You can get a downloadable map of this itinerary here.

***This guide is written by Jane. Jane is a Boston local who grew up right outside the city in Lexington, MA. She spent her 20s living in different cities across the U.S. including St. Louis, Indianapolis, and Philadelphia, but Boston will always be her home. She loves to read, hang out with her shorkie (shih-tzu/yorkie mix) Alby, and play Taylor Swift songs on her ukulele. Jane is excited to share the amazing city of Boston with all of you and hopes that you love it as much as she does!***

exploring boston by neighborhood.

When you think of Boston, you probably think lobster and clam chowder (or as the locals say, lobstah and clam chowdah), and to be fair Boston’s seafood is off the chahhhts, but, as you’ll see during your visit, Boston is so much more than its seafood.

Also, just as a word of general advice. When planning a visit to Boston, be sure to book restaurant reservations at least two weeks in advance. Boston is a small city with a lot of people, so getting a table day, or even week, of, can be challenging at some of its best restaurants, and you don’t want to miss out!

when to visit and where to stay.

While you can’t go wrong visiting Boston in the summer (New England summers are generally mild, think mid to high 70s with a light breeze and a proximity to the ocean keeps the humidity at bay, literally), my personal recommendation is to visit in the fall so that you can see the breathtaking changing-of-the-leaves.

If you want to be in the heart of Boston, I’d suggest staying in Back Bay. There are plenty of hotels around the Prudential Center, which is a good grounding point for visitors. The Prudential Center is the tallest building in Boston, home to many corporate offices and a large indoor mall, so knowing where it is can help you navigate the city. If you’re visiting for the history, you may want to stay closer to downtown near Faneuil Hall, where you will be walking distance to the historic Beacon Hill neighborhood and many other famous landmarks.

I’d also check out AirBNBs, if you want a cheaper option. Use the list of Boston neighborhoods below to find the perfect location for you.

cambridge.

Cambridge is home to Harvard, MIT, and some of the best bars and restaurants in the Greater Boston Area. Cambridge, while technically not part of the City of Boston, is just a short ride over the Charles River from Back Bay and is easily driveable, walkable, or bikeable (BlueBikes are available all around the city).

While in Cambridge, take a nice stroll through Harvard’s Campus, the beautiful brick buildings and green lawns are especially picturesque in the fall. Harvard is also home to the Harvard Art Museum containing Harvard’s MASSIVE private art collection, which is well worth a visit if you enjoy art. Right next to Harvard, is Harvard Square, where you can easily spend a few hours walking around exploring the various bars, restaurants, and shops.

Need a break after all the walking? Take a minute to relax with a spicy margarita on Felipe’s Rooftop (open weather permitting in the spring/summer/early fall) or grab a burger at Mr. Bartley’s Gourmet Burgers (a cool vibe and all the burgers are named after famous people who have dined there). If you like gourmet grilled cheeses and 90s nostalgia (and let’s be honest, who doesn’t?!), definitely check out Roxy’s Barcade, the front of the building looks like a regular restaurant, serving mouth watering grilled cheeses and one of the BEST fried chicken sandwiches I’ve ever had, but behind the restaurant, through a speak-easy-type secret door lies a vibrant, fun barcade full of all of your childhood favorite games, as well as a fully stocked bar. Roxy’s is in Central Square, just down the street from Harvard Square (just a quick T-Ride apart or easily walkable). Also in Central Square, The Little Donkey, has EXTREMELY cute creative cocktails, delicious tapas, and an INCREDIBLE raw bar.

If you’re looking for a chiller, more distinctly Boston vibe,  try the Druid, a traditional Irish pub located in Inman Square (about a 25 minute walk from Harvard Square), where you can get the best Guinness on this side of the Atlantic. 

back bay.

Back Bay is the heart of Boston in a lot of ways, and definitely one of the more touristy areas. But, it’s touristy for a reason, there are a lot of things to do and see while in this part of the city. 

The Reflecting Pool, located next to the Prudential Center and the Christian Science Center is a perfect place to relax. If you have time, I also suggest popping into the Christian Science Center to check out the Mapparium–a giant, three-story, walk-through globe. Duck Boat Tours also take off from this side of the Prudential Center (look for stands on Huntington Ave), which are a fun way to enjoy the city by land and by sea (travels along the Charles River, providing an amazing view of the city).

