FYI. In Boston it's not called "Little Italy", it's called the North End.

Just returned from 8 days in Boston. Great town for vacation! Absolutely unbelievable for driving. Don't drive in Boston unless you are a NASCAR-sanctioned driver.

Consider parking at the Boston Common garage. Walking distance to the hotel after dropping off the luggage and much cheaper than the Pru.

I have to agree on the signage thing. We had great maps, excellent written directions, and a good sense of where we were going, but got messed up by
1)missing signs,
2) signs posted too late to be of use,
3) signs with directional arrows that were too early -another street went in the direction of the arrow before the correct one- or
4) the arrow pointed hard 90'right, when our street was the one going 45" right.

Took us hours just to find our car drop off near the aquarium!

I've lived in a suburb of Boston for over 20 years, and I still get lost evertime I drive into downtown Boston. For the most part, signs are only on cross-streets, never on the street you are driving on. If you want to know the name of the street you are driving on, there are only 2 ways of doing this:

1. Note the names of a few cross streets. Then look at a map to see which through-streets they have in common. Then try to figure out which of the through-streets it is you are driving on.

2. Stop a pedestrian and ASK. This is by far the easiest method, assuming you can find a pedestrian who knows the name of the street :)

To make the situation even more difficult, most downtown streets are one-way, and they do not alternate directions. If you want to drive in the opposite direction, you cannot expect to just go around the corner to find traffic going in the direction you want.

I just want to second the suggestion to park near your hotel, at the Pru or another lot--please forget about trying to leave your car in some outlying T station!! That sounds like a total hassle to me, especially with kids and luggage. I live in a close-in suburb and drive into Boston all the time to go to the museums, aquarium, etc. with my kids. The only place I get lost (and I ALWAYS get lost there) is around the aquarium, because they keep changing the roads and signs due to Big Dig construction. But Back Bay is really no problem, especially as you're staying so close to the Mass Pike. I also think it would be great, if you have time, to get out of the city a bit, so having the car nearby would be a plus.

Just don't worry about it and have a great time!

I've lived in near every neighborhood of Boston (still do), including Back Bay. The Lenox is super easy to get to from the Pike.
For your reference, the cheapest parking lot near the Lenox is 3 blocks away on Dalton Street. Because there is a Sox game that day, it may very well be full, or you may get lucky with a spot. Or, Sunday meters are free. You can drive around to find a spot at a meter (avoid resident only spots, clearly marked) until later that evening and move the car to the garage that night or even early the next morning.
While Boston is not anywhere near as easy as driving in Manhattan, Back Bay does work like a grid. Instead of numbers (52nd street, 6th Ave, etc) the streets go by alphabet, and they are all one way streets that switch by the block. The Lenox is at the corner of Boylson and Exeter Streets, so you can drive down Boylston, turn left down Dartmouth, turn left down Newbury, go a couple blocks, turn left down Gloucester, and left again on Boylston to try and find a meter.
I agree that if you have a lot of luggage, parking at Riverside and T-ing it in doesn't really make sense. I'd personally feel more comfortable with my car in a garage rather than an open commuter lot. But that's just me =D
As for departing Boston from the garage, it's so simple. The on-ramp to get onto the Pike Westbound is a mere 3ish blocks away.

I have not read all the responses, but did you think of having to get from the BackBay Station to the Lenox. Its a pain to walk with your bags, but so closed for a cab ride.

Drive Drive Drive. It can be such an adventure. And to think , you know the language of the locals! Well, you can practice that Boston accent while "paakin da ca" :)

My daughter lives in Boston. She had a car that we parked in an Avis garage near symphony hall. I think it was on Westland avenue. You could look up Avis locations. It cost $10 a day. It is a very safe place and your car would be taken care of. You could leave it there on a long term basis and were also able to check it out if you wanted the car for any reason. This is not too far from the Lenox. It is walking distance. Boston is a very walkable town. The T is great. You don't need a car in town. Driving in town on a Sunday should not be a problem.

No one has asked this so I will.

If the company wants you to come to a conference and would have paid for your airfare to get there, won't they pick up the parking fee and/or mileage allowances?

The Lenox's website gives you directions to the hotel http://www.lenoxhotel.com/travel/index.htm and says that it's $38/day to park at the Pru Center Garage. If you're worried if parking will be available, have the valet park the car when you arrive,(then you're assured of a spot), tell him you want to get the car later, then park it yourself when the Sox fans leave town at the other less expensive garage recommended above. No worries about luggage or bears on the T.

At the Pru garage, you're charge all day after the first 5-6 hrs (don't exactly remember details). If you do this, you're better off just parking there for the whole 1st day and move to a cheaper lot afterwards.

Now that your trip has ended, how did the whole parking thing work out? And, of course, did you have a good time in Boston?? (Altho depending on your drive time back, you may still be in transit??) :)