Having visited Boston five times in the past twelve months, I’m finally ready to give some of my recommendations on Where to Eat, Play and Sleep in this amazing, historic and iconic, New England destination.
Honestly, it’s hard to know where to begin. After visiting Boston five times in the past twelve months, with an average trip lasting about ten days, I’ve barely scratched the surface. There are so many choices when it comes to where to eat, play and lay your head down to sleep in Boston! The city of Boston has an amazing food scene, incredible history and every type of hotel you can imagine. There is something for everyone, regardless of budget, interest and diet. Boston is definitely a vacation destination to put on your bucket list (especially if you’re a history buff).
If you know me, living in New England is a dream of mine, however, I’m not sure if that fantasy will ever materialize for this west coast girl. Regardless, I’m currently taking full advantage of the fact that my son is attending college in Boston and am happily eating my way through the city when I visit. There is so much history and things to do in Boston, I can only hope to see most of them in my lifetime.
When it comes to tackling Boston, especially if you are only there a week or a few days, learn to use the subway right away. Do not rent a car, it’s one of the hardest cities to drive (and park) in. Uber and Lyft are also readily available. However, assuming the weather is decent, I prepare to walk the city. It’s the best way to see Boston and get a feel for where you are. I average walking about twelve miles a day in Boston. Not only does this help counteract the ridiculous amount of food I consume, but I get to pop in and out of places I might have never stopped in before. Be ready for freezing temps, humidity, rain, snow and wind…pretty much anything depending on the time of year.
Before heading to Boston I highly suggest familiarizing yourself with the neighborhoods – there are twenty-three in all! And each neighborhood is so unique.
Boston Neighborhoods I Love
- Back Bay – this is where my son lives and it’s honestly one of the most picturesque parts of the city. So many of the homes and building facades found here could be sketched right on to a greeting card (and they probably are), it’s that charming.
- Beacon Hill – one foot in Beacon Hill and you feel like you’ve been transported back in time, but in a very good way. Cobblestone streets, incredible cheese shops and gorgeous homes make up this area. You feel like you’ve stepped into a Norman Rockwell painting.
- Chinatown- the Leather District – a fun and bustling hub of Chinese culture and you don’t want to miss Dim Sum (try Hei La Moon and China Pearl) in this area…it’s awesome.
- Downtown – lots of history in the downtown area, especially The Freedom Trail. Make sure to hit up the Downtown Crossing area for shopping and you’ll find the theater district in this area too, which is so pretty lit up at night.
- Fenway-Kenmore – this is where we usually stay! I’m a baseball fanatic and the Red Sox have always been a favorite team. There is nothing more unusual and amazing than to have a baseball stadium right smack in the middle of a big city and in this neighborhood. This area buzzes with excitement on game days and it’s a great central location in the city. The streets are lined with restaurants and bars, making it festive year round.
- North End – This is the hub for Italian-American culture and definitely one of the more visited neighborhoods in Boston. It feels like Europe. The air smells like Italian food and the streets are lined with bakeries where you can pick up your favorite cannoli or any Italian pastry you can imagine. Paul Revere’s House is also located here. It’s always busy and buzzing with people.
- South Boston – this area has exploded lately with the Seaport District. So much great food, museums and creative energy in this area. You could easily spend the whole day here enjoying time on the water.
What Food Is Boston Known For
- Lobster Rolls
- Baked Beans
- Boston Cream Pie
- Fenway Park Frank
- Clam Chowder
Where To Eat In Boston ~ Pricey/Fancy
- Fleming’s Prime Steakhouse – you’re here so you might as well get the Prime Tomahawk Steak (it’s amazing), the Caesar salad, Lobster Mac n’ Cheese and the warm apple turnover for dessert. You will be stuffed, but it will have been worth it.
- Abe and Louie’s – a fancy steakhouse (think white dinner jackets worn by the servers), but you must try the Maine Lobster Casserole if you’re not up for meat. All the classic sides are done extremely well and the warm rolls on arrival are perfection. Top notch service too.
- Grill 23 – so fancy! Get the 100 Day Aged Prime Ribeye (18 oz, charred salty crust, rich flavor…so tender you can cut it with a fork), it was amazing. A side of Grill 23 tots with truffle oil are also a must and their cocktail game is strong!
- Boston Chops South End – Very hip steakhouse in a former bank, with this gorgeous Amish bar built right in the middle. If you want steak, the prime bone-in-ribeye is the way to go (butter, garlic, and spices (like rosemary) and made in a cast-iron skillet ~ it’s meat decadence), but you also need to try the Double Cut Pork Chop with Carolina Dry Rub…wowzer. Make sure your table gets an order of the mile-high onion rings and the Poutine Style Twice Baked “Loaded” Potato. It’s all a requirement.
