Unforgettable Boston 3-Day Itinerary: Weekend In Boston
Welcome to the ultimate Boston 3-day itinerary! Although Boston is a smaller city than others in the US, it does not lack things to do. I have been visiting Boston my entire life and still find new things to do and see with every trip. You can spend a lifetime exploring everything Boston has to offer, but you can see the highlights in a few days.
You can fill your Boston 3-day itinerary full of history, delicious restaurants, beautiful parks, and waterfront trails! This guide has everything you need to know to create the perfect Boston 3-day itinerary, including travel tips, how to get there, where to stay, and the best things to do in Boston!
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Tips for Creating a Boston 3-Day Itinerary
Boston is a beautiful city full of so much to see, but there are a few things to know before you go. Here are a few things I think are crucial to consider before creating your Boston 3-day itinerary:
Boston’s weather is unpredictable. If you are visiting in the warmer months, I recommend bringing a rain jacket. In the winter months, I recommend bringing many layers as it can be very cold.
Your Boston 3-day itinerary will include a lot of walking, so it is important to have comfortable and supportive shoes. I always recommend wearing running sneakers because they provide grI always recommend wearing supportive sneakers because they provide great support.
Your trip to Boston does not have to be expensive. There are many ways to save money, including discount cards, discount codes, or purchasing tickets in advance to must-see sights in your Boston itinerary. There are also many free things to do in Boston!
Boston is an incredible city that you will fall in love with! Do not forget to visit many of the wonderful museums in the city.
Best Time to Visit Boston
Winter
Winter is one of the most underrated times to visit Boston. If you are okay with cold weather and snowy streets, you will love this quiet time to visit. I love walking down snowy streets, spending my days staying warm in museums and historic buildings, and going ice skating in the Boston Commons!
Spring
Spring in Boston is beautiful once the snow melts and everything blooms. The only downside to spring is it tends to rain a lot. If you are okay with some rain, you won’t be disappointed visiting Boston in the spring! We also love visiting the Public Gardens and Charles River Esplanade to see the stunning flowers!
Summer
Summer is one of the most popular times to visit Boston because the weather is warm, and all tours and facilities are open. We love walking around the streets of Boston in the gorgeous summer weather and sitting outside to eat. Summer is one of our favorite times to visit Boston!
Fall
Fall is one of the most beautiful times to visit Boston because the weather is perfect, and the foliage takes over the parks! New England is known for its fall foliage, and Boston is no different. Although the city has fewer trees than other areas, we have still found beautiful foliage!
Closest Airport to Boston
If you are flying into Boston, Boston Logan International Airport will be your airport because it's close to the city. The subway connects it with downtown Boston, so you can easily get into the city without a car.
How to Get Around Boston
Although Boston is a small city, I highly recommend mapping out everything on your Boston 3-day itinerary. It will allow you to figure out the best mode of transportation to use during your trip.
Walk: Boston is walkable, so I always recommend walking through the city as a way to get around. Walking is also a free option to see the city.
MBTA: The MBTA is a cheap and great way to explore the city. Boston’s subway system can be confusing, but you can use Google Maps to understand where a stop is and where the line will bring you. If you are flying into Boston Logan International Airport, you can take the MBTA into the city right from inside the airport.
Bluebikes: Bluebikes has over 300 bike locations in and around Boston, so you can pick up and drop off bikes wherever needed!
Uber or Lyft: Uber and Lyft are great options for getting around without worrying about parking.
Car rental: I do not recommend renting a car. Although it is doable, traffic and finding parking in Boston can be a nightmare. Boston also has a lot of one-way streets, so it is easy to get lost.
Best Places to Stay in Boston
Boston has over 20 diverse neighborhoods. The best neighborhoods to stay in, in my opinion, are Back Bay, Beacon Hill, Fenway Kenmore, North End, and South Boston for your Boston 3-day itinerary. These Boston neighborhoods are safe, beautiful, near many sights in your Boston itinerary, full of restaurants and bars, and have plenty of hotels.
