During summer when most New England locals head to the beach at Cape Cod, Nantucket or Martha’s Vineyard to enjoy the warm, sunny weather for a limited time, cities like Boston clear out enough to where you can enjoy the popular spots with less of a crowd to compete with. Both my boyfriend and I had previously visited Boston about five years ago on separate occasions, but we felt like we were due for a trip back to explore the city together. From the seasonal Lobster Rolls to a Red Sox game at Fenway Park, we had a perfect trip and can’t wait until we return!
Where We Stayed
Like every other city, we found the selection of Airbnb rental apartments in Boston to be conveniently/centrally located and more reasonably priced than hotels. Even booking less than two weeks before our trip with limited options, we were able to secure a place to suit our needs. It was very simple and the smallest sized studio we had ever stayed in, but it still worked out just fine. We are only in the Airbnb to sleep at night, so an expansive kitchen, living room, or balcony for example are never necessary.
My review of this unit in particular is that the location in the upper/central part of South End on Columbus Avenue could not have been more perfect. It was a charming neighborhood of brownstones, quiet but still easy to catch an Uber, close walking distance to cute shops and restaurants, and an easy walk to Back Bay, Beacon Hill, and Boston Common. It was an easy self check-in process, which we always prefer, only one flight of stairs up, clean, and modern enough for being such an old building. I will note that the bed is only a double, so I would not recommend it for anyone tall or for couples who like their space (ha). The shower was also quite small but the water pressure was great, which I personally care more about. It got very bright by 6am, so it was impossible to sleep in without an eye mask! Like I said, it was nothing special but it had the necessities.
If you ever have ANY questions about Airbnb, I’d be happy to help! I’ve stayed in at least 15 of them around the world.
Where We Went (by neighborhood)
Much like New York City or London but on a smaller scale, Boston is broken up into distinctive neighborhoods. From the Italian section in North End, to the upscale and charming Beacon Hill, and the up-and-coming, trendy area of South End, there’s something for everyone. Therefore, like many of my city and neighborhood guides, I’ve organized this post by neighborhood so that you can walk to each place listed within each section.
As seen in the movie, Spotlight, this cafe in the front and bar in the back is a well-loved locals spot located in the heart of the South End. We walked over from our Airbnb on our last morning before heading to the airport and first-hand witnessed the bustling vibe and popularity. There’s some seating inside as well as on the sidewalk patio, but it fills up fast. The croissants and muffins looked amazing but I went with a more hearty and savory egg burrito.
Many of my friends who have lived in Boston shared that Clery’s is the after work spot. Notice I didn’t say happy hour. That’s because the law here does not allow a sale on alcohol. However, many places will feature happy hour specials on food. Back to Clery’s, we loved how it was a traditional corner pub with neighborhood charm even though it is surprisingly part of a large restaurant group.
On a toasty mid-afternoon after checking in to our Airbnb, we started our South End exploration hop with a Pâté & Terrine plate and an Aperol Spritz. It truly hit the spot. It’s a small shop with a bar that was practically full. It was here that we noticed first-hand how friendly the locals were; receiving recommendations from both the bartender and a gentleman sitting next to us at the bar. Once again, we found ourselves following their suggestions to a tee that it dictated the next spot on our hop, Kava.
I’m half Greek and visited Greece a few months ago, so to think of going to a Greek restaurant in Boston worried me a little. However, this gentleman at The Butcher Shop bar recommended Kava as highly as the reviews I read, plus it was literally around the corner. It ended up being one of my favorite meals of the trip! The Oktapodi (tender grilled octopus, olive oil, lemon, oregano) and Keftedes (juicy, well-seasoned lamb meatballs) were outstanding. I paired them with the Tsipouro Mule (tsilili tsipouro, ginger beer, lime juice, jalapeno) and Spencer got some ouzo, of course. It was packed, so make sure to go soon after they open or book a reservation!
I love French wines, so this intimate wine bar with French tapas, a bar next to the open kitchen, sidewalk patio seating and a romantic glass-enclosed garden area pretty much sold me on stopping in. I ordered a glass of the 2017 Domaine Fouassier Sancerre Blanc from the Loire Valley of France, which was well worth the higher price tag. After Kava we didn’t have much of an appetite, but I’d love to go back here to try the food.