- High Tea at the Boston Public Library – the perfect way to spend an afternoon. The Boston Public Library is gorgeous and tea room is a great place to enjoy it. Fancy tea service and lots of loose leaf teas to choose from ~ our favorite tea is the The Cozy Copley.
- Craigie On Main – This place. It’s crazy good. If you can, order one of the impossible to get burgers. And what I mean by “impossible” is that they only make eighteen of them per night. And are only available in the bar. (get there at 5 PM if you want one.) The burger is its own half-pound masterpiece of flavor made with choice cuts of brisket and short rib. Bone marrow and suet are involved. It’s unforgettable.
Where To Eat In Boston ~ More Casual But Delicious Meals
- Citrus and Salt – I never anticipated finding my ABSOLUTE favorite Mexican food in Boston. It’s more like creative-coastal Mexican, with a Miami vibe. I love going for dinner, but I think I love going for brunch even more. In the evening the vibe is more clubby (loud music) etc., but during brunch it’s just lovely and hip and it looks like you’ve stepped into an Instagram filter. Here are some things you cannot miss when visiting…the Grilled Street Corn with Hot Cheeto Crumbs (omg), Guacamole – it’s unreal, the Warm Agave Glazed Blue Cornmeal Biscuits are off the charts, the Chilaquiles Rojo are perfection, the Chicken Waffle Tacos are to die for, the Raspberry Fre is a must, a pitcher of the white sangria is worthy of an award. End the meal with a Dole Whip (with an aged rum shot obviously) and Churro Bites. You will NEVER regret stuffing yourself here. Order an extra helping of the Hot Cheeto Corn to go because you will want seconds for a midnight snack at your hotel.
- Island Creek Oyster Bar – We’ve had so many amazing meals here. Start with a crispy oyster slider and a tray full of raw oysters (they will guide you on what to get). Rosemary’s Lobster Roll is not to be missed and neither is the Banoffee Pie.
- Mr. Bartley’s Burger Cottage – I have to say this is THE BEST BURGER I’ve ever had. Ever. This place is right across the street from Harvard. There might be a line and you’ll have to wait. It’s so worth it! They have a million hilariously named burgers, my fave is “The Viagra”, but the burger is the best because the meat is fantastic. You could eat it plain and it would be the BEST burger. Their secret recipe is just WOW. The restaurant is a fun, quirky, looks like the inside of a dorm room type of place. You must go.
- Tresca – located in The North End (Little Italy) this Italian place hits all the marks. I dare you to order the Veal Chop Parmesan that’s as big as your head. It’s prepared perfectly.
- Sumiao Hunan Kitchen – think upscale Chinese with a super quirky and modern vibe. This super hip bar and restaurant is one of the only places you can find Hunan Cuisine in Boston. They have a fun cocktail menu and we LOVED the Yellow River Beef with a side of Chinese Broccoli. This place can’t be missed.
- Eventide Oyster Bar Fenway – start with oysters, but finish it off with their Brown Butter Lobster Roll…it’s unmatched and crazy insane good.
- Limoncello – you feel like you’ve walked into an Italian family’s home for dinner. It’s lively, they talk to you loudly and it’s full of people all of the time. When you call to make a reservation, they will stop the conversation to yell at someone in Italian. It all felt normal. The bread, olive oil and olives on the table are welcoming. The Lobster Risotto is mind-blowing as well as the meatballs. And not to be understated is the Rosette Al Montasio Ed Olio Di Tartufo ~ you must order it. This place is most definitely a Boston treasure.
- Eataly – It’s epic. While there are many restaurants in Eataly to enjoy, we happen to love La Pizza & La Pasta. Their truffle fondue pizza is beyond delicious and I have not found a homemade pasta dish of theirs I did not like. This restaurant has some great Italian beers too. Skip dessert and head over to the walk-up gelato bar (in Eataly) for a double scoop.
- Boston Burger Company – Oh my gosh this place. The burgers and all their toppings are pretty wild, in a good way. Two of my favorite burgers are the VERMONSTER and THE KING. Taste them for yourself. However, make sure you save room for dessert and order one of their insane Freak Frappes…they will blow your mind…and your diet.
- Lucca – Another gem in the North End. Make sure to start your meal with the rosemary bread and meatballs to share. You won’t be sorry.
- Flatbread Co – This is a bit out of Boston proper, but easy enough to take an Uber. I am obsessed with Flatbread Co (a chain found mostly in New England). However, this particular Flatbread happens to have a candlepin bowling alley (much smaller bowling balls and thinner pins ~it’s both easier and harder than 10-pin) right inside the restaurant. How cool is that? Perfect place to take kids and play some games. Make a lane reservation!
