Boston Weekend Itinerary From a Local
From the European style architecture to some of the best universities in the world, Boston is truly amazing. Thinks clam chowder, the most authentic irish pubs outside Ireland, townies chatting about their favorite era of the Bruins in bars and street corners, and streets far too beautiful to be outside Europe. It is a great weekend destination because of it's small size - you can see a lot in a short amount of time. Read on to discover the best Boston Weekend Itinerary From a Local.
This post is all about your Boston weekend itinerary from a local.
What To Know About Boston
Established in 1630 by Puritans looking for religious freedom, Boston is the largest city in the northeast and is thought of by many as the birthplace of American history. It is home to some of the best universities in the world (Harvard, Tufts & MIT) and is commonly referred to as Beantown, although the locals don't call it that. The culture is strong and prevalent here - the pubs, sports pride, and accents are found throughout the city.
Where To Stay In Boston
Luxury Hotels In Boston
The Newbury - A luxury hotel set on the iconic Newbury Street and just steps away from the Boston Common. Originally opened in 1927 as a Ritz-Carlton, The Newbury beautifully maintains the old while keeping in modern. If you are looking for a luxury stay in Boston - this is your best option.
The Whitney Hotel Boston - The Whitney is a five star hotel in the fabulous Beacon Hill Neighborhood. This glamorous hotel has everything you need from an in house restaurant to free bikes to use. Make sure to stop by the most photographed street in the USA (Acorn Street) while at the Whitney in Beacon Hill.
Middle Range Hotels In Boston
The Colonnade Hotel - The Colonnade Hotel is a lovely option if you are looking for a fairly priced hotel that feels like a luxury. Located near the the oldest ballpark in MLB, Fenway, The Colonnade is modern clean and comfy .
Seaport Hotel- Located in the Seaport, this offers comfortable accommodation with views of the Boston Harbor. It is cozy with working fireplaces, room service, and beautifully appointed common rooms. There are amazing coffee shops and restaurants in the Seaport - be sure to try Tatte and Lola 42.
Budget Hotels In Boston
Battery Wharf Hotel - The Battery Wharf Hotel is a great option if you are looking to stay within a budget on your trip to Boston. It is one of the only options in the stunning North End neighborhood.
Club Quarter Hotel - The Club Quarter Hotel offers comfortable accommodation for a fair price set just a few steps from the iconic Faneuil Hall.
Best Tours To Take In Boston
If you want to learn as much as possible about Boston I would recommend taking a tour from a local guide! I wrote a post all about the best tours to take in Boston. Read full article here.
If you do any of these tours do this tour of Historic Fenway Park. You will learn so much about the oldest baseball stadium in the USA, and you will be able to see it without tons of crazed fans. Be sure to book this tour ahead of time because it will sell out.
When To Visit Boston
The best time to visit Boston is either the summer or the fall. My favorite month in Boston is October because of the gorgeous fall foliage and it is not too cold yet. Although if you want to extend your trip to The Cape and Islands definitely go in the summer.
What To Know Before You Visit Boston
Safety - Boston is a very safe city for the USA. But as always, take your normal precautions.
Climate - Winters - (20-30 degrees F) Summers - (70-80 degrees F)
Places to Avoid - Revere, Fall River, Malden, Lynn
Boston Weekend Itinerary From a Local
Day One
Morning - Newbury street and boston common
Newbury Street
Newbury Street has the best shopping in Boston. You will find luxury brands like Chanel and Gucci at the start of this one way street and more affordable ones like Urban Outfitters and Brandy Melville at the end of Newbury Street.
Newbury Street is a must see not only for the shopping but also to see the amazing architecture. You can't see these European style buildings anywhere else in the country.
If you get hungry on Newbury Street grab a bite from Stephanie's on Newbury or Joes. These are both local joints where you will find a great meal.
Boston Common
Located across the street from the start of Newbury Street is the Boston Common. The Boston Common is a lovely park that is a great escape from the city! The Boston Common has an adorable pond where you can ride the swan boats. The swan boats would be great if you are bringing kids on your trip to Boston!
The Boston Common is a great place to bring a book, coffee, and relax on one of the benches. This was one of my favorite things to do growing up in Boston. Right across the street is the Thinking Cup, a lovely local cafe.
