Boston is known for a lot of things: its rich history, its educational institutions, its passionate sports fans, its colorful autumns (and brutal winters), its culture, and its pride. While Boston may only be a short train journey away from the bright lights of New York City, it is a world away in terms of its pace of life. This charming New England city is one of the USA’s top city break destinations.
WHERE TO STAY
If you want to feel like an absolute rock star while you’re in Boston then book yourself in at the Four Seasons. If you’ve just come from New York, you’ll notice the rooms are about 487 times the size of your last hotel (you’ll actually be able to open your suitcase the whole way!), plus it’s in a prime location so you’ll be able to walk your way around the city. Also, book a stay at The Envoy Hotel right in the heart of Boston. Drop your suitcase in your room, then proceed directly to the rooftop bar for a sunset cocktail and a taste of the good life. You’ll be close to several popular local attractions.
One of my go-to places in Boston, flour bakery boasts a great selection of scrumptious pastries which makes it a perfect choice for breakfast. Who wouldn’t like a warm banana bread, a ham and cheese croissant, or brown butter cinnamon rolls to start the day? Besides pastries, they offer a variety of sandwiches and grain bowls. Flour offers consistently delicious, fresh, and affordable meals.
From flour bakery start walking towards the North End (Little Italy). Cross the Seaport Boulevard Bridge and stroll along Harborwalk which is public walkway that stretches 43 miles along Boston’s shoreline. Walking from flour bakery to the North End will take no more than half an hour. Make sure to stop at one of the wharves to get beautiful views of the harbor.
Visit the South End for even more Insta-worthy townhouses lining cobblestone streets. But our all-time favorite activity in Boston is walking the Freedom Trail, where you’ll learn fun facts about the Founding Fathers of our country that’ll come in handy at dinner parties.
Boston Public Market is located a few minutes-walk away from the North End and is open seven days a week. This indoor year-round marketplace offers fresh local foods produced in Massachusetts and New England. On Fridays and Saturdays from dusk to dawn, you can also visit historic Haymarket located nearby, on Blackstone, Hanover, and North Streets. Merchants gathered at the location of current Haymarket from around 1830-s. The produce is usually several times cheaper than in supermarkets, especially if you come by the end of the day.
One simply cannot spend 48 hours in Boston and not visit Brattle Book Shop, one of my favorite places in the city. Housed in a three-story building, Brattle is one of the largest used book shops in the country with 250 000 books in stock. Two floors feature general used books, while the third floor is dedicated to antiquarian books and first editions. My favorite space in Brattle, though, is the open lot outside with books for sale. Located in between two red brick walls, the lot houses carts with books that cost as low as one dollar.
If you’re staying at the Four Seasons you’ll probably just want to soak up all the goodness for a little while. Have a little rest in the most comfortable bed you’ll ever lay on, and check out the ah-mazing pool (don’t miss the sauna) and take in the views of the Boston Public Garden.
Once you’re feeling well and truly refreshed, venture out to the beautiful Boston Public Gardens and have a little walk around. Once you’ve got your greenery fix, check out Newbury Street for some seriously good shopping, or go the other way into the Boston Common—another park that makes up part of Boston’s famous Emerald necklace—a ‘chain’ of parks that resembles a necklace hanging from the Boston Peninsula.
****If you are a fan of the TV-show Cheers, the famous Cheers bar is located just outside of Boston Public Garden. Stop there for a beer on the way to Beacon Hill.
North of Boston Public Garden is located one of the most beautiful neighborhoods in Boston – Beacon Hill. With its narrow streets, brick sidewalks, historic homes with intricate iron work, and brass door knobs, Beacon Hill is one of those places where you wander around imagining what your life would be like if you had a couple million dollars laying around.
It’s going to be an awesome dinner tonight, but that’s because you’re about to go and get your sport on, but more about that soon. For now, get yourself a table at Antico Forno and take in all of the authentic Italian vibes.
Everything at Antico Forno is seriously delicious so go hungry and then share as much as you can fit in. If you’re a wine drinker, you’ll want to take a good hard look at the wine list because it is top notch and there are a few knock out reds on the list you’ll definitely want to try.
