Yes, it can be done. You can see the historic Boston in a weekend.

My first tip? Maximize your time. If you’re going to one area of town, make sure you do all the things you want to do and see all on the same day. That way, you’re not crisscrossing all over the city.

Here’s a sample itinerary based on my friend and I’s recent trip. We walked a lot of it and then other times we took an Uber. Don’t try to stress yourself out on trip. Know your limitations and relax in the back of a cab when you need to.

Day 1

This day, our flight got in right around 3pm, so we were able to get to our AirBnB and check in by 4pm. Once we checked in and got settled, we were ready to hit the ground running. Our AirBnB was in between the financial district and the theater district, so it was perfectly in the middle of all the things we wanted to do while visiting Boston.

Boston Tea Party Ships & Museum

Tea overboard! Become a revolutionist for a day and throw boxes of tea overboard in Boston Harbor while the tea party reenactors in period costume act out the historical event in detail.

Beacon Hill

If you’re interested in seeing the beautiful brownstone homes that Boston has to offer, you’ll want to visit the Beacon Hill area. This area is absolutely beautiful, but Charles street was our favorite. You can also take a trolley tour where the guide will tell you all about the historic homes and the famous people who lived there.

Acorn Street

This real cobblestone street from the 1700s gives you a glimpse into what the actual streets looked like for the colonists. While it’s a private street and can’t be walked/drove down, you can take a picture from the cross streets.

Cheers Bar

This underground bar was the inspiration for the 90’s sitcom, Cheers. You can grab a beer or just check out their memorabilia in this super touristy nod to the show.

Dinner at 75 Chestnut

This restaurant is definitely a favorite for locals. It offers outdoor seating, great cocktails, and absolutely delicious food. The staff was all super nice as well. If you go, make sure to get the Pineapple Elderflower Cosmo. Yum!

Day 2

Today is out first full day in Boston, so we plan on being gone all day. The name of the game today is history and food. Here we go!

Breakfast at Café Bonjour

When the number one breakfast place in Boston is three doors down from your AirBnB, you go. This place was delicious! I loved the French theme of the restaurant as well as the décor. The food was amazing. I had the Steak Tips and Eggs and it was SO good! I love anything with caramelized onions on it and this meal was delicious! It also came with homefries and you know this Texas girl loved that!

Freedom Trail

This was one of our favorite activities of the whole trip. Why? The Freedom trail is a 2.5 mile literal red brick trail you follow through the city in order to see a bunch of the most important historical buildings Boston has to offer from the era of the American Revolution.

You’ll begin your journey at the Boston Common Visitor Information Center located at 139 Tremont Street and conclude at the USS Constitution in Charlestown. Along the way, you will see places like:

• Boston Common
• Massachusetts State House
• Park Street Church
• Granary Burying Ground
• King’s Chapel
• King’s Chapel Burying Ground
• Benjamin Franklin Statue & Boston Latin School
• Old Corner Bookstore
• Old South Meeting House
• Old State House
• Site of Boston Massacre
• Faneuil Hall
• Paul Revere House
• Old North Church
• Copp’s Hill Burying Ground
• Bunker Hill Monument
• USS Constitution

We loved this tour! We also found this brochure to be super helpful in just giving us a brief synopsis of what we were looking at and why it was important. While we were on the trail, we made a few stops. We took our time, enjoyed a few restaurants’ specialty items, and meandered through town.

Quincy Market

This farmer’s market of sorts features food, live entertainment, and souvenirs. This place is super touristy, so be wary of that, but it was a great place to grab a cup of lobster bisque and a few souvenirs.

Skinny House

This famous narrow house is located at 44 Hull Street (right across the street from Copp’s Hill Burying Ground). This four story home boasts the “Most Narrow House in Boston” at only 10 feet wide. It’s sort of hard to wrap your mind around the fact that someone could live there. While there are differing stories on how this house came to be, this home is called the “Spite House” because both stories have it being built out of spite.

One story is that two brothers inherited land from their deceased father. While one brother was away serving in the military, the other built a large home, leaving only a shred of property that he felt certain was too tiny to build on. When the soldier returned, he found his inheritance depleted and built the narrow house to spite his brother by blocking the sunlight and ruining his view.

