Boston boasts a revolutionary history, delicious Italian food, and quaint cobblestone streets. It’s more of a town than a city, making it walkable and easy to explore in a weekend. It’s a great stop on a New England road trip or a weekend getaway in the northeast. This itinerary jam-packs Boston into a single weekend.
Let’s get into it.
Friday: Dinner and Jazz
In this itinerary, we are assuming you’re arriving in Boston in the afternoon on Friday. After checking into your hotel, you’ll go out in the South End for a night of Italian food and jazz. The South End is a charming neighborhood with Victorian houses and upscale eateries. You could walk to the South End from the city center, but at night I’d opt for an Uber.
Dinner at Coppa
Get ready to feast on Italian food in Boston. Coppa is a small upscale Italian spot in the South End. Its menu features smaller plates, pastas, and pizzas that are meant to be shared. Make sure you save some room for dessert for their decadent serving of tiramisu. You’ll need to make a reservation for Coppa in advance as its small dining room fills up quickly.
Jazz at Beehive
Two blocks away from Coppa is Beehive, a restaurant and jazz bar. There may be a line but the free live music makes it worth it. On the ground floor is a regular bar but down in the basement is where the music is (and there’s a bar there, too).
Saturday: The Freedom Trail
The Freedom Trail is a 2.5-mile path that takes you through the historic sites of Boston. It starts in the Boston Common and takes you all the way to the U.S.S. Consitution. Even if you aren’t a history buff it’s an easy marker to follow for a walking tour around downtown Boston.
Breakfast at Mike and Patty’s
For an easy breakfast on the go, visit Mike and Patty’s in Bay Village. The small breakfast sandwich counter is tucked into a little neighborhood that isn’t quite Back Bay or South End. The breakfast sandwiches are super tasty but be prepared to eat them on the street because there are only two counter seats at the shop.
On your way to Mike and Patty’s you’ll likely walk through the Theater District and Chinatown. You can stop at a Tatte, a local Boston cafe chain, for a coffee to enjoy on your walk.
Boston Common and Public Gardens
The Boston Common and Public Gardens are two parks right next to each other in the center of Boston. The Common is the larger of the two but the Public Gardens is the nicer park. The Gardens is home to a swan lake with a picturesque bridge and beautiful willow trees. Like any proper garden, the trees are marked so you can see which type of foliage is featured in the garden. It’s worth a stroll in each park.
The Freedom Trail
The Freedom Trail starts on a corner of Boston Common. There is a pathway or line made of bricks that guides you through downtown Boston. If you want to see all 16 stops it will take you about 2 hours to complete but I recommend using the Freedom Trail as a guide to take you through the historic districts of Faneuil Hall and the North End. Along the way, you’ll see sights like the Quincy Market and Paul Revere’s House.
Sam Adam’s Taproom
In Faneuil Hall, stop for a beer (or a flight) at Sam Adam’s Downtown Boston Taproom. It’s next to Quincy Market and other shops. They don’t brew their iconic Boston Lager on site but the keg is still fresh and delicious.
Lunch at Regina Pizzeria
The best pizza in Boston is at Regina Pizzeria. There are many locations around the city but you need to go to the original one on Thatcher St. in the North End. Like many places in Boston (and the North End) there will be a line but it’s worth it.
Cannolis at Mike’s Pastry
Make sure to save some room for dessert for cannolis in the North End. The three top spots for cannolis are Mike’s Pastry, Modern Pastry, and Bova’s Bakery but Mike’s is arguably the best and most famous. On busy days, all three bakeries will have lines out the door. Mike’s has multiple lines so just walk in and jump into one. It’s cash only and cannolis are $6 each.
Pro Tip: Bova’s Bakery is open 24/7 if you want to snag a cannoli during off-peak hours.
Dinner at Aqua Pazza
Aqua Pazza feels quintessentially Boston. It’s Italian cuisine that’s seafood-forward. It has delicious seafood dishes and local oysters but also non-seafood classics like chicken parm done well. Many restaurants in the North End are small and don’t have waitlists so try to get a reservation wherever you go.
Sunday: Back Bay and Beacon Hill
Breakfast at Metropolis
Start your day in the South End at brunch at Metropolis. It’s a small casual eatery with breakfast classics. They have a delicious warm blueberry muffin that you can split as an appetizer.
Copley Square and Boston Public Library
After brunch, head to Copley Square on Boylston St. and peek inside the Boston Public Library. It’s a beautiful building that will transport you to an Ivy League college campus. Depending on the day and season, there are occasionally open-air markets in Copely Square from food to vintage clothing.
Shopping on Newbury Street
Newbury Street is the shopping district of Boston. Even if you’re not in the shopping mood, it’s a pretty street to walk down with Victorian architecture and bay windows. There are commercial stores like Anthropologie and Doc Martens and local consignment shops that you should check out like Covet.
Charles River Esplanade
A couple of blocks from Newbury St. is the Charles River Esplanade. It’s a peaceful path along the Charles River for pedestrians, joggers, and cyclists. On the river, you’ll find many sailors and rowers on nice days. The view on the other side of the river is Cambridge, home to MIT and Harvard.
Beacon Hill
Beacon Hill is a historic neighborhood that’s gorgeous to stroll through. It has old, steep cobblestone streets like Acorn St. that tourists flock to. The main street with shops and restaurants is Charles St. which leads to the Charles River.
Late Lunch at Barking Crab
Before leaving Boston or New England, you need to indulge in a lobster roll. Barking Crab specializes in all kinds of shellfish and serves seafood in a kitschy restaurant on the water in the Seaport district. They have a patio that’s open in the summer months but indoor seating is available all year round.
Where To Stay
You’ll want to stay anywhere around the Boston Common or Public Gardens to be the most central. We stayed at the Omni Parker House, the oldest hotel in the United States. It’s where John F. Kennedy proposed to Jackie O. and where the Boston Cream Pie was invented. It’s also along the Freedom Trail, so I highly recommend it.
Getting Around
Boston is very walkable. The T is their underground transit system but it can sometimes take the same amount of time to walk as it does to wait for the train. If you’re traveling in a group, I recommend catching an Uber or Lyft. It’s worth the convenience.
A note on Uber and Lyft at Logan Airport: When you get dropped off at the airport by an Uber or Lyft driver, you will be dropped off in a parking garage, not at the departure terminal. Since many people are taking Ubers and Lyfts, it causes an influx of traffic so you might want to factor this into your travel plans.
Other Fun SPOTS
Fenway Park
In the summer months, catch a Red Sox game at Fenway. If you’re visiting in the off-season, you can still take a tour of the park and see the Green Monster, which is the giant wall that baseball players need to hit a ball over to get a home run.
Cambridge
Across the Charles River is Cambridge, which feels like an extension of Boston. MIT and Harvard are both in Cambridge but are actually quite far from each other if you choose to walk. On a summer day, it’s a nice bike ride between the two college campuses. If you have to choose between the two, visit Harvard Yard. It’s prettier and more historic.
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