itself, but other area hotels have plenty of vacancy.

Here’s a listing of Jauary events and hotels:

Ah ok, I know Chicago still gets tons of convention business in winter even with the awful weather. But, I imagine its location, two airports, and convention facilities outweigh the lousy weather.

Of course nothing can top Vegas on summer weekdays where you can stay on the Strip for low double digits.

And pay a $50 per day resort fee for a newspaper and free local calls! I love Vegas but the resort fees are nonsense.

Since you mentioned theatre, here are some plays from companies of various sizes that are running in your time frame:

https://www.huntingtontheatre.org/season/2019-2020/we-all-fall-down/

https://www.lyricstage.com/productions/the-cake/
http://freshinktheatre.org/2019-2020-season

Why does the MBTA make things so complicated? Taxi driver unions?

From what I understand I need to take shuttle from Logan to ‘Airport Station’ and then take the Blue Line to my hotel. Now, why are there separate fares for the Charlie Card and the Charlie ticket? Why can’t I just buy the card at any T station? I’ll assume they don’t allow you to just use a contactless card to pay fares.

The T isn’t really that complicated, just not connected to the airport all that well. There’s another way to get to your hotel that may be easier. Take the Silver Line (glorified buses) that pick up at each terminal, and will take you to South Station. Walk downstairs and take the Red line to Charles/MGH, which is about the same walking distance to the hotel as the Blue line Bowdoin stop. So, only one transfer.

Charlie Cards are intended for long term use and are plastic; Charlie tickets are paper and just for a short term use and cost a bit more. It’s a way to soak the tourists and infrequent riders.