Published: August, 2018
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Boston, Massachusetts

Boston is a perfect marriage of charm and history - a rich experience in so many ways!
— Katy Tanghe
  • More about your oliver guide:
  • Trip type: Family, City
  • Activity level: moderate
  • Ideal length of trip: A long weekend, however, if you have the time, add on a few days and plan a visit to the one of the other destinations nearby including the Cape, Nantucket, Martha's Vineyard, Provincetown, etc. - it is well worth it.

to & from

Boston Logan International Airport is your best bet and so convenient/easy. If you are not traveling outside of Boston, you do not need a car. You can use their subway/train system which is great or taxi/uber. However, if you are coupling your time in Boston with an excursion to Cape Cod or another spot, look into renting a car for only that portion of your trip.

Where to Stay

If you are going to Boston for just a few days, there is no shortage of great hotels to consider. If you are planning to stay for more than a week, then check out VRBO or AirBnB. Some good hotels for families include:



  • The Colonnade (Back Bay): The rooms are spacious enough to accommodate roll away beds and cribs and it has a rooftop pool that kids will love.
  • Marriott Boston Custom House: Updated and modern, this hotel offers a great spot to relax after a day of seeing the sights. It's proximity to the harbor and several other attractions is a big plus.
  • The Newbury Boston: Location, location, location. This wonderful hotel sits right at the south end of Boston Public Garden and at the tip of Newbury Street (luxury stores and boutiques). You really cannot beat this location. The hotel is charming with smaller rooms so plan to get two if you are traveling with two or more kids.
  • The Liberty Hotel: Once the Charles Street Jail, this modern and fabulous hotel is perfectly situated in one of Boston's most charming neighborhoods, Beacon Hill. This hotel is a perfect mix of luxury meeting history with a chic hotel bar and delicious restaurant. It's definitely worth checking out even if you don't choose to stay here.

Where to Eat and Drink

Whether you prefer Italian or seafood, Boston has some of the most wonderful food options you can imagine. The most famous is Boston’s North End – it includes more Italian restaurants than you can count. Equally in abundance are seafood restaurants – see below for some of our favorites.

  • 75 Chestnut: Located in Beacon Hill, this cozy place serves up American cuisine that will make everyone in your family happy. The steak and avocado salad was my favorite.
  • Union Oyster House: You can’t visit Boston and not pop in here. Its near the harbor and on the Freedom Trail. Have the clam chowder and look for JKF’s booth.
  • Pizza at Reginas – visit the North End location (original) – locals says it’s the best pizza in town.
  • The Green Dragon – pop in for a Sam Adams at the very spot where the founding fathers gathered to plot the revolution (it’s right next door to Union Oyster House).
  • Mike’s Pastry – grab a cannoli in this North End original.
  • Row 34 – the best place to grab oysters – especially if this is your first time trying them (eg kids). It’s casual and fun.
  • The Salty Pig – another fun spot for pizza except it’s not in the North End. Grab a seat on the patio!
  • The Saltie Girl – if you love seafood, this is your girl….classic and modern takes on everything from shrimp to sardines.

What to Do

You could play tourist for days and not see it all – below are some suggestions if you want to get the most out of a longer weekend.

  • The Freedom Trail – This 2.5 mile walk is the best way to see the most prominent historical sites in the city. You can either go on a guided tour or you can download the Freedom Trail app and explore on your own. This walk is a crash course in US history for kids and adults alike.
  • Boston Duck Tour – before you roll your eyes, if your kids are with you, this quick 80-minute adventure is great for anyone that has never been to Boston. It will not only outline city’s various neighborhoods, but orient you for the remainder of your stay. The guides are hilarious and our kids loved it.
  • Fenway – book a guided tour for your family. This ballpark has such a deep and interesting history. No matter your age, this a great way to experience one of Boston’s greatest sports treasures.
  • Boston Public Garden – this is a beautiful spot for a morning walk or an evening stroll. If you go during the day, take a ride on the park’s famous Swan Boats ( – these boats have been run by the same family for more than century.
  • Cambridge – just a quick train or uber ride from Boston, this historical gem is home to some of the country’s most elite universities including MIT and Harvard. Go to Harvard Square for great shopping/eating and take a stroll down Brattle Street to see homes that pre-date the Revolutionary War.
  • AdvenTours – if biking is a shared activity within your family, definitely check out this operator. They will deliver bikes/helmets to your hotel or you can visit them at 103 Atlantic Ave and take a guided tour. The bike paths in Boston are relatively new and really easy to navigate.
  • Beacon Hill – just across the street from Boston Public Garden, you will fall in love with this neighborhood. Great shopping, cafes and historical landmarks line the beautiful cobblestone streets.
  • Salem – If you have the time, grab a coffee and take the 45-minute train to this historical town. We did a walking tour with a private guide (no shortage of options). It’s well worth the visit to see The House of Seven Gables and to learn about the witch trials and Puritan history.
  • Boston Common – a great spot to bring a picnic and relax. It’s the oldest public park in the U.S.

inside scoop

Summer/early fall is a great time to visit Boston. If you want to tack on a trip to Nantucket or Martha’s Vineyard, September is ideal due to minimal tourists and warm weather.

  • If you can sneak away from the family for an hour or two to shop for yourself, you need to go to Beacon Hill (Charles Street) or Newbury St.

skip it

Cheers. It is located at on the southeast corner of Beacon Hill. It’s great for an exterior photo opp, but that’s it – the interior is not like the show and Coach won’t be bartending. Plus, your kids will have no idea why you are stopping.:)

What to Pack

Bring comfortable shoes/flats as there is a lot of walking (which you will want to do!) Bostonians are fashionable but not flashy so stick with packing the modern classics in your closet.

Boston, Massachusetts - Suggestions from the Oliver Community

  • Cynthia Pillsbury Says

    According to regular Boston visitor and Oliver Guide author, (Bora Bora) Kristen Kratus Island Creek Oyster Bar is not to be missed!

  • Nichole Rowles Says

    Mike’s Pastry does offer the best cannoli, but it has been discovered. To beat the very long line, order through Uber Eats. If you pick up at the shop, you’ll have your order in 3 minutes!

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