In Back Bay you’ll also find Newbury Street, which is a lively, very walkable street filled with restaurants, shops, and bars. On and around Newbury Street there are lots of places to dine, but here are a few of my favorites:  Stephanie’s (self-described as “sophisticated comfort food” & home to a build-your-own Bloody Mary bar during weekend brunch). Krasi (Greek small plates, delicious and chic, their website says it best: “Krasi is love. Krasi is life. Krasi means wine, literally. Krasi is about conversations and the people immersed in them. It’s about new friends, old friends, and turning strangers into friends.”). 

If you like seafood, you have to try the unique and delicious seafood hot spot, Saltie Girl (a short walk from Newbury Street on Dartmouth Street). You can be brave and order one of their more creative dishes like, fried lobster and waffles with sweet corn butter and spicy maple syrup or French burgundy snails with black garlic butter, or go traditional and get a classic lobster roll and bowl of clam chowder–whichever you decide you will not be disappointed. 

While in Back Bay, walk over to Copley Square and take a peak in the Boston Public Library, a BEAUTIFUL building that makes you feel like you’re at Hogwarts, and then walk over to the Boston Common, Boston’s much smaller version of Central Park. If you’re in the mood to do something super touristy, take a ride on the Swan Boats located in the center of the Common.

the south end.

The South End has some of the BEST restaurants in Boston, and SoWa (South Washington Street) located in the South End, has a trendy little shopping area, and a farmer’s market that is open on Saturdays in the summer and features local farmers, artists, and craftsmen.

For a quick bite or evening drinks, stop by Five Horse Tavern, which has a huge selection of craft beers, and self-described “locally-sourced modern American comfort food.” I’ve never had a meal I didn’t love from Five Horse, so you honestly can’t go wrong. 

If you like live music, The Beehive is a hip, loungey type restaurant that not only serves delicious cocktails, but has been rated as one of the “Top 100 Jazz Clubs in the World” by Downbeat Magazine and “Best of” by Boston Magazine. At the Beehive, you’ll find nightly live music, including Jazz, Blues, R&B, Electronica, Reggae, Latin, Country, Cabaret, and Burlesque. (To be honest, I think their food is a bit overpriced, but the vibes and drinks are worth checking out.)

Surprisingly, the BEST burger (in my opinion) in Boston can be found at Aquitaine, a trendy award-winning Parisian inspired French bistro. While this hot spot can be a little pricey, but worth it if you’re in the mood for a burger.

If you’re in the mood for something lighter, like tapas, Toro features Barcelona-style hot and cold plates that are unique, delicious, and great for sharing.

If you want a fun night out of dancing, strong drinks, and 90s throwbacks, head to Clery’s after dinner, where you’ll find a basement dance floor packed with college students full of life and liquor.

southie.

Confusingly, Southie, is an ENTIRELY  different neighborhood with an ENTIRELY different vibe than the South End.

Southie is quintessential Boston. It’s known for being the neighborhood where the Irish population in Boston settled, AND where the Irish mob was active historically.

If you’re visiting in the summer, definitely check out M-Street Beach for a real taste of Southie culture. Every day in the summer, the beach is filled with local Bostonians sunbathing, playing volleyball, and, usually, enjoying a few beers. (If M-Street is too packed, there is also Carson Beach and Castle Island nearby!)

Walking distance from the beaches, are some of Boston’s best restaurants and bars. If you’re planning a night out, Southie is a GREAT place to transition from dinner to drinks.

Broadway is the main street in Southie with bars and restaurants, and here are a few of my favorite places all within walking distance of each other if you’re looking to do a bar or food crawl.

Lincoln is a Southie staple, it has great food, (arguably the best burger in Boston, but as I mentioned above, I prefer Aquitaine’s in the South End), and generally has a pretty fun night crowd as well. Capo is a loungey, fun vibe, often with live music (in the basement area). If you’re looking for Italian food in the heart of Irish-Boston this is a great option!

While in Southie, definitely stop by Loco Taqueria and Oyster Bar for a delicious marg and local oysters! If the weather is nice, grab a drink at Playwright, which has a large open courtyard area with picnic tables.

Finally, if you’re looking to jump into a time portal and experience Southie of the past grab a bucket of bud lights and play some dahhhts at Tom English’s Cottage (AKA Tommy English’s). But make sure you bring cash because it is cash only!

fenway.

If you’re in Boston during baseball season, it’s well-worth spending the money to purchase red sox tickets to visit, in the words of The Town, “the Cathedral of Boston” (Fenway Park).

