Perfect Boston 2-Day Itinerary Exploring the City

Boston is one of the most beautiful cities on the East Coast, although I may be biased. I have been visiting Boston since I was a kid, and I will never get over how stunning the city is.

Although Boston is a smaller major city in the US, it does not lack things to do. You can spend a lifetime exploring everything Boston offers, but you can see the highlights in a few days.

You can fill your 2 days in Boston with history, delicious restaurants, beautiful parks, and waterfront trails! This guide has everything you need to know to create the best Boston 2-day itinerary!

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Tips for Creating a Boston 2-Day Itinerary

There are a few things to know before you plan your 2 days in Boston.

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, including a rain jacket and insulated jacket.
Your Boston itinerary will include a lot of walking, so it is important to have comfortable and supportive shoes.I always recommend wearing supportive sneakers because they provide great support and comfy socks.
Your getaway 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!

Best Seasons to Visit Boston

Winter is one of the most underrated times to visit Boston if you are okay with snowy and cold weather. You can enjoy walking down snowy streets, spending your days staying warm in museums and historic buildings, and going ice skating in the Boston Commons!
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 the potential rain, you will not be disappointed to visit Boston in the spring!
Summer is one of the most popular times to visit Boston because the weather is warm, and all tours and facilities are open. You can enjoy walking around the streets of Boston in the gorgeous summer weather and sitting outside to eat.
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, you can still find beautiful foliage!

Closest Airport to Boston

If you are flying into Boston for your getaway, Boston Logan International Airport will be your airport because it is 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 smaller major city, I highly recommend mapping out everything on your Boston itinerary to figure out the best transportation to use. I usually walk or use the MBTA.

Walk: Boston is walkable, and it is free! Walking around Boston is a great way to experience everything the city offers.
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/Lyft: Uber/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.

Where to Stay in Boston

The best neighborhoods to stay in are Back Bay, Beacon Hill, Fenway Kenmore, North End, and South Boston for your 2 days in Boston. These Boston neighborhoods are safe, beautiful, near many must-see attractions, 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. Some of the best hotels are:

North End

If you want to stay in Boston's Little Italy, 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:

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:

The Best Boston 2-Day Itinerary

Boston is full of history, delicious restaurants, fun activities, and waterfront trails, so you will love spending time in Boston! This Boston 2-day itinerary includes must-see attractions you need to add to your bucket list.

Pro Tip: Get a Go Boston Pass or a Go City Pass to get a discount on many of the must-see attractions in your itinerary.

Day 1 in Boston

boston skyline in boston 2-day itinerary

The first day in your 2-day Boston itinerary has an iconic tour that brings you to many of the must-see attractions throughout the city. You can 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. I have been on both, and I liked both of them.

The Boston Trolley Tour is the perfect way to get around Boston and explore many must-see attractions. It guides you around the city and allows you to get off and on whenever you want to explore the attractions. You can make the tour as long or as short as you want, and I recommend getting off at any 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 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

>>Go on the Boston Trolley

Faneuil Hall & Quincy Marketplace is an iconic place to visit in Boston and has stores, restaurants, musicians, and street performers. It is the perfect place to grab food and explore some historic sites! I love grabbing a quick snack before heading further into Boston.
- Time needed: 1-2 hours
- How to get there: On the Boston Trolley Tour or the State Street subway stop
The North End is arguably the best place to eat in Boston, especially if you love pastries and Italian food. The North End is considered the Little Italy of Boston and has delicious food. You can spend your time dining at various restaurants or walking around the cobblestone streets.
- Time needed: 1-2 hours
- How to get there: On the Boston Trolley Tour or the Haymarket subway stop
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 (I recommend doing both!).
- Time needed: 1-2 hours
- How to get there: On the Boston Trolley Tour or the North Station subway stop
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 is an iconic and charming street in Boston with boutiques, cafes, restaurants, and salons. It is eight blocks long and is a great place to shop or walk along while taking in beautiful buildings.
- Time needed: 1-2 hours
- How to get there: On the Boston Trolley Tour or the Copley subway stop
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 because it is an incredible experience!
- Time needed: 1-3 hours
- How to get there: Museum of Fine Arts subway stop

If you prefer to take a tour that does not allow you to get off, the Boston Duck Tour is for you! 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!
- Time needed: 1.5 hours
- Departure locations: Museum of Science, New England Aquarium, or Prudential Center

>>Go on a Boston Duck Tour

Day 2 in Boston

Are you ready to explore some iconic historic sites in Boston? You can walk to these sites along the Freedom Trail or take the subway to each. The Freedom Trail is my favorite way to see the city. Whether you are a history buff or enjoy learning, you will love everything on this day!

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!
- Time needed: 1-3 hours
- How to get there: North Stations or Haymarket subway stops
The Paul Revere House was built in 1680 and was where Paul Revere 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

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

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.
- Time needed: a few minutes
- How to get there: Along the Freedom Trail or the State Street subway stop
The Old South Meeting House was the iconic gathering spot for the Boston Tea Party on December 16, 1773. It 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

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. Whether you want to enjoy lunch with a view or a seasonal activity, you will love the Boston Common and Boston Public Gardens! If you visit in the spring, you have to visit the Boston Public Gardens! It is one of my favorite areas because of the stunning flowers.
- Time needed: 2-4 hours
- How to get there: At the end of the Freedom Trail or the Park Street or Boylston subway stops

If you have extra time in your Boston 2-day itinerary

If you have extra time during your 2 days in Boston, I recommend adding any of these attractions to your itinerary!

The Museum of Science is one of the world’s largest science centers and fantastic for all ages, with 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 and is perfect for the family!
- Time needed: 3-4 hours
- How to get there: Science Park subway stop

The New England Aquarium is an incredible highlight of Boston and has marine life from all over the world, including seals, jellyfish, turtles, sharks, and penguins. It is a great activity for the whole family!
- Time needed: 1-2 hours
- How to get there: North Station subway stop

>>Go to the New England Aquarium

Boston is home to incredible sports teams and venues, and you can catch a Red Sox, Bruins, or Celtics game. If you plan your Boston 2-day itinerary for the summer, I highly recommend attending a Red Sox game in the iconic Fenway Park! The area is also home to many delicious restaurants.
- Time needed: Half-day

The Best Restaurants For a Boston 2-Day Itinerary

You honestly cannot go wrong anywhere you decide to eat in Boston! I have rarely had a bad meal in Boston, so I know you will enjoy eating your way through the city! I highly recommend checking out these Boston restaurants for at least one meal and visiting a rooftop bar for sunset.

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.

Boston 2-Day Itinerary OVerview

Here is a quick overview of this Boston 2-day itinerary:

Day 1 in Boston:

Boston Trolley Tour OR Boston Duck Tour
Faneuil Hall
The North End
USS Constitution and Museum
The Prudential Center and Copley Place Mall
Museum of Fine Arts

Day 2 in Boston:

The Freedom Trail
Paul Revere House
Old State House
Boston Massacre Site
Old South Meeting House
Boston Common and Boston Public Gardens

If you are looking for a fun weekend getaway in Boston, this guide is the perfect place to start planning your trip. It has everything you need to create an incredible Boston 2-day itinerary, including the must-see attractions!