The capital of the British Virgin Islands, Road Town sprawls along the shore of Road Harbour, its namesake, a deepwater port on the south-central Caribbean coast of Tortola. (Road was once a common word for a harbor. Early writings refer to this area of Tortola simply as “The Road.”) Steep hillsides rush down to the shore on all sides, creating what looks like a giant amphitheater, with Road Town as the stage.

Road Town is like an adolescent who has reached the awkward stage. Planning here has been haphazard, the effects being poor traffic design, lack of parking, and spotty sidewalks. A recent effort to build more sidewalks, plant trees, and create crosswalks has made it a little easier to get around on foot, but it is still hard going for pedestrians. Plans for more traffic lights are unlikely to solve the traffic gridlock that strikes at rush hour.

Road Town possesses little of the old-world charm that exists in other port towns in the Virgin Islands. After all, it operated in the shadow of ports like Charlotte Amalie and Christiansted during the plantation era. A townwide fire in 1853 did not help things.

Despite its flaws, Road Town has a certain appeal, embodied by its ramshackle appearance, roaming chickens, and the constant ebb and flow of people.

Road Town’s main thoroughfare is Waterfront Drive, which follows the waterfront as far as the Crafts Alive shopping area before turning inland. Waterfront Drive ends at Road Town’s main roundabout, where the town’s central arteries meet, and runs roughly parallel to Main Street.

The best bets for parking in Road Town are the public lots on either side of the Road Town ferry terminal, on the waterfront.

Road Town is generally safe, even at night, although some areas are known for the criminal activity that tends to take place in them. Scatliffe Alley, a narrow road that runs from the Sunday Morning Well to the Fire and Rescue Station, is best avoided.