A Boston Art Getaway: Museum, Hotel, and Dining Tips
Contributor Hilary Nangle takes readers on a artful jaunt as she goes museum-hopping in Boston.
Boston’s Isabella Stewart Gardner Museum and its International Contemporary Art Museum (ICA) couldn’t be more different, which makes them a perfect pairing.
More than a decade had passed since I visited the Gardner Museum, and despite long wanting to visit the ICA, I’d never done so. So, when a friend asked me to join her on a Boston getaway and was willing to spend Labor Day museum-hopping, I said yes. Even better: We hit the weather lottery with sunshine and temps in the 70s. That weather encouraged us to explore two other, art-accented Boston icons: the Harbor Walk and the Rose Kennedy Greenway.
What we didn’t realize was that Labor Day, 2025, came early, falling on Sept. 1. That’s the infamous Move-in Day in a city that, when combined with its metro area, is home to somewhere between 30 and 50 institutions of higher learning with 150,000-200,000 resident students. (These numbers depend on how you define higher learning, whether you include neighboring cities and towns, and who’s doing the reporting.)
These students add youthful energy to one of America’s oldest cities, but they were everywhere – exploring the city, hugging friends on the sidewalks, sipping lattes at streetside cafes, visiting museums and historical sights, and clogging streets with all manner of vehicles as they moved their necessities in for the semester. But it didn’t stop us.
Walking the Rose Kennedy Greenway
After rendezvousing at the aptly named Boston Harbor Hotel, sandwiched between the harbor-hugging Harbor Walk and the Greenway, we began our city explorations with a stroll along the Greenway.
This 1.5-mile-long urban park, created when the elevated I-93 highway was relocated underground during Boston’s Big Dig, winds between the North End and Chinatown. It’s a sensual experience: Italian honey bees buzz, gardens burst with color, enticing floral aromas waft on the afternoon breeze, along with snippets of conversation. Along the way, fountains invite cooling off on a hot day: One is the centerpiece of a labyrinth, another mimics a stream with a waterfall, and some feature interactive sculptures.
Exploring the Harbor Walk
We returned via the harbor-hugging Harbor Walk, which ebbs and flows along the waterfront from the Battery Wharf Hotel to South Station and spills over to Seaport. On the stretch between the Aquarium and our hotel, we dawdled, lingering to watch the sky and water change colors as the sun dipped behind buildings, ogle art installations, and watch sailboats, water taxis, and excursion boats zigzag across the waters as gulls shrieked above. By the time we entered the hotel, daylight was ceding to nightfall.
The Institute of Contemporary Art, a Harborside Treat
As delightful as our walk was, we’d come here for an art immersion, and that was our focus on Labor Day. Warm and sunny with a sweet breeze, the day demanded that we continue along the Harborwalk to the International of Contemporary Art. The museum dates from 1936, but this eye-catching building, cantilevered over the harbor’s edge, opened in 2006, when the Seaport was in its infancy.
The ICA was offering free admission that day, so the galleries were hopping. We wandered through, taking in riots of color and mixed-media exhibitions for the 2025 James and Audrey Foster Prize, highlighting the works of Alison Croney Moses, Yorgos Efthymiadis, Damien Hoar de Galvan, and Sneha Shrestha.
I found Icelandic artist Ragnar Kjartansson’s video The Man, depicting blues pianist Pinetop Perkins on an upright piano set in a field, mesmerizing. A glass-walled space overlooking the harbor provided a place to sit and contemplate. But we couldn’t linger; we had tickets for a water taxi transit across the harbor to the ICA’s Watershed in East Boston.
Since the water taxi departed from a wharf adjacent to the ICA, the cruise across the harbor provided excellent views of the museum, with the boat reflected in the glass front, the Seaport; boats to-ing and fro-ing; and on the East Boston end, the docked Lightship Nantucket.
Open-Air Art at The Watershed
Once on land, murals painted on the walls of old warehouses hinted at the area’s revival. The Watershed opened in 2018 in a previously condemned copper pipe facility on the Boston Harbor Shipyard and Marina property.
Open only in summer, the Watershed presents one artist each season. In 2025, two related, thought-provoking installations by Chiharu Shiota exploring migration and home filled the galleries. In Accumulation – Searching for the Destination, vintage suitcases suspended from red ropes dangle from the ceiling. Similarly, Home Less Home uses red and black ropes. But in this walk-through exhibition, it’s ephemera—photographs, letters, passports—hanging from red-and-black ropes in a space that evokes a home, with eclectic pieces of furniture.
Both exhibits speak not only to the overall immigration experience but also to that of the many who settled in East Boston. I found each instilled a sense of solastalgia, the longing for something that is no more.