Before and after the game, the whole area around the park is filled with fun-loving red sox fans enjoying the many local bars and restaurants. Cask & Flagon, Game On, and Bleacher Bar are the most well-known and baseball-centric.

Cheeky Monkey is also worth a pop in, they carry a lot of local beers and have ping pong, pool, and shuffleboard tables. If you’re checking out the area around the park on a non-game night, take a look who is playing at the House of Blues, one of the best music venues in the city. Finally, be sure to check out Loretta’s Last Call, Boston’s only true “country venue” featuring weekly line-dancing, country music, and a build-your-own Bloody Mary bar during weekend brunches.

downtown-beacon hill & quincy market.

Faneuil Hall, named the “cradle of liberty” by our founders in 1742, is an absolute must see. Right next door to the historical Faneuil Hall is Quincy Market, a giant indoor and outdoor marketplace filled with history, shops, and local food. Grab a bread bowl of clam chowder from one of the local vendors and then take a stroll around the area, taking in the local historical landmarks. Sign up for a tour or grab a map and take a self-guided walk along the Freedom Trail to make sure you don’t miss any key spots! Stops include the Old North Church, the site of the Boston Massacre, Paul Revere’s House, and many more.

Beacon Hill is what people think of when they think of Boston. It has BEAUTIFUL cobblestone streets, classic colonial brick buildings, and is home to some of the most famous Boston landmarks. Take a stroll down Acorn Street and you’ll feel like you’re walking through colonial Boston! (Also, great place for an Instagram pic!)

If you’re looking for a sit down meal in the area, Granary Tavern has a great brunch! At night, the area around Fanueil Hall turns into one of the most popular destinations for young adults looking to enjoy a “few” drinks. If you’re in the mood for a fun night, sing some turns at Hong Kong’s karaoke or dance the night away at Ned Devine’s which often has a live band. If the weather is nice, enjoy the view with a delicious dinner or drink at Tia’s Waterfront, which overlooks the ocean.

north end.

The North End is another well-known area of Boston, best known for its Italian food and pastries, you honestly cannot go wrong with any restaurant you walk into on the popular Hanover Street.

Before or after dinner enjoy an espresso or latte at Caffe Vittoria, Boston’s first Italian Caffe. In addition to fabulous Italian food, Bricco has a beautiful and delicious espresso martini, as does Lucca. Prezza is another option with high-end mouth watering Italian delicacies.

For a classic slice of pizza Pizzeria Regina is a Boston STAPLE and lives up to the hype.

Mike’s Pastry is the most famous spot to grab a cannoli, but most locals will tell you Modern Pastry’s cannolis are far superior. Lucky for you the two pastry shops are just blocks away, so you can taste test them both and decide for yourself.

If you’re in Boston during August, the whole North End is filled with street celebrations on the weekends for St. Anthony’s Feast with food vendors and street performers.

seaport.

Growing up in the Greater Boston Area, I remember this area as large empty parking lots, but wow have things changed. Seaport is Boston’s newest neighborhood with a lively nightlife, delicious restaurants, and beautiful walkways by the ocean.

The Boston Tea Party Museum is also worth a visit. It’s a fun, interactive museum, literally located on a boat floating in the ocean. You’ll learn a lot and get to reenact tossing tea into Boston Harbor, hazzah! 

There are quite a few restaurants in the area, many of which offer outdoor seating with ocean views. Legal Harborside (is the original location and a Boston staple). Inside a large colorful tent on the water’s edge, is the Barking Crab, filled with picnic tables, delicious seafood, and fun vibes. Just down the street is the Lookout Rooftop, where you can enjoy nice weather, pretty views of Boston, and standard cocktails. In the summer, the CISCO Brewery Beer Garden is open, where you can play yard games while enjoying locally crafted beers and food.

lexington.

If you are a history buff and want to take a quick trip out of the City, take a 20 minute uber to Lexington, MA, birthplace of the American Liberty (my home town!).

Visit Buckman Tavern located right on the edge of the historic Battlegreen, where the shot heard round the world kicked off the American Revolution! (If you visit in April, you might be able to catch the reenactment of that famous battle, after which local churches host large pancake breakfasts.)

Before you  leave, take a quick stop at Rancatore’s for one of the  best ice cream cones you will ever have and then take a walk through Lexington’s quaint town center.