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Top 30 Destinations by Personality Type
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Boston, Massachusetts


Great Destination:


Value for Money:


Total Stars:


Personality Types that Like it Best

Because of history, Centric-Venturers and Centric-Authentics rate it highly but also appreciated by Mid-Authentics

Did you know…?

  • The Boston Marathon, mother of all city marathons, was first run in 1897 with 15 racers.
  • Boston hosted the first baseball World Series (Boston Pilgrims vs. the Pittsburgh Pirates) in 1903.
  • The African Meeting House was the first church built by free blacks in the U.S. (1806).
  • Boston has the moniker Beantown from the beans-and-molasses combo that is a local staple.
  • It’s a myth that the city’s streets were built atop cow paths; it just seems that way.

Beantown: From traditional to not really

In Boston, tradition and history sit comfortably cheek by jowl with liberal politics — so much so that any visitor will feel welcome, with the possible exception of vocal New York Yankees fans.

Once the home of staid hotels and set-in-their-ways restaurants, the city now boasts hot new chefs, cutting-edge eateries plus revitalized theater options. Shopping has become fun, too, with a mix of high-end, boutique and mass-market choices. Best of all, Boston offers distinct neighborhoods to explore, from the European charm of the North End, the once-depressed but now trendy South End and the always stately Beacon Hill. Even cruise ships are calling in Beantown with some regularity.

Boston is the unofficial capital of New England as well as the official capital of Massachusetts. Settled in 1630, the city is one of the country’s oldest, and visitors will feel that history in its narrow, twisted streets and lovingly preserved architecture. Its parks add to the charm, most notably the legendary Boston Common and its adjacent Public Gardens, both part of the so-called Emerald Necklace of parks that loop around the city.

Originating as an important seafaring city, Boston has always benefited from the influx of trade and immigrant cultures. Boston also is one of the world’s foremost cities of higher learning. There are some 100 colleges and universities in the city or environs, and the jewel in the crown, Harvard University, is the nation’s oldest (1636) institution of higher learning.

As with any city teeming with students, Boston and its environs have movie theaters showing independent films, talented musicians playing in the subways and vintage clothing shops and used bookstores vying for space amid the city’s more mainstream life.

All but the bravest should avoid driving in the city as the layout of the streets is incomprehensible and local drivers are renowned scofflaws; a robust public transportation system is a reliable solution. Boston is a great walking city, as well, particularly in the warm-weather months, thanks to the intimate size of its historic center and proliferation of resting spots.

Things to do for Venturers:

  • Visit in winter. Some of Boston’s best festivals take place in the snow, including the Festival of Lights and the Prudential Tree Lighting in December and First Night on New Year’s Eve.
  • Rent rollerblades for blading or jog along the Esplanade that flanks the Charles River, which also offers boating or ice skating, depending on season.
  • Love to ski? Within an hour-and-a-half of your hotel, there are several ski resorts offering both downhill and cross-country skiing.
  • Strap on ice skates and practice figure eights at the Frog Pond public skating rink in the Boston Common, or cross the bridge to Harvard Square for outdoor skating at the new rink at the Charles Hotel.
  • Take in a dose of foreign cinema at the annual Boston French Film Festival, held every July at Boston’s Museum of Fine Arts.
  • Kick up your heels at one of the nightclubs and bars that line the city’s famous  Lansdowne Street.

Things to do for Centrics

  • Walk the Freedom Trail, a 2 1/2-mile brick path that stops at 18 historic sites, or join a guided tour, where costumed actors spice up the history lesson with humorous patter.
  • Ply the smooth waters of the Public Garden lagoon in a classic Swan Boat, which offers 15-minute rides daily in summer.
  • Save your appetite for a foray into the International Marketplace food hall at Quincy Market, where stalls selling everything from clam chowder to chicken satay will assault your senses.
  • Stake out your spot on the lawn at the Hatch Shell concert stage on the Esplanade for a free summer concert or outdoor movie.
  • Spend the day exploring the U.S.S. Constitution — aka Old Ironsides — at the Charlestown Navy Yard at Bunker Hill Pavilion, accessible via water shuttle from the New England Aquarium.
  • Learn about one of Boston’s favorite sons at the John F. Kennedy Library and Museum, where multimedia exhibits include a re-creation of the Oval Office and examples of Jackie Kennedy’s clothes.

Things to do for Authentics

  • Splurge on a ticket to a Boston Red Sox game at Fenway Park, otherwise known as the Green Monster, and see if lightning strikes twice in the same century.
  • Relive the children’s classic “Make Way for Ducklings” by Robert McCloskey at the Public Garden, where bronze statues of the ducklings are usually crawling with young fans of the book.
  • Search for hard-to-find books or CDs at the Harvard Coop on Massachusetts Avenue (make that Mass Ave if you want to be understood by locals) or poke around among the kids’ books at Curious George Goes to Wordsworth in Harvard Square.
  • Indulge in a milk shake — it’s a frappe in Boston — at J.P. Licks ice creamery, a repeat Best of Boston winner.
  • Take in the best views of the city from the John Hancock Observatory in Copley Square.
  • Shop for fresh fruit and vegetables at Haymarket, the city’s largest outdoor market, on Fridays and Saturdays; top off the outing with a cappuccino at a cafe in the historic North End.

Additional Resources

For more information, consult the Greater Boston Convention and Visitors Bureau at