Day 1: The Freedom Trail
If you happen to be staying near the South End, To Go Bakery (314 Shawmut Ave; 617-482-1015; $3-7) is the spot for breakfast, packing in a host of regulars on their way to the many businesses, shops, and art galleries in the neighborhood. Stop in for fresh coffee or a yummy homemade muffin.
Sightseeing in Boston begins, but certainly does not end, with its history. Any visit should begin with a stroll through Boston Common, the country's first park, where the "redcoats" used to train and where farmers once brought their cattle to graze. It's also here where The Freedom Trail begins, on which the most important sites of Colonial and pre-Revolutionary history are located: The State House, The Boston Massacre Site, Old North Church, and the Bunker Hill Monument are among the most salient stops.
Not to be neglected is the Black Heritage Trail, a 20-block walk celebrating the history of Boston's African-American community. The trail begins at the African Meeting House at 8 Smith Court, the oldest black church building still standing in the United States.
For lunch, head down to the Quincy Market/Faneuil Hall complex (downtown, between Clinton and Chatham Streets), which was one of the first successful urban renewal projects in the country. Since then, its model has been copied so much that even this original seems generic: outdoor market with brick streets lined with Banana Republics, food stalls, banners, and bee lights -- you get the picture. It's fun for visitors, though, and worth a stop if you've got the munchies. Quincy Market has an endless variety and quantity of food, from fresh lobster to chicken enchiladas.
Closer the center of gay life in the South End sits Hamersley's Bistro (553 Tremont St; 617-423-2700; $24-37), which has been around for years, but stays at the forefront under the hand of celebrity chef Gordon Hamersley. Diners are treated to an ever-changing seasonal menu that features items like walnut-and-potato-crusted Arctic char with braised endive and celery root puree. The simple but sensational roast chicken entree is some seriously fine comfort grub, and the patio takes over a cozy corner that's ripe for people-watching.
If you have a hankering to head out afterwards, Machine (1254 Boylston St; 617-536-1950) offers a wide range of elaborately themed parties and events throughout the week, making it a great place for dancing, cruising, and watching videos nearly every night. Carved from the underbelly of Ramrod, Machine has steadily brought energy and a much-needed jolt to Boston's somewhat anemic club scene over the years. The club attracts mostly men but also a significant portion of women with ultramodern decor, several long bars, a huge dance floor, a cool video/light show, hot dancers and lots of space to move around. Upstairs, the Boston Ramrod (1254 Boylston St; 617-266-2986) is still the most popular leather/Levi's bar, with spectators welcomed.
The back bar dress code requires boots -- and Ramrod can be so strict about enforcing this rule that even guys with 17-inch biceps get turned away if their feet are shod with sneakers. On Saturday nights, either a significant article of leather clothing or a bare chest is also required (see Ramrod's website for an extensive description of the dress code).
Day 2: The North End
The North End, a densely woven, colonial-era neighborhood most famous for its Old North Church (193 Salem Street), where Paul Revere saw the "two if by sea" lanterns hanging in the steeple, is home to generations of Italian-Americans and, no surprise, some of the best restaurants and caf?s in the city. Buy a pastachotti (a delicious custard-filled pastry) from one of the many bakeries along Hanover Street, and wind your way through the narrow, twisting streets. Don't miss Blackstone Block, named after Boston's first settler, William Blaxton (or Blackstone).
On Blackstone Street, you'll find an outdoor produce market on Fridays and Saturdays. The North End has become less Italian and more yuppie over the years, but it remains a wonderfully atmospheric neighborhood for a stroll.
Boston's young and wealthy converge at Via Matta (79 Park Plaza, 617-422-0008; $16-30), which has a svelte boxy design that makes it ideal for power-flirting during lunch, brunch or dinner. A new patio spills onto the sidewalk overlooking the Park Plaza Hotel for those who wish to be seen sipping a Mimosa's a la belle etoile.
Nearby and loveably divey and campy, Jacques Cabaret (79 Broadway St, 617-426-8902) has been Boston's capital of drag for generations -- it features the scintillating Trani-Wreckage show every other Monday. The place puts on two shows and closes nightly at midnight, so be sure to arrive promptly to see the show.