Back Bay/Fenway Kenmore
These Boston neighborhoods are in the western part of Boston along the Charles River. Back Bay and Fenway Kenmore are near many attractions in your Boston itinerary, including the famous Newbury Street, Boston Common, Boston Public Garden, and Fenway Park. Some of the best hotels are:Beacon Hill
Beacon Hill is more of an upscale neighborhood in Boston. It is near Boston Common and Boston Public Garden and has many cute cafes and pubs.XV Beacon Hotel (on the pricier side)
North End
If you want to stay in the Little Italy of Boston, look no further! The North End is a place to eat, drink, and be merry because it has some of the best food and pastries in the city! The North End is also near many must-see attractions in your Boston itinerary, including Boston Harbor, TD Garden, and Faneuil Hall. Some of the best hotels are:Boston Marriott Long Wharf (on the pricier side)
South Boston
South Boston is one of my favorite neighborhoods. I highly recommend staying in the Seaport section of South Boston because it is near the water and has outdoor beer gardens, rooftop bars, and delicious food. Some of the best hotels are:Overview of the Best Boston 3-Day Itinerary
Below is a quick overview of everything in this amazing Boston itinerary! We will dive into each of these further.
Day 1:
The Freedom Trail
Paul Revere House
Old State House
Boston Massacre Site
Old South Meeting House
Boston Common and Boston Public Gardens
Day 2:
Boston Trolley Tour OR Boston Duck Tour
Faneuil Hall
The North End
USS Constitution and Museum
The Prudential Center and Copley Place Mall
Boston Common and Boston Public Gardens
Day 3:
Museum of Science
New England Aquarium
Museum of Fine Arts
Boston Sporting Event
The Best Boston 3-Day Itinerary
Boston is full of history, delicious restaurants, fun activities, and waterfront trails, so it truly has something for everyone! Whether you want to spend your days walking through museums or attending sports games, you will love spending time in Boston!
I have visited Boston more times than I can count, so I know the best places to visit! This Boston 3-day itinerary includes many must-see attractions that you can choose from depending on what you want to do and how you want to experience this beautiful city.
Pro Tip: Purchase a Go Boston Pass or a Go City Pass to get into many of the must-see attractions in your Boston 3-day itinerary.
Day 1 in boston
The first day in this Boston 3-day itinerary includes exploring some historic sites in Boston along the Freedom Trail! You can walk to these sites along the Freedom Trail or take the subway. I highly recommend walking the Freedom Trail because it is one of the best ways to truly see Boston. We still walk the Freedom Trail when we go into Boston because it is always a fun experience!
The Freedom Trail
The Freedom Trail is a 2.5-mile trail that brings you past historical sites throughout Boston, including the Boston Massacre Site, Paul Revere House, Old State House, and Old South Meeting House. I recommend beginning at the Old North Church and finishing near the Boston Commons. You can pay for a tour along the route, but I recommend a self-guided tour on the red-lined trail. I also recommend looking at the map ahead of time to familiarize yourself with it. I will also list a few highlights below! The Freedom Trail is a fantastic way to see many historic sites while enjoying the city views as you walk.
Time needed: 1-3 hours
How to get there: North Stations or Haymarket subway stops
Paul Revere House
The Paul Revere House was built in 1680 and was the home to Paul Revere. This house was where he lived during the American Revolution before he set out on his journey to warn the patriots about the British invasion. It is one of the only buildings from the 17th century that is still standing in a major city!
Time needed: 30 minutes
How to get there: Along the Freedom Trail or the Haymarket subway stop
Old State House
If you want to learn about Boston’s history, the Old State House is the perfect place to visit. It is considered one of the most important historical sites in Boston, and you can learn about colonial Boston and Revolutionary America.
Time needed: 1 hour
How to get there: Along the Freedom Trail or the State Street subway stop
Boston Massacre
On March 5, 1770, the Boston Massacre took place, where the Redcoats and Bostonians fought. Today, there is a marker on the ground, marking where it took place. The Boston Massacre Site is a quick stop to add along the Freedom Trail after visiting the Old State House and holds a lot of history.