- Bleacher Bar – Calling all baseball fanatics, this is such a cool and unique place. This restaurant/bar is literally located beneath the Fenway Park’s bleachers and has a view of centerfield. Order the pork belly Cuban sandwich and a bowl of chicken noodle soup…both are so good.
- Mamaleh’s Delicatessen – (open breakfast to late lunch) you will sit and agonize over the menu (it all sounds so good), so if I had to steer you towards something…splurge for the $42 smorgasbord of schmaltz on rye, chopped liver, potato kinish, meat knish, deli pickles and kreplach. It’s like a Jewish pupu platter. You will not regret your decision. Their dill cream cheese is also a game changer. Oy.
- Row 34 – we absolutely LOVED the Row 34 oysters. This is a hip restaurant in the Seaport district with great atmosphere. It’s very busy, but the acoustics are great so you can have a conversation. Make a reservation!
Where to Eat In Boston ~ Extremely Casual/Grab and Go
- Sal’s Pizza – You walk in and choose a slice and they pop it in the oven. Seriously the best crust ever! They also have an epic 19-inch, three-pound pizza if you’re really hungry.
- Tasty Burger – This is a solid burger joint in Boston (several locations). Always good and love their French fries. Perfect for grab and go.
- U Burger– Gourmet burgers at a quick and casual place (several locations in Boston). My fave is the Boom Burger and the handcut onion rings. You’ll be sad if you don’t get a frappe too.
- Noodle Street – Delicious. Generous portions. Inexpensive. Super casual.
- Bricco Salumeria – Literally tucked into an ally on Hanover Street in the North End, you’ll miss it if you’re not looking closely. You’ll feel like you’ve stepped into Italy upon entering. The best deli sandwiches on their homemade bread. My fave is the Panino Lady, but their meatball sandwich is pretty epic.
- Galleria Umberto – head to the North End for the MOST delicious slice of cheese pizza! And it’s only a $1.55 per slice…cash only. Here’s the thing, it’s Sicilian-style pizza (they do have other Italian eats) that is super cheesy, thick crust with just the right amount of chew. (If you are tired of thin crust pizza, this is your place.) Go early because they close when all the pizza pies are sold.
- Wahlburger – casual place and delicious gourmet burgers. Lots of locations, but we head to the one located in the Back Bay. The place is PACKED when there is a game at Fenway Park. And yes, Mark “Marky Mark” Wahlburg is a partner with his chef brother, Paul Wahlburg in this restaurant chain. It’s really hard to not sing the “Good Vibrations” tune when we’re eating there. The food is great for a quick bite. And they serve alcohol.
Where to Eat In Boston ~ Doughnuts/Bakeries
- Blackbird Doughnuts – Thank goodness my absolute favorite artisinal doughnut shop is located 3000 miles away from my home. First thing I do when I wake up in Boston is head over to their shop. Honestly, Blackbird makes the best yeast doughnuts, with the perfect chew. Their menu is seasonal with all types of fun flavors like tropical banana, strawberry honey or orange cranberry, just to name a few. A must try is their everything bagel doughnut…my favorite. Amazing cold brew coffee too. And the doughnuts are packed in pizza boxes, which somehow makes them even more irresistible. And don’t forget to order their doughnut cake for your next birthday celebration.
- Tatte Bakery – this bakery is culinary artistry at its finest. Not only does Tatte have the most welcoming and inviting atmosphere (many locations too), the pastry and breads are so beautiful. I never leave without a boxful of deliciousness. It’s impossible to choose just one or two items. And don’t forget your cardamom and honey latte.
- Flour Bakery & Cafe – warm baguettes from the steaming oven, buttery, raisin-filled brioche with sweet icing, silky-smooth chocolate cream pie, lemon curd cakes filled with raspberry preserves and the MOST amazing sticky buns you will ever find. The sticky buns are made with traditional yeasted French brioche dough and finished with cinnamon sugar/toasted pecans in a pan filled with brown sugar glaze. They are crazy good. And sell out so get there early. Make sure you have them warm it up for you.
- Mike’s Pastry – Famous, famous Italian bakery in the North End. There is always a line out the door, but it moves fast. Skip buying your cannoli here (you are going to get them across the street at Modern Bakery) and grab a dozen black and white cookies for your hotel room or the plane ride home. HOWEVER, if there are a few of you, make sure to grab la sfogliatella, otherwise known as “the lobster tail”. This gorgeous piece of pastry art is a giant flaky shell (on the outside) with a voluminous amount of white fresh cream filling on the inside. It’s light and rich at the same time. It’s not to be missed. Cash only.
