Boston Trip Planning & Itineraries

Day One: Boston Sightseeing

Freedom's the word in Boston - it's easy to plan your own itinerary with the value-packed Go Boston Card, giving you free entry to 70 of Boston's sights, attractions and tours. Or pick up a Boston CityPass, with discounted entry to Boston's five top attractions: the New England Aquarium, John F. Kennedy Library and Museum or Harvard Museum of Natural History, Museum of Fine Arts, Skywalk Observatory and Museum of Science. And to get around Beantown, jump on the Boston Hop-on Hop-off Trolley Tour - you can hop on and off at any of the 17, centrally located stops as often as you like. Of course, the wackiest way to get around is on a Boston Duck Tour. You get to see all the major landmarks and hear the history of the city as you tour Boston in a renovated World War II amphibious vehicle. And for the total Boston experience, follow in the footsteps of Paul Revere along the "Battle Trail" to Faneuil Hall, Quincy Marketplace and Beacon Hill.

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Day Two: Out and about in Boston

From historic walks and ghostly encounters to leisurely cruises by day or night, there are plenty of ways to get out and about in Boston. First, hit the pavements on a guided Boston walking tour. Follow the Freedom Trail with your camera in hand to capture sights from Boston's colonial era. Explore the exquisite architecture of the city's cosmopolitan Back Bay district or take a guided walk around historic Beacon Hill, an evocative 18th-century neighborhood of charming streets, brick sidewalks lined with gas lamps, hidden houses, and parade of doors and doorknockers. For more history, retrace that famous tea party on a walking tour of Boston's waterfront, or meet ghouls and witches on a nocturnal Ghosts and Gravestones walk with a 17th-century gravedigger. For more leisurely touring, step aboard a Boston sightseeing cruise on the harbor. A romantic dinner cruise is the perfect way to complete a day of sightseeing in Boston.

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Day Three: Day Trips from Boston

Boston is brilliantly positioned for all kinds of day trips, from colonial-era sightseeing to splashing across the water seeking whales. Start your foray into the Boston area's past with a visit to the historic Plimoth Plantation, a fascinating re-creation of 1620s Plymouth, or relive the 1690s witch trials on a day trip to Salem. Boston's Revolutionary story is complete when you visit Lexington and Concord, and there's more recent history at the fabulously opulent mansions and yachts of wealthy Newport. If you're lucky enough to be visiting Boston in Fall, don't miss the spectacular foliage on a visit to Cape Cod or the seasonal colors of New England. And to finally spot that whale, head out on a whale-watching cruise aboard a high-speed catamaran bound for Stellwagen Bank, the East Coast's most famous whale-watching destination.

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Harborside Inn of Boston

Ensconced in a respectfully renovated 19th-century warehouse, this self-proclaimed inn has B&B-style rooms with hotel-style service. Within a stone's throw of Faneuil Hall, the waterfront and the North End, the hotel strikes just the right balance between historic digs and modern conveniences.

Kendall Hotel

What happens when you set an artist and collector loose to remodel the interior of a firehouse-turned-hotel? If you're lucky, something like the hip, eclectic Kendall. When that artist/collector is also a co-owner, she's likely to take more chances on interesting colors, textures and amenities. At the Kendall, it works like a charm.

Copley Square Hotel

It's downright heroic when a fine hotel wins awards for its environmental vision. The Copley Square Hotel has adopted nearly 100 green initiatives, some of which are so simply practical that they border on brilliance. This superlative attention to environmental impact goes hand-in-green-glove when it comes to superior attention to its guests.

Isabella Stewart Gardner Museum

The magnificent Venetian-style palazzo that houses this museum was home to the wealthy lady herself until her death in 1924. A monument to one woman's exquisite taste for acquiring art, the Gardner Museum is filled with almost 2000 priceless objects, including outstanding tapestries, and Italian Renaissance and 17th-century Dutch paintings. The palazzo itself, with a four-story greenhouse courtyard, is a masterpiece, a tranquil oasis worth the price of admission alone.

Commonwealth Museum

Bone up on Boston's history at this newly renovated museum in the iconic Massachusetts State House on Beacon Hill. Interactive exhibits, personal stories, and a high tech theater truly bring the past alive. Highlights include a copy of the Declaration of Independence and Bill of Rights and the copper plate used by Paul Revere to engrave his image of the Boston Massacre.

Museum of Fine Arts

One of the finest collections in the country, noted for its galleries of French Impressionist masterpieces, works by American painters including Sargent and Copely, Japanese pottery and artifacts from ancient Egypt.