How To See Boston in 2 Days

Day 1

Breakfast 

You’re going to need your energy today, so let’s start things off with some morning deliciousness before embarking on your Boston adventure! Since your 2-day weekend itinerary begins with the Freedom Trail, here are some great breakfast options in the immediate vicinity worth checking out.
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Buttery, fluffy, popovers are as New England as it gets and Popover King does them better than anyone in town. There are as many varieties as there are tastes from popovers with lox and cream cheese, ricotta and berry compote, to honey-glazed with lavender crème filling. There’s also a wide selection of hearty, savory versions to go along with their gluten-free options. Don’t forget to pair these sublime treats with their incredible selection of hot and cold-brewed coffees!

Morning at the Freedom Trail 

Hop off and visit the Old State House, Boston Massacre Site, Old South Meeting House, and King’s Chapel Burying Ground. These are all great attractions along the Freedom Trail and many of them are free. The Old State House is the oldest public building in Boston and was where the Declaration of Independence was first read to the people of Boston on July 18, 1776. You can see everything here in about 90 minutes or less.

Designed by former Boston Herald travel writer, William Schofield, to better guide visitors to the most prominent landmarks, this color-coded, easy-to-follow trail takes you to the sites of some of the most pivotal events responsible for shaping Boston’s history. In addition to the places of interest already mentioned, you’ll get to see the U.S.S. Constitution. Affectionately known as ‘Old Ironsides’, this massive warship was among the first to be commissioned by the United States Navy and it still stands guard in the harbor where it was built, just north of the Charles River. Since you’ve got two days, it’s recommended you break up the two-and-a-half mile trail so you can leave some to explore the rest of your weekend.

Lunch on Marlborough and Newbury

Located mere blocks from the Charles River, the Corner Tavern is a warm, cozy, gastropub accented by brick and wood that exudes a cool, neighborhood vibe. The welcoming ambiance extends to its food; a menu full of creative spins on traditional pub grub like a chipotle-glazed meatloaf burger, 12-hour brisket tacos with chimichurri, and even a build-your-own grilled cheese!

Also located in Boston’s Back Bay, indulge in some of Beantown’s bounty of the sea with a visit to the Saltie Girl. The folks that run this establishment have a deep appreciation and respect for the sustainable delicacies found swimming in the local waters and their menu’s praises are sung loudly and proudly. Elegant, yet accessible, they feature dishes like fried lobster and waffles with sweet corn butter, crispy shrimp & chive dumplings, and mouth-watering seafood towers of every size imaginable!

Afternoon in The Seaport District

Easily one of Boston’s most transformative and ambitious large-scale urban development projects in recent memory, and thanks to sound planning and billions of dollars invested, it’s considered Beantown’s hottest neighborhood. This 20-block expanse of real estate along Boston’s waterfront offers a plethora of things to do to fill your afternoon. Enjoy a refreshing midday cocktail on one of the area’s several rooftop bars like the Envoy Hotel or the Lookout Rooftop Bar and take some gorgeous snaps of the surrounding skyline in between sips. If you’re looking to immerse yourself in some culture, head over to the Institute of Contemporary Art. Housed in a glass building every bit as dramatic as the art contained within, this 65,000-foot marvel of design includes temporary and permanent galleries, a 330-seat multi–purpose theater, a restaurant, bookstore, and education/workshop facilities. Want to satiate your munchies? The Seaport boasts tons of new restaurants from laid-back to upscale like the James Beard Award Winning Best New Restaurant, Menton. There’s also casual, Italian trattoria, Sportello, and all-day cafe, Tatte Bakery, for your post-meal coffee and pastry. Two of these blocks are dedicated to retail brands like L.L. Bean, Bonobos, and Warby Garber for those looking for a shopping fix. Of course, with all there is to see and do here, don’t forget about the simple pleasures of a leisurely, care-free stroll along the water’s edge.

Boston Tea Party Ships & Museum

Don’t make your way out of the Seaport District without exploring this highly-entertaining, interactive museum! BTPSM’s mission is to document the tumultuous tale of how this milestone event (The Boston tea Party) became the precursor to a full-blown revolution that resulted in a resounding victory for the 13 colonies during the War of Independence. The event is captured through innovative exhibits and a state-of-the-art multi-sensory panoramic film. You can even take part in a historical reenactment of the event itself by dumping boxes of tea over the port side of a ship into the Boston Harbor!

Theater District at Night

When night falls in Beantown, treat yourself to some drama! The good kind, of course! There is certainly no shortage of things to do in this crowd-pleasing neighborhood, some of which involve live performance like a night out at the enchanting Shubert Theater. Originally built with the staging of Shakespearean plays in mind, this magnificent 1,500-seat venue hosts touring Broadway shows, operas, music, and dance. Speaking of dancing, if you’re looking to mix and mingle, the district boasts several nightclubs like the Royale, with its super modern vibe and eclectic soundtrack or the Bijou, ground zero for experiencing some of the world’s premiere superstar DJs hyping a crowd to a frenzy! If laughter is music to your ears, go check out the crop of up-and-comers at Nick’s Comedy Stop, Boston Magazine’s Best of Boston 2018 Award Winner for Best Comedy Venue! If it’s a lit night out you’re after, these are great spots to let the sparks fly over your two-day weekend!

