North America

The Ultimate 3-day Boston Vacation

Any time of the year is a good time for a short three-day getaway in one of our favorite cities in the United States: Boston, Massachusetts.

Boston is one of the most popular cities in the New England region and is one of the oldest cities in the United States, making it an excellent destination to explore for three whole days.

Home to overly passionate sports fans and the World Series-winning Red Sox, a wealth of modern bars and food markets, and a rich history culminating in the American Revolution, Boston is effectively one big open-air museum. Below we’ve provided a three-day itinerary to help guide you around this east coast, cobblestoned, city.

Day 1

Kickstart your first day here with a trip to Faneuil Hall, Boston’s waterfront marketplace comprised of three historic buildings. Quincy Market is just one of the fantastic buildings that make up the marketplace and is home to an array of fresh food stalls serving anything and everything from pan-Asian cuisine to vegan delights. It’s here that you’re going to get your Boston diet on, thanks to the ample clam chowder, lobster rolls and cream pies for sale. Wander around for a while, sampling some of Boston’s best local produce.

In the afternoon, take a tour around Fenway Park, the home ground of the famous Boston Red Sox. The park is the oldest in Major League Baseball history, and if you’re not into baseball, this tour will blow your sox off (excuse the pun).

If you’re lucky to be traveling during the game season and the Red Sox are playing at home, you can try to get tickets to have the full baseball experience at its best. It will surely be worth your dollars, and if you’ve never been to a game before, the ecstatic atmosphere of being nestled among fans will make for a memorable day.

Photo by Osman Rana on Unsplash

Day 2

The second can begin with a visit to the Museum of Fine Arts, the oldest art institution in the country. Home to over 450,000 objects and classical, modern and French impressionist work, the museum is positively ginormous.

*Busbud tip: the museum closes on Tuesdays, so you might want to switch days 2 and 3 depending on the days you travel.

After an art-filled morning, you can spend the afternoon soaking up the city’s rich history with a 2.5-mile stroll down the Freedom Trail; a man-made path through Boston’s city center that follows the city’s involvement in the American Revolution. There are 16 historical sites to visit in total but if you’re pushed for time, start at the north end and call at the Old North Church, the Old State House Museum and the home of Paul Revere, a patriot of the American Revolution.

In the afternoon, head to the Trident Booksellers & Café. This quaint and quirky eatery is set inside a bookstore and serves an array of delicious cakes, smoothies and sweet treats, all to be enjoyed while reading any book of your choice from the shelves. It’s a real winner with bookworms and foodies alike!

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Day 3

If the weather is good, you really should save a whole day to spend enjoying the great outdoors. Start the morning with a short walk through Boston’s Public Garden, a green oasis and the oldest botanical park in America. You can also take the Harborwalk along the waterfront to admire the pier and shoreline.

Alternatively, if you’re ready to get your history on, head to the Boston Tea Party Ships & Museum. Here, you’ll learn about Boston’s famous involvement in the Tea Act of May 10th, 1773. Or, if you’ve woken up with a burning desire for epic panoramic views, head up to the Skywalk Observatory where you can enjoy 360-degree views of the city from the top of the Prudential Tower.  

In the afternoon, pick between a sunset sightseeing cruise or a whale-watching cruise out of Boston Harbor. Whale-watching season typically runs from April to October, so head down to the harbor to see if there have been any early sightings. If not, it might be worth jumping on the Sunset Sightseeing cruise instead to enjoy Boston’s skyline lit up with the orange evening sky.

Photo by Osman Rana on Unsplash

How to get there?

Busbud can get you to Boston to enjoy this city break:

Montreal to Boston

New York to Boston

Baltimore to Boston

Philadelphia to Boston

Pittsburgh to Boston

Providence to Boston

Albany to Boston

Ottawa to Boston


This post was written by Hannah Hilton, a UK-based freelance travel writer and keen photographer. Check out Hannah’s adventures on her website, and follow her on Instagram.