On Tuesday, I'm taking a trip to Boston with the American Teachers History Collaborative. I'll be staying at the Omni Parker House Hotel with about 40 other teachers. While there we already have planned to see Lexington and Concord, USS Consititution, Lowell Mills, and Plimoth Plantation. Tuesday is a travel day and I'm attending the Red Sox game that evening. My evenings are designated for free time, as is all day Saturday and Sunday morning before I return home. I'm looking for suggestions for evenings out/dinner, and what sight seeing you would recommend for Saturday. I'm leaning towards the Freedom Trail Walk, JFK Library, Tall Ships, Trinity Church, and Samuel Adams Brewery Tour, but am open for suggestions to lessen known "authentic" experiences. Thanks!

Try taking a stroll through the North End......Great Italian restaurants

The Brown Sugar Cafe on BU's campus is the best Thai restaurant I have ever set foot in.

If you like lobster, Tia's had a $24.99 twin lobster special a few weeks ago. I'm assuming they are still doing it. They were excellent. It is outside the Marriott long wharf.

+1 on the North End.  

I know that Italian restaurants are ubiquitous throughout the US but the area around Hanover Street in Boston has some of the most wonderful tiny places that will really make you a memorable meal.  Some of these places only have 15 chairs in them.  Shy away from the bigger places with large signage.  Go to one where the chef is in plain sight.  And, after a great meal and terrific wine, wander over to any one of the bakeries for dessert and espresso.  A great way for all that food to get settled leaving just enough room for a freshly made treat!  Then, wander back across the 'green' and window shop in Faneuil Hall area.  Its lots of fun and you'll enjoy the quaintness of old Boston.  

If you're there on a weekend, you'll also see the open air market.  It's quite a place.

BTW, I always send people to see the Granary Cemetery.  If you do the Freedom Walk, however, it will be one of the stops.

Rome

I'm not in Boston too often but whenver I am the woman insists on going to Vinnie Testa's. Pretty good

One of the best places I've ever eaten at was in the Chinatown section.  No idea what it was called.  Big wall of fishtanks.  You picked, they cooked.  I can't even remember what train we took.   25bucks on a geoduct clam.  These GIANT prawns, blackfish, chickenfeet, dimsum, Gallons of sake,    Went to a bar called Mr Wedgies (also in chinatown).  Not very friendly.   Found out a few days later their was a big gunfight in that area with two rival gangs.   I'd still go back for that clam though.

If you want seafood, eat at Legal Seafoods.  Really GREAT at upper midrange pricing.

I second that. Legal Sea Food.

Yeah they are. I won a $50 gift certificate there on a date once.

Okay, I've got to jump in now.  I've worked in hotels in Downtown Boston for years now and have eaten at MANY restaurants and made many reccomendations.  Our concierge staff keeps up with all the changes and can tell you where to go to get the best of whatever type of cuisine you want.  Now there's nothing wrong with chains like Legal Sea Foods or Vinny Testa's (we call them Vinnie's Testes) but if you're visiting from another region of the country do you really want to dine at a fairly generic chain?  DON'T DO IT!!!


Italian-

Follow a previous poster's advice and walk through the North End.  It is the best Little Italy in the country.  Yeah, some doof will come here shortly and tell you NY< NY but have you been there lately?  It's been over run by their China Town.  Our North End is still an Italian neighborhood and almost all of the restaurants are fantastic.  Just stroll around and look at the menus on display and choose a mom and pop place of your liking.  You won't go wrong.  My personal favorite is Artu on Prince Street but again, most are very good.


Chinese-

Go to China Town and try either Peach Farm or New Golden Gate.  Fantastic authentic Chinese, especially the seafood offerings.  I'd reccomend asking for a 2-3 lb lobster with ginger and scallions and the clams with black bean sauce.  You won't be disappointed.


Seafood-

There are many very good places but some of my favorites are Kingfish Hall, Atlantic Fish Company, and especially B&G Oysters.  There are many, many other good ones in all price ranges.


Steak

Wrong city but there are a few good ones.  Mostly high end chains though like Morton's, The Palm, Smith & Wollensky, Capital Grill, Abe and Loui's, and my favorite, The Oak Room.


PM me if you have any questions or need directions or whatever.  I'll get back to you with my phone number and put you on with a concierge if you'd like.  

By the way, go on the Harpoon Brewery tour instead of the Sam Adams tour.  Both are good but the Sam Adams brewery is in a shitty part of town while Harpoon is in the Seaport District, much closer to downtown and much safer.

#9 Park is a great place. Expensive but worth it if you want top notch contemporary american cuisine.