36 Hours in Boston and Cambridge

A quick weekend getaway guide to Boston and Cambridge - perfect for second-timers.

As a travel blogger, I find myself spending more time than I’d like touring my site’s analytics. It’s tedious, but I get to learn so much about the kind of content you’re interested in. And when $75 round-trip tickets popped up for one of the most frequently-searched destinations on this site, I took it as a sign and booked a flight.

With only 36 hours in Boston, I knew I’d need to be strategic in my planning to make the most of the limited time at the destination. But thankfully, much like the previous month’s trip to Philadelphia, this was a return trip for me, and those usual “must-dos” are already “have dones.”

Because of this, my weekend guide is focused on diving a bit deeper into Boston and Cambridge. You won’t find a stop at the USS Constitution, Mike’s Pastry, or Fenway Park on this list. Instead, you’ll find visits to more intimate museums, local shops, and, naturally, plenty of tasty food and drink. But before we begin, a little refresher:

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ABOUT BOSTON

One, if by land, and two, if by sea. If you’ve ever taken an American history class or watched a documentary travel series, you already know plenty about Boston’s history and other claims to fame: The Boston Tea Party, lobster rolls, Paul Revere’s midnight ride, Fenway Park, Bunker Hill, Harvard.

Known as the “Cradle of Liberty,” the city played a pivotal role in the American Revolution, and visitors can follow the country’s journey to independence along The Freedom Trail. The 2.5-mile-long path winds through downtown Boston, connecting 16 significant historical sites. Beyond its historical significance, the Boston area is a hub of education, culture, and innovation. Home to prestigious institutions like Harvard University and MIT, neighboring Cambridge has long been at the forefront of academic excellence and technological advancements. And no matter where you zoom in to on the map, distinct neighborhoods contribute to the region’s diverse and dynamic character, from architecture to cuisine.

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Five things you may not know about Boston

1. The Massachusetts State Dessert – the Boston Cream Pie – was born in the ovens at the Parker House in downtown Boston. (Not local? You can order one to be shipped to your door!).
2. Boston is home to the nation’s first subway tunnel, and you can still board the T at Park Street, one of the original stations that opened in 1897.
3. For better or worse, Boston’s nickname is “Beantown” – though the origins of the nickname are disputed (is it baked beans? Rum? Who knows, but it’s probably here to stay).
4. The Great Molasses Flood occurred in Boston’s North End neighborhood in 1919, unfortunately thwarting the adage “slow as molasses” and resulting in 21 deaths.
5. The Boston Marathon is the oldest annual marathon in the world, though it has come a long way since the inaugural race in 1897 with only fifteen participants.

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Boston is a city that is steeped in history, yet is perfectly situated for the modern-day visitor thanks to an easy-to-reach airport, great public transit, and dense neighborhoods. So come, tour this destination through the lens of a repeat visit, soaking up as much as possible in 36 hours:

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THINGS TO DO IN BOSTON AND CAMBRIDGE

Isabella Stewart Gardner Museum

The Isabella Stewart Gardner Museum is probably just as famous for the works it doesn’t have on its walls as the ones currently on display. In 1990, an estimated $500 million worth of art was stolen from the museum, a heist chronicled in the Netflix documentary This Is a Robbery: The World’s Biggest Art Heist. Walking through the galleries today, you’ll find empty frames patiently awaiting the return of their works.

And what impressive galleries they are! Built in the style of a 15th-century Venetian palace and completed in 1901, the ornate rooms and courtyard are such a treat for visitors today. Even on a dreary December day, the courtyard exuded light and warmth, inviting us to slow down and linger. Admission to this one-of-a-kind travel experience is only available with timed entry; purchase your tickets online before you leave for Boston.

→Isabella Stewart Gardner Museum // 25 Evans Way, Boston, MA 02115

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MIT Museum

Though the MIT Museum’s Kendall Square location is relatively new, the museum has been around since 1971. Founded with the purpose of making research and innovation accessible to all, the collection spans the arts and sciences. Wander the galleries, and you may find exhibits on AI, genetic technologies, the institution’s history, and more. I confess that some of the hyper-specialized subjects went over my head, but the collection is robust and there are plenty of interactive exhibits on display that cater to all ages and interests.