Day 2

Morning at the Freedom Trail 

Get thee a nutritious breakfast, or some trail mix, and complete your path toward Freedom! Some of the remaining landmarks to explore include the Park Street Church, whose 217-ft steeple was once the first observable structure to those approaching the city from the water. You’ll pay a visit to the Paul Revere House, where the eponymous artisan and patriot lived with his family and from whence he embarked on his legendary ‘Midnight Ride.’ You’ll encounter Faneuil Hall, a large, brick auditorium where colonial merchants, fishermen, and farmers conducted business and where many a fiery oratory aimed at the British Crown inspired a revolution.

Lunch 

Lucky you to find yourself in one of America’s great food capitals in search of a tasty lunch! If you’ve bravely resisted the urge to indulge in a creamy bowl of the local ‘chowda’ to this point, all good things come to those who wait. Located near the Freedom Trail, grab a seat at the Union Oyster House. Since 1826, this Boston institution has been a prime destination for delicious old-school eats. In addition to their signature clam chowder, make sure to make room for their other menu items like fresh oysters and clams on the half shell and one of the most scrumptious lobster rolls in the city.

Historic Buildings in Cambridge 

With your hunger in check and the remainder of the day to be seized, you’re ready to explore Cambridge! Less than three miles from the Boston metro area across the Charles River, you’ll find the home of some of the world’s most prestigious institutions of higher learning, namely Harvard University and MIT (the Massachusetts Institute of Technology.) MIT’s 168-acre campus features the work of some of the world’s best-known architects, ranging in a diverse collection of styles from the neoclassical, modernist, brutalist, and deconstructivist schools like Frank Gehry’s library and Eero Saarinen’s chapel. Also attracting the best and the brightest, is Harvard University and its campus. In addition to the well-known Harvard Yard and its several opulent libraries, the Harvard Museum of Natural History, though small, is well worth your time. Admission to the museum also grants you entrance into the Peabody Museum of Archaeology & Ethnology, which houses an exceptional collection of historic artifacts from around the world.

Boston Summer Nights Tour & Charles River Cruise

Seasonal tour • Runs from late May to early September

Elevate your Boston getaway with Old Town Trolley’s Boston Summer Nights Tour & Charles River Cruise, a must-have addition to your two-day itinerary! Begin your adventure with a captivating journey through Boston’s historic streets, where you’ll uncover the city’s fascinating past and iconic landmarks. As day transitions to night, embark on a magical Charles River Cruise and marvel as the skyline comes alive with shimmering lights. Whether you’re drawn to history or nature or simply seeking an unforgettable experience, this incredible night tour offers a unique perspective of the city’s charm. It is a perfect complement to your exploration of Boston’s vibrant culture and attractions.

Dinner 

Dinner time, already? Yum! All of this exploring really works up an appetite, so tantalize your taste buds by investigating some of these amazing eateries!
Your last night in Beantown should resonate in your memory long after you return home, so go big! Stillwater, located in the Downtown/Financial District, stands alone with its adventurous brand of high-concept comfort food. The whimsical menu is a melange of the familiar with more than a few culinary curve balls thrown in for good measure. Try the Everything Bagel popcorn, Vegan pork rinds, Chicken-fried ribeye, and Ritz Cracker-crusted fried chicken thighs.

If you’d rather play it safe with some refined, Old World French fare, then embark on the Grand Tour, a restaurant concept by renowned local chef, Michael Serpa. The bistro big-boys are impeccably prepared here like duck rillettes, artichoke soup, mussels, and two varieties of steak frites but you’ll still find plenty of surprises like escargot pie, and an entire menu dedicated to the delicate execution of vegetable cookery. Ooh-la-la!

See It All with Old Town Trolley Tours

Rated by Forbes as one of the Top-Ten Best Tours in Boston, this city tour is fully-guided and narrated by local history enthusiasts in a fun, yet, informative way aboard state-of-the-art stadium trolleys for maximum visibility with the convenience of all-day hop-on, hop-off access. That means you can get off at any of the various stops in the city and explore the surrounding area for as long as you like. When you’re ready to re-board, simply return to the nearest pick-up/drop-off point and hop-on for more Boston adventuring! When it comes to the famous Freedom Trail, the trolley is never too far away from either of the 16 places of interest outlined on the red-brick path. The Gold Pass covers all the major areas including Downtown, Beacon Hill, Back Bay, the Theater District, the Waterfront District, and includes FREE and reduced admission to some of the area’s most popular attractions. This is the best, most stress-free way to see it all during your visit to this dynamic and historic American city!