The good thing about boston is that it is hard to go wrong here. Problem is, it is very expensive. Unfortunately, I have no experience with hotels as I live off the T (subway). I would probably start looking for hotels in the copley/back bay area, this is the most expensive area of the city, but smack in the middle of everything.
For restaurants, I say Les Zygomates near South Station hands down will fit the occasion perfect (25-30$/plate). They have a room with a live jazz band, or you can sit out in the dining area and hear the band softly. Also, a great afternoon is spent on Newbury street. Only stores and restaurants are there. Plus the duck tours starts ver close by. THey take old WWII U-boats and put wheels on them and tour the city, and also go by water up the charles river. No trip to boston is complete without the north end for italian. Most romantic place to propose. Hundreds of italian restaurants and cafe’s are in this small neighborhood, virtually all are great (try Saraceno’s on Hanover).
A car is not needed in boston. The T reaches every area in boston and cambridge (don’t bother with the house of blues in cambridge, but Harvard Square in cambridge is full of great places). The Seaport area is within a 10 minute walk from downtown as well. In fact, everything in boston is within about 15 minutes of each other, either by train, cab or walking.
Hope this helped!
Thanks guys for all your help and support. I will have more questions later on, just don’t forget to check the board 