→MIT Museum // Gambrill Center, 314 Main St, Cambridge, MA 02142

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Boston + Cambridge Shops

Shopping wasn’t high on my list of priorities for this trip (plus I had only a little extra room in my backpack to contend with, thanks to flying on Spirit), but I had the chance to pop into two places. The Garment District in Cambridge is a must for any fan of thrifting, as the shop carries one of the biggest selections of secondhand clothing, shoes, and accessories I’ve seen in one place. Seriously, around every corner seems to be yet another room filled with racks and racks of clothing, and miraculously, everything is neat and organized. I found a chic wool coat in such great condition that it must have been brand new when the previous owner donated it (and yes, I made room in my backpack to bring it home!).

Across the Charles in Boston, I couldn’t resist a quick lap around Eataly. If you’ve never been to one of the outposts of this Italian food emporium, you’ll have to stop in while you’re in Boston. Warning: don’t visit while hungry!

→Eataly // 800 Boylston St, Boston, MA 02199
→The Garment District // 200 Broadway, Cambridge, MA 02139

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WHERE TO EAT AND DRINK IN THE BOSTON AREA

Krasi

I almost didn’t make it to brunch at Krasi as there were no reservations remaining in the days leading up to this trip – but I’m so glad I gave it one last search on Sunday morning. Availability for two seats opened up at the bar, and with just a few quick taps, they were ours. Named after the Greek word for wine (κρασί), this Back Bay Greek wine bar is equal parts refined and relaxed. Brunch, in my opinion, is the best time to visit as it offers a better value for many of the same delicious dishes. Plus, everything is served as mezze and begs to be shared over the morning’s gossip alongside any of the brunch cocktails with a Greek twist. I suspect Krasi is best approached as a group (more people means more plates!), but even as a duo, it was a delight to indulge in three of the dishes: The popular Dips and the daily Souvla finished off with a not-too-sweet slab of delicious Milopita. Reservations recommended.

→Krasi // 48 Gloucester St, Boston, MA 02115

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Mamaleh’s Delicatessen

For a great breakfast, it’s hard to beat Mamaleh’s Delicatessen. This Jewish deli has three locations in the area (in Boston, Cambridge, and Brookline), and serves up breakfast and lunch all day. I’m not one to pass up a good, fresh bagel sandwich, and a pastrami, egg, and cheese was just the ticket. But how to order it? I don’t know how busy the other locations get, but the Cambridge line was so long that it ended up reversing on itself in a confusing mass. We eventually gave up on waiting in the queue to order and ordered takeout online, enjoying our meal outside in the square (which I think was the right call!).

→Mamaleh's Delicatessen // Multiple Locations

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Moëca

I don’t know about you, but the first foods that come to mind when I think of Boston are seafood and pasta. Cambridge’s Moëca combines the two expertly, so even the most short-on-time traveler can indulge in some of the region’s favorite cuisines. I greatly enjoyed my meal at this neighborhood restaurant that responsibly sources its seafood and prepares it in new and exciting ways – so much so, that it deserved its own blog post. Find my post on Moëca here.

→Moëca // 1 Shepard St, Cambridge, MA 02138

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Neptune Oyster

When I visited Boston six years ago, I had every intention of ordering a lobster roll from Neptune Oyster. Well, those intentions were sidelined by a four-hour wait. For this trip, I went in with zero intentions of visiting Neptune Oyster – it was Michael who said, “Hey – isn’t that lobster roll place over here? Let’s just go see if there’s a line.” And apparently, that’s the ticket to gaining quick entry to this popular spot (well, that, and maybe trying to get a spot on a late, rainy Sunday afternoon).

The lobster roll was respectably full of large chunks of sweet and flavorful meat, piled carefully into a soft and squishy bun before being bathed in an amount of butter I’m glad I didn’t witness. It was heaven – and sharing was the way to go. You can have too much of a good thing, after all.

→Neptune Oyster // 63 Salem St # 1, Boston, MA 02113

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Area Four

“Well, I could eat pizza…” Michael trailed off, and soon we were making the quick walk from the MIT Museum to Area Four. Although it was nearly 4 p.m., the only free seats were at the bar (where, naturally, we were tempted to order a beer flight of local favorites). But soon we were diving into one of the restaurant’s long-fermented sourdough pizzas with a tangy crust with a perfect bite and chewiness. It was everything I wanted in a pizza – a great crust studded with charred spots, the right amount of tomato sauce, and a high-quality mozzarella. It wasn’t much of a stretch to polish off the whole thing!

