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in Lifestyle · October 23, 2018

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.

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

Kate Mitchell

Kate Mitchell is a blogger, chronic illness patient, and advocate who helps people understand chronic illness and helps chronic illness patients live their best lives.

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Having decades-long health problems sometimes mean Having decades-long health problems sometimes means coming across something in your health history that you completely forgot about⁣
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⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣ID: Screenshot of a thread post written by Kate Mitchell | Kate the (Almost) Great with the username katethealmostgreat. ⁣⁣The background is dark teal. All text is what’s above the first black square.⁣⁣⁣
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Here are some ways I practice self care, aka talki Here are some ways I practice self care, aka talking care of myself AND who I am as a person separate from illness⁣
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This is my Wonderful Things jar. Every day, I write down something wonderful or good that happened that day. ⁣
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I know it looks like I'm forcing Harley to sit like this, but he was making this face before I put my arm around him. Dog snuggle time is the best!⁣
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I got a Kindle this year and it has been amazing. It's so much easier on my body than lugging around books and it makes borrowing from the library a lot easier.⁣
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Yes, I share this all the time, but filling my pill boxes every 3 weeks make it so I stick with all of my medications. But the self-care part of this is that I don't have to take the time to refill a box every single week.⁣
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I’m Kate, a chronic illness patient and advocate sharing what my life is like with 7+ chronic illnesses. Follow me for more and check out my blog at katethealmostgreat.com⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣
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1️⃣ A glass jar on a desk with a lot of multi-color post-its inside⁣
2️⃣ Kate has her face in a golden retriever who is slumped onto her. They're in a teal room with a red rug. Kate is a brunette white woman wearing red pants and a gray sweater.⁣
3️⃣ A Kindle on dark mode in Kate's lap⁣
4️⃣ 3 open pill cases on a yellow bedspread ⁣
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#AlmostGreatHealth #AlmostGreatLife #SelfCare #ChronicallyIll #ChronicallyAwesome #SpoonieLife #Spoonie #ChronicLife #ButYouDontLookSick #InvisibleIllness #MentalHealthMatters #RetrieversOfInstagram #Readers #Kindle #WonderfulThings #GratitudePractice
What I Bring To the Doctor _______ Video: a pa What I Bring To the Doctor 

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Video: a pan of an exam room. White text reads “What I Bring To the Doctor ” and the “1. Planner/notebook
2. List of current medications 
3. Notes on my biggest concerns and questions 
4. My kindle for wait time” 
The intro to Maroon 5’s Priceless plays. 

