In this former capital of Bermuda, the first settlement landed in 1612, so this area – a UNESCO World Heritage Center – is steeped in rich local history. Just wandering its narrow streets with quirky names like Featherbed Alley and Old Maid Lane is fun, but do check out the evening Haunted History Walking Tour if your kids are interested in history and enjoy being spooked! Tours leave from Long Story Short in Tucker House on Water Street.