Hi Eunice,

Where in the city will you be staying? Are you looking for can't miss culinary experiences or more Boston experiences?

Here are a few of my favs. I'd say Toro and Legal Harborside are not to be missed - Toro for the food and Legal for the atmosphere! Tip Tap Room is an really good local every day sort of place.

Legal Harborside-Floor 1 & Marketa modern flagship restaurant from Legal Seafood. It's on Boston Harbor in the Seaport District which is a recently developed area. The first floor is casual and has traditional legal dishes, a raw bar, and new menu additions. I love the big bowl salad with lobster meat. You could grab beers at the Harpoon Brewery Beer Hall down the street before dinner!

Toro best tapas in Boston! A tiny restaurant on Washington Street in the South End. All of Ken Oringer's restaurants are amazing but this one stands out. The corn on the cob is the best :) Beware, it can get very expensive cause those tapas add up and they don't take reservations, so you may have to wait up to 2 hours!

The Tip Tap Room Trying to think of someplace less expensive but still great food and environment ;) Tip Tap Room on Cambridge Street in Beacon Hill came to mind! The theme is 'tips' (steak, turkey, fish, other crazy specials) and 'taps' (beer). The food is really good and it has big open windows on nice days.

1) For delicious fancy French food, head on over to Mistral on 223 Columbus Ave in Boston. I was really surprise on the large portions. 

2) For the best view, try Top of the Hub on Bolylston st in Boston. Food isn't that great though unfortunately. 

3) For something fun, I like having hot pot in Chinatown. Shabu Zen is the one I usually go to, but any place is good.

Hello again Eunice! Places that should not be missed during your stay in Boston:

• Mike's Pastry in the North End (Little Italy) for fantastic cannolis
  
• Faneuil Hall Marketplace is the most visited attraction in Boston, lots of small eateries and shops
  
• Boston Common for a nice springtime stroll
  
• Samuel Adams Brewery Co it offers a free tour of the brewery and is a well-beloved Boston drink
  
• Newbury Street for window shopping or actual shopping
  
• Top of the Hub is a bar at the top of the Prudential Center where you can see a 360 degree view of Boston
  

Ask me if you need any other places! There are so many wonderful things to do, I'm sure your boyfriend will take good care of you ;)

Boston is known for its seafood, oysters are very popular so try  Row 34 in Ft Point Channel.

A great neighborhood gem for authentic Northern Italian food is Erbaluce  in the Backbay.

Toro in South End has Spanish tapas, it is fun place to hang out. 

Eunice - An old tradition in Boston would have to be Durgin-Park in Faneuil Hall Marketplace. You can get New England Corned Beef and Cabbage, Yankee Pot Roast along with fish chowder.

Union Oyster House - oldest restaurant in Boston will definitely give you a sense of the tradition

Dont miss to visit Quincy Market and you will enjoy the best clam chowder in town!!

For seafood - Neptune Oyster or for Italian Rino's in East Boston or Trattoria Il Panino in the North End.

if you're a baseball fan then the Bleacher Bar is great! Food is okay but you can sit near a window and look onto Fenway Park! Different rules apply when Red Sox games are playing so check before going.   

I actually live in Boston (grew up in Detroit).
Here are some of my favorites, with $ symbolizing price:

Stephanie's: Great "meal" salads and great food. $$–$$$    (Nice outdoor seating on Newbury St. for people-watching)

Agree with Legal Sea Foods for seafood and view. $$ - $$$

L'Espalier on Boylston Street if you are really splurging. Artistic fine cuisine. $$$$

Clio Restaurant for sushi (near Mass Ave/Comm Ave intersection) $$–$$$

For the North End:
Mamma Mia's Restaurant & Pizzeria is the best, but upscale and pricey ($$$-$$$$)
Carmen(next to the Paul Revere house) is quaint and good ($$$)
Modern Pastry stuffs the cannoli when you order it, but Mike's has more varieties.  ($-$$)
Caffe Vittoriafor a cappuccino after dinner. ($-$$)

For Ice Cream: Toscanini's Ice Cream in Cambridge (near MIT); interesting flavors ($)

Places worth driving to:

J.T. Farnham's in Essex: Seafood chowder to die for and fried clams beat the more well-known Woodman's on a Food Network challenge; nice marsh views and great beaches near by, too. ($$) About 45 min north of Boston.

Best Lobster Roll:
Lobster Trap Restaurant in Bourne (just over the Bourne Bridge on Cape Cod...about 1 hour from Boston). Also have GREAT calamari.

In the city, try Belle Isle Seafood (near the airport).