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A 4-Day Itinerary to Boston

One of my favorite things to do for a vacation is to book a visit to a new city and spend a few days exploring it as if I were a local. One of my best tactics for finding the local hot spots is to head to a local coffee shop on the first day. I sit and sip at the bar, and when it’s slow, I chat up the barista. It’s one of the best ways to make a new friend and find all the secret gems in a city. It’s one of the best ways to make a new friend and find all the secret gems in a city.

 That’s exactly what I did when I went on a 4-day itinerary to Boston for the first time. I’ve since been back to visit Boston several times, so I’ve rounded up a few of my favorites (off the beaten path and touristy excursions still worth your time.) Ready? Let’s go! 

A 4-day itinerary to Boston

Day #1

Your first day in Boston should be all about settling into the city and finding your hotel. There are plenty of chain hotels that you can stay at if you want to go somewhere generic, but if you want to be a little more experimental, why not look into some of the different Airbnbs around? If you can, try to stay downtown so that you’re always close to the action, perhaps in one of the old industrial lofts that have been remodeled into living spaces. Can you say luxe? Then take my advice and find the closest local coffee shop. Chat up your barista, and remember to tip well.

Fenway Park in Boston
Image by David Mark from Pixabay

Day #2

There’s a ton for you to see and do in Boston, from watching the Red Sox at Fenway Park to taking in some arts and culture at the Museum of Fine Arts. Book lovers will want to visit the Brattle Book Shop, or if maritime history is your thing, then there are lots to love and learn about Boston thanks to its proximity to the Atlantic Ocean.

Day #3

Boston proper has so much to keep you busy, but there are beautiful day drives right outside the city limits. One option is to pay a visit to Martha’s Vineyard, which is easily accessible by bus, ferry, car, or plane. It’s arguably the best place to go if you’re into culinary tourism, and you want to experience the city by treating your taste buds and sampling the fantastic food that’s on offer. For something a little different, rent a car for a 40-minute car ride to Salem. Learn all about the Salem witch trials.

Statue of Paul Revere
Image by David Mark from Pixabay

Day #4

This last day should be all about ticking off any of the final few things you wanted to do and see before leaving the city. For some people, this means last-minute gift shopping, while for others, it means planning ahead for their next adventure. You can even get two trip experiences in one by cruising from Boston and sail to another destination. 


Now that you know what I’d recommend doing and seeing if you’re swinging by Boston for a long weekend, it’s time for you to go ahead and to start booking flights, trains, hotels, and anything else that you can pre-book to save some money and to take some of the weight off your mind. I hope you enjoy your 4-day itinerary to Boston!

Featured Image by usmc0491 from Pixabay