#AlmostGreatHealth #ChronicIllness #ChronicPain #RheumatoidArthritis #SjogrensSyndrome #Fibromyalgia #Endometriosis
💃🏼 Week 17 of #2025Weekly 💃🏼⁣
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1️⃣ She’s married!! ⁣
2️⃣ She married the best person in the world for her!!!!!⁣
3️⃣ I got dressed up! ⁣
4️⃣ The reality of doing fun things with chronic illness and pain is that then you have to recover from the fun things. It took … a while. One million percent worth it, but this is why I don’t do big events on a regular basis. ⁣
5️⃣ And then I had to be a person again for an appointment!⁣
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I’m Kate, a chronic illness patient and advocate sharing what my life is like with 7+ chronic illnesses. Follow me for more and check out my blog at katethealmostgreat.com⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣
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1️⃣ Kate stands hugging Emmie. They're both white woman. Emmie is in a wedding dress and Kate is in a red dress and wearing round tortiseshell glasses.⁣
2️⃣ Kate and Emmie stand next to Matt, Emmie's husband. He is a white man.⁣
3️⃣ Kate takes a mirror selfie. she's in the same red dress but now also wears a jean jacket and holds a cane and mask.⁣
4️⃣ Kate takes a selfie while giving a thumbs up. She looks tired. She's now wearing a pink flowery dress. ⁣
5️⃣ Kate takes a mirror selfie. She's wearing black shorts, a gray shirt, a jean jacket, a blue mask, and black aviator sunglasses. She has a bag over her shoulder and holds a cane.⁣
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On the one hand, you should always believe what pe On the one hand, you should always believe what people tell you about their bodies.⁣
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On the other hand, I’ve had so much ridiculous and unconnected health things happen that I do understand why people might not believe me.⁣
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⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣I’m Kate, a chronic illness patient and advocate. Follow me for more content for chronic illness patients and their loved ones!⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣
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Last week, I talked about how it surprised me how Last week, I talked about how it surprised me how systemic autoimmune arthritis can be. But something else that surprised me was how much pain can be caused by small things.⁣
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In this picture, I was getting ready to have an MRI on my knee. It has been bothering me a fair amount the last 6+ months, so I'm trying to do something about that. ⁣
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Unsurprisingly, some of the tissue is damaged, but it's not bad. What's probably causing it to bother me so much is a teeny tiny cyst. ⁣
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Baker's cysts are a type of cyst in the knee that are generally caused by arthritis. But having a cyst in my knee means that it's causing pressure on that damaged tissue. ⁣
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The body is a weird thing, and one of these weird things is developing tiny cysts that cause a lot of pain. ⁣
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I’m Kate, a chronic illness patient and advocate sharing what my life is like with 7+ chronic illnesses. Follow me for more and check out my blog at katethealmostgreat.com⁣⁣⁣⁣⁣⁣
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ID: Kate takes a mirror selfie. She's a brunette white woman wearing a hospital gown, scrub bottoms, black mask, round tortoiseshell glasses, and round tortoiseshell glasses. ⁣
🌸 Week 16 of #2025Weekly 🌸 ⁣ ⁣ 1️⃣ S 🌸 Week 16 of #2025Weekly 🌸 ⁣
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1️⃣ Spring has sprung … ⁣
2️⃣ … Which means I am overheating! ⁣
3️⃣ A quick view of NYC on my travels ⁣
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3️⃣ A picture of the New York City skyline behind a bridge.⁣
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If I met my newly diagnosed self for coffee ... ⁣
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I tell her how things would get worse before they got better. ⁣
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I'd tell her to stop eating gluten, dairy, corn, soy, and eggs immediately (although that would have been a lot harder in 2010, more than it even is now). ⁣
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I'd tell her that she still needs to keep advocating for herself. ⁣
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I'd tell her that having a diagnosis unfortunately doesn't mean everything automatically falls into place. ⁣
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I'd tell her that she'll develop many more illnesses but her quality of life will actually get significantly better. ⁣
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I'd tell her that she would eventually have to get her right foot fixed, although she does expect that.⁣
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I'd tell her that using a cane is not a sign of failure, but a tool to make life better.⁣
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(I did a sort of tongue-in-cheek post about this a while ago and thought I'd post a more serious one).⁣
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⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣I’m Kate, a chronic illness patient and advocate. Follow me for more content for chronic illness patients and their loved ones!⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣⁣
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The thing that surprised me the most about autoimm The thing that surprised me the most about autoimmune arthritis is how systemic it is. ⁣
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Like with most things, it's one thing to know the fact and it's something else to experience it. ⁣
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Yes, my joints are affected (a lot). ⁣
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But I've had enough serious infections thats I have to see an immunologist because we need to be aware of my antibodies and I sometimes need help recovering from illnesses. ⁣
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And, yes, I see pulmonology because of my asthma, but we also have to keep an eye out on developing rheumatoid nodules in my lungs. (So far so good!)⁣
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Not to mention that, when I developed POTS, the hospital admitted me to run every heart test to make sure that, at 26, I wasn't experiencing heart failure. ⁣
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Plus, when I developed endometriosis, I also went through a number of GI tests because one theory was that I had ulcerative colitis. ⁣
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Anyway, RA is so much more than "just" joints. If it wasn't, I wouldn't have to kill my immune system every 3 months like I am in this picture.⁣
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I’m Kate, a chronic illness patient and advocate sharing what my life is like with 7+ chronic illnesses. Follow me for more and check out my blog at katethealmostgreat.com⁣⁣⁣⁣⁣⁣
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ID: Kate takes a selfie in an infusion chair. She is a brunette white woman wearing a Boston Red Sox shirt, blue mask, and round tortoiseshell glasses.⁣⁣
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#AlmostGreatHealth #RheumatoidArthritis #RheumatoidDisease #Rheum #Autoimmune #AutoimmuneDisease #InvisibleIllness #ButYouDontLookSick #Sjogrens #SjogrensSyndrome #POTS #PosturalOrthostaticTachycardiaSyndrome #Dysautonomia
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