Best Places to Explore in Boston for Every Traveler
Why should you consider Boston for your next getaway? This historic and vibrant city offers something for every traveller. From its renowned museums and eclectic culinary scene to its endless shopping opportunities, there’s no shortage of things to explore.
Whether you’re a history buff, a foodie, a cultural seeker, a retail therapy lover, or simply looking for a memorable experience for the whole family, this city has it all!
In this guide, I’ll share everything you need to plan an amazing trip, including my favourite hotel options and a list of the best places to explore in Boston for every interest. Your epic Boston weekend awaits… Start building your perfect itinerary today.
Getting to Boston
There are several different options for making your way from Toronto to Boston. Deciding on the best plan for your trip will depend on your budget and preferred form of travel.
By Car
You can drive to Boston in approximately 9 to 10 hours if you prefer road trips. This is a great way to explore the many great locations available along the way. If you want to explore Quebec, you can travel to Boston via ON-401 E, stopping in Laval, QC and Montreal, QC. Alternatively, you can take your trip along I-90 E, visiting Buffalo, NY, Rochester, NY and The Finger Lakes. Either option is sure to be an incredible trip.
By Train
If your idea of a dream vacation involves a picturesque train trip, your trip would require two legs. First, you can travel from Toronto to New York Penn Station on VIA Rail, starting at $174 one way. From there, transfer to the Amtrak from New York to Boston, starting at $70 USD one way. The total travel time would be approximately 17 hours.
By Bus
Another public transit option would be to take the bus. Greyhound offers a 23-hour route from Toronto to Boston starting at $98 round trip. You can reduce your travel time to 21 hours by travelling with FlixBus, with prices starting at $132 for a round trip.
By Plane
Are you ready to get your trip started ASAP? The quickest option is to fly into Boston’s General Edward Logan International Airport. There are several flights to choose from, and the prices always fluctuate. At the time of writing this article, a flight with Air Canada starts at approximately $220 one-way for a 1 hour and 45 minute non-stop flight.
Best Hotels in Boston
When deciding on your accommodations, there are many options to consider. You may wish to book an Airbnb, stay at a local campsite, or try one of the many city of Boston hotels. The best part about travel is that there is no “right” choice, just the right choice for you.
To help you decide, here is a list of the top hotels in Boston (in my opinion):
Omni Boston Hotel at the Seaport
450 Summer St
Conveniently located near Boston Harbor, Omni Boston Hotel at the Seaport is an excellent option for those interested in spending most of their trip in the beautiful Seaport District. Not only are there many attractions and activities nearby, but the hotel offers everything you need for a relaxing getaway, including a heated rooftop pool and hot tub, an on-site day spa, and six dining options ranging from the contemporary menu at the Lifted Rooftop Restaurant & Bar to a more traditional Mediterranean-American menu at Kestra’s.
The Envoy Hotel, Autograph Collection
70 Sleeper Street
If you prefer a more contemporary and creative aesthetic, check out The Envoy Hotel, an award-winning hotel with easy access to the city’s downtown. Each guest room and suite features all the amenities, creative and unique décor, and beautiful city skyline views.
I recommend checking out Rooftop at the Envoy, the hotel’s rooftop bar and lounge. This is a popular spot for locals and visitors; it won’t take long to see why. Here, you can enjoy stunning views while enjoying a delicious meal and a refreshing cocktail.
The Langham, Boston
250 Franklin St
For those who would prefer a luxury hotel experience, The Langham, Boston, is the perfect option. Named the Best Hotels 2023 Winner by U.S. News and World Report, this elegant hotel offers a variety of different rooms suited for each type of traveller, from family-friendly rooms to professional options with larger workspaces for your next business trip. Onsite dining options include The Fed, a British-inspired cocktail bar with a menu of pub-style foods and Grana, a classic family-style Italian restaurant.
Best Places to Explore in Boston Based on Your Interests
Creating your perfect itinerary can be overwhelming with so many things to do in Boston – especially if you are visiting Boston for a short weekend away. To help with your planning, I have created the following guide to Boston’s best attractions, sorted based on your interests. Whether you’re a foodie wanting to try all the best restaurants in Boston or a history buff interested in visiting the area’s historical sites, there is something on this list for everyone.
