To maximize your time on Montserrat, it's best to make arrangements with a private driver-guide or sign up for a guided tour (eg with Montserrat Island Tours) rather than hire your own car. If you decide to go exploring on your own, keep in mind that roads are steep, many are unpaved and that signage is poor. Stop by the tourist office and the Hilltop Coffee House & Family Center for maps, directions and advice. Olveston House and Pont's Beach View both make lovely lunch stops.
If you're spending the night, start day two by hiking, kayaking or swimming to the deserted white sands of Rendezvous Bay beach in the morning for a few hours of sunning, swimming and snorkeling. Pick up a takeaway lunch from John at People’s Place and hit the tropical Oriole Trail to enjoy a picnic with a view from the top of Lawyer’s Mountain. Keep an eye out for the elusive Montserrat Oriole. Before leaving the island, meet some friendly locals over a bowl of goat water.