The other story is that two neighbors were quarreling and one built the narrow house so that it shut off the air and light from the home. No matter which story you believe, it’s still quite a sight to see.

The North End

I instantly fell in love with the North End, or “Little Italy” as it’s referred to. It’s a vibrant area filled with shops and restaurants – most of which stating how their red sauce, oysters, etc. are the best. While visiting this area, we found the best. Here’s where I recommend going.

Lobster Rolls at Pauli’s

For about $26, you can get a hot and buttered lobster roll and chips at Pauli’s. This place has been featured on the Food Network, has had tons of stars visit, and lots of success. But one bite into that hot lobster roll and you’ll know why. The buttered and grilled bun was the perfect vehicle for that mountain of lobster they put on top. Yes, $26 is pricey for a sandwich, but you definitely get your money’s worth. It was delicious and my mouth is watering for one as I sit here typing this up.

Cannoli’s at Mike’s Pastry

At just $5 each, you can grab one of their famous cannolis and man, are they good! Don’t forget your dollar bills though, because this place is cash only.

Dinner at La Famiglia Giorgio’s

We heard this place had the best “sauce” in town, so we decided to give it a try. Y’all, this place was amazing! I tried a classic – Chicken Parm – and it was SO good! The sauce wasn’t acidic at all (you know, that canned tomato taste) and the portion size was huge! I had two meals off of what they served me. They also gave us bread with an olive oil dipping sauce and served it with parmigiano Reggiano on top. I’ve never had it that way with cheese on it before, but now I won’t be able to have any without it. So good!

Day 3

For the last full day in Boston, the name of the game is to see the non-American Revolution historical places, pop culture references, and get a few souvenirs.

Breakfast at Café 26

Another delicious breakfast place we tried was Café 26. This breakfast and brunch place has a little bit of everything. Omelettes, English muffins, crepes, etc. they’ve got it all. I tried the Western Omelette with home fries and it was delicious. I always love starting off the day with a protein packed breakfast and we certainly needed it so we wouldn’t get hungry during all of our adventures!

Boston Pubic Garden

This beautiful garden has been around since the 1800s and is just gorgeous! You can walk around the grounds, take a ride on the swan boats, or have a picnic. It’s such a beautiful place to unwind.

Harvard Tour

We didn’t go to Harvard. We know nothing about Harvard except that’s an Ivy League school and super hard to get into. And yet, I think it’s a must see if you’re visiting Boston. The campus is absolutely gorgeous. You can walk onto campus without being a part of the tour, but I highly recommend taking the Hahvahd tour we did. It was inexpensive and an actual Harvard student led the tour. He talked about the history of the buildings, the faculty, the stories of how certain traditions came to be, and even a few tall tales. It was great!

Milk Bar

After walking around Harvard, we needed a little pick-me-up, so we stopped in Harvard Square at Milkbar, I’ve made their famous Birthday Cake before (with all 54824 ingredients) and it was amazing, but I’ve always wanted to try their Milk Bar Pie! I got my chance. It was SO yummy! It reminds me of a buttermilk pie (which I love), so I think I might be trying to make that at home next!

Lunch at Wahlburgers

Yes, we had dessert before lunch, it’s vacation, okay? After the Wahlburgers tv show came out, my friend insisted we go there to eat. It was such a neat place! There were movie and concert posters from the Wahlburger brothers’ accomplishments, Red Sox paraphernalia, and delicious food! We recommend trying the fried pickles and Jenn’s Chicken. I had Jenn’s chicken on a salad (and it was so flavorful), but I bet the sandwich version is just as good. My friend said the chocolate shake was good too. I imagine it would be a really fun place to watch a baseball game at since it’s so close to Fenway.

Fenway Tour

As a baseball lover, seeing Fenway was definitely on the list. Tours start every hour (when there’s no home game), and leave from the souvenir shop across the street. You can schedule a tour in advance or in store when you’re there. On the tour, you’ll see the inside of the stadium (including the Green Monster), hear the history of it, and maybe even a few tall tales too.

Where to Stay in Boston

We stayed at a place in between the Financial District and the Boston Common and it was perfect. If you need a place to stay, use the search bar below to find a place in your price range and area of town that you prefer!
Booking.com

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