Hi there,

The IC hotel is at a pretty good location. Can you just stay there for the other 2 nights? Otherwise, I'd look into any of the Back Bay hotels as those are near Newbury Street & Copley Place/Prudential where you can shop till you drop.

As for tours, probably the DUCK tour will be best as it goes on land as well as into the water. I think it still runs in mid-October.

P.S. Not sure what you mean by "unique" for Sunday brunch? Can you elaborate? Otherwise, I think dim sum in Chinatown is pretty unique...

As for romantic dinner places, I like Erbaluce in Bay Village. It's Italian though...

HTH

Sincerely, I have no idea how to define 'sophisticated' in regards to you or nightlife or lodging.

To me a sophisticated jazz fan would end up in a dive bar with a killer lineup that night rather then the predictable high priced high end more elegant jazz spots.

As far as lodging? What is sophisticated after Intercontinental which is fabulous and a lovely location? I could suggest the 4S or the Mandarin. I could suggest the W or I could suggest a little boutique hotel/b&b.

Unique Brunch? One of the grande hotel buffets? East Coast Grille? Pajama brunch at 247 Tremont? Elbowing up with the sophisticated brahmin at Paramount on Charles? Or scarfing down foodtruck offerings at the Sunday SoHo market followed by a Bloody Mary at one of the many Southend Sunday morning hot spots?

So you see, I have no real advice for you.

Romantic dinner? Sharing a burger and a ceasar salad on a sofa in the Bristol Lounge.

At the IC you are very close to Chinatown. Definitely dim sum for brunch, unless you live in NY or SF.

Jazz and French food at Les Zygomates in the Leather District, also near your hotel.

L'Espalier for a romantic dinner? Clio? Both in the Back Bay. XV Beacon? The restaurant at the MFA?

For lunch or a more casual dinner, Petit Robert Central in Downtown Crossing, only a few blocks from you.

More adventurous? I am exploring Allston these days. Pretty interesting Asian food there if you can stand the undergraduates.

Wherever you decide to stay I suggest you book immediately as I'm finding there's not a lot of availability in mid to late October.
I have a friend visiting and I thought it might be fun to spend an overnight in Boston but the hotel rates are way too high and I can't find any availability to book with hotel points!

You might like the Beehive for music and/or dinner: http://www.beehiveboston.com/

The Seaport area will be new to you--there is a three floor Legal Seafood with great harbor views, and quite a few other restaurants available. The Institute of Contemporary Art is located there as well. Both the Museum of Fine Arts and the Gardner Museum have new wings that are pretty fabulous, if that interests you.

Also check out Island Creek Oyster Bar and Eastern Standard, both in Kenmore Square.

Do make reservations for restaurants. October is a busy time in Boston.

I also like Mooo in the XV Beacon Hotel. It's a steak house mainly. And Oceanaire for seafood. Those two are more "romantic" than some of the other restaurants.

I like the Italian food at Via Matta, but I wouldn't say it was quiet and romantic. And you have the whole North End for Italian restaurants as well. Trade, quite near your hotel, is a busy restaurant. I like the food but it can be quite loud. Maybe a good place for lunch.

As a matter of curiosity, which dim sum restaurants are considered "good" places to go in Boston Chinatown?

sassy-cat: Have you ever used airbnb? Try that and make sure to select a place with several reviews. The reviews really help a great deal.

easytraveler, none of the dim sum places in Boston can measure up to the ones in San Francisco (well, south bay area I guess). I like Winsor Dim Sum cafe, but it's pretty small and no cart service. For cart service, Hei La Moon is okay but on my most recent visit, I get major food coma/headache afterwards which usually indicates MSG in the food (but I never had that problem in the past when we ate at Hei La Moon...)

yk, thanks for the names of the Dim Sum places. Well, I usually don't come East for Asian food, more for Italian and other European foods.

I was just reading about Mission Chinese Food in New York and how they're mobbed, so I had to read up on the original one in San Francisco, since I'd never heard of this restaurant. Sounds like dishwater really spiced up. But you never know what other people will like.

Thanks again!