For History Buffs
The city of Boston has a rich history. Founded in 1630 by Puritan settlers, it would soon become home to America’s first public school, the Boston Latin School (opened in 1635).
Throughout history, the city played a critical role in many historical events, including the Boston Tea Party, where 45 tons of tea were dumped in Boston Harbor, Boston’s occupation in the American Revolution War from April 1775 until “Evacuation Day” on March 17, 1776, and the great fire that destroyed much of the area in November 1872.
These events, and so many more, would shape the city and play a significant role in the country’s growth and development.
Today, there are many historical landmarks, museums, and sites of relevance to visit and learn about the many key events throughout Boston’s history. Here are a few I recommend if your visit is inspired by your love of learning about the past:
Boston City Hall
1 City Hall Square
Whether you’re just enjoying the bold architecture or taking a guided tour, Boston City Hall is a beautiful and impressive building that is an important part of the city’s history. Built in 1968, it was considered a controversial design at the time. Today, the building’s marble walls and floors, combined with the many modern art installations on display, create an impressive display.
Old State House
206 Washington St
Built in 1713, the Old State House is Boston’s oldest surviving public building. This location played a vital role in many aspects of the city’s history. It served as the seat of the Massachusetts General Court until 1798, was the site of the Boston Massacre, and it was on the balcony of this very building that the Declaration of Independence was announced. Today, it is one of the historical landmarks included on the Freedom Trail.
Boston Tea Party Ships & Museums
306 Congress St
Credited with igniting the revolution, the Boston Tea Party is not only an important part of Boston’s history but also a significant moment in the history of the United States. Visit the Boston Tea Party Ships & Museum to learn about this key moment. I recommend taking an afternoon to browse the many interactive exhibits and artifacts, tour full-scale replicas of 18th-century sailing vessels, and grab a cup of tea (or other refreshments) at Abigail’s Tea Room & Terrace.
Museum of African American History & Abiel Smith School
46 Joy St
The city of Boston is a key spot for African American history in the country. If this interests you, I recommend visiting the Museum of African American History’s Boston location. The museum includes the African Meeting House (1809) and the Abiel Smith School (1835). This location was central to the members of Boston’s Black Community, serving as a church, a school, and a community meeting place. In fact, the Abiel Smith School is the oldest public school in the United States. Exhibits and educational programs at the museum share the stories of those who played an integral role in the fight for educational opportunities for African American children.
Embrace Boston
Embrace Boston is a self-guided app that offers a unique way to learn about the city’s history. As it takes you around the city, highlighting locations of interest, the app will share historical facts and education as well as allow you to learn from stories and first-hand accounts of those involved. By giving a platform to those who may not otherwise be heard, the app’s developers are helping to dismantle structural racism in the city and beyond, creating a more inclusive future.
Live Like a Local Tour with Collin Knight
If you would prefer to learn about the city’s history through a guided tour, the Live Like a Local Tour is an excellent option. The tour will take you through the history of Roxbury’s Nubian Square, share critical moments in the civil rights movement, introduce leaders in the community over the years, discuss the rise of local Black-owned businesses, and highlight the impact of both modern gentrification and generational wealth in the city’s development. Our tour guide, Collin Knight, also took us to a local Jamaican joint and gave us time to shop.
The Paul Revere House
19 N Square
Built in 1680, the Paul Revere House is the oldest remaining building in downtown Boston. As the name suggests, the building was once the home of infamous patriot Paul Revere. Today, it has been transformed into a museum showcasing his life, accomplishments, and many business ventures – all of which are integral to the city’s history and development. You’ll also learn about his legendary Midnight Ride by reading Revere’s only words, which tell of his experience.
Paul Revere Statue
This impressive bronze statue depicts Paul Revere on horseback, completing his famous Midnight Ride. The important job of designing the sculpture was awarded to Cyrus Edwin Dallin after winning a competition in 1883. Despite his win, Dallin faced much resistance. It took seven versions of his model for one to be finally accepted in 1939. It was then constructed and unveiled in bronze in 1940.
Old North Church
193 Salem St
The oldest standing church building in Boston, the Old North Church, was built in 1723 and was named a National Historic Landmark in 1961. On the day of Paul Revere’s Midnight Ride, Robert Newman and John Pulling warned of the approaching British Army troops by hanging two lanterns in the windows of the church’s bell tower. Each year, the church welcomes approximately 500,000 visitors eager to learn about its crucial role in the start of the American Revolution.
