Guide For Planning A Fun Summer Trip to Boston

Boston Skyline

Top Tips for Planning a Summer Trip to Boston

Boston Skyline
Wikimedia Commons by: Matthias Rosecrans

If you’re thinking about where to go this summer, Boston is a great option. Now that Covid restrictions have been lifted, restaurants and attractions are open and the city is better than ever. Boston has some of the best historical sites in the country, as well as great restaurants and a cosmopolitan feel, thanks to generations of college students that keep the city feeling young. This year casual pop-up beer gardens and chic rooftop restaurants are adding extra fun to the city, so it’s a great time to visit.

The following are some of the most important things to know before you plan your trip to Boston this summer.

Don’t Drive If You Can Help It!

If you can avoid renting a car or driving in the city, it’s best. A study revealed Boston has the worst traffic congestion in the U.S., and the second-worst in North America, only coming in behind Mexico.

A much better option is to use public transportation or make it to most of the sites on foot.  If you drive into Boston, you will find that parking is outrageously expensive.  Try to find a hotel or rental with onsite parking where you can leave your vehicle the majority of the time.  For sightseeing use the subway system and enjoy walking the city.  Boston is a very walkable city with many attractions located at manageable distances from one another.  Another alternative is to take advantage of one of the hop-on, hop-off sightseeing tous that narrate the ride through the city and describe major attractions along the way.

The train system in Boston is called The T or (MBTA). For most things that are touristy in the city, you’ll be on the green and orange lines. There are also Lyfts and Ubers available as well.

Where to Stay

Faneuil Hall Marketplace Boston

There are a lot of great neighborhoods in Boston with beautiful hotels.  The main tourist areas are Back Bay, Beacon Hill, the newly developed Seaport area, and Faneuil Hall, all of which offer historic architecture and waterfront areas. In general, if you want a combination of historic sites and easy access to the harbor, you should think about staying in one of these areas rather than in the outskirts of the city.  If you want active nightlife, stay in Kenmore Square (Back Bay) or Allston/Brighton where a large number of college students reside.

If you want something whimsical and romantic, head to Beacon Hill, and for shoppers, the Back Bay is tops.

Do a Free Walking Tour

One of the best ways to really see Boston is to take a walking tour, and many are free. You can walk the famed Freedom Trail and the Black Heritage Trail.

The Freedom Trail is 2 ½ miles long, threading its way through historic Boston. You’ll see all the major monuments and sites that are associated with the city’s founding and the Revolutionary War. The trail starts in Boston Common and ends at the Bunker Hill Monument across from the USS Constitution and the Charlestown Navy Yard.

Sites that are located along the Freedom Trail include:

  • Massachusetts State House
  • Old Corner Book Store
  • Old South Meeting House
  • Faneuil Hall
  • Old State House
  • Paul Revere House
  • USS Constitution

You follow a brick road through the city, and there are markers and signs along the way.

There’s also something called Free Tours by Foot, or you can use Strawberry Tours. You can get oriented with the city, but you should plan to tip your guides.

Visit Boston Common and Boston Public Gardens

Swan Boats Boston Public Garden
Flickr by: Bill Ilott

If you’re planning a trip during a time of year when the weather is nice, make time for a stroll through the Boston Common. The park is incredibly popular in the summer, and there are walking paths throughout. You can go to Frog Pond, see the signature ducklings and enjoy being at the historic hub of the city.  Directly opposite Boston Common you will find the beautiful Boston Public Gardens. Originally opened in 1837, these lovely gardens were the very first public botanical gardens in America. Don’t miss the chance to take a swan boat ride on the pond.  No matter the time of year, the gardens are beautifully planted with vibrant blooms.

Don’t Miss The Back Bay

The Back Bay is an area that was at one time an actual tidal bay, where the indigenous population would catch fish. In the mid-1800’s the bay was filled in, and the Back Bay area was created with broad tree-lined streets, Victorian brownstone townhouses, and gas-lit sidewalks.  Look closely, you’ll be surprised to see the flame of the gas lights still shining on.

Trinity Church Copley Square Boston
Flickr by: Bill Damon

Newberry Street is famous for its high-end shops, cafes, and beautiful brownstones.  For more serious shopping at designer shops, the Prudential Center Mall is a short walk away.  Be sure to allow time to visit the Boston Public Library, the first large public library in the USA.  The architecture is impressive and the murals and artwork are unforgettable.  Likewise, the iconic Trinity Church in Copley Square should not be missed.

Make Your Way to Cambridge

Cambridge is a separate city that’s across the Charles River, and is the home to Harvard and MIT. Cambridge can be accessed by a ride on the T, and there are music venues, restaurants, and performing arts venues throughout the city. There are also green spaces and museums.  As an alternative, you could do a cruise on the Charles River for a shimmering view of both the city of Boston and Cambridge at once.

Other Things to Do In Boston

The choices are almost endless, but here are a few other options that you shouldn’t miss in Boston:

  • The Coit Observatory at Boston University. In the summer, there’s free stargazing on Wednesdays after 8:30 p.m. if the skies are clear.
  • Climb the Bunker Hill Monument. The Battle of Bunker Hill was one of the first major battles of the Revolutionary War. When you climb the monument, which is free, you can get a great view of the Boston skyline.
  • Go to Castle Island. This is in South Boston, and it’s home to Fort Independence. There are beaches and running trails, as well as a picnic area.
  • Visit the Aquarium and go on a Whale Watch or harbor cruise.
  • There are numerous museums representing fine arts and children’s interests.
  • Take in a RedSox Baseball game at legendary Fenway Park.

Finally, you should get a drink at the Sam Adams Taproom on State Street, or visit the brewery in Jamaica Plain.    And it should go without saying that a seafood dinner is a must!  Whatever your interests and tastes, Boston is a charming city with entertainment and fascinating sites for all.

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