When guests ask which hiking trail we'd recommend if starting out from Maho a favorite of mine would have to be America Hill. It's an "easy" walk from Maho to Cinnamon Bay, where one of the start points for getting to America Hill begins (the other would be on Centerline Road). Before or after the America Hill hike you can explore the ruins just off the road at Cinnamon, which have recently been transformed with a series of concrete and raised boardwalks (like ours!).
Be prepared for the start of the trail, it's a straight shot uphill for what seems like forever. Once the first part has been climbed its relatively easy navigating the switchbacks all the way to the top. Total hiking time going up from the Cinnamon ruins: 25 minutes or so
The views from the America Hill Estate House are incredible, and perhaps the only spot on St. John where one can view Peter Bay, Cinnamon Bay, Big & Little Maho, Francis Bay, and Waterlemon Bay - all at the same time. The Estate House itself is absolutely huge and beautiful, one which you'll spend plenty of time wondering how they ever carried so much brick, coral and concrete up the trail you just climbed!
Since you'll be so high above Maho & Francis Bay you can clearly see the white roofs of a few Maho tents. Bring a pair of binoculars and if the water is clear you can also see plenty of snorkelers between Big Maho and Little Maho. And if you're eyes are really good and the weather is clear you can see all the way to the West End of Tortola.
Caution: wear bug spray and listen for Jack Spaniards - towards the top you'll hear plenty of them buzzing around.