St. Leonard’s Catholic Church + St. Leonard’s Peace Garden
320 Hanover St
Another important historic church in the city of Boston, St. Leonard’s of Port Maurice Parish, was the first Roman Catholic Church in New England built by Italian immigrants. The church was first formed in 1873, but the current building on the property was built when church leadership recognized they needed a larger worship space. It was consecrated on November 6, 1899. In addition to the special history of the church, I recommend taking some time to enjoy the beautiful Peace Garden that has been planted on the property.
Long Wharf
66 Long Wharf
Constructed around 1710-1721, the Long Wharf played an integral role in commercial trade, slave trade, and early military history in Boston. It allowed direct access to unload and transport cargo from the vessel into the heart of Boston. While this was incredibly beneficial for business in the area, it was also leveraged by slave traders to bring enslaved people into the area. When you visit the wharf, take time to read about its role in the Mid-Atlantic slave trade on the marker that has been placed there to honour all who were impacted.
Innovation Trail (Cambridge) with Noah Puterman
While The Innovation Trail isn’t located in the city, it is one of my favourite places to visit near Boston. This walking tour can be found only 20 minutes from Boston, across the Charles River in Cambridge. You will learn about the many discoveries and innovations that took place in the area, putting Boston and the surrounding area on the map early in the country’s history. Plus, you’ll be introduced to some of the cutting-edge work being done today, continuing to move the area forward.
For Foodies
If your idea of a dream vacation revolves around exploring the culinary scene in the places you visit, you’re in luck. It is estimated that approximately one in every four Boston restaurants is foreign-born, making the city a melting pot of different cultures. With such a diverse population comes a wide variety of ethnic flavours and culinary delights.
Whatever flavours you are looking for, there are options available. The city is home to classic New England seafood, traditional American favourites, and an assortment of international cuisine. Of course, in addition to the many flavours and culinary experiences, there are also many spots throughout the city to relax and enjoy a creative cocktail or refreshing beer.
Here are my favourite restaurants, bars and taprooms in Boston:
Grace by Nia
60 Seaport Blvd #325
Owned by Nia Grace, a familiar face in the Boston restaurant scene, Grace by Nia offers a delicious Southern-inspired menu and a busy schedule of live music showcasing local jazz, soul, and R&B artists.
Stop by for a delicious weekend brunch featuring red velvet pancakes, Cajun home fries, and brown butter beignets. If you’re looking for a hearty dinner, the menu offers fried catfish bites, bourbon peach ribs, country-fried chicken, and many more Southern favourites.
Comfort Kitchen Boston
611 Columbia Road
If you are looking to enjoy delicious meals inspired by the flavours of the African diaspora, Comfort Kitchen Boston is the perfect stop. This black-owned, immigrant-owned, and women-owned restaurant offers a cozy and intimate dining space inside. If the weather is nice and you’d prefer to stay outside, enjoy your meal on their beautiful patio, where you will be surrounded by lush greenery and local artwork.
MIDA
782 Tremont St
For anyone craving traditional Italian cuisine, I recommend heading to MIDA. Chef and owner Douglass Williams combines a tasty menu with friendly and welcoming staff for an incredible overall experience. You’ll feel like you’re visiting family! Make sure to stop and say hello to Chef Williams during your visit. He loves meeting new people and learning where they are travelling from.
ZaZiBar
60 Seaport Blvd Atrium
Another one of the best restaurants in Boston, in my opinion, is ZaZiBar. With a creative cocktail menu and a Caribbean-Asian fusion menu, you’ll enjoy a unique dining experience. Chef Olrie Roberts, originally from Grenada, has an extensive resume in the culinary world, including attending Le Cordon Bleu in Boston and interning in Spain. He draws on all this experience to create dishes that will make your mouth water!
Fasika Café
51 Roxbury St
For foodies who love traditional Ethiopian flavours, Fasika Café is a restaurant you don’t want to miss. Defar, the café’s owner, and his wife are dedicated to authenticity in their menu. They even travel annually to Ethiopia to pick up spices in bulk. The whole family is involved in the restaurant’s operations, with Defar’s wife helping in the kitchen and his children serving customers. The result is a comfortable family atmosphere and authentic Ethiopian cuisine.
