I am SO excited to be sharing this blog post. I have visited Boston plenty of times and from my first visit I instantly became obsessed and fell in love with the city. Every time I visit this city my excitement and love for the city only grows. Honestly, what’s there not to love? The city is the perfect size, not too big and not too small, almost everything is within walking distance, the food is amazing, the city is right on the water, the buildings are beautiful, full of 19th century brownstones, cobblestone and brick roads, and there is just so much history on every street you turn down!
I’ve compiled a list below of a suggested tentative schedule, a full list of things to do during your trip and of course, some amazing food recommendations!
Staying for a long weekend? Here’s a tentative schedule for you to use with the must see things to do on your first trip:
- Walk around the city
- Fenway Park
- Newbury Street shopping
- Visit the Boston Public Library (It was closed when I went)
- Dinner at Eataly in the Prudential Center
- Boston Commons morning walk
- Quincy Market
- Union Oyster House for lunch
- Christopher Columbus Waterfront Park
- North End for Little Italy dinner
- Tatte Bakery
- Acorn Street
- Shop at Charles Street in Beacon Hill
- Walk the entire Freedom Trail
- Dinner at China Town
Things To Do In Boston
Take A Walk
On every trip I recommend this and will continue to. I highly suggest simply stepping out of your hotel and taking a walk around the area. Get comfortable with your surroundings and see what’s nearby you.
Fenway Park is a must see in Boston! The stadium has been around since 1912 and home to the Red Sox. The stadium is one of the oldest in the MLB and really cool to see in person. You can see a game (after COVID ends), take a tour of the stadium or just walk around the outside like we did to see some vintage, no longer used spots, such as the ticket booths!
The area surrounding Fenway park has a very fun vibe to it with lots of young adults, so stop by a restaurant and grab a beer or even a slice at Regina’s Pizza which is across the street.
I recommend this to all my art lovers out there! Tim and I enjoyed the Art Museum but agreed that it wasn’t a “must see” on the trip and that it could definitely be saved for a 2nd trip to Boston. Either way, the museum is beautiful and anyone who loves art museums and history will have an incredible time here.
While you’re in the area, walk around Berklee College of Music. You will see such an artistic group of students walking around, all with musical talent as they hold their instruments and hustle to class. Such a cool environment to be in!
Newbury Street Shopping
If you love the modern day and historical mix (well, then you’ll love all of Boston), then you will be obsessed with Newbury Street! It is packed with stores and boutiques all squeezed into a few blocks inside 19th century brownstones. The street is beautiful and always filled with people shopping and taking a stroll. It is incredible to see that THIS is what shopping looks like in Boston! Everything is placed in such beautiful buildings with a modern flare that comes from the store inside.
This is a must see on your trip! Quincy Market is directly in front of the historical Faneuil Hall, which is famous for being a meeting place for Patriots on the night of the American Revolution. Quincy Market is filling with walk up restaurants that range from seafood, desserts, American favorites, etc. The thing to get here though is of course, the clam chowder!
Quincy Market is surrounded by the North and South Market on each side of it which are filled with stores to shop at (yes, such as American Eagle – they literally put mainstream stores in these beautiful buildings and historical centers).
Christopher Columbus Waterfront Park
This Waterfront Park is directly across the street from Quincy Market (See what I’m saying now about how everything is all in walking distance?) and a beautiful little break to your day. The park is home to a huge dome that is entangled with vines and plants. It’s a stunning, peaceful site and you have the choice of grabbing a bench under the plants, or, a spot in front of the water. The waterfront is directly next to the park and if you go at the right time, you may see a local musician out performing.
If you’re with kids, the park also has a playground as well as the Greenway Carousel nearby!
Little Italy for dinner (North End)
This is an absolute MUST. There are no exceptions, you have to go to the Little Italy in Boston, located in the North End of Boston. The locals simply call it, The North End. The Little Italy here has a main 2-3 blocks filled with authentic, Italian food, because the majority of the population in the north side of Boston is Italian. I swear, I have never tasted better quality pasta in my life. Little Italy soon became Tim and I’s favorite place in Boston, so we made sure to stop there on each of our trips!