Perhaps the best patio seating in the South End, Banyan was packed outside and empty inside! They serve unique Asian fusion small plates, which I always love. We ordered the Cucumbers with black vinegar, peanuts, Korean chili flake and Fresh Rolls with cucumber, mint, Thai basil, carrot, peanut sauce. Both were super flavorful and delicious. To cool off the palette after those spicy cucumbers, I also ordered the refreshing Banyan G&T.
Another highly recommended spot opened more recently by a popular local chef was this modern Asian restaurant. We ordered the “Pretty Woman” option from the Cheap Date Night dinner that happens every Monday and Tuesday from 5pm to 10pm. There are 3 fixed menus for $45 each designed to be full dinner for two people or for larger groups looking to try new dishes. It was more than plenty of food for two people and such a great deal! It included Taiwanese Cold Dan Dan Noodles, another noodle dish with shrimp and lemongrass butter, Crispy Salmon Rolls, Ginger Scallion Bok Choy, and rice. Paired with cold sake, we really enjoyed it!
This chic and modern Italian restaurant with a hidden rear patio was recommended to us by a few foodie locals we met on our trip, so we had to try it out. Our favorite dish was the Fried Quail with salsa peverada, blueberry and shiso. It was so good that we are still wondering why fried quail isn’t on more restaurant menus! We also ordered the Tagliatelle with speck, arugula, black pepper, and Corn Risotto with mussels, garlic scapes, chili. We appreciated that the pastas are all housemade and smaller portions so you can try a few plates if you want.
Other Places To Consider
- Coffee Shops/Cafes – Flour Bakery & Cafe, Jaho
- SoWa Market – Sunday 10am-4pm only; pop up market on the weekends filled with artisans, entertainment and food
- Shops – Olives & Grace, Follain, Third Piece, Niche Plant Shop, Flock, Formaggio Kitchen
- Italian – Mida (classic Italian), Coppa Enoteca (Italian small plates), Bar Mezzana (coastal Italian)
- Other Cuisines – Toro (Spanish tapas), Gaslight Brasserie (French), Orinoco (Venezuelan), The Salty Pig (charcuterie), B&G Oysters (seafood), Trade (Mediterranean), The Gallows (New American)
- Drinks – Wink & Nod, Shore Leave, Beehive (Blues/jazz downstairs), Barcelona Wine Bar, Franklin Cafe
Back Bay & Beacon Hill
Although we had both been previously, the Boston Public Library is another must. The courtyard and “Harry Potter-esque” Bates Hall are gorgeous! It is a nice balance of being touristy and filled with students who are actually studying and reading. I would especially recommend visiting if you are a photographer.
This Boston staple is the most recommended spot for coffee/breakfast in the city, with Flour Bakery probably next in line. There are multiple locations around the city but we went to the one in Back Bay. It’s trendy and popular, yet authentic and local. At this location, there is a lot of seating (inside tables, coffee bar, outdoor patio) but even more people. Fortunately, many take it to go!
On our “must” list was this tiny seafood bar known for their lobster rolls and tinned fish. We went on a Monday, 15 to 20 minutes after they opened, and had to wait almost 40 minutes. I was shocked! Fortunately, there’s a bar next door (Met Bar) and they will call you when your table is ready. We sat at the bar and watched as they expertly filet a whole salmon and prepared other cold dishes. We ordered a lobster roll (cold, but you can also get it warm) and the NY-style smoked trout plate with an artisanal bagelette, tomatoes, capers, red onions… all the fixings. Both were so incredibly fresh and delicious. I mean, look at those lobster chunks!!! On a cooler day, I would totally come back for the warm lobster roll oozing with melted butter, and try more of their tinned/smoked fish plates.
I went to Cheers on my visit to Boston over five years ago, but honestly had never even seen the show. Now that I’ve watched most episodes thanks to Hulu, I was excited to go back! This location is the one they show in the intro for each episode, so if you’re a fan, it’s worth a visit. The bar downstairs does not look at all the same as in the show, but instead is filled with memorabilia and beer-filled Cheers mugs. There’s another bar upstairs as well as a gift shop, and a second location in Faneuil Hall. Don’t worry, we checked this location out too – see below!
Like Central Park, Boston Common and the Public Garden will always be worth a stroll around in any season. It’s beautifully maintained with everything from historic statues to benches facing the duck boats to beautiful flower gardens.