→Area Four // 500 Technology Square, Cambridge, MA 02139

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Dumpling Xuan

Dumpling Xuan had been on my radar before I arrived in Cambridge, but seeing people walking around with takeout from the restaurant sealed my fate to visit. With barely enough time and stomach space for one final meal before heading home, we made the call to order takeout as well, riding alongside the bag in the Uber and eating it all at the airport. With portability in mind, we ordered two types of dumplings: Taiwan-style fried dumplings and steamed pork and leek dumplings. Even thirty minutes later on an airport bench, they were still warm and flavorful within their homemade wrappers. It certainly made our delayed flight a little more bearable.

→Dumpling Xuan // 465 Cambridge St, Cambridge, MA 02141

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Coffee Shops

Remarkably, this guide features fewer coffee shops than I would have expected given the circumstances. But between the free coffee at breakfast at our hotel and the brisk December weather, I guess we had our caffeine bases pretty covered. Still, I had the chance to visit two cozy coffee shops during this quick trip. Ripple Cafe’s Cambridge location is conveniently located next to the MIT Museum (and next to our hotel – more on that in a moment) and offers a menu of coffee and espresso drinks, smoothies, and light lunch fare in its bright, minimalist space. Boston’s Thinking Cup was also abuzz with students at its Newbury Street location, and though not necessarily a small shop, felt snug and cozy – it’s the kind of place I’d like to curl up with a book if there wasn’t more city to explore!

→Ripple Cafe // 314 Main St, Cambridge, MA 02142
→Thinking Cup // Multiple Locations

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Bars & Breweries

When it’s dark and pouring rain at 4 p.m., where do you turn? In my case, I turned to Parla – a tiny bar with a big personality in Boston’s historic North End. It was easy to get distracted by the doodles and graffiti among the pages of the menu, but my focus was rewarded with an excellent reworked martini. Another great spot for a cocktail is not technically a bar – but with Stoked Pizza Co.‘s full, full menu of tiki cocktails and creative drinks, it very well could be (with dinner down the block at Moëca there was no room for a pie, but the beverages were perfection).

For drinks with a competitive edge, Roxy’s Arcade in Cambridge offers a large number of arcade machines in a small space. Bring plenty of quarters though – the game prices are some of the highest I’ve ever seen. And you know I love a good brewery, and I’m so glad we made time for a visit to the Satellite location of Remnant Brewing because we found friendly staff and inventive brews.

→Parla // 230 Hanover St, Boston, MA 02113
→Remnant Brewing - Satellite //  877 Cambridge St, Cambridge, MA 02141
→Roxy's Arcade // 292 Massachusetts Ave, Cambridge, MA 02139
→Stoked Pizza Co. // 1611 Massachusetts Ave, Cambridge, MA 02138

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Bakeries + Treats

Yes, there’s that famous cannoli place around the corner, but locals love Bova’s Bakery more (and for good reason!). Find a dizzying array of colorful cookies, cakes, and more in the cases without the wait. Plus it’s open 24/7!

And sure, it was winter during this visit, but that’s not enough to stop me from getting ice cream. Toscanini’s is the place to go for creative flavors, like their fan-favorite b3 (that’s brown butter, brown sugar, and brownies). Like all high-quality ice cream, the scoops are ultra-rich and you’ll feel sated faster – get a small serving or share a flavor or two with your (close!) companions.

→Bova's Bakery // 134 Salem St, Boston, MA 02113
→Toscanini's Ice Cream // Multiple Locations

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WHERE TO STAY IN CAMBRIDGE

The Kendall Hotel

After debating extensively over whether to stay in Boston or Cambridge, the charming Kendall Hotel made the decision for me, thanks to its perfect location, unique history, and approachable price. Once the Engine 7 Firehouse, today the property is a historic boutique hotel in Kendall Square. The building’s history is reflected in the common areas and each of the 77 guest rooms.