The streets are narrow and old, covered with the typical Boston 19th century brownstones, all smashed up in a row alongside each other. Walking through the streets will have you going through what feels like a maze, and you may even stumble upon The Paul Revere House as well!
Checkout my blog, “A Foodies Guide To Boston” for a deep dive into all my favorite spots to eat in Boston.
Discover Beacon Hill
Beacon Hill is hands down my favorite area in Boston. It is filled with some of the most beautiful homes and old, cobblestone or brick roads, pathways, etc. After researching, I found out that these homes are technically called a Federal-style and Victorian brick row of houses. All of these homes are pushed right up next to each other in rows and its such a relaxing time to just walk by them, block by block. I recommend going in the fall so you can see how cute these homeowners decorate their front steps with pumpkins, gourds and flowers.
- Checkout Acorn Street in Beacon Hill
This is one of the most picturesque spots in Boston. They even say that it’s the most photographed spot in Boston and I can completely see why. It is a very old street in Boston that brings you back to Colonial Boston, with a thin, beautiful cobblestone path to walk down.
I stumbled upon this while taking a stroll through Beacon Hill and fell in love! This little flower shop is so cute and filled with flowers displayed outside the shop as well as festive pumpkins and gourds in the fall. I can also assure you that the inside will have something you will want to take home, whether it be a little plant, bouquet, or new pot for your plant.
Walk Around & Shop On Charles Street
Charles street is located in my favorite area of Boston, Beacon Hill. It is filled with boutiques and antique shops, and of course the most important – a Tatte Bakery. Take a break during your walk to enjoy some baked goods and a little shopping.
Walk The Freedom Trail
This is another absolute must do in Boston. I highly recommend it because you will be able to see literally everything I told you to visit above – yes, everything. BUT, I suggest visiting all these places first so you can have time in each of them, enjoy them and make a mental note of when to get ‘off the trail” to stop at your favorite spots. So then, when you start the Freedom Trail, you’ll be able to see all these places (and more!) and know if you want to make another stop or not.
The walk is fairly easy, but I definitely recommend wearing comfortable shoes since it is 2.5 miles long. You will be walking on sidewalks, brick roads, cobblestone – everything – so just bring the right shoes. The trail takes you past 16 historical sites in Boston that are very significant to the United States history. It is incredible to see some of these old, historical buildings placed directly in the center of the city and skyscrapers. This walk will put a lot in perspective for you and make you fall in love with Boston even more.
- Of course, there is another easy stop to Tatte Bakery along the trail when you need a food break
- Climb to the top of Bunker Hill: Your walk will end at Bunker Hill, located in Charlestown. The monument is beautifully positioned in the middle of Charlestown on a hill. If you’re up for the challenge, you can walk all the way to the top of the monument, a total of 294 steps.
- Enjoy Charlestown: Charlestown is the oldest neighborhood within the city of Boston and you can definitely tell this as you walk through. Bunker HIll is positioned in the center of a square plot of land, with homes fully cocooning it. It is a beautiful site and I highly recommend walking around the homes after to take in their beauty. The style is different from the 19th century brownstone you will see in downtown Boston and Beacon Hill. They are full of color and life and are more square shaped. But, they have the same uniqueness as each home does in Beacon Hill, with front steps being decorated and each front door being uniquely different from the next. Walking around this neighborhood was incredibly peaceful. Enjoy the end of your walk along the Freedom Trail by grabbing a bench at Winthrop Square park.
Stop At A Local Book Shop
- Brattle Book Shop is a well known bookshop in Boston and looks so cute. It is known for rolling carts of books out into the alleyway next to the store front, for people to be outside and browse.
- Commonwealth Books is another cute bookshop, directly on the path of the freedom trail.