Even though there isn’t a specific attraction here, we were told by a couple friends that the Esplanade is worth a visit to ride bikes, go for a run, watch the kite boarders and crew teams, see the sunset or simply go for a stroll. It was a beautiful park along the water, and I’m always in my happy place by the water! Also, it felt as though it was 10 degrees cooler there than within the city.
Other Places To Consider
- Copley Square Farmer’s Market – Tuesdays only from 11am – 6pm
- Back Bay – Select Oyster Bar, Lolita, Puro Ceviche Bar, Moon Bar, Bukowski Tavern
- Beacon Hill – Bin 26, Toscano
- Shops (*many are closed on Monday) – Follain, Black Ink, Flat of the Hill, December Thieves, Holiday Boutique, Top Drawer
North End & Downtown Crossing
When visiting the North End, I recommend visiting Boston Public Market, then walking up Hanover Street past the Rose Kennedy Greenway to find all the most famous and authentic Italian places the neighborhood has to offer.
This cute coffee shop is conveniently located on Hanover and has everything from pastries to sandwiches. After walking around on a humid morning, we were looking for a quick break. While Italian pastries are most popular here, I found them all to be offering more dessert pastries than breakfast pastries, so I end up getting an iced chai tea latte and a chia pudding with berries instead.
If you love a classic brunch with loads of menu options that make your stomach growl, look no further than North Street Grille. My friends who live in the neighborhood recommended it to us, so we all went together as our first meal off the plane. The Sweet and Salty Sandwich with scrambled eggs, cheddar, bacon served on french toast (that you dip into maple syrup, of course) was a combination I never had before but now it certainly won’t be my last. YUMMY!
Famous Italian Pastries
The big question is: Mike’s Pastry or Modern Pastry? These two long-time rivals are a block away from each other packed with tourists and locals buying cannolis and other delectable sweets on a daily basis. Around the corner on a side street is the less famous, but equally regarded among locals, Bova’s Bakery. We walked in and looked around each one, shocked to find them near empty mid-morning on a Tuesday. Over the weekend you could hardly walk into the place! Word is that the lines move fast. Anyway, despite zero line, I didn’t end up buying anything. I know, I know… I should have. But they were cash-only, large portions, and I’ve had a lot of fantastic Italian pastries in the past! Maybe next time if I’m there later in the day. I do LOVE a quality cannoli though, that’s for sure. They had the classic and so many other yummy looking flavors like pistachio. Mmm.
I was so impressed by the variety of local food vendors at this market. Everything from cider donuts to ice cream (get the graham cracker flavor!) to smoked fish can be found here. It’s perfect if you’re with a large group, looking for a quick bite, want to picnic at the nearby park, or are looking for fresh ingredients to cook at home. Something for everyone and definitely worth a stop in!
Another popular area that is worth visiting once is Faneuil Hall Marketplace. Walk through Quincy Market for local food vendors, visit the second Cheers bar location, and check out some souvenir shops if you’re looking for gifts. It’s touristy, but it’s a nice place to stroll through even if you’re not looking to eat or drink.
This upscale speakeasy isn’t too hard to find thanks to a small sign outside, but it does appear to be a hair salon at the entrance! It’s expansive in size with various rooms, all dark, chandelier-filled with velvet couches and well-dressed bartenders. It can turn a bit clubby at night, but we loved going earlier for well-made cocktails. The food menu looked creative and delicious, but we didn’t stick around long enough for the kitchen to open.
Other Places To Consider
- Haley Henry
- Windsor Dim Sum Cafe
- Les Zygomates Wine Bar Bistro
- Ogawa Coffee
This new-to-me brewery, restaurant and rooftop in the Seaport District of Boston was a great introduction to the booming beer scene in the city. They had a very large industrial-modern space, and an equally impressive menu of their own craft beers, mostly sours, IPAs and stouts. I sampled a few (they don’t do flights) and went with the Double SeeSaw Peach – an American Gose Ale brewed with peaches. It’s a great place to hang out, for a group of any size, but worth noting that the rooftop does not open until 5pm.
