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St. John's Labyrinth of Trails

Updated: Jun 9, 2020

First donated by Lawrence Rockefeller in 1956, the Virgin Islands National Park makes up 75% of St. John and now includes an additional 5,500 acres of submerged lands. St. John, the Love City, is known for it's untamed beauty above and below the surface. Join us as we bounce from bay to bay and explore the countless trails that criss-cross the island.

Being a popular destination, getting to St. John is easy. Most major airlines fly into St. Thomas then it's a short 2-mile ferry or private boat ride across the channel. If you're staying on island, I highly recommend a 4-wheel drive vehicle; you can pick up your rental at the St. Thomas airport, drive it onto the car ferry and drive off onto St. John in the main town of Cruz Bay. Cruz Bay has everything necessary for a flourishing small community with many waterfront restaurants. But visitors don't come to St. John for the food, they come for spectacular vantage points that mark the end of many trails; they come for the sealife thriving in the protected waters; they come for a Caribbean adventure.

The north side of St. John is dotted with scenic mooring fields. Honeymoon Beach and Caneel Bay are the closest and most convenient with Lind Point Trail connecting to Cruz Bay. Unfortunately the Caneel Bay Resort is still going through legal battles from considerable damage sustained in the 2017 hurricane season, but things are progressing; hopefully reconstruction will begin soon. Passing the quiet and well-protected Hawksnest Bay, Kuma Too stops at Trunk Bay for the Coral Reef Underwater Park Trail. Yep, you read that right. It is a reef marked with descriptive plaques making it easy to record your experience in your vacation journal.

One of the largest mooring fields in the USVI is Maho and Francis Bays. Offering live music, cold drinks, and food truck grub, Maho Crossroads has a hippy-vibe with oversized shaded lounge chairs. Stretch out or grab a picnic table, let the music set the mood, as you take advantage of the strong WiFi and drink delivery. One morning in Francis Bay, Joe said, 'look, a donkey!' I didn't believe him and argued it must be a large goat. Peering through the binoculars, I was proven wrong, as two donkeys wandered along the beach. The resident 24-inch black tip shark can be seen swimming in stride as one strolls along the beach, and don't miss the 3-finned turtle as he surfaces for fresh air. The giant cove offers many rock ledges to search for hidden crustaceans and observe vibrant fish and coral. A dinghy excursion to Whistling Cay offers more snorkeling and a photo-op of the old Danish Customs house. For those looking to stretch their legs but not interested in an elevated heart-rate, check out the Francis trail. Beginning (or ending for those on land based travel) at the beach, a mangrove-shaded boardwalk circles a salt pond before transitioning to a dirt trail with an easy incline to a lookout over the bay and salt pond. The trail leads past modern ruins of a home before culminating at the street (the official trail head) leading to our next Bay, Waterlemon and Leinster Bays.

Named for the cay that protects the bay from the flowing channel, Waterlemon offers calm water for swimming, snorkeling, paddle boarding, and a scenic dinner view. Johnny Horne is a steeper trail but manageable for most able-bodies. The Johnny Horne Trail takes guests to jaw-dropping lookouts at the Old Danish Guard House ruins and Murphy Estate House atop Windy Hill. The more laid-back Leinster Bay trail, follows the rocky shore to the Annaberg Sugar Plantation ruins where National Park Service volunteers educate visitors. Before heading out, we wade into the protected shallow reef for great snorkeling at Leinster Bay.

Rounding the east end of St. John, Coral Bay offers more amenities such as grocery and restaurants. When open, Lime Out feeds hungry boaters the best tacos in the Virgin Islands at their floating taco bar. Depending on weather, we pop over to the seldom visited Flanagan Island nature reserve for the dreamt-about experience of total seclusion on an exotic island.

One of our favorite location on St. John is Saltpond Bay! Saltpond Bay, located at the southeastern end of the island, has a beautiful small secluded beach and is the starting point of Ram Head Trail; also a favorite! Ram Head Trail takes you along a rocky beach before leading up a lightly shaded hill opening to a stunning view of Blue Cobblestone Beach. The best part of Blue Cobblestone Beach, from the overlook and the actual beach that the trail runs along, is listening to the waves recede over the smooth blue and green pebbles. Joe and I each perched ourselves on a rock, closed our eyes, and took it all in for a few minutes before continuing on. The trail leads to Ram Head Peak with continuous photo opportunities of unabated ocean views, sheer cliff faces, colorful flora, soaring birds, and lively goats. The hour-long trek should be done before the heat of the day sets in! Back at sea-level in the bay, countless birds, including a family of American Oystercatchers, lead you around the salt pond to Drunk Bay. Don't leave Drunk Bay without adding a drunk rock-person to the collection!

A quick downwind sail takes Kuma Too to Lameshur Bay. Yawzi Point, a short charming trail, separates Great Lameshur and Little Lameshur Bays. The latter provides terrific snorkeling off a large beach. For the adventurer, this is a great starting point for the challenging Bordeaux Mountain Trail, Lameshur Bay Trail, and Reef Bay Trail; leading to Euphoria Point, Euphoria Bay, and the historic Reef Bay Factory, Estate, and Great House ruins, and the ancient Petroglyphs. The petroglyphs are rock carvings believed to be from the Taíno Indians from as early at 500 AD.

There are low-key walking paths that traverse the hillside and shores; some trails are no longer maintained or lack signage; and a few hikes will really challenge you. I like to think we live a healthy and active lifestyle, but getting to the Petroglyphs deep in the central valley of St. John really tested both of us. It gave me a whole new respect for hikers!

The reefs and sealife throughout St. John waters are among the very best in the Virgin Islands because of strict regulations to protect the environment. Colorful fish, friendly sealife, lazy turtles, vibrant coral, and impressive rock formations await under the surface in the many coves.

To learn about charters on board Kuma Too, visit

Until next time, Happy Sailing!

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