Art, Gardens, and a Heist at the Isabella Stewart Gardner Museum
From the avant-garde ICA, we time-travelled across Boston, arriving at the Isabella Stewart Gardner Museum around the turn of the 20th century.
Like the ICA, The Gardner is an experience, not simply a museum, and the mystery that adds to that experience is a wonder. Gardner, a Boston socialite, traveled extensively, especially in Italy, with her husband, Jack, and amassed an impressive personal art collection.
When she inherited $1.75 million from her father, she used it to buy more art. She wanted to share her collection with the public. With her husband, she began planning a museum that would also house an apartment for themselves, and their collection expanded to include architectural pieces and statuary they could incorporate into it.
The Back Bay Fens, part of Fredrick Law Olmsted’s Emerald Necklace, caught their eyes as a possible location. Jack died unexpectedly in 1898, but Gardner pursued their dream and purchased the land.
Working with architect Willard Sears, Gardner designed a four-story Venetian Palace with a magnificent, glass-ceilinged central courtyard. In 1902, after moving into her fourth-floor apartment, she began installing her collection in the galleries ringing the courtyard on the first three floors. When she died in 1924, her will stipulated that the arrangement of the artwork remain as she had designed it.
On March 18, 1990, thieves stole 13 pieces of art from the museum. Among those pilfered or cut from their frames were Christ in the Storm on the Sea of Galilee, A Lady and a Gentleman in Black, and Self Portrait, Age 23, all by Rembrandt; Concert, by Vermeer; Flinck’s Landscape with an Obelisk; five works by Degas, and Chez Tortoni by Manet. The vacant frames remain in their original places, a haunting reminder of the unsolved heist. (I recommend watching the four-part Netflix series This is a Robbery for more information.)
In some ways, the Gardner overwhelms visitors. Art fills every space, inside and outdoors. Before exploring the museum’s galleries, I sat on a wall in the Romanesque-style Cloisters surrounding the courtyard, trying to absorb the textures, colors, and artworks filling both. The courtyard’s floral displays change nine times throughout the year, and the flowers change weekly.
The adjacent Spanish Cloister, home to John Singer Sargent’s El Jaleo, opens to the Monk’s Garden, originally Gardner’s private garden, which provides a welcome, quiet reprieve to rest the mind. And we still had 24 rooms to discover, which we did.
In hindsight, we should have allowed the better part of the day to visit the Gardner and started first thing in the morning, before the crowds arrived. We could have toured at a more leisurely pace and rested over lunch on the café’s garden patio.
By the way, if your name is Isabella, admission is free.
Where We Stayed: The Boston Harbor Hotel
Straddling a huge, glass-domed, central arch, the Boston Harbor Hotel lives up to its name with a front seat on Rowe’s Wharf. This member of the Preferred Hotels & Resorts collection delivers everything you’d expect from a five-star property, including handsome, spacious guest rooms and suites; mine had a partial water view, my friend’s had a panoramic one.
Dining options ranged from a small shop with to-go items open from morning to early afternoon to a waterfront restaurant with indoor and outdoor seating. An inviting lounge promised “the city’s most extensive collection of fine scotches.”
Although neither of us brought workout or swimwear, we toured the recently renewed Rowe Wharf Health Club, a fitness facility in the hotel’s lowest level.
It wowed me with its state-of-the-art Matrix, Peloton, and Escape equipment; three private wellness pods (Echelon Reflect featuring more than 2,000 virtual classes, Hyperice Recovery with compression boots, and a multi-purpose pod); Halotherapy, salt, and infrared saunas; Full Swing golf simulator, indoor pool with lap lanes, and a fitness class room with scheduled classes.
Where We Dined and Sipped
Since we hadn’t made advance dining reservations, we winged it and ate early. On the first night, we broke our Greenway/Harbor Walk at State Street Provisions, splitting orders of oysters, Brussels sprouts, and a pizza. Despite no research or preplanning, we were pleased with our shared meal, and bonus points for an outdoor table.
On our full day in the city, we began with the hotel’s buffet breakfast, found lunch at Greco, a Greek takeout with a handful of tables inside and outdoors in the Seaport, and had dinner at Broadside Tavern, an Irish pub close to our hotel; I’d return for the fish and chips alone.
Afterward, we ducked into The Dark Bar, the hotel’s dimly lit lounge that feels more like old Beacon Hill than trendy Seaport. It’s reminiscent of an intimate library reading room, with prints depicting old Boston scenes, dark paneled walls polished to a golden gleam, and red leather couches and chairs grouped around tables. It provided the perfect haven to slip away from crowds, sip drinks, and rehash the day’s adventures.
Disclosure: The author was a guest of Boston Harbor Hotel, ICA, and the Gardner Museum but any opinions experessed in this post are her own.
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