Day 1

Freedom Trail/Duck Tour  → Faneuil Hall → Charles River Esplanade → Encore Casino 

A great thing about arriving in Logan National Airport is how close the airport is to the city and whatever hotel you may be staying at. A quick uber, taxi, bus, or subway trip will get you where you need to go within 10-20 minutes. After you’ve checked in and are settled in your hotel or Airbnb, the best way to discover the city is on foot. Boston is home to the Freedom Trail, an iconic 2.5-mile path that takes you to 16 historical sites throughout the city. You can print out a brochure and walk this at your own pace. If you prefer, you may also hire a tour guide. The Freedom Trail starts at the Boston Public Garden and leads you to notable sites, such as the Old State House, Old North Church, and Faneuil Hall. During the warmer months you can catch some street performers who have all sorts of captivating talents: dancing, singing, acrobatics, and entertaining crowds of people in Faneuil Hall. While here, you should also walk through Quincy Market and grab some food or dessert! If you are not interested in walking the city, you can always take a Boston Trolley or a Duck Tour, which takes you to many of the same places as the Freedom Trail! The cool thing about a Duck Tour is that it is an amphibious vehicle that can travel on land and water – pretty exciting!

After the Freedom Trail, you may be ready to relax back at your hotel, grab some food, or sit down for a drink. The city is full of restaurants and bars where you can sit back and relax until you are ready to continue exploring the city. 

To end your first day in the city, you can grab a box of pizza, a snack, or some drinks (or all of the above!) and head to the Charles River Esplanade to relax and watch the sunset. This is one of my favorite things to do in the city and it is a local hotspot as well! If you are looking for more adventure, you may also want to rent a kayak and explore the Charles River from within! Be cognizant of time and book ahead as kayaks are reserved fairly early on and closing times differ depending on the time of the year. Make sure to book your kayak adventure leaving from Kendall Square!

If you don’t want your night to end quite yet, you can always take a taxi or an uber to Encore Casino and head to one of the bars or spend your night testing your luck at the slots. 

Day 2

Back Bay → Boston Common/Boston Public Garden → Newbury Street/Boylston Street/Prudential Tower → Downtown Crossing → Fenway Park 

After you wake up, you can head towards Back Bay for some breakfast or brunch. If looking for brunch, try to make some reservations a couple days prior as Bostonians love to brunch! You can also grab a quick bite to eat at a coffee shop – there are tons in the area. Some of my favorites are Citrus & Salt, Stephanie’s On Newbury, and The Friendly Toast.

Once you are ready for some adventure, head to the Boston Common and Public Garden. I love to bring a blanket and sit on the grass watching the ducks in the pond. When the weather is warmer, you can ride on a swan boat in the pond to explore the park from the water. It is a fun, unique experience if this is your first time visiting the city. If you’re coming to Boston in the winter, then you can spend some time ice skating on Frog Pond! From the park, you can walk to Newbury street, which is one of Boston’s most famous streets. You can spend some time visiting the many little boutiques that line the street or grabbing a drink at one of the restaurants and bars. Parallel to Newbury Street sits Boylston street which is known for being the end of the Boston Marathon route. You can also find the Trinity Church, the Boston Public Library, and Copley Square (which has a very cool view of the John Hancock Tower – Boston’s tallest skyscraper!)

If you get hungry after a full afternoon, head over to Luke’s Lobster (off of Boylston Street) for some mouthwatering lobster rolls – my favorite in the city!  You can even head to the Prudential Building (second tallest building) to Eataly for some delicious dessert. You might also want to sneak in a bit of shopping while here! 

Continue to explore Back Bay and head towards Downtown Crossing, which is a lively outdoor shopping center. Right by there, you can visit the Omni Parker House, a historic hotel in Boston home to the Boston Crème Pie ! From here you can take a walk to the State House and explore Beacon Hill, one of the most expensive neighborhoods in Boston. There are many little roads to get lost in, including the Boston-famous Acorn street. 

 To end your day, head towards Fenway Park, home of the Boston Red Sox. The streets surrounding the park are filled with bars and restaurants, all of which have great beers and live music entertainment. You can even do some bar hopping and check out some of the unique bars like Bleacher Bar which is located right underneath Fenway’s bleachers. 

Day 3

Boston Museum → North End → Seaport District 

After you grab some breakfast, head over to one Boston’s many museums. My favorites are the Museum of Science and the Museum of Fine Arts. They always have unique exhibits so check out their websites before heading over! The Isabella Stewart Gardner Museum is also another great museum option in town. In 1990 it was the target of a major heist where the thieves stole $500,000,000 worth of artwork. If museums aren’t for you, the New England Aquarium may be more up your alley. The aquarium is home to a variety of fish, coral reefs, stingrays, epaulette sharks, African Penguins, and Myrtle the sea turtle. The aquarium also offers whale watching tours so you may opt to embark on a ship in search of whales in the Atlantic Ocean. It is an experience that you won’t forget – trust me! 

Once you have finished your museum or aquarium visit, you can make your way to the North End. This is my absolutely favorite neighborhood in Boston because it’s always bustling with energy and, most importantly, smells like a little piece of Italy. Make sure that you have an appetite because you are certainly going to want to enjoy a meal here. Some of my favorite places in the North End are Giacomo’s Ristorante (cash only), Bricco, and Trattoria Il Panino. You honestly cannot go wrong with these options – they are all to-die-for! Make sure to save room for a cannoli at either Mike’s Pastry or Modern Pastry Shop. Bostonians tend to take a side on whether they prefer Mike’s or Modern and now you can pick a side in Boston’s cannoli war too! You can spend some time exploring the narrow roads of the North End and learning more about the history of this area. 

A short walk or uber ride away, you will find Boston’s newest neighborhood, Seaport District. Seaport is a newer neighborhood in Boston with places to shop, eat, drink, and party! While here, you can have a drink at one of the many rooftops with a view of the city or have a drink by the water. Some great rooftops with a view are at Envoy Hotel’s Lookout Rooftop & Bar, YOTEL Sky Lounge, and Legal Harborside. In the wintertime, Envoy Hotel has heated igloos on the rooftop so that you can enjoy the view even when it is cold out! Seaport is also another great place for breweries. Some notable mentions are Harpoon Brewery, Trillium Brewing Company, and Cisco Brewers Outdoor Beer Garden.

You can end your trip in Boston with some of the most amazing views in the city with a cold drink in hand! 

P.S. If you are looking for even more activities, check out our Ultimate Guide to Boston!