Boston is a classy and charming New England destination that you cannot miss while travelling to the East Coast! As one of the oldest cities in the United States, Boston is made up of 23 neighborhoods each offering unique architecture, history, and culture. If you are familiar with Boston, you may know of its rich history and the role that the city played during the American Revolution with the Boston Massacre, Boston Tea Party, and Battle of Bunker Hill. Not to mention, it’s a city of many firsts! Did you know that the Boston Common was the United States’ first public park or that the Boston Latin School was the nation’s first public school? Pretty neat! Today, Boston is home to over 50 universities, some of the Country’s best hospitals, and thousands of start-ups. It is booming with construction and recently had a new skyscraper added to its beautiful skyline – One Dalton. 

I have lived in Boston for 23 years now and am constantly discovering new hidden streets, restaurants, and activities. One of my favorite aspects of Boston is that it has four seasons that highlight the beauty of the City. In the fall, you can see the famous New England foliage that features vivid red and orange colors. Despite the occasional blizzard, a highlight of winter is walking down quiet streets lined with oil-lit lamps in Beacon Hill, or going ice-skating on the Frog Pond. Come springtime, the city is blooming with tulips and cherry blossoms, and runners take their mark to compete in the Boston marathon. Summer in the city is also bustling with locals and tourists alike, all enjoying the warmer weather. 

And of course, I can’t write a blog post about Boston without mentioning our amazing sports teams! Whenever you visit Boston, make sure to check out a sports game with some rowdy, local fans and wicked awesome energy! Here’s my comprehensive and ultimate guide of where to go, what to see, and what to do while you visit Beantown! 

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Cultural

1. Walk the Freedom Trail

If you’re a history buff or simply looking for a unique and fun activity, you should plan to walk the Freedom Trail. The Freedom Trail is an iconic 2.5 mile path that takes you to 16 historic sites throughout the city. You can choose to take a self-guided walk on your own, which is made easy with red bricks leading the way, plaques on the ground at each site, and a printable brochure. If you prefer to go with a guide, there are numerous tour operators available!! Some of the sites include the Old State House (which is also the site of the Boston Massacre), the Boston Public Garden, and Faneuil Hall. I will cover many of these destinations throughout this article so you can learn more and choose your preferred way of sightseeing during your time in Boston.

2. Take a Duck Tour

If you are short on time, tired of walking, travelling with kids, or just looking for a fun, lighthearted way to explore a new city, then I highly recommend hopping on a Duck Tour. These ‘Ducks’ are WWII style amphibious vehicles that can travel on land and water. The tour will take you throughout the streets of Boston and then will dive into The Charles River for some amazing views of the city! The tour is fully narrated and engaging for people of all ages. Get ready to quack at pedestrians as you learn about Boston’s impressive history. This tour can be booked ahead of time from many different departure locations, and typically lasts about 80 minutes. 

3. Visit Boston’s Many Museums

While in town you can discover Boston’s renowned museums that are suitable for kids, history buffs, and art lovers! Some top ones are the Museum of Science, the Museum of Fine Arts, and the Isabella Stewart Gardner Museum. If you are traveling with children, then the Museum of Science is a fun, kid-friendly place to go and spend an afternoon. There is a planetarium, a number of live presentations throughout the day, and interactive exhibits. The Museum of Fine Arts has over 500,000 works of art and often has many special exhibits. The Isabella Stewart Gardner Museum is another art museum in the city with paintings, sculptures, decorative pieces and a picturesque courtyard. In 1990, the Gardner Museum was the target of a major art heist where the thieves stole around $500 million worth of artwork. To this day, the theft remains unsolved and there is a $10 million reward for information leading to the recovery of the works of art! 

4. Tour Historic Landmarks in Charlestown

Charlestown is the oldest neighborhood in Boston and home to many historical landmarks and sites. The Bunker Hill Monument, a 221-foot granite memorial, commemorates the Battle of Bunker Hill, which was a battle fought between British and Patriot forces during the Revolutionary War. Tourists can choose to climb the 294 steps to reach the top of the monument, or simply admire from below. Charlestown is also home to USS Constitution, the oldest warship in the world, which is docked in the Navy Yard. Hollywood has taken note of Charlestown and chosen this location for some well-known blockbuster films like Good Will Hunting and The Departed! 

5. Awaken Your Musical Side at Symphony Hall

Symphony Hall is Boston’s main concert hall and home to the Boston Symphony Orchestra. The stage, walls, ceiling, and floor all slope in a way that helps to project the perfect sound to the audience. The architectural design inside the hall is breathtaking with Greek and Roman statues lining the upper walls and an astounding 4,800 pipe organ. 

During the holiday season, the Boston Pops host exceptional shows with Christmas music across multiple genres where everyone can listen and sing along. They even bring along a Santa! It is a tradition for many Bostonians to see the Boston Pops during the holidays. I went for the first time in 2019 and plan to make this a fun yearly experience!

