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A weekend itinerary for Boston



As the cultural hub of New England, Boston makes the perfect weekend destination. It’s compact, walkable city center means that you can easily take in its amazing history and fascinating cultural highlights in a couple of days, and you’ll even have time to dip into the fantastic foodie scene that has sprung up in Beantown. Check out the guide below, the perfect way to spend a couple of days in the city before taking a cruise out of Boston or taking the train from NYC. If visiting Boston, take it all in and be sure to capture every moment to look back on.


Start off in the North End with a coffee and a pastry at one of the amazing delis in this traditionally Italian-American neighborhood. Before diving into the historic city center, take a walk southwest through the gorgeous cobbled streets of Beacon Hill, snapping away freely at the picturesque and charming 19th century brownstones that make up this photogenic district. Explore leafy Boston Common, and take your first dip into Boston’s rich history at Park Street Church and the Granary Burying Ground, where patriots like Sam Adams and Paul Revere are buried.

Head back north, and grab a quintessential Boston lunch of clam chowder at the Union Oyster House. Check out Faneuil Hall Marketplace, full of excellent shops, market stalls and street entertainers, then head up Hanover Street and into Boston’s remarkable past. Check out the Paul Revere House, the colonial-era home where he began his legendary ride, as well as his statue outside the Old North Church.

In the evening, take a stroll on the pretty Boston Harborwalk, a lovely pedestrian-only walkway offering fantastic views of the harbor. Double down on Boston’s amazing seafood with dinner at Fin Point Oyster Bar and Grille, and finish the night off with a nightcap at The Outlook on top of the Envoy Hotel and one of the best views in Boston.


Set your sights on Boston’s hip and sophisticated South End for your second day in town. Get your day started at the South End Buttery, then wander down to the South of Washington Market, a fantastic collection of stalls, pop-up shops and independent boutiques which is probably the best shopping experience you can have in Boston. Spend the rest of the morning walking around this delightful district, which is full of splendid Victorian architecture, beautiful leafy parks, and a wonderful array of independent galleries, studios and showrooms.

Grab a spot of lunch in the casual, relaxed surrounds of The Friendly Toast, then head north into the Back Bay neighborhood. Check out Trinity Church, designed by Henry Hobson Richardson, then explore the magnificent Boston Public Library, a proper temple to literature. Continue with the literary theme and soak up the atmosphere in the many independent bookstores that are scattered around this district, and grab a coffee at Trident Booksellers and Café.

Finish up your weekend in Boston with the most authentic and fundamental experience you can have in the city, a ballgame at Fenway Park. Whether in the late afternoon or early evening, the atmosphere here is sizzling, and no trip to Boston would be complete without seeing this glorious cathedral to the national pastime.

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