The 2 Best City Walkings in Boston

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Boston is a city steeped in history and charm, and one of the best ways to experience this is through a walking tour. Whether you’re a local looking to learn more about your city or a tourist wanting to dive deeper into the culture and history, walking tours offer a unique and immersive experience. With so many options to choose from, it can be overwhelming to decide which tours are worth your time. In this post, we’ve rounded up the best walking tours in Boston that are sure to leave you with a deeper appreciation for the city and its rich history. So put on your walking shoes and let’s dive into the best walking tours Boston has to offer.

The 2 Best City Walkings in Boston

  1. The Revolutionary Story Tour an Epic Walking Tour of Boston
  2. Small Group Guided Walking Food Tour in Boston

The 2 Best City Walkings in Boston

1. The Revolutionary Story Tour an Epic Walking Tour of Boston

Explore Boston’s rich revolutionary history on this epic walking tour that takes you through the city’s most iconic sites. Led by an experienced guide, you’ll learn about pivotal events, from the Boston Tea Party to the Siege of Boston, and the brave individuals who played a key role in the city’s revolutionary history. Starting at City Hall Plaza, this curated route is designed to take you beyond the crowded Freedom Trail and explore lesser-known historical sites that offer insight into Boston’s past. With a small group size, you’ll enjoy personalized attention as you experience both modern Boston and the city’s rich history. This tour includes entrance into Faneuil Hall (when open), an expert guide, 14 of the 16 Freedom Trail sights, and the option to engage with costumes, actors, scripts, or partisanship. Gratuities are optional. Join us for a walking tour that’s both informative and entertaining, a must-do for history buffs and anyone interested in Boston’s heritage!

2. Small Group Guided Walking Food Tour in Boston

If you’re a food lover visiting Boston, there’s no better way to experience the city’s culinary delights than by taking a small-group walking food tour. On this tour, you will explore Boston’s North End neighborhood, famous for its Italian heritage and delicious food offerings. The tour is designed for small groups of up to 12 people to ensure a personalized experience. During the tour, you will visit several local businesses where you will sample some of the best seafood, pasta, sandwiches, and pastries Boston has to offer.
The tour includes a menu of starters that features Boston’s famous New England Clam Chowder, a traditional Italian sandwich, bakery pizza, handmade lobster ravioli, and cannoli. These starters are followed by a delicious secret dish that will be revealed only on the day of the tour. As you explore the North End, your knowledgeable guide will share insider stories and tips about the area, which will make your experience more enjoyable.
Remember to come with a hearty appetite, as the tour is designed to give you a full meal’s worth of food! Choose between several convenient start times and spend the afternoon exploring the North End, one of the best neighborhoods in Boston for food lovers.

Frequently Asked Questions About Boston

Boston is one of the most popular tourist destinations in the United States that receives millions of visitors each year. The city offers a plethora of attractions, museums, historical sites, and cultural events that satisfy the needs of any traveler. Travelers coming to Boston for the first time often have many questions regarding the city’s culture, food, transportation, and places to visit. In this blog post, we will answer some of the most frequently asked questions by tourists about Boston.

1. How Do I Get Around Boston?

Boston is a very walkable city, with most of its attractions located within walking distance from each other. However, Boston also has a comprehensive public transportation system that includes buses, trains, and subway lines. The Massachusetts Bay Transportation Authority (MBTA) operates this system, and you can buy a CharlieCard, which is a reusable smartcard that contains stored value or a monthly pass.Taxis and ride-sharing services like Uber and Lyft are also available in Boston, but they can be expensive during peak hours, and you might face heavy traffic. If you are traveling with a group of people or have a lot of luggage, you might consider hiring a car service.

2. What are the Best Times to Visit Boston?

The best time to visit Boston is undoubtedly during the fall from September to November. The foliage colors are breathtaking, and the weather is pleasant, making it a perfect time to explore the city’s outdoor sites. However, the peak tourist season starts from June to August, which is also a good time to visit, but the hotels are costly, and they book up quickly. Another popular time to visit is during the spring, from March to May, but the weather can be unpredictable, with occasional rainy days.

3. What are the Must-Visit Attractions in Boston?

Boston is renowned for its rich history and cultural heritage. Some of the must-visit sights include:

  • The Freedom Trail – a 2.5-mile-long trail that passes through 16 historically significant sites.
  • The USS Constitution Museum – the world’s oldest commissioned naval vessel afloat and a museum dedicated to the ship and its history.
  • The Museum of Fine Arts – one of the most comprehensive art museums in the world that showcases a broad range of art, from ancient Egypt to contemporary art.
  • Fenway Park – home to Boston’s beloved baseball team, the Boston Red Sox.
  • The Boston Tea Party Ships and Museum – an interactive museum that showcases the American Revolution and the events leading up to it.
  • New England Aquarium – one of the most prominent aquariums in the world with a vast collection of marine life, including sea turtles, penguins, and sea lions.

4. What are the Best Places to Eat in Boston?

Boston’s food scene is vibrant and diverse, offering various local specialties and international cuisines. Some of the must-visit places to eat include:

  • Mary Chung – a Chinese restaurant famous for its Suan la Chow Show and Tea Smoked Duck.
  • Lobster Roll – serves the best lobster rolls in Boston with a secret blend of spices and hot butter.
  • Mike’s Pastry – a legendary Italian bakery located in the North End that serves mouth-watering cannolis, tiramisu, and other sweet treats.
  • The Union Oyster House – one of the oldest continuously operated restaurants in the United States that is famous for its fresh seafood and chowders.
  • Legal Sea Foods – a seafood chain restaurant that serves high-quality seafood dishes and drinks.

