Fun Things To Do in Boston: A 3-Day Guide

As you guys probably know by now, I love Boston, which has been my home for the last 4 years. But I’ve been visiting Boston for most of my life, as I grew up in the Portland area of Maine, 2 hours north of Boston. There’s so much to do in the city! To help you figure out how to spend your time here and see as much as possible, I’ve pulled together this 3-day guide full of fun things to do in Boston. There’s history, food, shopping, and more in this guide. Happy visiting!

Whether you live in Boston or are visiting for a weekend, there's plenty to do in this New England city. Boston lifestyle blogger Kate the (Almost) Great breaks down a 3-day travel guide to Boston full of fun things to do in Boston.

Fun Things To Do in Boston: Day 1

Duck Tour – This is a special kind of tour around Boston! According to their website, “The fun begins as soon as you board your “DUCK”, a W.W.II style amphibious landing vehicle. […] You’ll cruise by all the places that make Boston the birthplace of freedom and a city of firsts, from the golden-domed State House to Beacon Hill and the TD Garden, Boston Common and Copley Square to the Big Dig, Government Center to fashionable Newbury Street, Quincy Market to the Prudential Tower, and more. […] And just when you think you’ve seen it all, there’s more. It’s time for “Splashdown” as your captain splashes your DUCK right into the Charles River for a breathtaking view of the Boston and Cambridge skylines, the kind of view you just won’t get anywhere else” (x).

Mike’s Pastry – You haven’t gone to Boston if you haven’t gone to Mike’s. They have amazing desserts, especially cannoli (their website’s title is literally “Home of the Cannoli”). They can be very full due to their well-earned reputation, so don’t plan to just pop in quickly. “Founded in 1946, Mike’s Pastry is located in Boston’s historic North End on Hanover Street. Michael Mercogliano (the “Mike” behind the famed Mike’s Pastry) created the one-of-a-kind cannoli that keeps loyal Bostonians and tourists coming from around the world to enjoy” (x).

Dinner in the North End – If you like Italian food, you have to go to the North End, as this is the Italian section of the city. There are a ton of Italian restaurants, big and small, and I’ve never gone to a bad one. As the North End website says, “where else can you get a caffe latte, an Italian newspaper, an American history lesson, a great dinner and a moonlit harborside serenade all in the same evening? No where else but in Boston’s North End” (x).

Cheap things to do in Boston

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Fun Things To Do in Boston: Day 2

Brunch – Who doesn’t love Brunch? There are so many places to go in Boston. My family’s go-to spots are Stephanie’s, Aquitaine, and Frenchie. You can check out other places from Thrillist’s list of brunch places, Eater’s list, and TimeOut’s list.

Museums – There are so many museums in Boston! I looooove the Museum of Fine Arts. They have such a gorgeous collection, including exhibits about New England history and impressionist art, my favorite section. Plus, wheelchairs and rollators are free, which makes it even better in my book. The Museum of Science was always my favorite place to visit when I came to Boston when I was growing up. There are so many different exhibits, so there is sure to be something that your family will enjoy. While I’ve never been, my mom and sister rave about the Isabella Stewart Gardner Museum.

Shopping – There’s so much shopping in Boston! Newbury Street is the most famous, and it’s “Eight blocks filled with salons, boutiques, and fabulous dining. Boston’s Newbury Street has something for everyone” (x). The Prudential Center has shopping and restaurants. And “Here you’ll find unique shopping, including places like Vineyard Vines, Lord & Taylor, Saks Fifth Avenue, Sephora, and Vera Bradley. Plus you’ll find a variety of popular activities, and restaurants such as wagamama and 5 Napkin Burger, and it’s all under one roof” (x). Connected to Prudential is Copley Place, “Boston’s most distinctive shopping destination with 75 fabulous stores including Neiman Marcus, Barneys New York, Tiffany & Co., Jimmy Choo, Rigby & Peller, Legal Sea Foods, Yves Saint Laurent, Salvatore Ferragamo, David Yurman, Louis Vuitton, Christian Dior, Burberry, and Versace” (x). Newbury is outside while Prudential and Copley are inside.

Cheers – There are 2 locations of the famous bar where everyone knows your name. The original is on Beacon Street, and the replica is at Quincy Market. “You’ve seen the TV Show. You know and love the characters. Now experience the Boston pub that inspired it all – Cheers on Beacon Hill, previously known as the Bull & Finch Pub. This really is the place where everybody knows your name. Just step inside and see why. Founded in 1969 as the Bull & Finch Pub, Cheers Beacon Hill became the original inspiration for the setting of the TV show Cheers. In fact, the year that the Cheers show premiered on television (1982) Boston Magazine chose the Bull & Finch Pub as the “Best Neighborhood Bar” in Boston. We’re still an intimate neighborhood bar – our neighborhood has just gotten a little bigger!” (x).

Best coffee shops in Boston

Fun Things To Do in Boston: Day 3

Freedom Trail – This is a 2.5 mile trek through Boston that goes to various historical sites in the city. It is free to walk this on your own, but there are tours that require purchasing tickets. “Preserved and dedicated by the citizens of Boston in 1951, the Freedom Trail is a unique collection of museums, churches, meeting houses, burying grounds, parks, a ship, and historic markers that tell the story of the American Revolution and beyond” (x).

Old State House – This is “the birthplace of the American Revolution in Boston”. There are two tours available, the tour of the Old State House and the Boston Massacre tour. And if you’re in Boston for July 4, they read the Declaration of Independence, the same place it was read in 1776.

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Fenway Tour – If you like the Red Sox or baseball, you have to go on a Fenway tour at some point in time. We did this for my birthday one year and it was awesome. You go when the park is basically empty, so you get to see a really interesting view. More specifically, “Fenway Park is a place where dreams are made, traditions are celebrated and baseball is forever. See the home of Red Sox Legends, Williams, Yaz, Fisk and Rice. Visit Pesky’s Pole and sit atop the world famous Green Monster which stands 37 feet 2 inches high overlooking leftfield. Our experienced tour guides will provide a thrilling, one hour, walking tour of Fenway Park. Bilingual tours are available in Spanish and Japanese with advance notice. We welcome all fans to Fenway Park, home of the Boston Red Sox and the pulse of Red Sox Nation” (x).

What looks most enjoyable to you?

Like this post? Check out:

Best Places To Go in Boston, New England Trips This Spring and Summer, What To Do in Boston This Fall, A Weekend in Boston

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