City Guide to Boston, MA

City Guide to Boston, MA

Planning a trip to Boston, MA is fun but can also get a bit overwhelming since this cosmopolitan city has so much to offer. You can experience delicious Italian dining, catch a baseball game live, take a walking tour and learn about the city’s rich history, enjoy a first-rate concert…and the list goes on. So how do you figure out what to do on your Boston area vacation?

Whether you’ll be taking a Boston trip for the first time or you’re seasoned at Boston travel, you’ll find plenty of inspiration about what to do and see during your upcoming Boston vacation in our city guide below.

Top Things to Do on Boston, Massachusetts Vacation

As one of America’s oldest cities, Boston is a creative hub of culture, art, food and more, boasting a plethora of charming attractions, with something for everyone. Rated as one of the most walkable cities in the country, it’s also a joy to explore by foot with a comfortable crossbody bag or tote bag.

In our Boston travel guide below, discover our top recommendations for what to see when you visit Boston.

  •  Fenway Park

If you’re a huge baseball fan (and even if you’re not), one of the most fun and popular things to do in Boston is to catch a Red Sox game at Fenway Park. Watching the game on TV just doesn’t compare to experiencing it in the stadium in the company of other fans!

  •  Boston Common

Considered to be America’s oldest park, Boston Common is the start of the Freedom Trail (see below) but is also a wonderful place to spend a relaxing day outdoors when the weather is beautiful. Frog Pond, a lovely pool in the warmer months and a fun skating rink in the winter, is located here. 

  • The Freedom Trail

Starting at Boston Common and passing 16 important Boston landmarks, the 2.5-mile Freedom Trail is a self-guided walking tour. You can also take a guided tour through the Freedom Trail organization. Guided tours are offered on specific subjects or themes, including African American Patriots, North End, Revolutionary Women and more.

  • Quincy Market

Historic Quincy Market is a Boston food hall where you’ll find a variety of delicious foods, from steaming chowder and lobster rolls to oysters on the half shell and ice cream and more. After grabbing a bite, head to the North Market next door to shop local retailers.

  • The North End 

A one-square-mile waterfront community, Boston’s North End is famous for its Italian food, historic buildings and streets, restaurants and shops. Get your fix of great Italian dining here (and satisfy your sweet tooth at one of the many bakeries). Enjoy strolling the streets, which include some of the oldest streets in Boston. If you’re a history buff, be sure to visit The Paul Revere House.
  • House of Blues

Attend an A-list performance at Boston’s iconic House of Blues. Just be sure to book your tickets before your visit, as they tend to sell out quickly!


Use this guide to plan your itinerary and get ready for your exciting trip, filled with top Boston tourism spots that both locals and visitors love. Shop at Briggs & Riley to find the perfect bag for your visit.

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