Nubian Markets
2565 Washington St
I included this on the foodie list for the incredible food available at the café, but Nubian Markets is so much more than just a restaurant. Created by Ismail Samad and Yusuf Yassin, this location combines a café, marketplace and a gathering space serving as a community hub for both private and public events. Dedicated to celebrating the African diaspora through food, you will find flavourful meals and fresh ingredients to bring home and cook for your own creations.
Sam Adams Downtown Boston Taproom
60 State St
What foodie adventure is complete without finding a place to relax with a cold drink? The Samuel Adams Downtown Boston Taproom just steps away from the iconic Samual Adam statue, is a 3-floor taproom and rooftop deck. Choose from the many beer options on tap for a relaxing evening with friends, or make it a meal with their classic pub-style menu.
For Cultural Seekers
Another benefit of visiting a city with such a diverse population is its impact on the area’s art and culture scene. Boston’s art and music are inspired by its rich history and vibrant presence. From renowned art museums to historic concert halls, there are so many cultural experiences to explore.
As you visit Boston, take the time to enjoy some of the many world-class performances and stunning art galleries. It’s easy to immerse yourself in the city’s lively arts scene – making it a go-to destination for many arts and culture-focused travellers.
If this sounds like you, here are a few places to visit in Boston during your trip:
Institute of Contemporary Art
25 Harbor Shore Drive
Founded in 1936, the Institute of Contemporary Art/Boston is dedicated to supporting artists and inspiring a love for contemporary art. Here, you will see many creative, moving, and thought-provoking displays and art installments. You can take a guided tour, where you will learn about the talented artists and their work from knowledgeable guides or take a self-guided tour of the building. They also offer hands-on activities and performances for children on the last Saturday of each month called “Play Dates.”
Boston Symphony Hall
301 Massachusetts Ave
If your love of the arts is focused more on music, why not enjoy a performance by the talented Boston Symphony Orchestra at their home concert hall, Boston Symphony Hall? The building opened its doors in 1900 and is well-known for its incredible acoustics, which earned it recognition as one of the world’s top concert halls. The hall also hosts many other talented musicians and musical ensembles. You can see a complete list of events and purchase your tickets online. As you enjoy your performance, look around to see the 16 statues on display throughout the hall, each representing a Greek or Roman person who is related to music, art, or literature in some way.
Museum of Fine Arts Boston
465 Huntington Ave
With over 100 galleries of art representing different art genres and periods, the Museum of Fine Arts Boston is considered one of the world’s best art museums. Before you visit the city, check the museum’s program calendar to see if any events are running that you would be interested in. You can also tour the many collections and exhibitions with a guided tour or by using the free multimedia tours on the MFA Mobile app. With several cafés throughout the building, you can easily grab a bite to eat, enjoy a gourmet coffee, or even relax with a craft beer or glass of wine.
For Retail Therapy Lovers
Of course, one of the fun aspects of visiting a new location is the opportunity to discover the unique shops, vendors, and small businesses that call that city home. For those visiting Boston, this area is no exception. Throughout my recent visit, I had the opportunity to check out several markets and shopping-focused regions in the city, picking up some memorable souvenirs and supporting local small business owners.
Whether you’re looking to plan a complete retail therapy getaway or simply looking for the best areas to visit in Boston to find the perfect gift for a friend or family member (or yourself), these are the places I recommend adding to your Boston itinerary:
Faneuil Hall Marketplace & Quincy Market
If you’re looking for a one-stop shop to check out a wide assortment of local retailers, look no further. Faneuil Hall Marketplace features 200,000+ square feet of retail space, allowing you to browse over 80 local makers, business owners, and other retail shops. Built in 1742 and expanded in 1826 to include the Quincy Market, Faneuil Hall brings together shipping, live music, food carts, and restaurants for the perfect afternoon of retail therapy.
Black Owned Boston
100 Seaport Boulevard | 623 Tremont St
If, like me, you are interested in supporting and learning about the many Black-owned businesses in Boston, this is the perfect place to start. Created by Jae’da Turner, Black Owned Boston is dedicated to connecting consumers and Black-owned business owners in the city, building a more inclusive community. The network features over 1,600 businesses representing a variety of different industries in Boston and the surrounding area. Many of these businesses are also showcased in their Bos. Shop South End (on Tremont St) or in their many pop-up markets and events (on Seaport Boulevard).
