Start from 130 curated places around Boston, MA, then choose the recommendations that fit your guests.
Restaurants & cafés
Neptune Oyster
42-seat North End oyster bar with the city's deepest raw bar and an outsized hot-buttered lobster roll. Counter seats, no reservations, lines that are part of the experience.
Bricco
Hanover Street upscale Italian, intentionally lower-key than the showier North End rooms, with a pasta program that emphasizes hand-cut over machine and a wine list that runs unusually deep on smaller Italian growers.
Trails & outdoors
Arnold Arboretum
265-acre Harvard-owned tree collection in Jamaica Plain, designed by Frederick Law Olmsted as the south anchor of the Emerald Necklace. Free, leashed dogs welcome, and 15,000 species labeled if you want to learn what you're under.
Great Blue Hill
Boston's only real summit hike — 600-foot Great Blue Hill in the Blue Hills Reservation south of the city, with a stone observation tower on top and a skyline view that earns the rocky scramble. Three miles round-trip, moderate-to-strenuous depending on the route.
Things to do
Museum of Fine Arts
Encyclopedic museum with one of the country's deepest Egyptian collections, a Monet hoard that rivals Paris, and a glassy Linde Family Wing of contemporary galleries. Half a day minimum; a full one if you're an art person.
Isabella Stewart Gardner Museum
Gilded-Age collector built her own Venetian palazzo in the Fens and stuffed it with Rembrandts, Titians, and Vermeers — then left a will saying nothing can ever move. The central courtyard alone is worth the ticket, and the empty frames from the 1990 art heist are still on the walls.
Landmarks & sights
Freedom Trail
The 2.5-mile red-brick line stitching together 16 Revolution-era sites from Boston Common to the USS Constitution. Walking it cold is the move — the brick guides you, and rangers run free talks at several stops in summer.
Boston Public Garden
America's first public botanical garden, designed around an ornamental lake with the Swan Boats Bostonians still ride every spring. The willow-shaded lagoon and the bronze Make Way for Ducklings statues make it more storybook than park.