Last fall my family and I flew to the east coast to spend a weekend in Boston. It’s a thanksgiving tradition for us to explore a new city together, and Boston did not disappoint. Small-town charm meets big-city style in this bustling city. After spending only a couple of hours in Boston I knew it was unique. I’m not usually a fan of big cities, especially New York, but Boston managed to capture my heart. Plan a trip to this historic American city with my Boston weekend itinerary. Explore the Freedom Trail, enjoy the harbor views, feast on seafood, and stroll through Little Italy.
Where to Stay in Boston
I ended up booking this Airbnb for my family and it was the perfect fit. I honestly don’t think we could have been in a better location. The Back Bay area is one of the most wonderful neighborhoods in Boston. Picture tree-lined streets with brick sidewalks, traditional brownstones, and cute neighborhood coffee spots. Tim was a great host. He provided us with all the local Boston hot spots.
*If this is your first time using Airbnb make sure to sign up with this link to receive $65 off your first stay!
What Time of Year to Visit Boston
When is the best time of the year to visit Boston? The weather is superb from June to October, but you’ll also find many tourists thinking the same thing. We visited in late November and got lucky with warmer than normal temps and sunny skies. If I was ever to visit again I would plan a trip for early-mid October in order to see the fall leaves changing.
*Photo by Centre Reality Group
Getting Around Boston
Walking is a must in Boston. I wouldn’t even consider renting a car unless you’re taking day trips to visit nearby Salem or Cambridge. We had no issues with exploring the city on foot. It’s free, convenient, and you’ll be working off all those extra calories from the cannoli’s you’ve been eating. Of course, walking is weather dependent so you can also try Uber or public transportation.
*We averaged 6.5 miles of walking a day and occasional took an Uber ride.
BOSTON AREAS TO EXPLORE:
I’ve broken up this Boston weekend itinerary into different areas we explored during our weekend stay. As you’ll notice, most is food. But hey, what’s traveling without tasting local cuisine? We had everything from lobster rolls to soup dumplings during our trip. My favorites are indicated with a star*.
South Boston & Backbay Area
*Mike & Patty’s – Boston’s Best Breakfast & Lunch Sandwiches! Takeout only.
Blackbird Doughnuts – fresh doughnuts, coffee, and soft-serve treats daily from six locations across Boston.
Coppa Enoteca – an intimate restaurant featuring Italian small plates.
*Barcelona Wine Bar – tapas shaped by Mediterranean, Spanish, and South American influences
FoMu – vegan ice cream shop
Luke’s Lobster Back Bay – delicious lobster rolls!
*Tatte Bakery – cute local bakery/café with multiple locations around the city. I tried their seasonal latte and it was scrumptious!
China Town
Gourmet Dumpling House – try their soup dumplings and scallion pancakes.
*Gong Cha (bubble tea) – I had the brown sugar boba and it was 10/10
Happy Lamb Hotpot – my first hot pot experience and it certainly won’t be the last!
Central Boston
Brattle Book Store – if you’re walking by this bookstore stop in and support this small business!
Boston Public Market – is an indoor, year-round marketplace featuring New England artisans and food producers housed under one roof.
Union Oyster House – Boston’s oldest restaurant, serving seafood and New England specialties in a historic setting on the Freedom Trail.
Little Italy
Neptune Oyster – lines form early for the raw bar & warm, buttered lobster rolls at this tiny, high-end oyster bar.
Salumeria Italiana – a cute shop selling a range of Italian groceries, including meats, cheeses, pasta & sauces.
*Mike’s Pastry – the cannoli’s are out of this world.
The Daily Catch – Sicilian-inspired seafood and pasta est. 1973.
*Giacomo’s Boston North End – is a casual, reasonably priced Italian restaurant with some of the best pasta dishes in the city. Be warned, there is almost always a line.
North Boston
Freedom Trail – is a 2.5-mile-long path through downtown Boston that passes by 16 locations significant to the history of the United States.
Central Rock Gym – rock climbing gym chain found in many parts of the city. We climbed at the North Boston location.
I hope you got some tips from this Boston weekend itinerary! Let me know in the comments if you plan to travel to Boston anytime soon.