A Weekend in Boston Itinerary
It’s you’re planning to a spend a weekend in Boston, I’ve got your Boston Itinerary right here! These are all the restaurants you’ll want to check out, neighborhoods to visit, guided tours, and places to stroll!
This was such a last minute trip!
My husband had been to Boston, Massachusetts before for a quick conference and came back raving about it. So when we needed a northern destination to check off of our bucket list on the way up to Canada, we flew into Boston Logan International airport for a weekend trip. I’ll be honest, this was a last minute trip so I got several of the recommendations on this list from my good friend and my sister. Both of them had been before and knew what I’d love to see and do!
I had always heard that the best times of the year to visit Boston was between September and November and luckily, the timing worked out perfectly for us. Cool morning and sunny afternoons, we clocked in about 15,000 steps a day and ate our weight in cannoli’s, pizza, and more!
A 2-3 day Boston Itinerary
- Newbury Street: A shopping area lined with 19th century brownstones. They have tons of high end stores and boutiques. Even if you aren’t planning on buying anything it’s great to walk around and take in the sights!
- Boston Public Library: This is a beautiful work out art! For as long as I can remember, I’ve always wanted to visit Bates Hall with its iconic green lamp room! Then walk across Boston’s Copley Square to the Trinity Church.
- Acorn Street: This is one of the most photographed streets in the city! This row of houses is considered highly prestigious and there are signs everywhere that say it’s a private lane. Visitors are asked to respect it and stay off of the street. But you can always stand at the corner and check it out!
- Charles River Esplanade: Gives you a beautiful view of the Boston skyline!
- Beacon Hill: A great neighborhood to check out on the way to or from Acorn Street. The old corner bookstore (Beacon Hill Book Store) is beautiful and you could spend hours getting lost in there!
- Boston Commons: You can start walking the Freedom Trail here. The Freedom Trail start in the Boston Common, to the Old North Church in the North End and the Bunker Hill Monument in Charlestown. This is rich in America’s history.
- Boston Public Garden: Make way for Ducklings are located here and they are the cutest! You should also check out the Lagoon Bridge.
- Harvard University: Absolutely stunning college campus located in Cambridge, MA. We weren’t really planning on adding this to our itinerary and since we skipped the Freedom Trails (a dream for a history buff, but we just aren’t) we decided to use the afternoon to Uber into Cambridge. Afterwards, head to the amazing Uyghur restaurant in the food reccs!
- Quincy Market: Historic market located right across from Faneuil Hall Marketplace in Downtown Boston. These are both great place to check out and grab a few souvenirs, clam chowder, and for crowd watching.
- Isabella Stewart Gardner Museum: tickets are $20 for general admission and they do offer a beautiful afternoon tea service at the cafe for an extra cost. Though it is a bit pricey, so definitely budge for this if it’s something you’d enjoy!
- Catch a Red Sox game: if you’re a baseball fan, this is not to be missed. The Boston Red Sox play at Fenway Park during the season.
- Boston Ghosts and Gravestones Trolley Tour: This boards off of 200 Atlantic Ave, right in front of the Marriott. This is steps from the Boston harbor. We had dinner at Regina’s Pizza, grabbed Mike’s then walked over for the tour. Keep in mind that though it is a trolley tour, there are several times you have to hop off and walk (sometimes up hill) to historic landmarks such as the Granary Burying Ground and King’s Chapel Burying Ground. We had a few people on the tour that hopped off and didn’t come back, because of mobility issues. The tour guide carries a little lantern as you walk to burying grounds and honestly, for an all-things-spooky fanatic, this was one of my favorite things to do in Boston! Buy tickets here.
- Boston Duck Tours: This is a great way to see the city if you are short on time on a guided tour without having to leave the duck mobile! The tour guides take your through sites such as the Theater District, Massachusetts State House, Fenway Stadium, and many others before giving you a water tour! We started the tour from New England Aquarium and returned there before walking around the harbor front for a bit.
Where to Eat in Boston:
- Regina’s Pizza: With locations all over the city, we opted for the first and most famous one in North Boston.
- Located at 11½ Tatcher St. Boston, MA
- Mike’s Pastry: I have an un popular opinion! I didn’t care for Mike’s Pastry. There was so much hype surrounding this dessert shop and honestly, it was kind of meh. Overly sweet, not much flavor to the desserts. But you should still try it for yourself! A quick heads up, they only accept cash!
- Modern Pastry: We didn’t get a chance to try this shop, but I wouldn’t be doing my Boston itinerary justice if I didn’t mention it. Many people try both this and Mike’s and like to pick their favorite!
- Ogawa Coffee: They had the most amazing drip coffee. And my thing is, if you can do drip right, it’s worth checking out!
- Bruegger’s Bagels: For a quick, grab and go breakfast!
- Pressed Cafe: Located in Back Bay, this is a great little breakfast spot.
- Located at 105 Huntington Ave. Boston MA 20199.
- Yankee Lobster: A great place to catch some fish and chips, clam chowder, and lobster rolls! Boston is all about the seafood!
- Located at 300 Northern Ave, Boston, MA 02210.
- Silk Road Uyghur:A tiny hole-in-the-wall that packs a flavor punch. Serving up pan-fried noodles with spices, this is not to be missed.
- Located at 645 Cambridge St, Cambridge, MA 02141
- Tatte Bakery and Cafe: There are locations for this coffee shop all over the city. The shakshuka and the poached eggs on avocado toast along with the pistachio croissant were divine!
- Located at 70 Charles Street Boston, MA 02114 (this is the Beacon Hill location but there are others in Back Bay, South Boston, Fenway, and several others)
FAQs about Boston:
I’d say 2-4 days depending on how quickly you can get through attractions and how much of a history buff you are! If you are into history, give yourself plenty of time as there is plenty to see in Boston!
Yes, and you should! Boston is not a city where you want to drive! Instead opt to clock in plenty of steps and use Uber for when your feet just can’t handle another step. The key is to center yourself in the city based on the places you’d like to visit so that you are walking and not Ubering everywhere.
I would say that Boston has something to offer for everyone and is definitely worth adding to your itinerary. With that said, would I fly from Houston to Boston just to see Boston? No. But I would definitely recommend it as a city to hit on your east coast tour!
Layers! Depending on the time of year you visit, Boston can start off cool and warm up throughout the day before it dips again in the evening. Layering is the best way to stay comfortable.
Of course, these are just some of the many things to do in Boston, so if I missed your favorite, feel free to leave it in the comments below 🙂
If you like this, you might also like:
- Fall Things to do in Woodstock, VT
- Experiencing Fall in Stowe, Vermont
- Girls Trip to New York
- 19 Tips for Visiting the Wizarding World
- A Weekend in Chicago