Guided Tours

Taking advantage of Boston’s [1] reputation as a “walking city,” Boston By Foot (77 North Washington St., 617/367-2345 or 617/367-3766 for recorded information, www.bostonbyfoot.com [2], $12 adults, $8 children 6–12) offers architectural and history tours of several Boston neighborhoods, including Beacon Hill [3], the Back Bay [4], and the North End [5].

Boston By Foot also offers tours of the Freedom Trail [6] for children, and a unique Boston Underground tour that explores closed-off subway tunnels and the construction of the Big Dig.

Boston Trolley Tours

In 1898, Boston [1] produced the first subway in America. Since then, the city’s tourism industry has done seemingly everything in its power to twist that form of transportation into as many silly (albeit often quite fun) ways to see the town as possible. Here are the most popular:

Boston Upper Deck Trolley Tours: If it looks like there’s a party going on inside these trolleys as they roll down the street, it’s probably because there is. They come equipped with everything from strobe lights and disco balls to plasma TVs, bubble machines, and wireless microphones (departing from Long Wharf, 617/742-1440, www.discoverbostontours.com [7]).

Duck Tours: A full fleet of authentic WWI amphibious vehicles have been converted into “ducks” that take passengers on a narrated tour of the city’s streets and the Charles River, encouraging them to “quack” throughout the tour (departing from the Prudential Center and the Museum of Science, 617/267-3825, www.bostonducktours.com [8]).

Beantown Trolley: These trackless trolleys stop at upwards of 20 major Boston [1] museums and attractions, and allow passengers to take as many round-trips in a day as they like (800/343-1328, website [9]).

Silver Trolley Tours: The one-hour, narrated tour aboard silver trolleys made in Maine come complete with DVD players, air-ride suspension for comfort, and free tickets to either the Sports Museum (year-round) or a Boston Harbor Cruise (in summer). Children under 12 ride free (departing from various locations, 617/363-7899, www.cityviewtrolleys.com [10]).

Boston Harbor Tours

No matter how many tours visitors to Boston [1] go on, many miss seeing the city from one very important angle: the ocean. Viewed from in and around the harbor, the city’s skyline is not only immense, but astoundingly peaceful, and offers an entirely new perspective and sense of place.

To that end, there are a number of ways of getting out on the harbor that don’t require a private charter. One of the easiest means is the Lighthouse Cruises offered by Boston Harbor Cruises (departing from Long Wharf, 617/227-4321, www.bostonharborcruises.com [11]). The voyages last five hours, are narrated by members of the American Lighthouse Foundation, and pass numerous lighthouses—including Boston Light, the oldest lighthouse station in America, and Thacher Island, the only operational twin lighthouses in the country.

Rather do your wining and dining offshore? Spirit of Boston dancing and dinner cruises (departing from World Trade Center, 617/748-1450,www.spiritofboston.com) lays out candlelit tables, an enormous buffet, and live music on its enormous boat.

Likewise, the huge dinner cruises offered by Odyssey Cruises (departing from Rowes Wharf, 866/307-2469, www.odysseycruises.com [12]) play everything from live jazz to pop dance tunes while you dig into dinner and take in the ever-changing water view.

On a more hands-on note, passengers are encouraged to participate in sailing when they cruise aboard the schooners Liberty or Liberty Clipper (depart Long Wharf, 617/742-1422, www.libertyfleet.com/ [13])—replicas of early-1800s schooners used by New England fishermen.