If you’re lucky enough to be in Boston while the basketball is on, you have to get tickets to a Celtics game. Even if you’re not into sports, I promise you’ll have fun, just take a seat and start cheering! The ice hockey is also pretty great to watch
If you have any energy left in you, it’s time to say goodbye to beer in plastic cups and hello to some of the best cocktails in Boston. Jump in a cab and head to Drink in Fort Point. Drink is a little different than your average cocktail bar in that they have no menus, just bartenders who know their shizz. All you need to do is tell them what you feel like drinking and they’ll making something 18 times better than what you felt like.
Hopefully your head isn’t too sore after last night because there’s lots to see today!
Start your second day in Boston at South End Buttery, a café located in the South End neighborhood of Boston. Their menu features a wide selection of breakfast items from muffins and croissants, to sandwiches and burritos, to oatmeal and yogurt parfaits.
South End Buttery is also one of the filming locations for Academy Award winning movie Spotlight. In the movie, the Boston Globe journalist Sasha Pfeiffer (played by Rachel McAdams) interviews one of the victims in the case she is investigating at South End Buttery.
The neighborhood of South End was designed from scratch by Charles Bulfinch, the architect who also designed Massachusetts State House and the Boston Common. Despite the name, the neighborhood is not located directly to the south of downtown Boston and should not be confused with South Boston (also known as “Southie”).
Head to Harpoon Brewing for lunch. If you’re mad on beer, you should do the public tour which starts at 1pm. This includes about 15 minutes where you can taste as many beers as you can manage, and even if you’re not mad about beer, there are plenty of options you’ll want to try, just ask them about the combo that tastes like apple pie!
Start making your way to Cambridge to soak up all of the college vibes at Harvard University. Cambridge is an easy train ride away and when you step into the streets you’ll feel like you’re in a completely different city. Meet your Harvard Tour guide on the edge of the campus and then let them take control. With a seriously beautiful campus, some pretty fascinating history and a couple of bizarre Harvard traditions to learn about, you’ll most likely finish the tour wishing you were a student again.
Now you hit up all the sites, It’s time for some shopping.When it comes to shopping in Boston, Back Bay’s Newbury Street is the trendiest destination. Rain or shine, its sidewalks are filled with throngs of shoppers from all over the world. Though this stretch may be the most popular, Boston has plenty of other great places to shop.
A few streets away from Newbury, and only 2 miles from the Boxer, Copley Place is a high-end mall with a wide range of designer brands. Whether you’re shopping for clothes, accessories, or jewelry, it has everything from Burberry to Salvatore Ferragamo to Tiffany & Co. For a delicious dinner after a day of shopping, head over to Fogo de Chao, a brazilian BBQ restaurant where a variety of meats are served endlessly until you eat you full and give up.
Or try Downtown Crossing, located at the intersection of Washington, Winter, and Summer streets, is one of Boston’s most bustling shopping districts. Part of its allure is the fact that a stretch of Washington and Winter streets are only accessible to pedestrians, allowing a relaxing shopping experience. The area specializes in department stores like Macy’s, Primark, Marshall’s, and H&M.
Depends on where you go shopping, and if you stay in Cambridge, go to the Little Donkey. This will undoubtedly be one of the best meals you eat on your US trip. The cocktails here are ridic—don’t miss ‘the one in a grapefruit’ which literally comes in a grapefruit—and the wine list is solid.
Little Donkey has an amazing raw bar with some of the best ceviche we’ve ever eaten, so you absolutely need to try some of those. We let our waiter bring out whatever they thought was best and were not disappointed.
If you’re into jazz, you’re going to be in your element tonight. Scullers Jazz Club is probably the most well-known jazz club in Boston—it’s been around for close to 30 years after all—and they host some of the best talent going around. Take a look at the calendar and find a show you like the look of. If they don’t happen to have any shows on while you’re in town, check out Beat Brasseries which is in Harvard Square (these guys also do jazz brunches on the weekends) or the Beehive which has live music every night of the week.
Start your day right at The Friendly Toast in Back Bay for breakfast. The menu is as long as your arm which isn’t surprising considering there is a whole section dedicated to benedicts, another section dedicated to pancakes and plenty of other goodies. The Friendly Toast does a dang good boozy brunch—mimosa flight anyone?—so why not have a drink… you’re on holiday after all.
If you’re not too hungry and just want coffee, stop by The Thinking Cup for a seriously good cup of joe.
Finish up that last mimosa and head to the Skywalk Observatory for the very best view of Boston. Grab a set of headphones and learn about Boston and its history as you check out the views.
If you’ve got some spare time, check out the Museum of Fine Arts—you could honestly spend an entire day walking around this gorgeous museum.