5. Are there any Day Trips from Boston?

Boston is situated in a region filled with spectacular natural scenery and historical landmarks. Some of the fantastic day trips from Boston include:

  • Salem – a historic town famous for its witch trials and rich maritime history.
  • Cape Cod – a scenic peninsula with white sandy beaches, lighthouses, and quaint seaside villages.
  • Newport – a picturesque coastal city with a rich colonial heritage and some of the most opulent mansions in the United States.
  • Provincetown – a vibrant and eclectic town located at the tip of Cape Cod, offering galleries, restaurants, and Whale Watching tours.
  • Plymouth – a historic town that marks the landing place of the legendary Pilgrims in 1620 and has several historical sites to explore.

6. What is the Weather Like in Boston?

Boston has a humid continental climate with hot summers and cold winters. The temperature in Boston during the summer months can reach up to 85°F (30°C), while in winter, they can drop to 20°F (-6°C). Boston experiences occasional snowstorms during the winter months, which can lead to flight cancellations and significant delays.

7. Is Boston Expensive?

Boston can be expensive, especially during peak tourist season or events like the Boston Marathon. Accommodation, food, and transportation can be costly, especially in prime locations. However, there are many affordable options, including hostels, budget restaurants, and transport passes, that allow travelers to explore Boston without breaking the bank.

How to Spend Your Time as a Tourist in Boston

Boston, Massachusetts, is a city steeped in history and culture, which makes it a perfect destination for tourists. Boston offers a wide variety of tourist attractions ranging from historical landmarks to world-class museums, beautiful parks, and delicious cuisine. Whether you’re visiting Boston for a day trip or a week-long vacation, there’s no shortage of things to see and do.In this guide, we’ll outline some of the best ways to spend your time as a tourist in Boston. From exploring Fenway Park to walking the Freedom Trail, you’ll find plenty of inspiration to make the most of your trip to Beantown.

1. Explore the Freedom Trail

The Freedom Trail is a 2.5-mile long path through downtown Boston that takes you to 16 historical sites. The trail is marked by a red line that winds through the city streets, making it easy to follow.Don’t miss important landmarks in the Freedom Trail like the Paul Revere House, the Old South Meeting House, and the Bunker Hill Monument. These sites offer unique insights into the Revolutionary War and the city’s rich history.


  • Wear comfortable shoes as the trail involves a lot of walking
  • Start your tour early in the day to avoid the crowds
  • Consider purchasing a Freedom Trail guidebook for an in-depth experience

2. Visit Fenway Park

Fenway Park is one of the most iconic baseball stadiums in the world and home to the Boston Red Sox. You can take a guided tour of the historic park or catch a game and experience the unique atmosphere that only Fenway Park can offer.


  • Book your tour or tickets in advance to avoid disappointment
  • Visit the Fenway Park Team Store for unique Red Sox souvenirs
  • Try some classic Boston food at Fenway, like a hot dog or a lobster roll

3. Visit the Museum of Fine Arts

The Museum of Fine Arts in Boston is one of the most comprehensive art museums in the world. It houses more than 450,000 works of art from every corner of the globe, including works from renowned artists like Monet, Picasso, and Rembrandt.


  • Check the museum’s website for special exhibits and events
  • Consider purchasing tickets in advance for popular exhibits
  • Don’t miss the Museum’s expansive Asian Art collection

4. Walk Commonwealth Avenue Mall

Commonwealth Avenue Mall is a tree-lined park in the heart of Boston that connects the Back Bay neighborhood with the Boston Public Garden. The park is home to many statues and memorials and provides a great spot for a leisurely stroll.


  • Visit during the fall to see the beautiful foliage
  • Take a guided tour of the park for a more in-depth experience
  • Bring a picnic lunch and relax on the park benches

5. Enjoy a Lobster Roll

No visit to Boston is complete without trying a classic lobster roll. This New England favorite is a sandwich made with freshly cooked lobster meat on a soft, buttered roll.


  • Try the classic warm lobster roll with melted butter or the cold lobster salad roll with mayo and celery
  • Visit one of Boston’s many seafood restaurants for the best lobster roll experience
  • Pair your roll with a local craft beer or a glass of Chardonnay

6. Visit the Isabella Stewart Gardner Museum

The Isabella Stewart Gardner Museum is a creative and intimate environment that allows visitors to explore the private collection of Isabella Stewart Gardner, a passionate art collector and philanthropist. The museum is a treasure trove of art and includes art from ancient Rome and Egypt, as well as contemporary art, textiles, and sculptures.


  • Explore the unique museum garden area
  • Join the museum’s guided tour for an immersive experience of the artwork
  • Check the museum’s website for upcoming exhibitions and events

7. Stroll through the Boston Public Garden

The Boston Public Garden, situated in the center of the city, is a beautiful park that features a pond, a famous bridge, and swan boats. The gardens are the perfect spot for a romantic picnic or an afternoon stroll with friends.


  • Take a boat ride on the park’s iconic swan boats
  • Visit the park’s famous Make Way For Ducklings statue
  • Grab a coffee from the park’s cafe and relax by the pond
ConclusionBoston is a city that is filled with history, culture, and beautiful attractions. Whether you’re visiting for a day or a week, there’s plenty to see and do. By exploring the Freedom Trail, visiting Fenway Park, enjoying a lobster roll, and more, you’ll experience the best that Boston has to offer. So get ready to be immersed in the rich history and culture of this beautiful New England city.

The 2 Best City Walkings in Boston

Discover the world’s most captivating museums with our expertly curated tours.