Dinner At Chinatown
I wouldn’t say this is a must for everyone’s first visit, since the China Town in Boston isn’t as large as say the one in San Francisco – but for people like me, who are obsessed with China Towns AND dumplings – yeah, I recommend making a stop. More on where to eat below!
Checkout Broadway Street and the Downtown Crossing
Broadway Street is beautifully lit up at night by a few theatre signs and is a nice stroll while you discover more of the city. They also have a 4-way street called the Downtown Crossing which is a shopping area completely paved and for pedestrians only, no cars are allowed.
Eataly + Shopping In The Prudential Center
I highly recommend stopping at the Eataly in the Back Bay area. Some of the best Italian food and pizza I had was from there and it’s always so fun being fully thrown into Italian Cuisine while walking through the market. Food recommendations below!
The Eataly is located in the Prudential Center, which is a shopping center with stores such as Saks Fifth Avenue, MAC, LOFT, Kate Spade, Barnes & Noble, etc. Ready for more shopping? This mall leads into Copley Place, which is a very high end shopping center with stores such as Tiffany & Co, Jimmy Choo, Louis Vuitton, Dior, etc.
Walk Along The Harbor Walk
The harborwalk is a paved walkway that lines the Boston Harbor. It runs a distance of 47 miles from East Boston to the Neponset River. Take a stroll down the harborwalk to get amazing views of the city and the shoreline.
Visit The Modern Seaport District
Something new I did on my 2nd trip to Boston was visit the Seaport District! Once you head over the Congress Street Bridge, you enter the Seaport District (South Boston Waterfront) which is a bit opposite of Boston’s usual 19th century brownstone buildings, historical sites and monuments at every corner. Instead, you are surrounded by an extremely modern, up and coming area. The Seaport District is a newly redeveloped area on the South Boston waterfront. The streets are filled with huge, tall, fully glass paned apartments, restaurants, bars and hotels. When I went, the area was filled with young adults and seemed like a fun space if you’re into a young environment and modern, up and coming city life.
Book Your Stay
Where To Stay:
- Back Bay: The hotel I stayed in during my first trip was in the Back Bay of Boston. We stayed in the Hilton Boston Back Bay hotel. I recommend this area since you can walk to a bunch of places such as Newbury Street, Fenway Park, Boston University, Museum of Fine Arts, Boston Public Library, Prudential Center, etc.
- Theatre District: The next hotel I stayed at during my 2nd trip was at The Courtyard Marriott in the Theatre District. This was a great area as well because it was a close walk to the Boston Commons, about a 15 minute walk to Beacon Hill and just a block from China Town.
Booking On A Budget:
Hotwire is one of the best sites I use to book all my hotels during my trips at a great price. I’ve used them plenty of times and every time it has been a great experience, a very nice hotel and the lowest prices! Hotwire gives you a last minute, discounted room that hasn’t been booked yet. Read more about Hotwire in my “NYC Travel Guide.”
Like I said earlier, Boston easily became my favorite city yet. How much I love the city and vibe it has is indescribable. I get excited just thinking about it! It was the one city where I felt so at home in. It gave me that feeling that one day, down the road, I could maybe see myself there. For Wisconsinites – a homey feeling is what we long for, it’s instilled in us, and it’s one we always think we can’t find anywhere but in our home town – well, not true – I felt it in Boston. I felt that homey feeling with a twist of excitement and nerves! Nerves because I knew there was the possibility that I wanted to live there.
There’s really nothing you can hate in Boston. Obviously, every city has its issues, that is never not going to happen. But Boston has that perfect mix of history and modern day. It soothes the feelings you may get when you wish you were born in a different era, but, it also hits on those feelings you get when all you want is new, exciting and up and coming. Boston ticks all the boxes. It was incredible to see all of the old, historical buildings placed directly in the center of the city, wrapped around modernized skyscrapers. That’s what makes Boston the best. It’s old and new. Vintage and modern. Its past and present.
Get out there and see it for yourself!