This Boston winter guide provides you with a 2-day Boston itinerary that allows the perfect amount of time to explore all the sites and learn about the city’s rich history. A winter weekend in Boston is a great way to explore the city because you won’t have to deal with large tourist crowds and prices for accommodation and travel are much cheaper compared to warmer weather months!
Boston Winter Guide: Common Questions
Is Boston worth visiting in the winter?
Yes! Boston in the winter months is great time to visit with more affordable prices. Make sure to pack for the cold weather and you will have a great time.
Is Boston walkable in the winter?
Depending on the amount of snowfall, sidewalks may be covered with snow. If it only snows a few inches, then the snow is typically removed quickly.
Why is Boston so famous?
Boston is famous for its American Revolution history, beautiful architecture, and prestigious universities.
What is the cheapest month to visit Boston?
December to March is the cheapest time due to the cold weather. Take the opportunity to find a good deal on flights and lodging!
Is 2 days enough time in Boston?
You will be able to see most of Boston’s attractions in 2 days, making for a perfect winter weekend getaway.
Getting To and Around Boston
Getting to Boston
Flying
The closest airport is Boston Logan Airport; only 3 miles from downtown, taking about 10 minutes.
Getting Around Boston
Walking
Luckily, all the major sites within Boston are all within walking distance! Make sure to pack comfortable shoes and some thick socks, and you will be just fine getting around the city by foot.
Subway
Public transportation in Boston is really good and we took advantage of this quite a bit since we were staying in Somerville. Plan your stops before by utilizing this map.
Trolley
There is also a guided tour option that provides you with hop-on-hop-off access to all the major sites. This is a great alternative if you want more context into the major attractions or if walking long distances can be troublesome for you.
We had the luxury of having two friends as local tour guides who showed us all the main attractions in Boston. If you want more options for your Boston winter travel guide, check out my 12 things to do in Boston when it’s cold.
Boston Winter Guide Breakdown
Day 1
Isabella Stewart Gardner Museum
The Isabella Gardener Museum is a perfect addition to your Boston winter guide because it’s an indoor activity that gets you away from the cold!
This museum has pieces from popular artists such as Rembrandt, Whistler, Titian, and Botticelli. Another interesting fact about the Isabella Gardner Museum is that some pieces were stolen in an unsolved art heist in 1990. I watched the Netflix documentary “This is a Robbery: The World’s Biggest Art Heist” specifically about this museum and it was fascinating!
- Admission: Adults $22, Children 17 and under free
After the Isabella Stewart Gardner Museum, take the tram to Park Street to explore the Public Garden.
Boston Public Garden
The Boston Public Garden is 24 acres of beautiful scenery. Even though the winter isn’t the best time for blooming flowers and picnics, there are still two main Boston attractions that are worth seeing:
The Lagoon
This was a surprising activity that was not initially on our itinerary. The lagoon in the Boston Public Garden completely freezes over in the winter and you can walk on it! As someone from North Carolina, I was amazed by the frozen pond and had so much fun exploring the pond and the little island.
The lagoon in the Public Garden was initially maintained for ice skating until a dedicated rink was created in the Boston Common Park.
Make way for ducklings!
Within the Boston Public Garden, make sure to add the infamous Make Way for Ducklings statue to your Boston winter travel guide. Dedicated to Robert McCloskey and Make Way for Ducklings, a very well-known children’s book, that features the Boston Public Garden.
Throughout the year, the ducklings are decorated for various seasons and events pertinent to Boston. While we were visiting, they were supporting the Boston Bruins!
Wander Around Beacon Hill
A Boston winter guide is not complete without visiting the Beacon Hill neighborhood. Beacon Hill is a quintessential neighborhood in Boston known for its quaint streets and colonial charm. There are several independent shops and cafés throughout this neighborhood. I recommend visiting the Beacon Hill Books and Cafe, a tall multiple-story bookstore with different genres on each level.
Make sure to check out Acorn Street, which is one of the most preserved streets in Boston. It has a cobblestone path that is a reminder of colonial history.
Shopping Newbury Street and Architecture on Commonwealth Ave
A shopping day is a great way to escape the cold! Newberry Street offers a wide range of stores from Hermes to Princess Polly. Along the street, you will also stumble upon several galleries and churches that are also a great way to save some money and take advantage of the indoor things to do in Boston.
Walk along Newbury Street or admire Boston’s beautiful architecture along Commonwealth Avenue to get to your next stop on your Boston winter literary, the Boston Public Library.
Explore the Boston Public Library
A perfect indoor thing to do in Boston during the winter is to visit the Boston Public Library. The Library’s architecture is stunning and it is so cool to wander around the library and admire the art painted on the walls. There is so much detail within each room, it is truly stunning!
Ice Skating on Frog Pond
Ice Skating on Frog Pond is a perfect way to end the first day of your Boston winter itinerary because it is such a fun winter activity that adds to the charm of the city as you skate around in America’s oldest park and admire the skyline.
- Admission: $10 for anyone over 58 inches and free for anyone under
- Rentals: $15 for adults, $10 for kids
Day 2
Freedom Trail
Day 2 of the Boston winter travel guide will be based heavily on Boston’s pertinence to the American Revolution. You can’t visit Boston in the winter without exploring the sites on the Freedom Trail.
Even though this is mainly an outdoor activity, there are several churches and monuments you can tour to get breaks from the cold. This is the main attraction for things to do around Boston, there are so many sites related to the American Revolution!
Tip: Want to spice up the Freedom Trail? Make it boozy! With so many pubs and bars, you can easily turn the Freedom Trail into a bar crawl.
Finish your Day in the North End
One of the best things to do in winter around Boston is to warm up from the cold with a cozy plate of pasta. The North End of Boston is known as being the city’s Little Italy. We went to Al Dente and it was DELICIOUS. The pasta is handmade and we had a great experience there.
Another delicacy in the North End neighborhood that is a must-do on your Boston winter travel guide is to try both Modern and Mike’s pastry shops. There is a long-running debate about which is better so you need to try them both and decide for yourself!
Note: Mike’s and Modern Pastry are cash-only, so remember this when visiting the pastry shops.
Let’s Connect!
Interested in more Squeeze with Louise content? Follow @squeezewithlouise on Instagram so you never miss a post!
Thank You
Thank you for reading my post. I would appreciate your thoughts about how to spend 2 days in Boston in the winter, and how this blog post helped you plan your trip.
Interested in Other Travel Locations?
Click below to see my articles on places in the following destinations:
This ‘Boston Winter Guide: A perfect Weekend Itinerary’ guide might contain affiliate links, meaning I might make a small profit if you choose to book at no extra cost to you. This helps me provide you with quality content for free. Thank You
Thank you for reading my post. I would appreciate your thoughts about the Boston Winter Guide: A perfect Weekend Itinerary and how this blog post helped you plan your trip.
