Downtown Boston is filled with buildings erected in an age when no architect would dream of designing a building without decorative friezes, elaborate scrollwork or statues and gargoyles.
Today, they are all the more delightful because you don't expect them. You're walking down Washington Street near Filenes when, who knows, a glint of light catches your eye and you look up - to see a series of gargoyles looking down at you from their precarious perches.
One of the more amazing doorways in the city is to a building on Stuart Street at Berkeley Street. It was once the headquarters of Salada Tea (what is now the Grill 23 restaurant used to be a room where clerks made out orders for large volumes of tea). Today, Salada is long gone, but the bronze and stone friezes of elephants and ships, boxes of tea and tea farmers remain, a memorial to the day when Boston clippers were the fastest way to China.
One of the best places to enjoy these details is Downtown Crossing and the neighboring financial district. Go down on a Sunday, when, at least in the Financial District, you've pretty much got the place to yourself.

Cambridge/Harvard Square

It's not just that it's surrounded by the historic buildings of Harvard University. Or that it has more book stores per square block than any other place in America. Or that you get to see more unusual haircuts than anywhere else in greater Boston.
Harvard Square is unique because it is all those things - and more. It is the unique mixing - the tweedy profs with pipes side-by-side with the skate punks down by the Pit.
Recent years have seen the Square become something of an overgrown Anymall, U.S.A., as the local stores get bought out and replaced (nice to have known ya, Tasty!). But there are still plenty of unique things about the Square, from Cardullo's imported foods to the serious chessplayers outside Au Bon Pain. Equally important, Harvard Square rivals Quincy Market as the outdoor entertainment capital of Massachusetts. On your average spring or summer day, there's music for every taste - from folk to Inca to classical. And rare is the day there isn't some guy on a unicycle - or juggling flaming bowling pins across from Wordsworth.
And bookstores! There are women's bookstores and children's bookstores; foreign-language and science-fiction bookstores. You can look down and see bookstores in basements or look up and see bookstores on second floors. And, yes, in a district hard by Harvard, there are stores that sell textbooks.
And what of dear old Harvard? It's everywhere (it even owns many of the buildings in the Square) - so you might as well not try to ignore it. Walk the ivied Harvard Yard. Pat John Harvard's shoe (fun fact: nobody knows what he really looked like, so the face on his statue is really that of a friend of sculptor Daniel Chester French). Take a tour of the various Harvard museums (Glass Flowers, anyone?). You'll feel smarter in no time (just remember, you can always tell a Harvard man - you just can't tell him much).

Quincy Market/Faneuil Hall

Today, "festival markets" are a dime a dozen - every city, it seems, has a collection of old brick buildings turned into chic little stores and endless restaurants. But the one that blazed the path was Boston's Quincy Market. Back in the mid-1960s, James Rouse, then a city planner, had a revolutionary idea: Instead of abandoning downtown to decay, why not build a fun marketplace that would not only attract tourists, but keep workers downtown after dark.
Fortunately, Boston already had a set of buildings almost perfectly designed for that: Faneuil Hall and Quincy Market. The former, built in 1742 as a wholesale market, also has a large meeting hall upstairs - where ol' Sam Adams inspired (or inflamed, depending on your point of view) the locals into taking up arms against the crown. When Boston began growing rapidly in the 1800s, it built Quincy Market to provide additional market space.
Today, Quincy Market is the most visited tourist destination in Boston. It's changed over the years - it's a bit less Boston, a bit more Anymall, U.S.A. (with both Warner Bros. and Disney stores). But don't worry - it's still very much the vibrant place. There are street performers and zillions of people. And you'll still find more lobster items (from candy lobsters to lobster T-shirts to stuffed toy lobsters) than anywhere else in the world.

The North End

If Boston is the most European of American cities, then the North End is Boston's most European of neighborhoods.
Walk along its narrow, curving streets and catch quick glances of hidden courtyards and flower-bedecked fire escapes. Listen to the animated Italian conversations of the retired gentlemen sitting outside the Caffe dello Sport. And breathe in the scent of the nearby sea - when you're not taking in the scent of garlic or olive oil from the seemingly inexhaustible supply of restaurants.
The North End has always been a European community. For decades, immigrants from Europe have found a home here - just beyond the docks and just down the winding streets that followed the curve of the ever expanding shoreline. First the Irish, then the Jews, today the Italians.
And like previous groups, the Italians have retained many of the customs of their homeland. One of those is the hosting of festivals to honor the patron saints of the towns from which they or their ancestors came. On more than a dozen weekends, various societies honor the saints with Masses, processions, food and music. The festival for St. Agrippina di Mineo is an example. For several hours, men with some muscles carry a one-ton statue of the saint (martyred after resisting the advances of the Emperor Valerion), bedecked with dollar bills, around the neighborhood. They stop frequently at other saint's societies, churches and the like. Meanwhile, a street fair takes over a good part of Hanover Street.

The South End

The South End is a neighborhood of Boston about one square mile in area with about 35,000 residents. It straddles Washington Street, Boston's main north-south street and includes two other main north-south streets: Tremont Street and Columbus Avenue and one main east-west street: Massachusetts Avenue. The South End contains the largest collection of original Victorian bowfront rowhouses anywhere in the U.S. and was listed on the National Register of Historic Places in 1973.
The South End (aka, Southie) has always been known for it’s large population of Irish Catholics. This is also where the infamous St Patrick’s Day parade takes place. Nowadays, it’s a bit on the scummy side, though it’s historical value is still high.