6. Throw Tea Off of the Boston Tea Party Ship

The Tea Party Ship & Museum is a floating museum that represents an important time in history where the American colonists fought the injustice of taxation without representation. There are reenactments by actors and historians, and you can even throw tea overboard like the colonists did on December 16, 1773! The tour lasts for about an hour and is certainly a unique way to experience Boston’s history.

7. Interact with Animals at the New England Aquarium

The New England Aquarium houses thousands of aquatic animals ranging from jellyfish to green sea turtles. In the center of the building is a four-story ocean tank filled with various types of fish, Myrtle the sea turtle, stingrays and a vibrant Indo-Pacific coral reef. There are plenty of interactive exhibits where you can touch stingrays, epaulette sharks, sea stars, and hermit crabs. There is also a fur seal exhibit where you can watch the seals do fun tricks! My personal favorite is the penguin exhibit with over 60 African penguins and rockpoppers. The aquarium also has whale watching tours, which is an incredible experience! You can easily spend a few hours admiring all that the aquarium has to offer.

Shop – Dine – Nightlife

8. Visit Boston’s Major Streets for Shopping and Dining

One of my favorite things about Boston is how walkable the city is, especially when the weather is nice! You can spend an entire afternoon shopping or dining along Newbury Street, which is known for its many cute little boutiques and high-end retail shops that meet everyone’s needs! 

Parallel to Newbury Street, you will find Boylston Street, which also offers a multitude of retail and dining options. However, it is mostly known as the final stretch of the Boston Marathon. From Boylston, you can watch the runners cross the finish line!From Newbury or Boylston, you can walk to the Prudential Building, the Boston Public Garden, or Downtown Crossing. Downtown Crossing is another shopping district with different stores, restaurants, and a cinema.

9. Enjoy a Mouthwatering Meal in the North End

The North End is Boston’s own ‘Little Italy’ and is constantly bustling with tourists and locals alike. The aromas of fresh, homemade pasta and pizza fill the air of the North End, and the food tastes even better. All of the restaurants in the North End are absolutely delicious, but I must say that Giacomo’s Ristorante, located right on Hanover Street, is my absolute favorite. The chicken parmigiana, mussels, garlic broccoli, and the mozzarella marinara are to die for. After you fill up on delightful Italian food, your next stop should be to head over to either Modern or Mike’s Pastry for a cannoli. Bostonians tend to take a side on whether they prefer Modern Pastry or Mike’s Pastry, but I would say that I am more of a Mike’s fan. While here, you should try both and become part of Boston’s own cannoli war! 

The North End is not only a destination for restaurants, but it also has a great history. While in the neighborhood, be sure to check out the Paul Revere House, the Old North Church, and Christopher Columbus Park. The Old North Church was founded in 1722, and is Boston’s oldest surviving Church. The lamps hung from the church’s steeple informed Paul Revere whether the British were coming by land or sea!

10. Have a Drink at the Bell in Hand Tavern

The Bell in Hand Tavern was founded in 1795 and is now the oldest tavern in the United States. The name comes from the original owner, Jimmy, who was the town crier for fifty years. Today, the Bell in Hand is a hot spot for those looking for a cold beer and live music. 

11. Spend an Evening in Seaport

Seaport is an increasingly popular area to explore in Boston, becoming a new hub for many restaurants, breweries, and nightclubs. If you are looking to taste a classic Boston beer, head down to Harpoon Brewery and enjoy some brews and pretzels. Harpoon puts on a ton of festivals and events, so be sure to check out their website before you visit. While there, you can also sign up for a tour of the brewery! 

There are also many bars, night clubs and restaurants. Some fan favorites for a night out are Drynk Bar and Lounge, Scorpion Bar, Kings, the Grand and the Lookout Rooftop and Bar. During the summer you can find people out and about until 2:00 A.M. partying at many of these locations. The Lookout Rooftop and Bar is located at the Envoy Hotel and is a hot spot year-round. During the summertime, you can spend a day there drinking, dancing, and catching amazing views of the city. In the winter and colder months, you can still see the beautiful city views with a drink in hand but from the comfort of a heated igloo. Pretty cool – pun intended! If you’re looking for some food, I would recommend that you check out The Barking Crab or James Hook & Co. – Both have delicious lobster rolls! 

12. Shop at the Prudential – One of Boston’s Tallest Buildings

The Prudential Building is the second tallest building in Boston after the John Hancock Tower. The tower is a premier shopping center with stores like Tesla, Warby Parker, Peloton, Under Armour, and many, many more. You can also visit a variety of restaurants including Eataly, an Italian marketplace that offers a variety of dining options, retail counters, and gelato stands. 

13. Take the Samuel Adams Brewery Tour

If you are a beer fanatic, you can head over to the Samuel Adams Brewery and learn about Boston’s own craft beer. While on the tour, your guide will teach you about the ingredients that Sam Adams uses, the brewing process and you can even sample a few different beers (as long as you are 21 years of age). The classic tours are first come, first serve so make sure to factor this into your schedule if you plan a visit!

