Boston
Do you ever travel somewhere and just feel at home? For me, that’s always been Boston. I love the small town feel in the midst of a big city, plus all the history and delicious food. Growing up, my parents and I would spend about three weeks every summer on the Cape for 10 straight years. Sometimes we would venture into Boston when we flew into Logan International or we would drive up for the afternoon. So my introduction to the city was at a young age. As I got older and could explore it at my own pace I would do long weekend solo trips. Then my fiancé, Dayne, and I moved to New Jersey three years ago, putting us within driving distance. So we usually trip to make it up there 2-3 times a year. All this to say, I have spent a lot of time compiling the perfect weekend itinerary/travel guide to one of my favorite cities! I hope you enjoy.
Depending on where you are coming in from will depend on your departure time and arrival method. I have included two options for Day 1 depending on driving in from the NYC area or if you plan to fly into Boston Logan International Airport.
Day 1: Travel Day + Arrival (Driving from North Jersey/NYC)
Start drive around 9am north toward Boston
Make a pit stop in Mystic, CT to stretch legs and get lunch at the famous Mystic Pizza!
From where we live it takes about 2 hrs. 45 mins to get to Mystic
Dayne and I ordered small build your own ($14 before toppings) then walked down by the river to enjoy the weather and views
If you’re looking for a little coffee pick me up you can check out: Mystic Depot Roasters, Lighthouse Bakery, Sift Bake Shop or for a little spooky witchy vibe visit The Cloak and Wand!
Get back on the road and continue drive to Boston (1 hr. 30/45 mins.)
Road Trip Sidebar: If you are a fan of Samuel Adams Beer, you’ll be close to the company’s original brewery in Jamaica Plain!
The tours range in price and time - we chose the Sam Signature Experience ($15/45 mins)
Note: the parking for this brewery is a little tricky since it’s in the middle of a neighborhood so make sure you have plenty of time to park and walk
Get to Boston mid/late-afternoon and head to hotel or Airbnb
Neighborhoods I recommend:
Downtown/Financial District*- Right in the middle of the action, lots of hotels and Airbnb locations to choose from plus close to several public transit stations (the T).
North End - Here you’ll experience the hustle and bustle of Boston’s Little Italy while also enjoying all the wonderful smells from the local restaurants and bakeries
West End* - Right near Boston’s Little Italy, the West End makes travel easy as you are close by major transit stations, close to the famous Mass Gen Hospital and right on the Charles River. You’re also close to a few bridges that connect you to Charlestown and Cambridge.
Beacon Hill - This picturesque historic neighborhood is home to beautiful brownstones, Instagram worthy backdrops, local shops, and close to the Boston Gardens and Common. If you can’t find a place to stay in this area, I still recommend exploring it for a few hours.
Back Bay* - Another neighborhood in the middle of the action, Back Bay plays host to Copley Square, Trinity Church, the Boston Public Library, and the Finish Line for the Boston Marathon on Boylston Street.
Cambridge* - Located across the Charles River from Downtown Boston, Cambridge is home to MIT and Harvard University. This city is scenic, quiet, and perfect for anyone who wants to escape the large crowds.
*Places I’ve stayed in Boston
Once you are settled/checked in and refreshed head out to the North End for dinner at one of these amazing restaurants:
If you plan to go here you need to make reservations WELL in advance or be prepared to wait a long time - however it is 100% worth the wait.
After dinner, make sure to get a little treat at one of the many delicious bakeries in the North End! I always opt for a cannoli from Modern Pastry.
In case you didn’t know, there’s a longstanding cannoli rivalry between Modern and Mike’s Pastry (right across the street) that locals and tourists go back and forth on. Modern has a traditional feel (ironic considering the same) while Mike’s has a wide selection of cannoli flavors. Amongst my family and friends, we choose Modern but I’ve talked with others who prefer Mike’s - so now it’s up to you!
Also make sure to bring CASH when going into North End bakeries. Several of them do not take card at all.
Day 1 Alternative: Travel Day + Arrival (Flying into Boston Logan International)
Fly into Boston Logan International Airport
If you can make it happen, fly in earlier so you can maximize your day.
Also, if you are only planning to be in Boston and the surrounding cities during your trip, there’s no need to rent a car! The transit system is easy to use, cheap, and very clean.
Once you get all your luggage head for Ground Transportation/shuttles and look for the free to ride Massport Route 22, 33, or 55 shuttle that will take you to Airport Station
Once at the Airport Station, take the inbound Blue Line (toward Bowdoin) into Downtown Boston.
Depending on where you are staying will depend on which stop you get off on but usually it’s convenient to get off at the Government Center as that puts you right in the middle of the city.
My go-to app when using any sort of public transportation is Google Maps! Just put in your origin then destination and it will pull up the different lines and times you can choose from.
Also the T has tap-n-go turnstyles so just have your card ready!
If any of this is confusing or overwhelming do not worry someone will help you out. Look for an official transportation employee or ask a fellow traveler!
The trip from the airport into the heart of Boston usually takes 20 minutes
Once you get off at your stop and get your bearings, head toward your hotel or Airbnb
Neighborhoods I recommend:
Downtown/Financial District*- Right in the middle of the action, lots of hotels and Airbnb locations to choose from plus close to several public transit stations (the T).
North End - Here you’ll experience the hustle and bustle of Boston’s Little Italy while also enjoying all the wonderful smells from the local restaurants and bakeries
West End* - Right near Boston’s Little Italy, the West End makes travel easy as you are close by major transit stations, close to the famous Mass Gen Hospital and right on the Charles River. You’re also close to a few bridges that connect you to Charlestown and Cambridge.
Beacon Hill - This picturesque historic neighborhood is home to beautiful brownstones, Instagram worthy backdrops, local shops, and close to the Boston Gardens and Common. If you can’t find a place to stay in this area, I still recommend exploring it for a few hours.
Back Bay* - Another neighborhood in the middle of the action, Back Bay plays host to Copley Square, Trinity Church, the Boston Public Library, and the Finish Line for the Boston Marathon on Boylston Street.
Cambridge* - Located across the Charles River from Downtown Boston, Cambridge is home to MIT and Harvard University. This city is scenic, quiet, and perfect for anyone who wants to escape the large crowds.
*Places I’ve stayed in Boston
Once you are settled/checked in and refreshed head out to the North End for dinner at one of these amazing restaurants:
If you plan to go here you need to make reservations WELL in advance or be prepared to wait a long time - however it is 100% worth the wait.
After dinner, make sure to get a little treat at one of the many delicious bakeries in the North End! I always opt for a cannoli from Modern Pastry.
In case you didn’t know, there’s a longstanding cannoli rivalry between Modern and Mike’s Pastry (right across the street) that locals and tourists go back and forth on. Modern has a traditional feel (ironic considering the same) while Mike’s has a wide selection of cannoli flavors. Amongst my family and friends, we choose Modern but I’ve talked with others who prefer Mike’s - so now it’s up to you!
Also make sure to bring CASH when going into North End bakeries. Several of them do not take card at all.