AFTERNOON
Go To a Game
The first thing you will learn in Boston is that we are crazy about our sports. Go to a Red Soxs, Celtics, or my favorite, a Bruins game. The Patriots' stadium is in Foxborough which is far from Boston.
Day Two
morning
Faneuil hall
Faneuil Hall is a huge market place located near the Boston waterfront. It is a melting pot of culture. There is Indian food, Spanish food, you name it. Along with the food stands and restaurants, there are cute booths with homemade clothes and crafts.
AFTERnoon
North End
You cannot go wrong with food in the North End. Walk into any restaurant and have an amazing meal. My favorite restaurant all around in the North End is the Daily Catch. I also love Carmelina's, Giacomo's, and Pizza Regina.
Almost all of the restaurants in the North End do not take reservations. So ethier arrive early (especially on a weekend) or be prepared to wait in line. During the weekdays you should not have to wait for long, if at all. If you do have to wait, it is well worth it.
After your amazing meal in the North End walk to the water, it is right next to all of the restaurants.
Day Three
Morning
Beacon Hill
One of my favorite places in the city is Beacon Hill. Beacon Hill is absolutely gorgeous with it's cobblestone streets and brick homes and shops.
Start off your morning at Tatte in Beacon Hill. Then wander the streets.
Make sure you stop by the most popular streets in Boston, Acorn Street, located in Beacon Hill.
Afternoon
Cambridge
Home to Harvard University, Cambridge has one of the most intelligent zip codes in the world. There is so much to do in Cambridge. You can take a tour of Harvard University or explore Harvard Square. Harvard Square has a bunch of cafes and shops.
If you have extra time check out...
The Isabella Stewart Gardner Museum and Museum of Fine Art is great if you don't have much extra time in Boston. Should take no more than 2 hours to visit.
If you have an extra day in Boston I would recommend visiting the Cape and Islands or Salem depending on the time of year. If you are visiting Boston in the summer you should spend the day on the Cape and Islands. If you are visiting Boston in the fall go to Salem, MA and learn about the Salem Witch Trials.
⭐Go to the Cape for a day trip (especially if it's summer!)
⭐Day Trip to the Salem Witch Trials
The Best Food In Boston
Coffee & Breakfast
Tatte -Not only does Tatte have insanely good coffee, but they also have some of the best pastries and breakfast in town. Try the honey havala latte.
Blue Bottle - Blue Bottle is not unique to Boston, but it is still one of my favorites in the city. This minimalist coffee shop serves up amazing, but expensive lattes.
Thinking Cup - Located right on Newbury Street the Thinking Cup is the perfect place for a shopping break. It has the ultimate Boston vibes with the dim lights and eclectic decor.
Kanes Donuts - From the classic honey dipped to the creme brulee these donuts are so good!
Lunch & Dinner
The Daily Catch - The Daily Catch was my childhood favorite. This is seriously the best pasta I have ever had. Make sure to try the squid ink pasta. (walk in only)
Stephanie's On Newbury - Stephanie's is great for lunch in the middle of a busy day shopping. In the summer you can enjoy their outdoor dining right on the street. (reservation)
Carmelina's - Located in the North End you will find incredible Italian food at Carmelina's. (walk in only)
Giacomo's - Located in the North End you will find delicious Italian food at Giacomo's. (walk in only)
Pizza Regina - Pizza Regina is the best pizza you will find in Boston.
Dessert
Modern Pastry - Desserts are made fresh daily and located in the North End.
Bars
Where To Go From Boston
If Boston is just your starting point on a longer trip here are some places that would be a great second stop on your trip.
If you want to explore more of the Northeast I would recommend seeing York, ME - Portsmonths, NH - Nantucket, MA - Provincetown, MA
Related Article - 15 Places To Visit In Massachusetts
Boston Weekend Itinerary From a Local Wrap Up
Boston is such a fun city. I hope that this step by step Boston weekend itinerary from a local helps you plan the perfect trip. If you liked this post I think you will love my Complete Guide To Nantucket Island and my guide all about 5 of the best towns in Cape Cod, Massachusetts.
10 comments