14. Test Your Luck at Encore Harbor Resort and Casino

In 2019, Massachusetts added its very own casino located right outside of Boston in Everett. The casino is a sight-to-see with glass chandeliers, a carousel made of flowers, and a Popeye sculpture that weighs more than 2,000 lbs. Even if you do not gamble, there are a ton of things to do. The casino features many restaurants, bars, and a nightclub. You can also spend time exploring the Harborwalk with beautiful gardens and waterfront views. There is ample free parking at the casino, and it can also be reached by bus or by ferry.

Explore

15. Visit the Boston Public Garden and Boston Common

The Boston Common and Public Garden were the nation’s first public park and garden, respectively. The Garden and the Common are found adjacent to one another in the heart of the city. At the main entrance of the garden stands a statue of George Washington on horseback with the beautiful City skyline in the background. During the warmer months, the Common is full of street performers, people riding the Swan Boats, and locals laying on the grass enjoying the weather. When the flowers begin to bloom in the springtime, the entire garden becomes full of vibrant and multi-colored tulips. There is also an assortment of trees within the park that give the garden a beautiful, picturesque feel. In the winter, the Frog Pond in the Boston Common is a hopping spot for ice-skating. 

16. Experience Faneuil Hall and Quincy Market

Faneuil Hall is a must-do when you come to Boston. It is the location where Samuel Adams and other colonists gave heartfelt speeches encouraging independence from Great Britain. Today, it is a marketplace with shops, restaurants, and extraordinary street performers where crowds of people gather and explore. Next to Faneuil Hall you can find Quincy Market, which is a popular place to grab a quick meal with many different food stalls ranging from oysters to ice cream. Even if you are not hungry, I recommend walking through the market and maybe something will catch your eye that you simply can’t resist! 

17. Walk Around Beacon Hill

Beacon Hill is a quaint, historic neighborhood in Boston, that happens to be one of my favorites to explore! It is beautiful all year round, with brick sidewalks, brownstones, and gaslit lamps along the roads. Beacon Hill is known to be one of the most expensive neighborhoods in Boston, with home prices starting in the millions. At the top of ‘the hill’ resides the Massachusetts State House, which stands tall with its magnificent dome gilded with 23k gold. As you walk around Beacon Hill, make sure that you stop by Acorn Street. This river stone-lined road is one of the most photographed streets in Boston!

18. Take a drive to Cambridge

Just outside of Boston lies the city of Cambridge, which is the location of Harvard University and MIT. There are many different ‘squares’ in Cambridge that have plenty of delicious eateries, boutiques, and businesses. Harvard Square is home to part of Harvard’s campus, and is an exciting place to be especially during the summer. A trip to Harvard square would not be complete without stopping at Felipe’s Taqueria for some Mexican food and margaritas! Kendall Square is another popular area with many start-up companies,known by many as “The Most Innovative Square Mile on the Planet”. From Kendall, you can walk to Memorial Drive and the Longfellow Bridge located along the Charles River for spectacular views of the city!  

19. Relax at the Rose Kennedy Greenway

The Rose Kennedy Greenway is a 17-acre park that passes through many Boston neighborhoods. During the warmer months, the park is full of kids playing in the water fountains, food trucks, and entertainment. It’s a great place to relax and enjoy the fresh air!

Adventure

20. Kayak or Walk Around the Charles River

The Charles River, referred to by Bostonians as ‘The Charles’, is an 80-mile-long river that runs through 23 cities beginning in Hopkinton, MA and ending in the Atlantic Ocean in Boston. Many universities are located along The Charles, including Harvard University, Boston University, and MIT. Around the river there are many parks and the famous Esplanade, where you’ll find kids playing and people biking or running. In the spring and summer, the river is full of people kayaking, rowing, sailing, and enjoying the beautiful views of Boston’s skyline. This river is also the location of Boston’s Fourth of July celebration and the Head of the Charles Regatta, which is the world’s largest distance rowing race held in October. 

21. Catch a Ball Game at Fenway Park

Fenway Park, home of the Boston Red Sox, is the oldest Major League baseball park in the country! From the park you can gaze upon the infamous Citgo sign that lights up the Boston skyline while enjoying a Fenway Frank and singing Neil Diamond’s ‘Sweet Caroline’ during the eighth inning. Fenway Park is full of tradition and history, so catching a ball game here is a memorable experience. If you aren’t interested in baseball, then you can spend an afternoon bar-hopping in the Fenway area. When visiting Boston outside of baseball season be sure to head over to Bleacher Bar, located beneath Fenway’s bleachers, to grab a drink while having a view of centerfield. It’s quite a unique experience!

22. Hop on a Ferry to the Boston Harbor Islands

There are 34 islands located in the Boston Harbor that are open for public recreation! During the summer, you can catch a ferry to one of the islands and enjoy the many hiking trails, beaches, and camp sites available. There is even a war-era fort that can be found on George’s Island! Spectacle and George’s Islands are two of the most popular spots and can be reached by a ferry from Christopher Columbus Park. After visiting these two and Thompson islands, I highly recommend adding this to your Boston bucket list!

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All in all, there is so much to do and see year-round while travelling to Boston. The city has something to offer everyone who visits and I am lucky to call it home! We hope you enjoy your visit!

xx,

Carla