Summer is in the air, ushering in high time for al fresco meals, rooftop bars, and summer Fridays. There’s no time to take advantage of a three-day weekend like the present, and when it comes to a quick getaway, we at The Root have our sights set on New England’s de-facto capital, a hub of classic architecture, riverfront revelry, and Black history: Boston.
Whether you’re taking the kids on an educational jaunt or enjoying a reunion with friends, we’ve crafted a 72-hour itinerary just for Root readers.
DAY 1
10:30 AM: Caffeinate in the stacks
Set the tone for an academically excellent trip at the charming Beacon Hill Books & Café. Admire the well-preserved Federalist architecture as you peruse their diverse catalog of new releases and classics. The café offers the full suite of caffeinated drinks along with light bites, the perfect fuel as you curl up in one of their plush chairs and leaf through the first five pages of something that catches your eye.
Noon: Get a lesson in Boston’s Black history
Boston’s Beacon Hill neighborhood isn’t just a perfectly preserved portrait of colonial architecture and cobblestone street charm. Before the Civil War, it was home to the highest concentration of African-Americans in the US. This makes it the perfect place for Boston’s Museum of African American History. In this inspiring space, exhibitions dive deep into African-American life in the 18th and 19th centuries. Opening in early June, their latest showcase The Emancipation Proclamation: A Pragmatic Compromise explores the facts and context around the Union’s motion to free slaves just prior to the Civil War, which changed the course of history.
2 PM: Take a walk through time
Beginning from the museum, the Black Heritage Trail covers 1.6 miles of Boston’s North Slope neighborhood, approximately a 90-minute tour. Book your slot online for a park ranger to guide you through the area’s significant homes and community spaces of abolitionists and educators including the 54th Regiment Memorial (commemorating the first Black regiment of the Civil War), the Abiel Smith School, and the African American Meeting House.
5 PM: Enjoy a decadent meal
Pop over to the South End for a homemade plate of pasta at one of the city’s lauded Black-owned dining establishments. Mida boasts a minimalist luxe ambiance and a menu of creative, italian-inspired dishes, including glazed duck wings and rock shrimp carbonara pasta. Say hi to chef/owner Douglass Williams, who was named one of the Best New Chefs in America by Food & Wine in 2020.
8 PM: Hit up a jazz cabaret
Your first 24 hours in the Bean wouldn’t be complete without a little nightlife, and Wally’s Café will not disappoint. Every Friday and Saturday night, this jazz club, established in 1947, hosts their virtuosic house band to jam out standards and new classics. Set your party up with a couple martinis in this intimate, exposed-brick space, and consider your night made.
DAY 2
11 AM: Brunch it out
Brunch just hits different at one of the city’s most talked-about Black-run eateries Comfort Kitchen. Dinner reservations at this James Beard-nominated establishment in Dorchester are booked out months, so your luck may be better earlier in the day, when dishes like tandoori chicken sandwiches, nepalese dumplings, and momos parade out of the kitchen to leisurely locals. Enjoy the early summer weather by snagging a seat on their charming patio.
1 PM: Stop and smell the roses
Walk off that decadent first meal of the day through the garden of your dreams. Located in Roxbury, the Isabella Stewart Gardner Museum features a vast collection of artifacts highlighting the decorative arts of Europe, Asia, and the Americas. But the crown jewel of the space is the massive central courtyard. The flowers on display rotate seasonally, so every time you come back you’ll see a different spread of blooms. Don’t miss out on their latest exhibition, opening June 13th, Portraits from Boston With Love, featuring a spectrum of portraits from Boston, New York, and Dallas photographers reflecting the varied LGBTQIA+ experience.
3 PM: Elevate your vacay style
Naturally, shopping is next on the list of to-dos. Hit up one of South End’s chicest Black-owned boutiques House of Culture. This atelier was founded by stylist Patrick Petty, who discovered his love for tailoring observing his preacher father’s style as a youngster. Their selection boasts fits for an array of occasions, from bold-printed sportswear to shimmery cocktail dresses. Be your most extra self and pick up something that will make you stand out for a night on the town.
6 PM: Sail into the sunset
A trip to Boston wouldn’t be complete without taking in its harbor vibes. For an extra special experience, book a golden hour jaunt on the Classic Harbor Line. Sip a gratis glass of Champagne as you pass such maritime landmarks as the U.S.S. Constitution, Fort Independence, Marriott Custom House Tower, U.S.S Cassin Young, You’re on a boat, and you’ve officially arrived.
8:30 PM: Twist and shout
Saturday is the perfect evening to indulge in a bougie night out, and we’ve got the place. The Black-owned Grace by Nia is a contemporary twist on the supper clubs of the 1930s and ‘40s, featuring a playful menu of upscale soul food like chicken and waffles, chargrilled oysters, and catfish bites alongside a full bar pouring seasonal cocktails on draft like the Tropical Mule with vodka, papaya juice, and ginger beer. Live music — jazz, soul, and R&B—is the centerpiece of this experience, with different acts every night.
DAY 3
9:30 AM: Make a self-care pitstop
Boston’s surrounding hamlets contain an array of charming eateries and shops that you don’t want to sleep on. First, stock up on self-care products at the Black-owned emporium ANNIKAPURE in Dedham. Discover skincare, cosmetics, fragrances, and home decor all made with natural ingredients alchemized personally by the owner Annika Cox. It’s the perfect place to grab a souvenir for your bestie back home or as an indulgent treat for yourself.
1 PM: Order up a pizza pie
Before heading back into town, pop over to Allston to hit up Rock City Pizzeria, a Black-owned pie joint with plenty of local flavor. For his tasty menu of casual eats, Haitian-born proprietor Joseph Charles’s enterprise was recognized as one of four US businesses recognized by the Champion Black Business initiative, and awarded a $25,000 grant courtesy of with a 25K grant courtesy of ESPN, Andscape, and Shark Tank. Tomato pie is the star of this menu, but don’t sleep on the wraps, salads, and calzones, too.
3 PM: Hit the books
Burn off your lunch back in Boston by strolling the stacks at Frugal Bookstore, a Black-owned indie bookstore in Roxbury. Then take one of your new reads to Nubian Square and admire the vibrant murals celebrating the creativity and resilience of the city’s Black community.
5 PM: Get inspired by public art
Unveiled in Boston Common in 2023, the Embrace Boston Monument is one of the city’s most striking pieces of public art. Designed by artist Hank Willis Thomas, this sculptural tribute to Martin Luther King Jr. and Coretta Scott King creates a canopy out of the intertwined arms of the two civil rights leaders. This allows viewers to literally walk into their embrace. It’s a moving tribute to the enduring impact of the Civil Rights movement.
7 PM: Take in the view
As the sun sets on your Boston trip, it only makes sense to watch it from the greatest observation deck in the city. Head over to the Back Bay to View Boston, a rooftop vista located on the 52nd floor of the Prudential tower. Ascending to the building’s summit, you’ll enjoy creative animations enhancing the natural views of the city. At the top, take in 360-degree panoramas of the pink sky (with a cocktail for maximum relaxation).
Rediscover this diverse harbor town and book a summer trip to Boston today!
This post is a sponsored collaboration between Meet Boston and G/O Media Studios.