Boston guide-the must do’s of a long weekend

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Last updated on March 23rd, 2018

Boston guide-the must do's of a long weekend
Each US State has its own slogan on their number plates.

Boston guide – the must do’s of a long weekend

The most European American city you can find yourselves in. Full of history, style, sport and great sea food. Home to two of the most prestigious Universities in the world, Harvard and M.I.T

Boston is the kind of city where you can spend a lot more than a weekend to explore it. No matter how long you had to spend here, you would still find new things to do, great sights to see and the thrill of exploring the place as if it was your first time.

Take me for example. I have lived in the North Shore of Boston for 1 year, where I thought I thoroughly explored it then. I came back at least another 5-6 times since and this city never ceased to amaze me. You can read all about my first experiences of Boston and how this city is the right one to discover America, here!

Thanks to its compact size, (compared to some other American megalopolis), and completely walkable downtown, you can certainly take advantage of a long weekend here. See some of the most essential and picturesque corners this place has to offer and indulge in some delicious seafood Boston is known for.

Here are the best of Boston highlights for your long weekend

The Freedom Trail

This is a unique way to see some of the most important historical sites that Boston has to offer, (16 to be precise). A 2.5-mile red trail that you can walk and see some of the following sites:
Massachusetts State House
Granary Burying ground
Benjamin Franklin Statue and Boston Latin School
Old State House
The Paul Revere House
Old North Church
U.S.S. Consitution
Bunker Hill Monument

There is no specific start point for the Freedom Trail to begin your historical journey of Boston. Being very well marked throughout its route, you can skip some of the sites or spend more time on others. You can pick up some nicely marked maps for free along the way. The Freedom Trail Foundation, offers some great public tours with the ‘Freedom Trail Players” which you can also book ahead of time. You will be walking along with 18th-century players dressed up in costume and providing some more in-depth knowledge of each site.

Boston Commons Park

This, amazingly enough, is the oldest city park in the country, (founded in 1634).
Whichever way you decide to spend your long weekend in Boston, you simply have to include at least a 2-hour stroll through this park. I usually left this last, after having walked either the Freedom Trail, or wandered through the city. I would get something to eat, (usually a baked Lobster Roll..yum), and sit on one of the many benches just watching the world go by.

A fun, leisurely activity I did on one of my first few times I visited this public park, was to hop onto one of the Swan pedalled boats and take it for a ride along the park’s lagoon.

Boston Commons has seen many transformations across the centuries, and several historical events have taken place here. Some of which include:
The 1860’s civil war recruitment
Most of its iron fencing was given away for scrap metal for the needs of WW II
Anti Vietnam war gatherings
Rallies for civil rights, (even Martin Luther King, Jr rallied here)

Faneuil Hall Marketplace

There is no question about whether you should visit this place! It is actually 4 places into one:
Faneuil Hall
Quincy Market
North Market
South Market
Full of street entertainment and set on a cobblestone promenade that you will be able to walk, people watch, laugh at magicians and other street entertainers.
Quincy Market was added to the hall in 1826 and built according to Greek architectural style. It was always such a great joy to enter on one side and go through the endless eateries inside. Deciding what to pick was always fun. International cuisines included: Greek, Italian and of course American.
I would always go for some Greek cuisine no matter what else I decided to devour there. Satisfying my hunger for the much missed Greek cooking and getting over the sweet nostalgia of home and mama’s cooking.
Other favourites included various seafood dishes, (lobster rolls of course), and the famous ‘Clam Chowder’. If you do enjoy seafood, you should definitely try a hot, creamy cup of Clam Chowder.

Walking through the hall and passing by its 18 restaurants and 35 eatery stands will satisfy even the most culinary demanding connoisseurs. When you finally exit this ‘delicious’ edifice, several pushcarts of arts, jewellery, local artisan items are waiting for you alongside the walls of this building. You can find some unique souvenirs, and it’s great to speak to some of the local artists and small entrepreneurs here. More shopping can be done in the buildings of South and North Markets as well.

Your visit in Faneuil Hall Marketplace can easily take at least half of your day. It is a fun place to be, and it will give you a great taste of what Boston and New England are all about.


Only a 10-minute walk from Boston Commons and you will find yourselves in one of the prettiest areas of Boston. Beacon Hill can easily be claimed as the true essence of what Boston is.

A mixture of old-style, elegant brick houses and cobblestone streets, (beautiful Acorn Street). Gas-lit street lamps with tree-lined pavements, are all there to transport you to another era.
A must for photography enthusiasts. Visit the gold-domed State House at the top of Beacon Hill and capture beautiful shots. Wander around the charming streets of one of Boston’s most desirable neighbourhoods and try one of the many eateries on the West by Charles Street.

A cruise along Charles River

Charles River runs through many of the above sights, and you can get a feel for most them in as little as 90 minutes. It will be a great way to cruise by Cambridge, (the University town), and get a glimpse at Harvard University Campus, the M.I.T., as well as historical and cultural sites such as the Esplanade Park, Beacon Hill and the Back Bay.

There are several cruise operators you can choose from. Pick an old-fashioned river cruise boat or even relax on romantic gondolas. There are also 3 different types of cruises you can embark on, depending what you feel like seeing.

The Charles River Tour, (approx. 60 min): with panoramic windows that you can enjoy most the sights since this is an all-around cruise.

The Sunset Cruise, (approx. 75 min.): during the summer months. Catching the sun rays across the river and some of the most beautiful reflections on top of famous landmarks.

The Architectural Cruise, (approx. 90 min.). If you had to pick only 1 cruise – this would definitely be the winner. This river cruise will offer great insights by expert guides on both historical and contemporary architectural landmarks along Boston Harbour, |Charles River Locks and Basin and more.

You can get more details on the different Charles River cruises and their schedules here! (link)

Summing it all up

There is obviously a lot more to do and see in this great city! This first “Boston guide” series attempts to introduce you to some of the main sights and attractions that you could see over a long weekend.

If you manage to fit in all 5 activities, you will fly back home having had a pretty good idea of what this incredible city has to offer. Having a yearning for your next visit and more to see.

In my next post, we will look at some of the many museums, galleries and different activities that you can try, but even then, Boston will have you coming back, time after time, after time.

Boston: Capital of Massachusetts

Population: 673,184, (as of the 2016 pop. census) – Largest city in New England

Greater Boston area population: 4.8 million – the 10th largest area in the US

Boston is one of the oldest cities in the United States, founded in 1630 by settlers from England.

It was the scene of several key events of the American Revolution, such as the Boston Massacre, the Boston Tea Party, the Battle of Bunker Hill, and the Siege of Boston.

Some of the most renowned and highly ranked universities in the world are located near Boston. Three universities with a major presence in the city, Harvard, MIT, and Tufts, are located just outside of Boston in the cities of Cambridge and Somerville, known as the Brainpower Triangle

Source: Wiki-Boston

The 'Million Dollar' question? (click below to find out)

As mentioned earlier, I have been to Boston and New England area numerous times! Being such an incredible area however it would certainly lure me back for yet another visit. Visiting Boston is more than just going to a city – it feels like a never ending exploration!

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