Considered one of the most important sites on the island, this cupola-topped building on Front Street is also one of its most emblematic. First built in 1793, the shingled structure was the home of the town’s founder and namesake, Captain John Philips, a Scottish captain in the Dutch navy. In addition to multiple renovations, the former residence has been a fire station, a post office and even a jail. At the top is an artisan wooden pineapple—the symbol for hospitality—and inside the tower’s belfry are 25 bells.