To save a little, Michael and I opted for the smallest room option, the Classic Queen. This room has all the essentials in a petite package: a comfortable bed, a small sitting area, a closet, plenty of outlets (plus a wireless charging pad!), and an in-room coffee maker. The hotel knows how to make the most of the space, though, by adding chic Jonathan Adler toiletries, a lap desk for working, silky-soft plush robes, and a Dyson sonic hairdryer.

Breakfast is a hearty affair, with all the classics like eggs, bacon, and pastries, plus the makings for breakfast tacos (my go-to!). The hotel also offers wine tastings in the restaurant on the weekends and upstairs in the rooftop retreat during the week. With friendly service, clean and comfortable rooms, and a location mere steps from the Kendall T station, I can’t recommend this hotel enough – if I find myself in Cambridge again in the future, it’s the first place I’ll look.

→The Kendall Hotel // 350 Main St, Cambridge, MA 02142

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WITH MORE TIME IN THE BOSTON AREA

With more time in Boston, I’d have loved the chance to wander a little more and spend time in the city’s parks and along the Charles River. I’d also love the chance to enjoy more local restaurants, bars, and shops like the ones listed below:

Restaurants

• The Neighborhood Restaurant & Bakery – a Somerville institution
• Tonino – a cozy newcomer with hard-to-snag reservations
• Puritan & Company – classic New England fare
• Oleana – the spot for Baked Alaska
• Yume Wo Katare – mostly ramen, sometimes a surprise menu
• Bagelsaurus – yummy-looking bagels and bagel sandwiches
• The Q – hot pot in a lounge setting
• Zhi Wei Cafe – dumplings, noodles, rice dishes, and so much more
• Gufo – a cute Italian spot by the folks behind SRV
• Moon Bar – a casual offshoot of a popular fine dining spot

Bars

• haley.henry – tinned fish and natural wines
• The Koji Club – the city’s first sake bar
• Mahaniyom – handcrafted cocktails and Thai tapas

Shops

• Make & Mend – a secondhand craft supplies shop
• gather here – notions for sewing, knitting, and more
• ouimillie – a lifestyle boutique with discerning taste

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Thank you to the Isabella Stewart Gardner Museum for generously providing media passes for this visit!

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TRAVEL TIPS FOR BOSTON + CAMBRIDGE

Boston is a relatively easy city to reach from much of the U.S. with direct flights landing at Boston Logan International Airport across multiple airlines daily (Boston also has three Amtrak stations that serve regional rail passengers). Public transit (bus, taxi, or ferry), rideshare, and taxis are all readily available to get you from the airport to your hotel.

Travelers staying in Boston or Cambridge will be glad to know that the city is easy to navigate by public transit, and in many cases, a rental car might even be considered a burden. Pick up a CharlieCard at a fare vending machine at one of the T stations (what Boston calls its subway stations) or at a retail location, and load it with either a daily pass or cash value. Visitors staying three or more days will likely find the most value in purchasing the 7-Day Pass (for this quick trip I opted to pay per ride).

When should you visit Boston? Well, I’ve had the chance to visit the city in both the summer and the winter, and I prefer the former for one reason you might not expect: the amount of daylight. The sun sets around 4:15 p.m. as you near the Winter Solstice, and it does impact your experience as a traveler (for comparison, the sun sets at 5:15 p.m. in Charlotte, even though we’re in the same time zone). Weather-wise, summers are hot and winters are cold, with November and December being the rainiest months (something I experienced during this trip!).

One thing that felt unique to me about visiting Boston compared to other regional cities of equal size is that many bars and restaurants are closed on Sundays. You expect this, say, in a small town in the South, but it surprised me a little to find this to be the case in Boston. I don’t say this to scare you away from visiting on a Sunday – there are still plenty of places open, of course – but just as an encouragement to verify the hours while building your itinerary.

And lastly, though I’m always a little reluctant to talk about it, safety. Boston and Cambridge both felt immensely safe to me, and I would feel perfectly comfortable walking alone in the areas we visited during this trip. But as always, you should keep your head up and your city smarts about you.

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FINAL THOUGHTS ON SPENDING 36 HOURS IN THE BOSTON AREA

Is 36 hours enough time? No, never for Boston.

But it’s enough to explore more of what makes this city such a classic destination. And with inexpensive direct flights from Charlotte and other domestic destinations, it’s a great city to return to year after year, season after season.

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Questions for you

What are Sundays like where you live?

How do you like your lobster rolls?

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