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Lisa Owen

While in transit between Iceland and San Diego, I took a quick look around one of America’s oldest cities. Boston was founded in 1630 and is now one of the major university cities in the United States. It is filled with historical buildings and parks perfect for a stroll – and in the winter months, they’re often covered with a layer of fresh snow.

If you only have a day to spend in Boston, here’s some budget suggestions on how to spend your time and check out some of the highlights. The east coast city is easy to get around and the suggested itinerary can be done on foot or by going a couple of stops on the subway – known as the ‘T’.


Start your tour of Boston with a visit to Harvard University. It’s accessible on the T from the Harvard Square station. While it’s not mind blowing, it’s a nice walk through the courtyards between the red brick buildings if you have the time.

From Harvard University, you can choose to head down Broadway Street to get to Downtown Boston but it’s about a 45 minute walk and there’s really only houses to see along the way. But to save some money and get some exercise, I decided to walk down, crossing one of the bridges spanning the Charles River to reach the Downtown area.

The bridge leading off Broadway Street offers good views of the Boston skyline on a sunny and still day. There’s a number of bridges you can walk across along the Charles River to get some good views of the city.

Boston bridge

If you don’t feel like walking, hop on the T from Harvard Square and head down to the Back Bay stop.


From the Back Bay T stop, Newbury Street is only a 10 minute walk away. Newbury Street was once underwater and formed part of the Boston Harbour, but was filled in and became one of Boston’s most prestigious addresses.

Today, Newbury Street is filled with retail stores and restaurants and is the top spot for high end shopping. But if shopping is not your thing, take a look at the Boston architecture along the wide boulevard.

Have a coffee at the Thinking Cup café during your wanderings.

From Newbury Street, head downtown and you’ll reach Beacon Hill – one of the oldest parts of Boston.


Head down Charles Street in Beacon Hill and you’ll see shops, homes and cafes of all kinds housed in historical buildings. Charles Street is also great for a coffee stop if your time on Newbury Street was taken up by shopping.

Beacon Hill is another of Boston’s most prestigious suburbs, although interestingly enough, part of it is built on landfill.

Beacon Hill backs onto the Charles River and was named because of the former beacon on Boston’s highest point to warn of invasion. Beacon Hill is easy to spot by the gold domed Massachusetts State House across from the Boston Common.

Beacon Hill


Leading off Charles Street is Boston Common and the Public Garden – both very pretty in winter if it’s snowed recently. Boston Common was established in the 1600s and is America’s oldest public park.

Boston Common has had a variety of uses since the 1600s – it was a beach when the Charles River was at high tide, it once housed the town gallows, and was also used for military training. Boston Common started being transformed into a public park during the 1800s as Beacon Hill started to be turned into housing estates.

Public garden


After wandering through the local parks, head into Downtown for a shopping fix, lunch or a combination of the two. All the popular department and chain stores are there including H&M, Primark and Macy’s. For my budget food fix, I discovered Bruegger’s Bagel Bakery (bagels are delicious, just saying). Bruegger’s is a chain bagel shop but has a great selection of New York style bagels in a range of flavours which you can simply top with a generous serving of cream cheese or a range of deli style fillings.


After you’ve had some lunch, you can start exploring the Freedom Trail. It starts in Boston Common, and winds its way through the Downtown area and near the harbour. The trail is 2.5miles long and features 16 historically significant sites related to the American Revolution.

The Freedom Trail includes museums, churches, meeting houses, burying grounds, parks and a ship.

Freedom trail

Guided tours run several times a day and cost $US12. Tours can be booked online. A tour is not necessary though – just follow the red brick line. Each site has information on the front about its historical significance and you can start at any point of the trail. I started the trail at Feneuil Hall and then onto the Paul Revere House, but later doubled back to State Street to see the sites between Feneuil Hall and Boston Common.

Faneuil Hall was the site of America's first Town Meeting.


While on the Freedom Trail, make a detour to the Boston Public Market, which is located near Feneuil Hall and the Holocaust Memorial.


The Boston Public Market is an indoor gourmet market with a range of meats, fish, nuts and cheese products as well as organic fruit. There’s also ice cream and juice stalls. All food  is locally sourced from the New England area. My favourite stalls were the ones selling crispy apple cider doughnuts (delicious!) and stone ground chocolate (the chocolate stall has some samples to try for your chocolate fix). You can pick up a mini apple cider doughnut for $US1.

The market is closed Monday and Tuesday but open from 8am to 6pm Wednesday to Sunday.

If you have more than a day….

If gets dark in Boston over winter about 4.30pm, so if you’re up early or have more than one day in Boston and have a car, you might want to head out to the Blue Hills Reservation. There’s a range of woodland trails through the reserve. The trails are well maintained and offer an easy walk, and there’s also a pretty lake. I was lucky enough to have friends in Boston who drove me out there.

The area is especially pretty after recent snow, but it can get chilly out there in winter, so wear layers.

Blue hills

Things you should know:

  • Tourists can buy a reloadable paper ticket for the T subway. Each journey costs $2.65. There’s five T lines but each station has easy to read maps and signs.
  • Boston is a great city to walk but the subway is well connected if you need to pick up the pace.
  • You can catch the subway from the airport into the city’s central subway station Downtown Crossing. Take Bus 33 (it’s free) from the airport to the Blue Line subway station – it only takes a couple of minutes. You can get off on State Street – which is only one stop from the central station - or change lines to the Orange Line to get to Downtown Crossing.
  • Boston can get very cold in winter. You’ll need a good coat, flat boots in case of snow, and layers.
  • If you’re need wifi, look for a Starbucks store.

Lisa Owen is a pint-sized Australian following her dreams to travel to as many places as she can, and loves to share her photography, travel hacks, hiking adventures, and food discoveries along the way. At last count, she has travelled to more than 40 countries in between working in public relations and discovering hidden gems in Australia's great outdoors. Instagram: @_thelittleadventurer Facebook: The Little Adventurer Australia  

The views, opinions and positions expressed by the author and those providing comments are theirs alone, and are meant as travel inspiration only. They do not reflect the opinions of Cover-More Insurance. You should always read the PDS available from your travel insurance provider to understand the limits, exclusions and conditions of your policy and to ensure any activities you undertake are covered by your policy.