
Our charter began at CYOA Yacht Charters in Charlotte Amalie, St. Thomas. Just minutes from the STT airport, CYOA is a convenient place to start a sailing vacation. We provisioned in town at Pueblo and got ready to set sail on our 47-foot Fountaine-Pajot Salina, Island.

First stop: St. John. This lush island is surrounded by peaceful bays, which are perfect for daytime visits and overnight stays. We stopped in Hawksnest Bay on the northwest corner and experienced our first of many pristine views, where the water was clear and the snorkeling excellent. Because 75 percent of St. John is U.S. National Park, the mooring fields are all well maintained with well-marked channels noting the dinghy path to white-sand beaches.

St. John was teeming with wildlife. The wild donkeys were especially adorable, but we were thrilled to find all of these creatures during our hikes and swims.

If you enjoy incorporating hiking into your charters, St. John is an ideal destination. There are dozens of hikes ranging from .2 miles to 12 miles that climb over luscious hills, pass by antiquated ruins and often end at pretty beaches. Our favorites were Lind Point trail between Caneel Bay and Cruz Harbor, Johnny Horn Trail between Waterlemon Bay and Coral Bay (pictured here) and the Ram’s Head/Petroglyph trails from Lameshur Bay. All were well marked and maintained. We found this to be a helpful hiking guide.

Here, our boat is anchored in Leinster Bay, seen from atop the Leinster Bay trail. Beware that the beach leading to the Annenberg Ruins (in the left of this photo) does not have a dinghy landing, though most cruising guides indicate otherwise. Instead, you’ll have to pull your dinghy ashore in Waterlemon Bay. Note, also, that the National Park Service prohibits dinghy anchoring and would prefer you haul your dinghy ashore and tie it to a tree or rock.

Next stop: Cinnamon Bay. We found the mooring field in Francis Bay to be the most calm, so we picked up a mooring ball there are dinghied over to Cinnamon Bay. There, beside the soft sand beach, we found rentals for kayaks, windsurfers and Hobie Cats; shower and trash facilities; and, of course, more trailheads leading to more great hiking.

No trip to St. John is complete without a visit to Skinny Legs in Coral Bay. The iconic bar is famous for its island-pub food, its Caribbean drinks and its laid back atmosphere that attracts all sorts of characters. Because the anchorage in Coral Bay is crowded with live-aboards, we opted to hike to Skinny Legs from Leinster Bay. The 4-mile round-trip jaunt was just difficult enough to make us feel as though we deserved our rum punches.

One of St. John’s most beloved attributes is its lack of crowds, especially compared to its neighboring British Virgin Islands. Moored here in Little Lameshur Bay on the island’s south coast, we had the bay completely to ourselves, allowing us to enjoy an unspoiled view of a spectacular sunset. That evening, we took the dinghy ashore and used a National Park grill and table on the beach for a fun on-shore picnic.

If you plan your route right, the U.S. and British Virgin Islands can be visited through a series of comfortable reaches. Our sails between St. John and Jost Van Dyke, then Jost Van Dyke and St. Thomas, were just that.

After arriving on Jost Van Dyke and clearing into customs in Great Harbor, we took the dinghy to the Soggy Dollar Bay in White Bay. The hammocks and painkillers were as good as ever and we were pleased to see that someone had installed mooring balls in this often hectic anchorage.

With its smooth water and good winds, Sir Francis Drake Channel is excellent for kiteboarding.

Next stop: Sandy Spit. Just minutes from Jost Van Dyke, this picturesque island is worth a stop to enjoy the nice snorkeling to the east and the pretty white-sand beach that surrounds it.

The Virgin Islands are built around chartering, and you’ll be hard-pressed to find an anchorage nowadays without well maintained mooring balls. In the U.S. Islands, charter boats must visit an honors-system pay station and drop in $15. In the BVI, a mooring field-keeper will visit your boat in a dinghy to collect $30.

Though the North Swell was down considerably, the Bubbly Pool on Jost Van Dyke still made for a fun-filled visit.

To access the Bubbly Pool, moor in East End Harbor, walk past Foxy’s Taboo, and follow the beach path just over a mile. Be sure check in these shallow mangrove pools along the way—they’re known to have some great sea life, including squids, sharks and octopus.

Our final hike took place on Sandy Cay. To access this hike, swim or dinghy ashore and enter the woods at the clearing with the trailhead. The first half of the hike is forested and replete with wildlife sighting—keep your eyes peeled for hermit crabs, iguanas, tarantulas and more. The second half climbs above the trees to an exposed, rocky path. As long as you’re wearing shoes, you’ll love this part of the hike, with its excellent views of the Sir Francis Drake Channel and surrounding islands.

The Sandy Cay hike ends back at the beach, where it’s a race to cool off in the ocean.

In addition to great wildlife and sunny views, Sandy Cay is covered in coconut trees. They’re tricky to take apart, but once you muster through, the fruit is worth the effort.