Boston is such a great city, and while one guide can’t possibly include all of the best restaurants or bars or activities, you can definitely fit a little bit of everything in 48 hours.
Living in Chicago, I love exploring different neighborhoods in the summer, so I wanted to do the same in Boston. This guide will take you to Back Bay, Cambridge, Seaport, the North End, Downtown and Fenway and treat you to Italian, Mexican, Asian Fusion, Seafood and Farm-to-Table.
So book that flight to Boston, and use this as a guide to enjoy the best food, drinks and activities the city has to offer. (For a more in-depth look at some of the restaurants and bars on this list, check out The Boston Guide post.)
day one
Check into your hotel and make your way to Yvonne’s for a late afternoon, early evening drink before the bar gets packed. You’ll want to test out one of their inventive cocktails and grab a spot on one of the couches to regroup after a morning of travel.
After a drink or two at Yvonne’s, take a quick stroll past the park on your way to dinner. The city of Boston is extremely walkable, so take the time to gain awareness of your surroundings as you head to the North End. You’ll also be grateful for the exercise as you sit down for Boston’s best pasta and pizza.
There are a plethora of choices for Italian in the North End, like Panza, Al Dente and Bricco. I’d recommend making a reservation in advance and asking for a table by the window to do a little people watching.
After dinner, head over to Mike’s Pastry, a local favorite for cannoli’s and other pastries. Grab it to go as you walk back towards your hotel (or grab a ride if you’ve over-indulged).
day two
Depending on your hotel’s location, head to Thinking Cup or Caffe Nero for your morning coffee and breakfast. You’ll need the extra caffeine for a full day as you take your coffee to go and head to one of Boston’s most historic neighborhoods.
On the northern side of Boston Common lies Beacon Hill, one of the most well-known, sought-after neighborhoods in the city. Once you’ve walked down a few of the quaint streets and alleyways, you’ll understand why. Be sure to check out Acorn Street and grab a picture—it’s known as one of the most photographed streets in the city.
After you’ve gotten your Beacon Hill fix, hop in a cab to the Museum of Fine Arts ($25 admission) prior to the museum opening at 10. You can spend the whole morning there (with 450,000 works of art, it’s one of the largest collections), or you can head to the Isabella Stewart Gardner Museum ($15 admission), which houses a world-class art collection, collected by Isabella and her husband in the late 1800s to early 1900s. Not a museum fan? Head to Fenway Park for a tour.
You’ll have worked up quite an appetite after hours in the museum, so head to the South End for your lunch reservation (you’ll need one!) at Myers + Chang. The brunch menu, including a Fried Egg Banh Mi and Nasi Goreng with Pork and Pineapple, is not to be missed and you’ll want to try 2-3 plates per person.
After lunch, hop in a cab and head to Cambridge for a self-guided or Harvard student-guided tour of the campus. Check out the boutiques and shops lining the downtown street and enjoy a quick daydream of what life would be like as a student there.
Once you’ve snapped 100 photos of the beautiful buildings, ivy and trees around campus, walk on over to Alden & Harlow for your dinner reservation (you’ll need one here too!) If you’re interested in trying the “Secret Burger” you’ll want an earlier reservation and request a seat at the marble chef’s table to get a front row view of the action in the kitchen as they whip up inventive dishes like Chicken Fried Rabbit. Don’t miss the Pickled Verrill Farm Corn Pancakes as a savory dish that will feel like dessert.
If the dessert options at Alden & Harlow aren’t your speed, head over to Tatte Bakery for an after-dinner dessert or a late-night snack for back at the hotel. I’d also recommend snagging a pastry or two for Sunday breakfast.
day three
After a day and a half of indulgent meals, you might be craving some form of heavy exercise. Boston has a ton of specialty boutique gyms that offer drop-in rates, like Barry’s Bootcamp (they just opened a new, gorgeous studio in Back Bay), Equinox, Exhale and CorePower Yoga. If you’ve chosen Barry’s, be sure to take advantage of the Oribe products in the locker room and hit up the fuel bar for a smoothie. I recommend the Dirty Chai-Town, a banana, peanut butter, chai spice and almond milk smoothie that makes the 60-minute high-intensity workout worth it.
Post-workout, head to the waterfront to check out the boats and walk through Faneuil Hall and Quincy Market. If it’s nice out, grab a seat on the patio at Legal Sea Foods and get your seafood fix with New England Clam Chowder or a Lobster Roll.
On your way back south, stop by the Boston Seasons patio, a pop-up experience with beautiful views of downtown and beer served out of an airstream.
After downing a cold beer, walk through downtown as you head towards Boston Common and Boston Gardens, taking a peek at the swan boats and snapping a few photos of the statues throughout.
Once you’ve made it to Newbury Street, the window-shopping (or actual shopping, your choice!) begins. The eight-block stretch is home to boutiques of all price ranges and the walk-up house-style shops continue the Boston charm you’ve enjoyed all weekend.
Pop into the Boston Public Library for a quick look at Bates Hall, one of the most well-known rooms in the building. The library also offers art and architecture tours should you be interested.
If you’ve got time before your trip home, grab an early dinner at Citrus & Salt—I promise you won’t regret it. The bright and airy restaurant, themed as “MexiCali Coastal” is the perfect spot to wind down after a long weekend and you can’t forget to order the Blue Agave Cornmeal Biscuits that come with smoked canela butter and poblano-pepperjack spreads.
Boston seems nice I think I’d like it there