The Boston Tea Party, Paul Revere’s Ride, The Boston Massacre… Boston is filled with history – starting with its colonization in 1630 by Puritan settlers – which makes it one of the oldest municipalities in the US. And it’s not just historic – it’s charming as well – and that’s because even though it’s a “big city” – it never quite feels that way. Thanks to its cobblestone streets, brownstones, tours via trolleys, marketplace, and colonial-era structures, it feels more like a small-town atmosphere than a bustling urban center. And that’s what makes it so appealing. Check out our offerings below then contact our destination experts to book your Boston (spring, summer, winter or fall) break!