Our Boston Travel Guide

To the point Boston is a fast-paced city where there is never a dull moment! Find ideas for your future stay for you and your family, there is something for everyone.
Milesopedia recommends this card from Scotiabank

This post is also available in: FR

Come and visit Boston for a weekend, this city so loved by Canadians and Americans!

Between discoveries, cultural walks, family activities and restaurants, you will be charmed! Overview of the 24 hours stopover of Jean-Maximilien and Jean-Francois during their mini world tour in one week in September 2019!

Boston, an emblematic city of the United States

Boston is the capital of Massachusetts. This city with its characteristic red bricks is known in the world for its famous university, Harvard. Impossible not to know!

This city can be visited in as little as 24 hours during a stopover! However, in order to enjoy it, we suggest you spend a few days there to get a feel for the lively atmosphere.

So many things to do there, we love to go! Between walks, museums, shopping, sports, shows, etc. In addition to the classic city tours, we offer other activities to make you feel like a local!


What to do in Boston?

The unmissable Freedom Trail

For those who don’t know the city, this is the best way to start your visit! Indeed, the Freedom Trail is a path traced on the ground that visitors can follow to discover different places or emblematic buildings of the city. A fun and active way to discover the history of the American Revolution!

Boston, city of champions

Boston brings together the crowds and especially sports fans! Boston’s major professional sports leagues have won numerous titles since the new millennium.

Experience the thrill of the game with them and come to Fenway Park to see a Red Sox game! Coming in the winter? A new 6,000 square foot skating rink has just opened in the last few weeks: The Rink, 401 Park by the Trillium Brewing, theme nights are expected. Another skating rink in Seaport is also available.

Another idea is to participate in the Boston Marathon, the oldest marathon in the world, or come and cheer on the participants. To know the dates of the next marathons, consult this site!

Children also have their place with races for children under 14 years old!


Shopping session

Looking to refurbish your wardrobe or just window shopping? Go to the beautiful Newberry Avenue. With its beautiful houses, you will be charmed by the corner and the nice stores. Something to inspire you for the season!

boston —

Observing the city

In addition to the stores offered by the Prudential Center, you can head to its observatory and admire a 360 degree view from the top!

Stroll along the Charles River esplanade and then look out over the city from the Longfellow Bridge . We recommend going at sunset for an even better experience.


For a different view of the city, try the water cab! You can go from one pier to another and for example reach Pier 6 to enjoy a cocktail.

boston —-

Boston, city of culture

Boston has a performance hall, the
symphony hall
. With several concerts on the program, this is an opportunity to enjoy yourself in a different way. Do you have children and think it’s not for you? Think again!

A series of concerts are held especially for families with children from 3 to 8 years old. A good way to educate children about music. Discovery of the stage and activities are planned before the show.

The Harvard campus and its museums

Visit Harvard University, America’s oldest university, with a guide and stroll through its surrounding gardens. We loved the immersion. Don’t miss the souvenir store or the bookstore located on campus!

In addition, Harvard has a museum of archaeology and ethnology as well as a museum of natural history!

boston —

For the family

The city offers many activities for families. Here are some ideas:

  • Boston children’s museum
    to develop their skills or take a walk in a Japanese house for example!
  • Explore the science museum which has several exhibits for young and old,
  • Have a picnic at Franklin Park where there is a zoo and playgrounds,
  • Enjoy the wading pools at Boston Common Frog Pond in the summer. In winter, the space is set up as an ice rink. Shows and movie nights are even organized there!

Gastronomic pleasures

Let’s say it right away the choices are not lacking and we recommend you to reserve to be sure to enjoy the beautiful tables.

boston —

Some ideas:

  • Sit down at
    Bostonia Public House
    for a simple, casual family meal, a sure bet that’s part of one of the city’s best restaurants, chosen by TripAdvisor members in the 2019 Travellers’ Choice Awards.
  • Would you like to enjoy a craft beer? We recommend the company
    Dorcherster Brewing
    which offers a nice selection.
  • Enjoy a Lobster Roll at James Hook & Co
  • Boston magazine just named Tasting Counter the best restaurant in the city. Located in Sommerville, the chef cooks in front of you and offers a great experience for your taste buds.
  • Is Sommerville too far for you? You’ll find a variety of great booths at Boston’s Time Out Market with several events taking place there.
  • Finish a walk with a stop at Mikes Pastry to taste their canollis, reputed to be the best outside Italy.


