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Boston holidays sing from a different hymn sheet to most cities across the pond. This city's stashed with long-standing landmarks, cobbled streets and waterfront avenues that belong on a postcard.

City with character

City breaks to Boston aren’t your run-of-the-mill American getaways – the city’s one of the biggest and most unique personalities on America’s east coast. Winding, intricate lanes set it apart from its big-name counterparts, and the whole place is stamped with a European influence. In Downtown Boston, you’ll see Greek columns fronting buzzy Quincy Market, plus Gothic apartment blocks and a red-brick fire station on pretty Boylston Street. The cobbled streets of Beacon Hill, meanwhile, are like hopping into a quaint English town.

Ace architecture

The city’s Financial District is crane-your-neck territory, thanks to a modern crop of cloud-nudging skyscrapers. It’s the old-school stuff that’s really worth a look, though. The Freedom Trail snakes through the city, dot-to-dotting its way between 16 historic landmarks. The gold-domed Massachusetts State House, the obelisk-shaped Bunker Hill Monument and one of the oldest properties still standing – the Paul Revere House – are all on the route. Elsewhere, Boston Public Library’s McKim Building is inspired by Parisian architecture, and looks like a cathedral inside.

Waterfront sights

City breaks to Boston spoil you with a hefty helping of waterfront views. It’s right by an island-dotted bay – which has a couple of beaches spaced out along it. The Charles River wriggles inland from here, and has an esplanade beside it that’s peppered with blossoming trees. The Back Bay district cosies up close, with its stock of indie shops and fashion boutiques. South Boston, meanwhile, is like the city’s Swiss army knife – it’s got beaches, museums and some of the most authentic Irish bars in its locker.

Beer, baseball and back to school

In the west of the city, you’ve got a ‘famous names convention’ going on. Sample the most famous tipple, Samuel Adams beer, on a tour of the brewery. If you’re feeling peckish after a tot or two of the good stuff, pick up a hot dog at Fenway Park – this baseball stadium’s one of the most iconic in the nation, and its franks are award winners. For a smidge more history, head across the river to Cambridge, where brainiacs swot up at the Harvard and MIT universities.

At a Glance

  • Shop around Quincy Market
  • Take a tour of Fenway Park
  • Get a dose of history on the Freedom Trail
  • Prep for your trip with our Holiday Extras
  • Get your visa through our visa and travel authorisation partner Sherpa

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