Charles River
Charles River / iStock.com / Marcio Silva
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Beacon Hill
Beacon Hill / iStock.com / LUNAMARINA
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Fenway Park
Fenway Park / iStock.com / vivalapenler
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Local Seafood
Local Seafood / iStock.com / VICTOR PELAEZ TORRES
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The Mapparium
The Mapparium / The Mary Baker Eddy Library
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JFK Presidential Library
JFK Presidential Library / iStock.com / Marcio Silva
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The Freedom Trail
The Freedom Trail / iStock.com / SpVVK
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Boston
Our Review
Deal Expert / Travel Blogger

One of the United States' first cities and home to some of the world’s most celebrated universities offers a quaint mix of history and modernism in an easily walkable city. Ships pull into the centrally located seaport area, which just happens to abut the gentrified Southie neighborhood, home to some of Hollywood’s favorite themes.

What We Love

John F. Kennedy Library: Camelot comes alive at the waterfront Presidential Library and Museum dedicated to the short-lived term of the 35th president. See writings, letters, gifts, and even some of Jackie’s famous fashions at the interactive collection. Serious Kennedy-philes will want to check out the adjacent Edward M. Kennedy Institute that celebrates the nearly 50-year senate career of the clan’s youngest son. 

Mapparium: The three-story glass world map circa the mid-1930s was the brainchild of architect Chester Lindsay Churchill. The visit is an all-sensory experience that includes lights, music, and views of the shifting borders of our world.

Best Known For

Freedom Trail: Think of it as the 2.5-mile yellow brick road of our nation’s birth. The brick and cobblestone pathway winds through the city past such important sites as the North Church, Paul Revere’s House, the State House, Boston Common, and the Boston Massacre site.

Fenway Park: There are endless historic churches in town, but the cathedral where all Bostonians worship is home to the “Green Monstah.” Fenway Park is one of the country’s oldest — and most alluring — baseball stadiums. Throughout the year, backstage tours are offered when games aren’t being played.

Who It's Best For

History Buffs: Boston is also home to the country’s first public library (a beauty), the first public school, the first university (none other than Harvard), and one of the most popular bars in TV history. It’s loaded with museums, performance centers, and Colonial architecture a go-go.

Seafoodies: Lobster, chowder, and fish and chips are likely to be found on any menu in town.

Don't Say We Didn't Warn You

Tides Predict Departure Times: Larger ships need more time to maneuver out of the old port. You may be disappointed by the fact that your time in town can be cut short based on the tidal chart.

Leave the Driving to the Locals: The Big Dig (a behemoth road project) concluded years ago, but its shifted lanes and the general “get out of my way, guy” attitudes of local drivers mean renting a car is more of a headache than it's worth. Plus, parking is a challenge.