Updated: Oct 21, 2019
Hi there! My name is Ashleen Chappuis (@a.bit.brighter) and I’m thrilled to explore Boston with you!
As the birthplace of the American Revolution, Boston is known for its history, but with a thriving job market and new cruise ship terminal, this rapidly growing city is hard at work on its modern reputation.
Boston is a very walkable city that’s great for a long weekend or as a home base for a larger trip around New England. The city is spilt into over 20 neighborhoods and across the Charles River from another city, Cambridge, so there are plenty of options for visitors looking to spend a longer time in the are as well.
The best time to visit Boston is June through September, though May and October can be beautiful if you’re lucky! Late spring here is on the cooler side, think 50’s to 70’s, but the streets are busting with color. Flowers are blooming in every window box on Beacon Hill, the trees in the Commons are coming back to life, and the locals are excited to shed their winter coats for some time in the sun. Don’t be surprised if the whole city seems to be out in shorts on the first really nice day of the year!
The summers are warmer, generally in the 70’s and 80’s, and with the warm weather comes rooftop patios, outdoor seating, and open windows all around town. Touristy areas tend to fill up around this time as the number of cruise ships picks up and more out of town visitors decide to take advantage of the nice weather to see the city. However, if you go a little ways off the beaten path, you’ll find a relatively calm city waiting for you to explore.
The early fall sinks back down to between the 50’s and 70’s as the leaves start to turn. You’ll find leaf peepers and locals wearing flannels and boots while enjoying the crisp fall air and all things apple. This is the best time of year to take a trip up north to Vermont or New Hampshire to see the mountains covered in shades of orange and red.
Late fall to early spring is cold, and Boston is a bit bleak so the city has 2 public outdoor ice rinks to try and brighten the mood. Visitors at this time tend to be going north for skiing or snowboarding or just in town for the holidays. A couple of Christmas markets pop-up around the city, and Boston puts up a big tree in Faneuil Hall that is well worth checking out!
Regardless of when you visit, Boston has a lot to offer. In this itinerary, we’ll visit some classics, a few local favorites, and a couple of hidden gems. Ready to get going?
Boston Day 1
The very first place to start in Boston is the Commons and the Garden. These two neighboring parks are situated downtown and create a patch of peace in all the hustle and bustle. The Commons is the larger park where a lot of Boson’s outdoor festivals are held. The Garden, on the other hand, is a bit more picturesque with flowerbeds, statues, and a small pond. It’s the setting of Robert McCloskey’s children’s book, Make Way for Ducklings, (you can visit a statue of Mama with all her ducklings in the Public Garden) and home to Boston’s swan boats, which take you around the pond and the little island made just for ducks.
Once you’ve gotten a chance to look around, head over to the information desk near Park Street Station in the Commons to start the Freedom Trail. If you want to hear about the local history from someone wearing colonial garb, stop inside the booth to buy tickets. As a big fan of walking tours (and people wearing costumes outside of Halloween), I’d recommend getting tickets. However, if you’d rather do it yourself, the Freedom Trail is free! Just follow the red line painted on the street. Keep a close eye on it because as you move, the line will switch between being red paint on tar, red brinks lined with silver stones, red bricks in cobble stones, and just red bricks going in a different direction than the other bricks making up the sidewalk.
As you work your way down the trail, either with a tour guide or on your own, you’ll end up at Faneuil Hall. This historic market was where the first protesters fought against the Sugar Act and later against all of British Rule. It was such a big deal back in the day that George Washington celebrated the US’s first birthday at Faneuil Hall!
Nowadays, this market is known for having street performers, shopping, and wide variety of food stands. If you’re traveling in a large group or are a picky eater, this the perfect place for you to have lunch! As the largest food hall in New England, it is bound to have a vendor selling something you’ll like. I’d recommend grabbing a classic lobster roll or a slice from one of Boston’s oldest pizza places, Regina Pizzeria, for lunch, and, if you’re looking for something sweet for afterwards, some chocolate chip cookies from the ChipYard or a cupcake from Magnolia Bakery. Fun fact, chocolate chip cookies were invented in Massachusetts!
