Seven Days Around St. John

The smallest of the three U.S. Virgin Islands offers a wealth of adventures for charterers.

Trunk Bay, St. John, U.S. Virgin Islands Brocreative/

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I know what you’re thinking: a week to cruise around one little island? Having run charters on my Lagoon 410 Guiding Light for nearly a decade, my answer is: You bet! 

With the pandemic came a renewed interest in the US Virgin Islands, especially for US citizens, who found the nearly 20 square miles of St. John to be as ripe as ever for a fun, easygoing experience. Here’s a taste of what a week around St. John looks like. 

Day One: Pick up or meet your boat. I prefer to start in Red Hook because it is on the east end of St. Thomas and a good jumping-off spot. If you start in Charlotte Amalie, simply add a ­two-hour upwind motor to get to the east end. The first stop is on the southwest corner of St. John: secluded Rendezvous Bay. Tuck up into the eastern part of the bay just off a rocky beach. Here you have the choice of two snorkeling spots. The one to the left is against the cliffside, and you will be amazed at the variety of sea creatures. The second spot is on the opposite side of the boat. This one is from the edge of the beach all the way out to the point, where you’ll find large rocks, walls, and overhangs covered in coral and fish. It’s a bit deeper (in 15 to 25 feet of water) and more advanced, but it’s amazing.

Day Two: The first stop will be in Reef Bay to hike up to see the 500- to 1,000-year-old pre-Colombian petroglyphs and the last active sugar factory on St. John. This factory is also the only one that brought in steam equipment. After the hike, head half a mile or so to the east and snorkel Tektite Point in Great Lameshur Bay. NASA and the National Oceanic and Atmospheric Administration ran underwater tests here back around the late 1960s. Finish your day at Salt Pond Bay, where you will find only five other boats because you have to take a mooring while inside the US national park that makes up two-thirds of St. John.

Day Three: Start your day with a sunrise hike out to Ram Head, one of the most ­popular hikes on St. John. Other highlights of Salt Pond Bay are the wonderful beach, turtles and snorkeling. If you want a more adventurous snorkeling itinerary, then check out the cliff between Salt Pond Bay and Blue Cobblestone Beach to the south (also where the Ram Head hike goes by). You can walk from the beach to the other side of the peninsula and check out the artwork people have made from coral on the beach at Drunk Bay. Around 2 or 3 p.m., head around Ram Head with the boat and anchor in Coral Bay so that you can have dinner at Skinny Legs, a funky little burger-and-sandwich joint that people love.

Day Four: Spend the morning snorkeling along the mangrove-lined bays of Otter and Water creeks in Hurricane Hole. This is one of my favorite snorkeling spots in the whole Virgin Islands because it has coral, sponges, fish, and other creatures in and on the mangrove tree roots. It is very different from what you find elsewhere. After snorkeling, head back to Coral Bay to grab lunch at Lime Out, a taco boat that has “lily pads” for your group to hang out in. Next, head to the east coast of St. John and Newfound Bay, which I can almost guarantee you will have to yourself. Make sure you are comfortable with reef navigation because you’ll need to sail between two reefs on a lee shore to enter the bay. You must have good light, so get there early. Once inside, you can tuck in behind the southern reef for an amazing view of the British Virgin Islands. If the weather is favorable for snorkeling outside the reef, it’s well worth it. Otherwise, explore the entrance to the bay on both sides. Rays fly through this bay all the time.

Waterlemon Cay
Surrounded by a reef, Waterlemon Cay features some of the best snorkeling in the US Virgin Islands. Shane McClellan

Day Five: It’s time to enjoy a 4-mile downwind sail to Waterlemon Bay, which has some of best examples of soft corals in the Virgin Islands. The best snorkeling is on the back side of Waterlemon Cay, reportedly the last place in the islands that pistol duels took place. You can also enjoy the beach and walk over to Annaberg Sugar Plantation, which is the most popular historic site on St. John and has the largest of the five windmills on the island. Up on the hillside from the anchorage, you will find a garrison house.

Day Six: Beach day! Choose among four major beaches and a handful of small beaches, all within a 1-mile area. Each beach has its own atmosphere: Francis is quieter and has a boardwalk hike; Maho has food trucks; Cinnamon is the national park’s campgrounds; and Trunk is one of the most beautiful. My favorite is the small beach to the west of Cinnamon Beach. You will probably have it to yourself. You can moor at any of the bays, but I prefer Francis Bay because it is the calmest and provides the best breeze. Another choice is to spend the night in Caneel Bay or off Honeymoon Beach, and dinghy around the corner into Cruz Bay to enjoy dinner and nightlife in town.

Day Seven: You can snorkel Whistling Cay and hang out on another beach in the morning and early afternoon before heading downwind to Christmas Cove. This is a popular anchorage outside the national park. There is great snorkeling along a 5-foot ridge at the head of the bay, as well as around the Fish Cays in the middle of the bay. The best part of Christmas Cove is having pizza for dinner from Pizza Pi, a boat built specifically to dish out traditional New York-style pizza. 

After 11 years of running charters in the Virgin Islands and Eastern Caribbean, Capt. Shane McClellan is setting sail for the Greater Antilles, including Cuba and Belize. Follow him at

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