Many people refer to Boston as being the “best of both worlds,” meaning it’s large enough to offer endless things to do (especially for people in their 20s and 30s) and it’s small enough to not feel overwhelming, like some say about New York. Bostonians are immensely proud of it’s history and accomplishments. Boston continues to support education, arts, and push for social equality making it a very safe place to travel.
Getting around the city is easy and affordable. The public transportation (the “T”) makes Boston a wonderful option to travel solo, with a group of friends, or on a family getaway. It also doesn’t hurt that it’s easily one of the prettiest cities in the country.
The best time to visit Boston is at the tail end of summer (August) and all through fall (November), because the crowds are smaller and you can really embrace all the best outdoor activities that New England has to offer. If you come late enough into fall, you’ll get to experience the New England fall foliage in all its glory.
Many people come to Boston to experience American culture and history. While there are endless tourist attractions geared toward that aspect of the city, like walking the Freedom Trail and visiting Paul Revere’s House, there’s so much more.
1. Do it for the gram in Beacon Hill.
Beacon Hill is one of Boston’s most sought after neighborhoods to live in and visit. BH is also home to the most photographed street in the US – Acorn Street. Don’t believe me? Google it!
With beautifully built brownstones displaying flower pots, custom door knockers, quintessential New England window shutters, overgrown ivy and gardens tucked away in secret alleys, Beacon Hill is seriously #facadegoals (especially if you come during Halloween or Christmas). A few popular spots are in front of Rouvalis Flowers, Chestnut Street and Louisburg Square. John Kerry’s house in Louisburg Square is also a popular spot for picture takers. If you visit in the morning, you’ll avoid crowds, but if you come in the evening, you’ll instantly be transported to Europe with its gas-lit streets and pretty sunset views.
Beacon Hill is also home to a ton of equally adorable, locally-owned shops that line Charles Street. For food try Figs, Tatte Bakery and Sweet Cupcake. For shopping check out Follain, Dress Boston, The Holiday Boutique and NRO.
Pro-tip: Get to Acorn Street before 9am to avoid engagement shoots and other tourists trying to get that perfect snap.
2. Get artsy at one of Boston’s most beloved art museums.
The most popular are the Museum of Fine Arts and the Isabella Stewart Gardner Museum, which are in walking distance of one another. A few other less-popular, but equally as moving museums are the Institute of Contemporary Art (ICA), the Museum of Science and the Harvard Art Museum. If you enjoy supporting local artists, I suggest SOWA – an outdoor art and food market in Boston’s South End neighborhood. Make sure to check their operating hours beforehand.
Pro-tip: See if you apply for free entrance at any one of these museums via the Bank of America Museum on Us program for card holders.
3. Indulge in Italian culture and cuisine in the North End.
Although Boston is known for it’s seafood, you might be surprised to know the Italian food scene brings in people from all over the world. For dinner, try Bricco, Mamma Mia’s or Monica’s Trattoria. For dessert, Mike’s Pastry, Bovas and Modern Pastry are all local favorites.
4. Catch a baseball game at Fenway.
If you don’t know already, Boston takes its sports very seriously. With Fenway Park’s perfect location, it’s easy to walk or take the T from just about anywhere in the city to catch a game. I suggest an evening game, so you can do a little bar hopping in the area afterwards. In the summer, the heat can get a little bit unbearable if your seat isn’t in the shade.
If you can’t sit through a full game or you’re really in it more for the selfies, you can opt for the one hour walking tour! And if you’re a hockey or basketball fan, TD Garden is located in the heart of the West End.
5. Explore Boston by water.
One of Boston’s best features is its proximity to the ocean and it’s endless water activities. One of the most touristy, yet absolutely enjoyable attractions is a duck tour – an experience where you can tour the city by land and water.
You can also go whale watching, charter your own a sailboat/cruise ship or ride the Codzilla speedboat, all out of the Boston Harbor.
For a more tranquil experience, try renting kayaks in the Charles River. If you do so, go during the evening to catch the most beautiful sunsets.
If you just want to take a quick dip on a nice warm day, try the public swimming pool, Mirabella Pool, in the North End or a roof deck pool, like the one at the Revere Hotel.
And lastly, Boston does have a beach! While it’s nothing like Maui, it is clean enough to stick your toes in or go for a quick dip. Carson Beach is located in South Boston (Southie) where you’ll find endless 20-somethings playing beach volleyball and having a good time.
6. Shop till you drop.
You can think of Boston’s shopping scene by location. Copley Square is home to the Copley Mall and the Prudential Center. Here you’ll find big retailers like Saks Fifth Avenue and Barney’s. Boston’s first Eataly also opened here in November 2016.
Right next to Copley Square is Newbury Street, which is one of Boston’s most recognizable landmarks. Newbury street has a wide collection of boutique shops and extremely high end retailers of all kinds. Adding to the charm of Newbury street are the countless restaurants with outdoor patios. Try Lolita Cocina or the Saltie Girl if you’re in the area.
Beacon Hill, Harvard Square and the South End are home to smaller, locally-owned, yet pricier boutiques with a wide range of goods. Check out SAULT New England, Olives and Grace and Uniform if you’re in the South End area.
Pro-tip: Swing by Faneuil Hall, but do not plan your day around it, as it is a very touristy area and not worth too much of your time.
7. Nom on a lobster roll.
You can’t come to Boston without having a lobster roll or a bowl of clam chowder! For the most part, there are 2 types of lobster rolls – warm and cold. For a warm roll with delicious savory butter try Luke’s Lobster. For a very filling cold roll with mayo, try James Hook + Co.
8. Enjoy dinner and drinks with a view.
Pro-tip: Skip the Skywalk Observatory at the Top of the Hub. Instead, go enjoy some eats at the restaurant on the 52nd floor for free (you just have to pay for the food of course).
9. Step outside of Boston-proper, into the city of Cambridge to enjoy a day in the sun.
Cambridge is home to Harvard University and the popular Harvard Square area where you’ll find all types of dining and shopping experiences. For dining check out Giulia, Alden & Harlow or Beat Brasserie. For shopping check out Mint Julep and Black Ink.
Pro-tip: Bring or rent a bike so you can travel between Boston to Cambridge. You’ll get to experience beautiful city views as you cross the bridge between areas.
10. Take the fast ferry to Provincetown, Cape Cod.
To experience Cape Cod without the 2-3 hours of traffic, hop on the Boston Harbor Fast Ferry for ~$80 round-trip to Provincetown, which sits at the very tip of the Cape. Spend at least half a day strolling through picturesque New England streets and bring or rent a bike to get to one of the many beautiful warm sand beaches. Don’t leave without eating some fresh local seafood.