After lunch, mosey on under the archway to Christopher Columbus Park. Situated on the water, this little park is a great spot to relax and watch the boats come in. If you’re looking for a photo-op, the vine covered archway is perfect for a Boston-themed picture.
From the park, head right along the water towards Boston Harbor Cruises and the Aquarium. Both places are a great way to spend the afternoon, so pick one based on the weather, how much time you have, and how you feel about boats.
Boston Harbor cruises offers sunset cruises, tours of the Harbor Islands, and whale watching trips lead by guides from the Aquarium. As a former whale watching guide myself, I would do the whale watch. On these trips you’ll have a chance of seeing Humpback, Minke, and Fin whales along with seals, birds, and, sometimes, dolphins! Amazing sights to see, just be sure to check the website for times and tickets so you don’t miss your boat!
If you’re spending the day at the Aquarium, note that it is the largest in all of New England. You can touch the rays, walk along the three-story tall tank in the middle, and play with penguins using a fish flashlight! Throughout the day there are different shows that teach you about the wildlife, including one with rescued seals, so be sure to look at their schedule when you get in.
Not looking to spend money this afternoon? That’s ok, the Aquarium has a small tank with gray seals out front that is free for anyone to look at. You just have to walk around the line at the ticket booth to find them.
After your aquatic afternoon, it’s time to stroll around Boston’s historic North End. This neighborhood is home to dozens of Italian restaurants, bakeries, and grocery stores. It’s a food-lover’s paradise with options for every budget!
If you’re looking for cheap eats, head no farther than Ernestos. They have the best pizza (a big claim, I know) and sell a quarter pie for around five dollars. Looking for a sit down place? Trattoria Il Panino has authentic Italian food in a cozy atmosphere. In the summer, they open up a whole wall to make you feel more outdoors. However, if you’re looking for fine dining, Bricco, which is owned by the same people, has some delicious options. Plus, they bake all their own bread in-house in the little bakery out back.
The North End is a bustling neighborhood, but once you start down the alley next to Bricco, you enter a different, much older world. The bakery, Bricco Panetteria, is down a flight of stairs and overs only a handful of breads, but each one is handmade and heavenly. The little grocery store next door has Italian imports and a sweet older couple behind the counter who seem to have been there forever.
For dessert, you have to go to Mike’s Pastry! This bakery is famous for their cannoli and one of the most well-known shops in Boston. The line to the counter is normally long, but moves quickly, you’ll see how once you get inside.
If you aren’t tuckered out yet, head over to Union Street for a row of local bars. Since they’re right downtown and near the T, these bars tend to be busy every night of the week. Signs out front will advertise cheap beer options while bars on the side streets will be pricier but offer better cocktails.
Boston Day 2
Start your day off right with one of Boston’s trendiest breakfast spots, Tatte, in Harvard Square. This local chain is booming for a reason. Ten years ago, there was only one Tatte bakery, famous for their cookies, and now, there is one in nearly every neighborhood in Boston. Thanks to Tatte, shakshuka has taken the city by storm so don’t miss out on this Middle Eastern and North African classic!
After breakfast, take a walk around Harvard. You can learn more about the school on a tour (the historic tours are not to be confused with the prospective student ones) or just enjoy the beautiful architecture on your own. If you’re looking for the real student experience, be sure to stop in the Harvard Bookstore for great staff recommendations and the COOP for all your Harvard memorabilia.
There are a lot of cute little stores to check out and a lot of great places to eat. If you’re hungry already, consider having lunch at The Border Cafe or Bartley’s Burger Cottage. Both places have loved for their uniqueness. The Border Cafe serves authentic Tex-Mex with a 90’s country flare, and Bartley’s dishes out some cult-favorite burgers while bringing you closer to your neighbors, literally since you will be sharing a table in this busy little eatery!
From Harvard, take the Red Line to Downtown Crossing. Have your camera ready for when you go over the Longfellow Bridge between Kendall/MIT and Charles/MGH. This is the pretties spot on any of the lines, and since the bridge is under construction and trains need to go slow over it, you will have plenty of time to get a good photo!