Time needed: a few minutes
How to get there: Along the Freedom Trail or the State Street subway stop
Old South Meeting House
The Old South Meeting House was the iconic gathering spot for the Boston Tea Party on December 16, 1773! This iconic spot is an old Congregational Church and now a museum, where you can learn more about the history of Boston and the building.
Time needed: 1-2 hours
How to get there: Along the Freedom Trail or the State Street subway stop
Boston Common and Boston Public Gardens
The Boston Common and Boston Public Gardens are located in the heart of Boston and are at the end of the Freedom Trail. The beautiful parks offer gardens, picnic areas, ponds, Swan Boat rides in the summer, and ice skating on Frog Pond in the Winter, making it the perfect place to add to your Boston 3-day itinerary in every season! Whether you want to enjoy lunch with a view or enjoy a seasonal activity, you will love the Boston Common and Boston Public Gardens!
Time needed: 2-4 hours
How to get there: At the end of the Freedom Trail or the Park Street or Boylston subway stops
Day 2 in boston
The second day of your Boston 3-day itinerary has an iconic tour that brings you to many of the must-see attractions in Boston. You can either spend your day on the Boston Trolley Tour or the Boston Duck Tour. Both tours bring you to many of the same attractions but are two different experiences.
The Boston Trolley Tour allows you to get off and on, while the Boston Duck Tour does not have the option to get off. We have been on both and loved them! The tour you choose will depend on how you want to experience Boston!
Boston Duck Tour
If you would prefer to take a tour that does not allow you to get off, the Boston Duck Tour is perfect for you! The Boston Duck Tour is a great way to many Boston highlights. The main difference between the Boston Duck Tour and the Boston Trolley Tour is the Boston Duck Tour travels by land and water, which is a fun experience! If you are looking for a quick tour that drives past many must-see attractions and you are not interested in getting off, the Boston Duck Tour is perfect for you!
Time needed: 1.5 hours
Departure locations: Museum of Science, New England Aquarium, or Prudential Center
Boston Trolley Tour
The Boston Trolley Tour is the perfect way to get around Boston and see many must-see attractions. It guides you around the highlights and allows you to get off and on whenever you want. You can make the tour as long or as short as you want, and I recommend getting off at any of the stops that interest you! Although your original trolley tour will leave once you get off, you can get on another that passes by. I recommend seeing the list of attractions, so you can plan ahead where you will get off! I will list some of the highlights below as well!
Time needed: a full day
Departure location: New England Aquarium
Faneuil Hall and Quincy Marketplace
Faneuil Hall and Quincy Marketplace is the first stop on the Boston Trolley Tour and has many stores, restaurants, musicians, and street performers. It is the perfect place to grab food and explore historic sites you may have missed on your first day!
Time needed: 1-2 hours
How to get there: On the Boston Trolley Tour or the State Street subway stop
The North End
The North End is another incredible place to eat, especially if you love pastries and Italian food. The North End is considered the Little Italy of Boston and has some of the best food in the city, in my opinion. You can spend your time eating or walking around the cobblestone streets. We always love our meals in the North End; the food is delicious!
Time needed: 1-2 hours
How to get there: On the Boston Trolley Tour or the Haymarket subway stop
USS Constitution Museum
The USS Constitution and Museum has two historic ships and an interactive museum. You can either visit the museum or board the USS Constitution ship!
Time needed: 1-2 hours
How to get there: On the Boston Trolley Tour or the North Station subway stop
The Prudential Center
If you are looking to shop, the Prudential Center and Copley Place Mall are perfect for you! They have a large mall, stores along the street, and many delicious restaurants. The Prudential Center is also home to the iconic Eataly!
Time needed: 1-2 hours
How to get there: On the Boston Trolley Tour or the Prudential and Copley subway stop
Newbury Street
Although it isn’t a stop along the tour, you can visit Newbury Street when you get off at the Copley Place Mall. Newbury Street is a charming Boston street filled with boutiques, cafes, restaurants, and salons. The eight-block-long street is a great place to shop or walk along while taking in the beautiful buildings.
