Search
Travel

Art Insider’s Guide to Boston: Where Art, Design, and History Converge

Late summer to early fall is a particularly rich moment to visit—when crisp New England air mingles with world-class contemporary exhibitions, architectural gems, and a new wave of hospitality that defines a quiet, confident luxury

By Scott Drevnig
Rooftop lounge with modern seating, cityscape view, and sunset sky.
Terrace at Raffles Boston. Photo: Courtesy of Raffles Boston

Boston may be synonymous with American history, but these days its cobblestoned streets lead to just as many cutting-edge galleries as colonial landmarks. Late summer into early fall is a particularly rich moment to visit—when crisp New England air mingles with world-class contemporary exhibitions, architectural gems, and a new wave of hospitality that defines a quiet, confident luxury.

Fenway: Four Museums, Countless Perspectives

Begin in Fenway, Boston’s cultural heart, where four art institutions sit within walking distance.

Robotic arm interacting with a wooden panel featuring Indigenous art design in a modern indoor setting.
Nicholas Galanin. Installation view, Aáni yéi xat duwasáakw (I am called Land), (2025). Photo: Mel Taing. Courtesy of the artist and Peter Blum Gallery, New York

Start at the Massachusetts College of Art and Design’s free MassArt Art Museum (MAAM), currently a key venue for the inaugural Boston Public Art Triennial (through October 31). Twenty ambitious works—by emerging and notable talents like Swoon and Nicholas Galanin—spill across public sites from the Fenway neighborhood to the suburbs, transforming the city into an open-air museum. Download the interactive map and let the city itself become your gallery.

Interior courtyard garden with lush greenery, blooming flowers, and classical architecture, featuring sculptures and arches.
Summer Blues display at the Isabella Stewart Gardner Museum. Photo: Troy Wade
Elegant historical room with a decorative wooden table, ornate chairs, paintings on red walls, and a patterned rug.
The Titan Room at the Isabella Stewart Gardner Museum. Photo: Sean Dungan
Historic dining room with green wallpaper, vintage chairs, and framed portraits on the walls.
Dutch Room of the Isabella Stewart Gardner Museum. Photo: Sean Dungan
Interior view of a room with a large framed painting on the wall, ornate architectural details, and blue tiled floor.
Isabella Stewart Gardner Museum. Photo: Courtesy of Isabella Stewart Gardner Museum.

From there, wander to the Isabella Stewart Gardner Museum, the Venetian palazzo of Boston’s most eccentric collector. Renzo Piano’s elegant glass expansion contrasts nicely with the original building. This season, the late Ming Fay’s “Edge of the Garden” (through September 21) fills the courtyard galleries with fantastical fruits, seeds, and shells—an otherworldly meditation on nature’s quiet wonders.

Portrait of a man seated at a table, holding a silver teapot, wearing a white shirt and dark vest.
John Singleton Copley Paul Revere, (1768). Photo: Museum of Fine Arts, Boston. Gift of Joseph W. Revere, William B. Revere and Edward H. R. Revere
A painting depicting a historical scene with George Washington on a white horse, soldiers crossing a river in a snowy landscape.
Thomas Scully, The Passage of the Delaware (After Treatment 1819). Photo: Museum of Fine Arts, Boston. Gift of the Owners of the old Boston Museum

Just blocks away, the Museum of Fine Arts, Boston (MFA) is a temple to both art history and architectural vision, with Foster + Partners’ daylight-filled Art of the Americas Wing. Treasures abound throughout the museum from Monet’s water lilies—Boston holds the largest Monet collection outside France—to Gauguin’s Where Do We Come From? This summer, “Van Gogh: The Roulin Family Portraits” (through September 7) offers an intimate look at the painter’s most personal series. Over lunch at the glass-ceilinged New American Café, admire Dale Chihuly’s towering Lime Green Icicle Tower.

For a more experimental edge, cross the street to the School of the Museum of Fine Arts at Tufts, whose small gallery is well worth a visit.

Modern hotel lobby with artistic ceiling installation, stone reception desk, plush green sofa, and large windows letting in natural light.
City level lobby at Raffles Boston. Photo: Courtesy of Raffles Boston
Contemporary spiral staircase with wooden steps and metal railing, surrounded by indoor plants and large windows with sheer curtains.
Spiral staircase at Raffles Boston. Photo: Courtesy of Raffles Boston
Luxury hotel suite with modern decor, featuring a comfortable seating area, abstract artwork, and a city view through large windows.
Guest suite living room. Photo: Courtesy of Raffles Boston
Stylish rooftop lounge with elegant seating, a well-lit bar, and city skyline views at night.
Blind Duck Speakeasy Photo: Courtesy of Raffles Boston

Stays Steeped in Style

The wave of creativity extends to Boston’s newest hotels. Raffles Boston, the brand’s North American debut, blends materials and patterns reminiscent of the city’s iconic history and architecture. Guest-only spaces include the serene Amrita Lounge, an indoor pool, and a Guerlain Spa. Corner suites feel like private art-filled apartments. Don’t miss drinks at the jewel-box speakeasy Blind Duck. At Amar, a beautiful room accessed via the hotel’s 17th floor sky lobby, expect seafood with Middle Eastern inflection—and sweeping sunset views. (Guests also enjoy exclusive MFA perks, from complimentary tickets to curator-led tours.)

Across the River: Modern Icons in Cambridge

Hop over the Charles to Cambridge’s MIT campus and discover their extraordinary collection of public art. At the List Visual Arts Center, pick up a self-guided art map, then set out to spot more than 50 works by Henry Moore, Sarah Sze, Olafur Eliasson, Alicja Kwade, and Spencer Finch, woven across campus architecture by Saarinen, Gehry, Holl, and Aalto. Don’t miss Sanford Biggers’s newest commission, the inventive Moghadam Building, and SANAA’s music building.

Nearby, the Harvard Art Museums, unified under Renzo Piano’s glass canopy, place Rothko beside Ming-dynasty scrolls. A short walk away, the Carpenter Center for the Visual Arts—Le Corbusier’s only North American building—reopens early this fall after restoration.

Skyline of Boston with tall skyscrapers and waterfront view under a partly cloudy sky.
South Boston seaport district from the Boston harbor. Photo: Mark Nassal/Alamy

The Seaport’s Contemporary Pulse

Back on the Boston waterfront, the Institute of Contemporary Art by Diller Scofidio + Renfro dramatically cantilevers over Boston Harbor, its galleries shifting between emerging voices and global stars. This summer: Stanley Whitney’s “How High the Moon” and Christian Marclay’s “Doors” (both through September 1), along with Sara Cwynar (through September 7). In warm weather, a seasonal ferry carries visitors to the ICA Watershed, where vast industrial spaces host immersive installations.

Lively restaurant interior with colorful tiled floor, green plants, elegant chairs, set tables, and large windows on the side.
Contessa. Photo: Major Food Group

The Dining Scene

In May 2025, the Michelin Guide announced its expansion to Boston—designations will be revealed later this year. Until then, try the Seaport’s Woods Hole Pier, where the focus is sustainably sourced seafood with sweeping harbor views. For a brunch worth lingering over, Contessa atop the Newbury Hotel offers Ken Fulk–designed opulence and panoramic vistas of Boston Common. If you’re chasing buzzy tables, look to No Relation for its omakase counter or Bar Vlaha for inventive Greek cuisine.

In Boston, art isn’t confined to galleries—it’s stitched into the city’s streets, parks, and skyline. Visit now, and you’ll find a place rooted in history yet constantly reinventing its own future.