- Modern Bakery – This is where you’re going to get your cannoli…their ricotta filling is just better. And it’s right across the street from Mike’s. In fact, go to both places and have your own blind-tasting of cannoli just for fun. Cash only.
- Sofra Bakery – If you can only get one thing, make it the Egg Samdwich! It’s heavy on the exotic ~ spiced feta butter, halloumi cheese, and bacon on house-made brioche. It will be a good morning after indulging in this.
Not only does Boston have some amazing restaurants with exceptional eats, there are a plethora of sporting events (with all of their championship teams) and points of interest around every turn. Your biggest decisions when visiting Boston will be deciding what to experience first. The possibilities are endless.
Where to Play (Have Fun) In Boston
- The Freedom Trail – the Freedom Trail is actually paved into the sidewalks. It’s a line carved into the sidewalks that connects sixteen locations that are significant in American history. You can walk it yourself or you can hire a guide dressed in historical clothing who will take you around and explain it all to you. Either way it’s pretty fascinating, but the guides are super fun and stay in character.
- Boston Public Library – I mentioned having high tea here, but you’ll also want to take an architectural tour. The library is a stunning mishmosh of 19th century to modern era architecture, with a robust art collection. Make sure to peek into gorgeous Bates Hall while you’re here.
- Cambridge Center Roof Garden – most people don’t even know this exists. This clandestine garden sits on top of a multi-story parking garage in Cambridge’s Kendall Square (go to the parking garage at 4 Cambridge Center and follow the signs to the green oasis that has a beautiful view of the city.) Bring your lunch on a sunny day. There’s even a ping-pong table.
- Mapparium – at the Mary Baker Eddy Library – this is a three-story stained glass globe and you get to stand inside it. Your geography skills will be tested as you try to identify countries, some that no longer exist. It’s honestly very cool.
- Harvard Natural History Museum – this was one of our favorite museums. The glass flower collections were just wow. Great mammal hall…again wow. The birds, bees, arthropods…all just wow. So worth a visit. Great for the whole family. You will be impressed.
- Boston Public Garden – I’ve visited the garden in the fall, summer and spring…all were beautiful, but spring was especially extraordinary. The tulips and all the flowers blooming. The garden is peaceful, whimsical and full of history and located right in the middle of the city. Make sure to find the famous duckling statues.
- Swan Boat Ride – also found in the public garden and available for rides at certain times of the year. These swan boats date back to the 1870’s and are pretty magical.
- Warren Anatomical Museum – there will be those of you who just want to visit the Museum of Fine Arts and that’s fine, but if you want to see something weirdly different, this is your place. Most come to this museum to see the skull of Phineas Gage, a mysterious medical miracle who survived being impaled in the head by an iron rod, and whose personality completely changed after it happened. If that’s not macabre enough, make sure to see their collection of impressive kidney stones.
- Boston Tea Party Reenactment – this is what started the American Revolution and they love to reenact the tea party in the Boston Harbor. You even get to dump the tea into the sea. A must.
- Most Photographed Street In the USA – Acorn Street in the Beacon Hill neighborhood. Make sure to take a peek and bring your camera. It’s a beauty.
- Observation Deck at Independence Wharf – kind of a semi-hidden gem that not many know about (470 Atlantic Ave in Boston). Great views of the harbor and surrounding high rises. Bring binoculars and a photo ID (you need an ID to get up there). You’ll have views of Harbor Island and can watch the planes coming in and out of Logan Airport. There are a few benches too.
- Fall Foilage – one of the most beautiful cities in the fall, especially when framed with fiery orange leaves.
- Arnold Arboretum at Harvard University – basically a tree sanctuary (not on the main Harvard campus, but close) with beautiful nature walks and perfect for a picnic. However, if you are in town for Mother’s Day they celebrate “Lilac Sunday” with the most impressive collections of lilacs in all of North America. It’s a must see.
- Fenway Park – if you’re in town during baseball season, grab tickets and see a game at the oldest baseball park in America. Fenway Park is small so almost all seats are good. If you can’t make a game, make sure to take the tour of the park, it’s a great one.
- Celtics Game– if the Celtics are playing, head to TD Garden and watch. It’s so easy to get there and back on the subway from where ever you’re staying. Boston is pretty much the center of the sports universe, so when in Rome. And Boston fans can be very entertaining.
- Newberry Street – a completely enchanting eight block street in the Back Bay. Lots of boutique shops, dining, art galleries. The perfect place to stroll on a warm evening.
