Traveling to new cities is enriching and eye opening, however it can feel daunting if you are not sure where to start! This guide is meant for you to enjoy some of the best parts of Boston in a few days’ time.

Boston was founded by Puritan colonists from England in 1630. It plays a major role in the history of the United States. It quickly became the political, financial, commercial and educational center of New England.

72 Hours in Boston

Day 1

Arrive at Boston Logan Airport!

This airport is very convenient, as it is right in the city. You can take the silver line or arrange for private transportation to your accommodations.


The Freedom Trail

The Freedom Trail is a wonderful way to explore Boston, especially on the day of your arrival.

Walk this historical path at your own pace or connect with one of our local guides who will make you feel like an expert by the time you are done. The Freedom Trail is about 4km total and contains 16 historical sites for you to explore.

Feel, learn and see how the American Revolution unfolded. Take a look at Boston Freedom Trial to Copley Square Walking Tour. 



Time to sit back after your long walk and decompress with a savoury lunch. You can´t go to Boston without trying clam chowder. Creamy, hearty and comforting, clam chowder is a local and classic favourite of New England.

Union Oyster House is right near the famous Faneuil hall as well as the Freedom Trail.

Fun Facts: Union Oyster House is one of the oldest restaurants in the United States. It opened in 1826 and has been serving diners continuously ever since. Union Oyster House is the oldest restaurant in the country to have its doors open consecutively for this many years. In addition, the building is listed as a historic landmark.


Harborside Walk

After your lunch, it is time for some relaxing and beautiful views along the harborside of Boston. This area of the city is quieter than the hustle and bustle downtown. Take in the yachts, boat activity and green areas as you explore the lovely skyline of Boston.

The Rose Kennedy Greenway is a public park that is lush and perfect for escaping the busy city. Featuring ocean views and greenery, it provides locals with a little piece of nature in a major city. This park hosts contemporary public art, which is updated and changed regularly.



Dinner in the North End

The North End of Boston is like walking into a small city in Italy. It is the oldest residential neighbourhood in Boston. Enjoy the maze of narrow streets, bustling bakeries and the aroma of Italian cuisine.

Maurizio´s has won many awards for its contemporary Sardinian Cuisine:

There are hundreds of restaurants to choose from, but this one is tucked away and not as easy to spot. This restaurant is cozy, comfortable and makes you feel at home.

Fun Facts: Boston made itself bigger through landfills. You may be walking in an area that was once water. In 1630 the Puritans arrived to a very different layout of the city than you see now. The landfills promoted areas for park spaces, created more land to expand the city and were necessary for building Boston Logan Airport.


Day 2

Americans love their big, hearty breakfasts! Have a filling American style breakfast/brunch at the Friendly Toast in the Back Bay. The retro style and funky interior make this a fabulous spot to stay for a few hours.

Remember the old soda fountains from American Diners? The Friendly Toast serves up soda fountain treats. These old-fashioned treats are a great compliment to the contemporary food in this kitschy diner.

Newbury Street

After you´re nice and full, make your way to Newbury Street. This famous area of Boston boasts major clothing designers, high end restaurants on a picturesque tree-lined street.

Keep an eye out for celebrities, as Boston is a hot spot for films. This street is exactly where the rich and famous gather.

Make your way to the Old South Church after you have taken in Newbury Street. It was built in 1669 and was designed in the Gothic Revival style.


Lobstah on a Roll is a sandwich shop serving up enormous lobster rolls. Lobstah is a play on the distinct Boston accent. Notice how the locals pronounce their R´s and you will understand why this sandwich shop has its name.

New England lobster is fresh, delicious and a classic culinary delight that can´t be missed.

This eatery is located in the chic and diverse South End neighbourhood of Boston. The gorgeous apartment buildings, stylish streets and general vibe in this area sets it apart from other neighbourhoods.

Fun Facts:  The South End was built on tidal marshes. It also has the largest Victorian row house district in the country. This is comprised of over 300 acres.


Duck Tour

Perhaps you have heard of the famous Boston Duck Tours. You will see the city through land and water on the replica World War II vehicles. These vehicles can run on both land and water. Soak in the historical facts and walk away feeling like you are an expert on Boston History.

                                                                                                                               (Picture by Rawhead)

Dinner in Beacon Hill

Considered one of the most beautiful parts of Boston, Beacon Hill is adjacent to Boston Common and Public Garden. You can´t miss the gold-domed State House of Massachusetts. Talk a long walk through the Boston Common, the oldest city park in the United States.

Fun Fact: Before the American Revolutionary War, the Common was used as a camp by the British.

Boston is known for its Irish settlers. In fact, the largest ethnic group in Boston are those of Irish decent. You may notice that you can´t really go anywhere in this city without seeing an Irish Pub.

Emmets Irish Pub and Restaurant encapsulates the feeling of being in Ireland. You will have an original Irish pub experience; if you are lucky, you can take in some live Irish music. Order a perfectly poured pint of Guinness and excite your taste buds with traditional Irish food.


Day 3


South Street Diner is a 24-hour diner in Boston with a casual atmosphere and to-die for Boston Cream pancakes. This diner has been rated as one of the best 24-hour diners in the country.

Sit at the counter for an authentic American Diner experience and observe the constant flow of customers. You will see people of all ages and backgrounds flocking to this laid-back eatery.


Guided Bike Tour of Boston

You have walked, you have been on the duck boats, but you have yet to bike! See Boston in a whole new way with fantastic guides. Not a big biker? No problem! You can book a bike with electronic assistance for some help with pedalling.



Americans love baseball and Bostonians love their Red Sox. Fenway Park is a historic landmark in the USA; it is not a landmark to be missed. Feel the sporty vibes in this hub of Boston.

If you are in Boston during baseball season, buying tickets to Fenway can be challenging and expensive. If you are lucky enough to score seats, go for it, however simply walking around this area of Boston both in and out of season will still provide you with the Red Sox fever.

Bleacher Bar is an authentic experience for lunch. Relish in American style pub food underneath the bleacher section of Fenway Park. This unique spot showcases views of centerfield. Feel like you are in the stadium, cheering on the beloved Red Sox!

Americans love their sports bars and Bostonians are no different. You can´t come to Boston without eating at one of the many sports bars in the city. Bleacher Bar goes one step further with its authentic location underneath Fenway.

Fun Fact: Fenway Park is the oldest baseball stadium in the USA that is still in use.


Boston Tea Party Ships and Museum

This is a floating museum depicting the famous Boston Tea Party. Highly interactive and set on a barge in the water, you will feel like you are a part of history in the events leading up to the American Revolution.


Dinner on the waterfront

Tia´s serves American food with ample outdoor seating. Taste the sea as you overlook the harbour. This humming restaurant is a perfect way to end your last evening in Boston. Tia´s has a fantastic cocktail menu and is frequented by locals.


Day 4

Your trip has sadly come to an end, but hopefully you feel confident in your historical knowledge of Boston and are still talking about the classic New England food you got to experience.

In need of a quick breakfast before you depart? Americans love their bagels. Finagle a Bagel has a few storefronts in the city. Try a new bagel you have never seen before!



Boston, like every city, has a whole lot to offer. If it is culture, food or simply just the mentality of the people and the aura of its places.

If you are hooked with the idea of going to Boston than don’t forget to sign up for our 5 secret tips.

But even more important, we would like to hear from you:

What are your thoughts about Boston? Is there anything missing in this guide? Do you have open questions? We love to discuss travel so go ahead and fire away, there are no wrong comments!

Also, please let us know how your trip went and what was the most exciting part about it.



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