From March to November, meet the area's waterlogged residents while on a Boston Harbor Cruises whale watch. Along with a naturalist from the New England Aquarium, sail from the Boston Harbor (where the infamous Tea Party took place) to the Stellwagen Bank Marine Sanctuary in Massachusetts Bay, home to humpback, fin, and minke whales, as well as dolphins and seabirds.
It's difficult to visit the city and not stumble across the Public Garden and Boston Common, but most visitors don't realize that these beloved sanctuaries are actually part of the Emerald Necklace. A string of nine parks designed by Frederick Law Olmstead, the Necklace features lesser known spaces with tree-lined trails, geese-dotted ponds, and picturesque picnic spots.
Best Day Trip
Drive or take the ferry to Provincetown, located on the tip of Cape Cod. Dip fresh catches in butter at the Lobster Pot, climb the 252-foot Pilgrim Monument, or try the breakwater walk, a 1.2-mile rock bridge that leads to a deserted island. Finish the day off with the ultimate Provincetown experience-enjoying one of the many drag shows.
Off the Beaten Path
Skip the Freedom Trail and head to Coolidge Corner for a more intimate look at history. Tucked away on a quiet street is the John Fitzgerald Kennedy National Historic Site, the quaint home where JFK was born. Step inside for a vignette of Kennedy family life, then join a neighborhood walking tour to hear stories from the former president's childhood.
Most Iconic Experience
Fenway Park is a place of worship in Boston. For a new perspective of the park, watch from the Bleacher Bar on Lansdowne Street. The bar's garage-door window is part of Fenway's outfield wall, so patrons feel like they're on center field during the game. For the full experience, cheer on the Sox with a Sam Adams Boston Lager in hand.
Boston's Little Italy, the North End, transforms after dark. After pasta dinners, residents and tourists alike flood Hanover Street, hunting for fresh cannoli from Modern Pastry and Mike's Pastry. Escape the crowds at the old-school Caffe Vittoria to sip a cappuccino or grappa, an Italian brandy. It's the perfect precursor for a late-night show at the nearby Improv Asylum.
The neighborhood of Charlestown boasts its own miniature version of the Washington Monument. The obelisk commemorates one of the Revolutionary War's early battles, the Battle of Bunker Hill in 1775. After climbing the nearly 300 steps to the top of the Bunker Hill Monument, visitors are rewarded with views of downtown Boston and the iconic Zakim Bridge.
In the 1950s, an MIT fraternity measured the length of Harvard Bridge by using a fellow student-five-foot-seven Oliver Smoot. One night they carried Smoot across the bridge, marking out his length on the sidewalk. By morning, they had their measurement: The bridge came out to 364.4 Smoots, plus or minus one ear. That same MIT fraternity repaints the measurements on the bridge every year.
Neighborhood to Explore
Stroll the South End's shaded streets and stop at the specialty shops: Follain for organic beauty products, Olives and Grace for small-batch foodstuffs, and Ore Jewelry for handmade pieces. On summer Sundays, browse vintage finds and local wares at SoWa Open Market. Enjoy dinner at Picco, featuring brick-oven pizza and homemade ice cream, followed by live jazz at the Beehive.
Park yourself on the stone steps of the Boston Public Library and look out onto Copley Square, the Romanesque Trinity Church, and the glassy Hancock building. This part of Boston is a major pedestrian intersection, with commuters coming in from the nearby train station, skateboarders grinding along the square's fountain, and shoppers toting their hauls from Newbury Street.