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Start a two-day trip to Boston by spending a morning in Beacon Hill, with its quaint cobblestone streets, gas lamps and rows of elegant houses (you can ogle Senator John Kerry's digs on gorgeous Louisburg Square). Have a picnic lunch on the Boston Common, and then go for a ride on pedal-powered Swan boats in the Public Garden next door. From there, it's an afternoon of upscale boutiqueing, high-end spa-ing and perhaps ice cream at Emack & Bolio's as you make your way down Newbury Street. Find dinner along nearby Boylston Street, a steak at local favorite Abe & Louie's is a study in old-school dining.
Your second day should begin with a tour of Fenway Park to get a feel for the sports fanaticism that grips the city every spring, summer and fall, and then make your way back to the Prudential Center to board a Duck Tour, taking in the rest of Boston from both land and sea (well, river, but close enough). Round out the trip with some art, the small intimate collection at the Isabella Stewart Gardner Museum, or if you still have some zing in your step, the larger and encompassing treasures of the Museum of Fine Arts.
On day one:
Morning: Tour the city’s famous landmarks like never before aboard an amphibious Duck Boat, with a trained ConDUCKtor as your guide. From the city streets to the Charles River, this fun-filled experience is wholly one-of-a-kind, with quacking encouraged!
Afternoon: Lined with stores, galleries and restaurants, Newbury Street is a shopping Mecca and must-see destination. Afterward, venture to Charles Street in quaint Beacon Hill to browse the unique shops followed by a sweet treat at Isabella’s Curly Cakes. Be sure to snap a photo on the city’s most picturesque street, Acorn Street.
Evening: Savor mouthwatering Italian cuisine in Boston’s oldest and most vibrant neighborhood, the North End. Finish the meal with an old world Italian dessert at Mike’s or Modern Pastry.
On day two:
Morning: Step back in time on the Freedom Trail, a 2.5-mile red brick path that passes the city’s most famous historic sites such as Faneuil Hall, the Paul Revere House, the Bunker Hill Monument and the USS Constitution.
Afternoon: Venture across the Charles River to America’s oldest and most prestigious university. Take “The Unofficial Hahvahd Tour,” guided by students and filled with behind-the-scenes stories you won’t hear anywhere else. Afterward, have lunch at one of the many restaurants in the buzzing and eclectic Harvard Square. Don’t forget to buy a souvenir at the Harvard Coop!
Evening: Indulge in housemade pasta, house aged steaks and fresh New England seafood in The Bristol Lounge at Four Seasons Hotel Boston. Sip one a signature cocktail while taking in the ambiance of “Boston’s Living Room.” Following dinner, treat yourself to the “Let’s Split It,” a chocolate devil’s food cake tower layered with truffle ganache, vanilla buttercream and crème de cacao.