At Downtown crossing, switch to the Orange Line for a couple stops and get off at Haymarket. This is right where you were yesterday, however, depending on the day of the week, this area looks very different. Haymarket, held on Fridays and Saturdays, is a big outdoor market selling produce that is generally at peak freshness or a day or two past that. It’s a Boston tradition that is so popular, the city opened up a year-round public market right next door.
Instead of heading towards the North End like we did yesterday, follow the Green Way. This thin strip of park used to be a major highway that cut through Boston before the Big Dig, which put that highway underground. On weekends, the Green Way is full of stalls selling food, crafts, and farther down, local wine and beer. Be sure to sample all of it as you wander closer to the Seaport.
The two most buzz-worthy pop-ups in the area are Trillium and City Winery. Both have permanent spaces in the city, but tables at each are so sought after, they made outdoor spaces for people who just want to try the beers and wines outdoors. Just make sure to have a valid ID with you to get in!
While on this journey along the Green Way, be sure to walk along the water for a bit and take some photos under the archway at the Long Wharf. That is, if there isn’t a wedding taking pictures using this pretty backdrop. Then take a detour up Broad Street for Mr. Dooley’s Irish Pub. Famous for their live music, this pub is what a lot of people think of when they think of Boston, historic, cozy, and when the music’s playing, a bit rambunctious!
When you’re done walking the Green Way, you’ll hopefully be ready for dinner and in luck since you’re near the Barking Crab, a seafood restaurant on the water that is featured in too many movies to count, and Gourmet Dumpling House in Chinatown. You haven’t lived until you’ve tried their mini juicy dumplings!
After dinner how about a show? Right next to Chinatown is Boston’s theater district, which has big shows like the Lion King, Rent, and Cats as well as comedians, classical concerts, and more. Try to research what show you’d want to see before to make sure your timing lines up and tickets don’t sell out!
Boston Day 3
For our third and final day in Boston, we’re going back to where we started (I told you, the city is not that big!) to spend the morning shopping on Newbury Street. This is Boston’s high-end shopping area with luxury stores and trendy chain restaurants. It’s also home to several beautiful and historic churches for those who’d rather marvel at stained glass windows than window displays.
Another must see in the area is the Boston Public Library. Hear me out on this! There are two parts to the library; the true library part that is used by hundred of book fans each day and the museum-like part of the library that is great for relaxing with a good book and posing for Instagram.
If you liked the fountain at the library, you are going to love the first stop on our afternoon of Boston culture, the Isabella Stewart Gardener Museum! This former mansion is a photographer’s dream. Inside is a courtyard that feels like the Garden of Eden, especially on a cold, wintery day. It is home to variety of art, from ancient tapestries to watercolors to painted imported from far away lands, all collected by Isabella Stewart Gardener herself for this museum, which used to be her home.
On top of beautiful garden and priceless collection, this museum holds one of Boston’s greatest mysteries. In 1990, a total of thirteen works of art were stolen. These pieces have never been seen since, but the museum leaves their frames empty in the hopes that one day, they will all be found and returned.
After an afternoon of art and history, get ready for some baseball! Boston is home to the oldest major league baseball stadium in the United States, Fenway Park. Going to a game is a fun time even if you don’t like baseball. If you’re not following the game, you can focus on getting a Fenway Frank and a beer during the innings when there are no lines.
If there are no games going on, you can tour the stadium to learn more about its ups and downs and the team’s history. If there is a game going on but you can’t get tickets, you can watch from the Bleacher Bar, which looks out over the field. This bar is fun to visit even when there isn’t a game because it gives you a bird’s eye view of the stadium for the price of a drink!
For your last evening in Boston, stick around the Fenway area to see the nightlight. This neighborhood is sweet spot between a number of college campuses, one of Boston’s most popular concert venues, and Fenway park, so there are a lot of bars to check out and the dress codes are very relaxed. If the Red Sox played a home game, Landsdown, the most popular club nearby will be packed with a mix of high heels and baseball caps, though generally these aren’t on the same people, so whatever you’re wearing, you’ll fit right in. Other places to check out are the Cheeky Monkey and the Yard House.
Thanks for traveling with me, and I hope you liked Boston as much as I did!