  • Meet at the Underground Underground located in Ink Block, transformed into an urban park. You will be able to observe artists creating street art. You will find a dog park, fitness activities, accessible by subway or car (parking available).
  • Cruises or boat excursions are offered at the port, why not go to meet the whales?
  • How about a family fitness session at Fallon Field in Roslindale!
boston —

Around Boston (by car)

There are several family-friendly activities within a 2.5-hour drive of Boston:

  • Is your visit scheduled for this winter? Take a trip to North Woodstock where you’ll discover ice castles! Slides, thrones, fountains and many other attractions such as a walk in the woods will give you a new experience!
  • Are you a roller coaster fan? The amusement park
    Six Flags
    in New England will make you live great emotions. Go to their site, you could get free tickets when you sign up for their newsletter!
  • You like nature and heights? A rope course is available 2.5 hours from Boston, visit the
  • Are you in the Worcester area? Visit the Ecotarium museum where your child will learn about physical science or the environment.

Getting there

With points & miles

There are many flights between Boston and Canada.

From Montreal, for example, it costs 7,500 Aeroplan Miles one way. It is also possible to use AIR MILES miles (which is the best use of Dream Miles thanks to short-haul flights).

Here are 3 credit cards that offer Aeroplan or AIR MILES miles:

Alternatively, you could also find a low-cost flight and apply your travel points to the cost of the flight! American Express Membership Rewards points, Scotia Rewards points or HSBC Rewards points can be used here!

Or use BMO Rewards points through the BMO Travel Portal!

Here are 3 great travel credit cards we recommend:

Boston Airport to Downtown

From Logan Airport, it’s easy to get downtown. Take the Silver Line bus at Terminal A. It is free and runs approximately every 10 – 15 minutes.

boston —

Where to stay?

The member hotels of Marriott Bonvoy

In Boston, there are over 100 hotels that are members of the Marriott Bonvoy loyalty program.

During a 24-hour stopover, we chose to stay at the Courtyard Boston Downtown. Find our photo report here.

Courtyard by Marriott Boston Downtown 05

Best Western Rewards member hotels

There are also a few hotels in and around Boston that are members of the Best Western Rewards loyalty program!

Our choice will be the Best Western Plus Boston Hotel for its location.

bw plus boston

For the complete list, check this page!

If you want to earn Best Western Rewards points, the easiest way is to sign up for the MastercardMD Best Western RewardsMD credit card MastercardMD Best Western RewardsMD

Hilton Honors member hotels

For those who prefer Hilton Honors loyalty program member hotels, there are several in Boston!

Our choice will be the Hilton Boston Back Bay for its location near Newbury street.


Here are some other great Hilton Honors locations conveniently located in Boston:

Hilton Honors points are not readily available in Canada. However, it is possible to have Hilton Honors Gold status which allows you to get an upgrade and free breakfasts at all Hilton Honors member hotels!

This is one of the many benefits for travellers from the PlatinumMD from American Express which is currently on offer:

Three credit cards with no conversion fee

Don’t forget to have a free credit card with you for your foreign currency transactions! That’s 2.5% savings on every transaction!

Here are the top 3 card s with no conversion fees in Canada, ideal for travelers:

City passes

Passes are available to get discounts on your visits. You can get information and buy them on the spot at the tourist office for example or in advance on the internet. You can choose from the Boston CityPass, the Go Boston Card.

To inspire you!

For a short stay in Boston, I recommend the travel guide Escale à Boston.

The Stopover to Boston guide is ultra-practical thanks to its easy-to-understand at-a-glance structure and to use on site. The first section, “The Best of Boston,” highlights the best the city has to offer and makes it easy to plan your Boston getaway. The “Explore Boston” section then offers a dozen turnkey itineraries so that you don’t miss a thing in the city’s various neighborhoods. For each itinerary, a clear and precise double-page map indicates the route, in addition to locating attractions, cafés, restaurants, bars, nightclubs, theaters, boutiques and hotels. It’s impossible to miss anything! What’s more, a system of stars and “coup de coeur” labels guides the reader to the addresses that stand out.

The “Boston Practical” chapter, packed with information delivered in a succinct and easily identifiable manner, rounds out the book and gives you useful information on flights, weather, accommodations and more.

In addition to all this, there are additional maps – general view of the city, zoom on the downtown area, map of the metro.

Once on site, ask at the tourist office of course! Go there to buy for 3$ the Freedom Trail map for example (translated in French) or to pick up some ideas of escapades in the area.


I suggest you check out the Boston Magazine or Massachusetts website before your next visit! You will find the dates of future festivals for example or ideas for outings. This is the magazine to follow!


Our map of Boston

This post is also available in: FR

Come to discuss that topic in our Facebook Group!
4.1 Milesopedia Rating
Mother of two young children, pharmacist, travel hacker's wife and frequent traveller, Audrey shares her advices and destinations recommendations on milesopedia.

Suggested Reading