Seaport District
This bustling neighbourhood is known for several things, including a vibrant arts scene, several incredible restaurants and, the reason I am including it on this list, 70 unique shops and stores, including luxury boutiques, clothing shops, outdoor stores, pet-focused retailers, and more. One of my favourite spots is East End Books, a full-service bookstore with print books, e-books, audiobooks, vinyl albums, magazines, and more all in one spot. With so many shops in one area, there will surely be something for everyone.
SoWa Open Market
500 Harrison Ave
Does your retail therapy focus more on local crafters and makers than luxury retailers? If so, you should check out SoWa Open Market. This open-air farmer and artist market runs every Sunday, from May to October, from 11 am to 4 pm. Here, you will find many incredible vendors, including local farmers, bakers, crafters, chocolatiers, artists, and more. There are also food and beverage trucks on-site, allowing you to grab a bite while you feed your need to shop. The market is also located near the many galleries, art studios and retail shops on SoWa’s pedestrian-only Thayer Street.
For Families
Travelling with the whole family is an incredible way to make memories and expose your children to the wonders of the world around us. However, it also means familiarizing yourself with the kid-friendly stops and events available during your trip. While most people focus on the historical and cultural options in Boston for adults, there are also some great things to visit in Boston for the younger travellers among us!
The following attractions are either designed specifically for children, making them a great choice for families visiting the area, or they offer programming and attractions that make them suitable for all ages. Start planning your family-friendly Boston getaway with these must-see places:
Boston Children’s Museum
308 Congress St
If you’re looking for an opportunity to turn your family vacation into an educational experience, add the Boston Children’s Museum to your itinerary. Dedicated to educating visitors of all ages, the museum offers three floors of interactive exhibits, STEAM (science, technology, engineering, art, and math) workshops, and arts programming (music, dance, theatre, and visual arts). There is so much to do that you can easily spend an entire afternoon exploring the museum without seeing everything.
New England Aquarium
1 Central Wharf
Another fun, family-friendly attraction in the city, the New England Aquarium, is a great place to see and learn about thousands of aquatic animals. As you tour the aquarium, visitors of all ages will be introduced to the over 1600 animals that call the location home and learn how to help protect marine life in your daily routine. They hope to inspire a love of the ocean and a passion for conservation efforts.
Simon’s Theatre
1 Central Wharf
Located inside the aquarium, Simons Theatre offers a unique way to learn even more about marine life. The theatre features a massive five-story tall screen where you can see 3D films that will immerse you in the natural world, making you feel like you are coming face to face with wildlife. If your kids enjoy visiting the aquarium, Secrets of the Sea 3D will introduce them to some of the ocean’s most incredible animals.
All Travellers: Take a Tour with Boston By Foot
Unlike all the other attractions on this list, I couldn’t place Boston By Foot in any one specific category. Why? With many daily and weekly walking tours, they have options to suit nearly any type of traveller. For example, Boston By Little Feet is designed for children, making it the perfect choice for family-friendly travel. Meanwhile, The Dark Side of Boston will introduce you to many of the true “tales of misery, misfortune, and murder” in the city (clearly not for younger visitors).
During my trip to Boston, I went on the tour: “Black Voices: Writers for a 19th Century Revolution.” As we walked through the city, we were introduced to many of the talented Black writers who lived and worked in the city, using their writing skills to focus on the topics of slavery and the revolution. This included David Walker, Dorothy West, and Pauline Elizabeth Hopkins. We were shown locations where they raised their families, lived at various stages of their lives, and those that played a key role in their writing efforts and their fight against injustice. I highly recommend it for those interested in the city’s role in the revolution.
Your Boston Adventure Awaits
Whether you’re a history buff, a foodie, a cultural seeker, a retail therapy lover, or simply looking for a memorable experience for the whole family, there are so many amazing places to visit in Boston. From its renowned museums and rich arts scene to its many restaurants and endless shopping opportunities, it won’t take long to fill your itinerary for your next vacation.
So, what are you waiting for? Start planning your epic Boston getaway today!With my comprehensive guide, you have all the information you need to create a personalized itinerary that suits your interests and preferences (or the preferences of your whole family). From transportation and accommodations to the best places to explore in Boston, I’ve got you covered.