A more popular brewery with more widely distributed beers is Harpoon. I had visited previously, but have since become much more of a beer connoisseur. Only a 10-15 minute walk away from Trillium, it’s definitely worth a visit. I ordered the UFO sampler flight with the Big Squeeze, Hefeweizen, Raspberry, and White. We also ordered the salted pretzel with bacon ranch sauce (really good) and IPA cheese sauce (not good; too grainy). Tip: If you’re interested in a brewery tour, you can join for free if you “like” them on social and show the host. Easy enough!
One of the most popular restaurants in the Seaport District, serving Greek fusion, plays on the idea of a modern-day ouzeri in Greece. It’s lively, welcoming, and gets very busy! We ordered the Spanakopita Grilled Cheese with spinach, feta, kasseri on a Kalamata olive loaf served with tomato soup to eat, which was a fun twist on such a comfort food classic. To drink, I ordered the Cuke Skywalker with gin, a vermouth blend, cucumber-rhubarb syrup, lime and mint. That is, until I started sharing my boyfriend’s ouzo flight. We ended with a shot of mastiha (a sweeter raisin liqueur).
While I’m usually not one for chains, this Legal Harborside location in the Seaport has a 3rd floor roof deck facing the water and fishing piers. They also served some of the best frosé I’ve ever had! We didn’t eat anything here, but you can expect to find a selection of steaks, seafood and sushi on the menu.
Other Places To Consider
- The Lawn on D
- Shops – Away, Outdoor Voices, For Now
- Yankee Lobster
- Row 34
- Cisco Brewers
- Lookout Rooftop & Bar
This chef-driven spot in East Cambridge near MIT had a cool industrial vibe and a variety of interesting small plates, craft beers and cocktails. My kind of place! I ordered the Snow Day with Ginger Shrub, maple, ginger beer and the addition of Tito’s because it was actually on the menu as a mocktail. Never overlook the mocktails! We enjoyed the laidback, friendly service here and would go back. No special occasion needed!
This sleek neighborhood cocktail bar above popular restaurant Alden & Harlow in Harvard Square was one of my favorite spots on the whole trip. For starters, I had one of the best creative versions of a gin & tonic I’ve ever had. It’s called “A Matter of Trust” made with Japanese gin, nori boba, honey, and tonic in a highball glass. The boba were super interesting and had a umami/savory/salty taste. Somehow, it worked! The people were very friendly and for being nice-looking, it still felt casual and approachable. The upstairs bar is absolutely gorgeous, but doesn’t open until later. Next time!
A couple fellow bar go-ers and the bartender at Longfellows recommended this Mexican restaurant around the corner for frozen margaritas on the rooftop. The food looked and smelled amazing, but we weren’t hungry at the time. I was surprised to learn that it’s actually a chain, but that wouldn’t stop me from going back. The frozen marg was really delicious and apparently much stronger than their marg on the rocks! Who would’ve thought?
This creative seafood and raw bar by the same people as Alden & Harlow and Longfellow Bar serve local $1 oysters, as well as pizzas, pastas, and absinthe too. The smoked and salted peel & eat shrimp were super tasty, and obviously we got the oysters too! We ended up having a great chat with a woman at the bar next to us, who shared great restaurant recommendations like Cafe Sushi.
I had read very positive reviews of Cafe Sushi but for some reason was under the impression that it was omakase only, but it’s not! Fortunately, it was one of the places Alice, our friend at the Waypoint bar, recommended to us the most. We ordered the Chef’s Selection of five pieces of in-season fish topped with unique condiments, O-Toro fatty tuna, Unagi eel from Maine, and Uni. The fish was incredibly fresh and high-quality, like Kadence, our favorite Orlando restaurant. They also had fantastic service and sake selections to choose from.
Other Places To Consider
- Loyal Nine
- Alden & Harlow
- Brick & Mortar
- Henrietta’s or Benedetto at The Charles hotel
Last, but certainly not least, Fenway Park is a must! Whether it’s baseball season or not, you can still visit the oldest ballpark in MLB. The Red Sox were playing the Toronto Blue Jays when we were there, so we decided to check it out for both of our first time. We took an Uber from Cambridge, bought the cheapest tickets they had available (about $35 each), walked around the stadium, and sat in our bleacher seats for an inning or two. Although a short visit and not being invested in the game itself, we still enjoyed the spirit and charm all around and didn’t regret buying the tickets. I did, however, regret getting a Fenway Frank. Don’t be fooled by the catchy alliteration! Guilty.