Start & Finish: Ferry docks in Cruz Bay.
Time: 3 to 7 hours, depending on beach time, bar stops, and pedestrian detours.
Best Time: Any warm, sunny day.
Worst Time: Any rainy day, when you are likely to get stuck in the mud on bad roads.
Important note: Before you begin this tour, make sure you have at least three-quarters of a tank of gas, because there are only two gas stations on St. John, one of which is often closed. The more reliable of the two stations is in the upper regions of Cruz Bay, beside Route 104. Ask for directions when you pick up your rented vehicle. And remember to drive on the left.
Head out of Cruz Bay, going east on Route 20. Within about a minute, you'll pass the catwalks and verandas of:
1. Mongoose Junction
This shopping emporium, a major island attraction, contains some unusual art galleries and jewelry shops.
Continuing east on Route 20, you'll pass:
2. Caneel Bay
Past the security guard, near the resort's parking lots, are a gift shop and a handful of bars and restaurants. Continuing on, you'll see within a mile the first of many stunning vistas. Note the complete absence of billboards and electrical cables, a prohibition rigidly enforced by the National Park Service.
In less than 3 miles, you'll come to:
3. Hawksnest Beach
Hawksnest is one of the island's best beaches. Continuing your drive, you'll pass, in this order, Trunk Bay, Peter Bay (private), and Cinnamon Bay, all of which have sand, palm trees, and clear water.
A few steps from the entrance to the Cinnamon Bay Campground is a redwood sign marking the beginning of the:
4. Cinnamon Bay Trail
Laid out for hikers by the National Park Service, this 1-mile walk takes about an hour. Its clearly marked paths lead through shaded forest trails along the rutted cobblestones of a former Danish road, past ruins of abandoned plantations.
A short drive beyond Cinnamon Bay is the sandy sweep of Maho Bay, site of one of the most upscale and eco-friendly campgrounds in the Caribbean. Shortly after Maho Bay, the road splits. Take the left fork, which merges in a few moments with an extension of Centerline Road. Off this road will appear another NPS signpost marked DANISH ROAD; this detour takes you on a 5-minute trek along a potholed road to the ruins of an 18th-century school.
At the next fork, bear right toward Annaberg. (Make sure you don't go toward Francis Bay.) You'll pass the beginning of a 1-mile walking trail to the Leinster Bay Estate, which leads to a beach good for snorkeling. In less than a minute, you'll reach the parking lot of the:
5. Annaberg Historic Trail
The highlight of this driving tour, the Annaberg Historic Trail leads pedestrians within and around the ruined buildings of the best-preserved plantation on St. John. During the 18th and 19th centuries, the smell of boiling molasses permeated the air here. About a dozen NPS plaques identify and describe each building within the compound. The walk takes about 30 minutes. From a terrace near the ruined windmill, a map identifies the British Virgin Islands to the north, including Little Thatch, Tortola, Watermelon Cay, and Jost Van Dyke.
Back in the car, retrace your route to the first major division, and take the left fork. Soon a sign will identify your road as ROUTE 20 EAST. Stay on this road, forking left wherever possible, until you come, after many bends in the way, to:
6. Emmaus Moravian Church
At the sandy bottomlands you'll see an elementary school, a baseball field, and, on a hilltop, a simple barnlike building known as the Emmaus Moravian Church. This church, with its yellow clapboards and red roof, is often closed to visitors. Near its base yet another NPS walking trail begins: the 1.5-mile Johnny Horn Trail, known for its scenic views and steep hills. You will now be about 13 miles east of Cruz Bay.
The roads at this point are not very clearly marked. Avoid the road beyond the elementary school below the church; it's pretty, but leads only to the barren and rather dull expanses of the island's East End. Instead, backtrack a very short distance to a cluster of signs that point to the restaurant Shipwreck Landing. Follow these signs heading south about a mile to:
7. Coral Bay
Claimed by the Danes in the 1600s and used to unload Danish ships, the bay still contains a crumbling stone pier. This was also the site of the first plantation on St. John, which was established in 1717 and abandoned long ago; it predates the far-better-developed facilities of Cruz Bay. You can also follow the posted signs to see the remains of Fort Berg, which stationed the soldiers that suppressed the 1733 slave revolt. Today, Coral Bay shelters a closely knit community of yachting enthusiasts, who moor and live on their yachts between excursions to other parts of the Caribbean.
Ringing the bay's perimeter is a widely spaced handful of restaurants and bars. One of these is called:
8. Shipwreck Landing
This is an ideal place to drop in for a meal or a tropical drink. You can sit amid palms and tropical plants on a veranda overlooking the sea.
After your break, continue driving south along Coral Bay, perhaps stopping in at another of the two or three shops and bars beside the road.
Backtrack north along Coral Bay to a point near the Emmaus Moravian Church, which you'll see in the distance. At the cluster of restaurant signs, turn left onto Route 10 West (Centerline Rd.), which has high-altitude views in all directions as you follow it back toward Cruz Bay. (An alternate, but much steeper, way is King Hill Rd., which merges later with Rte. 10 W.)
Within 7 or 8 miles, Route 10 merges with Route 104 (Gift Hill Rd.) just after the island's only hospital, the St. John Myrah Keating Smith Community Health Clinic. Take Route 104 and begin one of the steepest descents of your driving tour. (Use low gear whenever possible, and honk around the many blind curves.) When the land levels off, you'll see, on your left, the entrance to the most imaginative pieces of modern architecture on the island, the postmodern:
9. Westin St. John Resort & Villas
If you're a gardening or architecture enthusiast, stop in for a look at a hotel whose inspirations include ancient Mesopotamia, colonial Denmark, and the coast of California. What makes all of this even more impressive is that it was built only a few years ago on what, at the time, was unusable swampland.
From here, your return to Cruz Bay entails only a short drive along Route 104, through a slightly urbanized periphery of private homes.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.