Time needed: 1-2 hours
How to get there: On the Boston Trolley Tour or the Copley subway stop
Boston Common and Boston Public Gardens
If you did not have a chance to explore the Boston Common and Boston Public Gardens on the first day, this is your chance! The beautiful park offers gardens, picnic areas, ponds, Swan Boat rides in the summer, and ice skating on Frog Pond in the Winter, making it the perfect place to visit in any season! Whether you want to enjoy lunch with a view or enjoy a seasonal activity, you will love the Boston Common and Boston Public Gardens!
Time needed: 2-4 hours
How to get there: The Boston Trolley Tour or the Park Street or Boylston subway stops
Day 3 in boston
The third and final day of the Boston 3-day itinerary has a few different options! You can explore museums and aquariums, spend time at a sporting event, or both.
Museum of Science
The Museum of Science is one of the world’s largest science centers and is fantastic for all ages! There are many interactive exhibits, including an electricity theater, a planetarium astronomy center, science presentations, and an IMAX theater. It also has an entire section for kids with hands-on activities.
Time needed: 3-4 hours
How to get there: Science Park subway stop
New England Acquarium
The New England Aquarium is an incredible highlight of Boston. It has marine life from all over the world, including seals, jellyfish, turtles, sharks, and penguins.
Time needed: 1-2 hours
How to get there: North Station subway stop
Museum of Fine Arts
The Museum of Fine Arts is one of the most comprehensive art museums in the world, featuring over 450,000 pieces of art. Even if you are not a fan of art, I highly recommend adding the Museum of Fine Arts to your Boston itinerary.
Time needed: 1-3 hours
How to get there: Museum of Fine Arts subway stop
Boston Sports Game
Boston is home to incredible sports teams and venues, and you can catch a Red Sox, Bruins, or Celtics game. If your Boston 3-day itinerary is planned for the summer, I highly recommend attending a Red Sox game in the beautiful Fenway Park!
Time needed: Half-day
The Best Restaurants for Your Boston 3-Day Itinerary
Boston has some of the best food, so you cannot go wrong anywhere you decide to eat! I highly recommend adding many of these restaurants to your Boston itinerary and checking out a rooftop bar for sunset. Below are some of my favorite places to eat!
Food
Regina Pizzeria - This will be your go-to place for all things pizza. And yes, the pizza is worth all of the hype!
Union Oyster House is one of the best seafood restaurants in Boston.
Giacomo’s Ristorante is one of the best Italian restaurants. It is so good and worth every penny.
Dessert
There is a debate about which pastry place is better: Modern Pastry or Mike’s Pastry. Both are classic pastry spots you need to visit. Some say they are overrated, and I will not disagree, but their pastries are AMAZING, especially their cannolis. They have anything your heart desires!
Rooftop Bars
Legal Harborside is one of my favorite rooftop bars because they have great food and drinks. The line can get very long, so I recommend arriving early.
Lookout Rooftop Bar is another rooftop bar in Envoy and is open year-round, with patio furniture in the summer and igloos in the winter. Although the drinks are expensive, the views are worth it.
Breweries/Beer Gardens
Harpoon Brewery offers a tour of their brewery and tastings of their beer selection.
Trillium Garden is a seasonal beer garden and has food trucks on site.
Cisco Brewers is another seasonal beer garden with an extensive list of beers, cider, wines, and frosé.
If you are looking for a weekend getaway in a beautiful city, Boston is the perfect location. This guide has everything you need to create an incredible Boston 3-day itinerary!
Hey, I’m Nichole!
I am the creator behind Nichole the Nomad, the home of my explorations around the world, mountain hikes, and beautiful pictures taken along the way. I have a deep passion for capturing the world in a beautiful light and sharing my experiences.
I created this blog to share my travels, show how beautiful the world is, provide tips and tricks for traveling, and encourage you to explore. Whether you want to travel across the world or explore what’s in your backyard, I hope this blog inspires you to get outside and find your adventure!
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