- Shop on Charles Street – if you are looking for a less crowded, but iconic Boston shopping experience, this is your street. Antique shops, gourmet grocers and little indie shops are what you will find here, with less tourists. However, you are going to feel every bit of real estate envy in this area. A turn down any side street and you are transported into a world of street lamps, carriage houses and cobblestone roads. It’s magical.
- Walk the Commonwealth Avenue Mall – Commonwealth Avenue is a major street in the Back Bay of Boston, but at one point becomes a tree-lined parkway as you head towards the Public Garden. The homes are gorgeous along either side and it’s one of the most beautiful and peaceful walks in the city.
- John F. Kennedy Presidential Library – right on the water. We really enjoyed this. So much history and I loved seeing so many of Jackie’s outfits on display.
- The Isabella Stewart Gardner Museum – a beautiful art museum (love the garden). Fun fact…the entrance fees to the museum are discounted if you wear Red Sox memorabilia and free if your name is Isabella.
- Architecture Boat Tour – perfect for the architecture buff. Panoramic views of both historic and contemporary architecture from the Charles River Basin, the Charles River Locks, and Boston Harbor. If the weather is nice, you’ll want to do this.
- Charles River Esplanade Walk – one of Boston’s most beloved parks, located right on the Charles River. This is where I take my morning walks when I’m in the city. Located in the Back Bay.
- The Sport’s Museum – located right inside TD Garden on level five and six (where the Celtics and Bruins play). All kinds of historical Boston sports memorabilia. The museum tour will take you to TD Garden arena’s top floor, where you get to pay homage to all the arena’s championship banners. There are lots. During the off-season, you get to check out the visiting team’s locker room.
- The New England Holocaust Memorial – This is not a museum or a “fun” activity, but a memorial. I highly recommend reading about the memorial first and all the symbolism found in the artistry. It’s very well thought out. Located downtown on High Street, try visiting in the evening as it’s quite impressive with all the lights, but very, very sobering.
The choices are endless for a large city like Boston when it comes to where to stay and the type of accommodations you prefer. Boston hotels are not inexpensive by any means (unless it’s winter). I know lots of people, with bigger families, choose to go the Airbnb route and have had decent luck in Boston. With all the places we’ve stayed, the Back Bay neighborhood of Boston is our favorite. It’s centrally located and in one of the most beautiful parts of the city. We can walk almost anywhere from the Back Bay and have always felt safe.
Staying out of city limits (15-20 minutes away) to get a good deal on accommodations is a possibility. However, if you are in Boston to experience the city, don’t do this! You want to be able to walk outside your hotel and smell the food, see the sites and get to know the streets. There is nothing like this city so you might as well enjoy it.
Where to Sleep (at a Hotel) in Boston
- Marriott Residence Inn Back Bay/Fenway – we love, love staying here because the location is perfect. We are steps away from Fenway Park, Kenmore Square, Newberry Street, the Charles River…it’s all so close. If you have a student at Northeastern, Boston University, Harvard, Tufts, MIT, Berklee etc you are close. There are so many restaurants and bars right out the hotel door. The rooms are bigger than regular Boston hotels and you have a full kitchen. (And they are NICE rooms.) Breakfast is provided, which I never eat, because there is just too much great food in Boston. They have a lovely rooftop patio with bar service in the evening. Perfect for a family, but it’s not cheap.
- Intercontinental Boston – if you want to be fancy, this is it. It’s a luxury waterfront hotel with incredible views. It’s close to the North End, the aquarium, Faneuil Hall marketplace and the city’s business district. The rooms are lovely and have huge bathrooms. I highly recommend splurging on the club level rooms, mostly because their club level VIP InterContinental Lounge is like whoa. The food they have going at breakfast and in the afternoon is pretty sweet. However, don’t overeat because you will miss all the amazing Boston food.
- Hotel Eliot – This hotel is a small, boutique luxury property in the Back Bay. It’s lovely! It has an amazing sashimi bar too. Think timeless elegance with modern comforts. Great location. You will love this place.
- Hotel Commonwealth – also in the Back Bay, a very nice luxury hotel with incredible subway access (right across from Kenmore Station). This place is gorgeous and feels very urban and hip throughout.
- Encore Boston Harbor – this hotel opens this month. Every day I get an email from Wynn Hotels trying to lure me to stay at their newest luxury palace casino. If it’s anything like the Wynn and Encore properties in Las Vegas, you will be just fine here.
My hope is to continually update this guide as I visit more and more of Boston. There is just so much to see and eat!!
Please feel free to add your Boston suggestions in the comments, I would love to know all your favorites!
Also let me know if you want to know where any of the above pictures were taken.
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