Sailing the Virgin Islands: How to Spend a Week Aboard

People often spend a lot of their mental energy thinking about the future. I know I do. We plan, worry, and anticipate things that may even be years down the line. We like to be ready for what’s coming. Some of this future-mindedness detracts from our life - it causes us to lose track of the present moment, and we end up perpetually missing out on what’s going on right in front of us. But sometimes, planning for the future feels almost just as good as what we’re planning for itself! Travel falls into this category. 

The trip planning process, while stress-inducing for some, may actually be a source of happiness even greater than the trip itself. We imagine ourselves living the adventure before we’re even there, and this anticipation is exciting. But what’s better about the planning part is that, for one, it covers a longer period of time than the trip itself, and two, there will always be that sense of mystery and curiosity of what lies ahead! Just like reading a good book, our minds love this. 

So come with me, let your mind drift off to turquoise blue waters and lush green mountainsides…That’s where we’re going. It’s called St. John.

Day 1:

After spending our first night aboard, we’ll do any last provisioning needed in Charlotte Amalie and just take the morning slow. Maybe a quick car tour of the island with a stop at Northside Grind for some locally roasted coffee. Then the adventure begins! 

We’ll pick up the anchor and leave St. Thomas behind us as we head for St. John. Our first stop is Rendezvous Bay, on the southwest corner of the island. This anchorage lies just outside the boundaries of the Virgin Islands National Park, and we’ll likely have it almost all to ourselves! There is some good snorkeling right off the boat. Beginning shallow, with spotty coral heads and rocks, the underwater landscape transitions into deeper, bouldering rock formations with bustling sea life as we swim south along the bay. Previously spotted creatures include eels and green sea turtles. 

Upon coming back to the boat after a refreshing afternoon swim, outdoor showers and happy hour are in order. To celebrate our first full day of the charter, we’ll gather on the bow for some sunset snacks and a cocktail. Cheers to the next few days of exploration!

Day 2:

An early morning wake up is necessary to get moving to our next destination - Reef Bay - as there are only two day-use moorings available and they often go fast. From here, we’ll make an energizing breakfast or pack some GoMacro bars in our backpacks to accompany us on the 4-mile hike. Only steps from the beach, we’re immediately rewarded with the beautiful ruins of a sugar mill. We’ll then follow the hermit crabs along a flat section of trail, warming ourselves up before the ascent up the mountain begins. Though it’s nice and shady in the lush understory, we’ll have worked up a sweat by the time we reach the top. Breaths of fresh forest air and views from high above the water are well worth the effort.

After a swim to cool off, it’s lunchtime! We’ll take this moment to enjoy the secluded bay, with nature as our only neighbor. And then on to our next stop, a personal favorite…Salt Pond Bay. Here, we’ll find only three moorings, so again, it can be a gamble whether or not they’re unoccupied. A rocky outcrop lies in the middle of the bay, home to the easiest and most rewarding snorkel of the trip! From one of the moorings, you’re practically on top of the reef already when you jump in - no need for a long swim. There are lots of fish dancing around, but the few big and beautiful elkhorn corals are the star of the show for me, as a coral biologist. The little baby corals making a comeback always bring me happiness, too. 

Day 3:

Our third day begins with another hike! But don’t worry, this one is shorter and even more rewarding. If you’re an early bird, we can even start before sunrise in order to watch the sun come up over the ocean from the nearly 360-degree viewpoint up top. The Ram’s Head trail begins along the rocky beach of Salt Pond Bay and continues up and out to the end of the skinny peninsula. Windy, rugged, and beautiful. 

After this little adventure, we’ll sail around that very peninsula and into Coral Bay. For marine bio enthusiasts, a stop in one of the mangrove-lined creeks of Hurricane Hole is a must. Mangrove snorkeling is always a unique experience. It’s fun (at least for me) to identify the diverse algal species, sponges, and little fish that live among the mangrove roots. 

By the time we’re done with this very adventurous morning, we’ll be more than ready for some tacos at Lime Out. The floating taco bar in Coral Harbor is a crowd-pleaser for sure. With about a dozen circular rafts and a swim up bar on either side of the floating, lime green restaurant, this is the spot for a unique and fun lunch. Their tacos are stuffed to the brim with fresh ingredients. With an ice cold, craft margarita in hand, you will be one happy sailor! 

The afternoon can be spent relaxing aboard or wandering around the quiet town of Coral Harbor. There might even be more abandoned, mast-less boats in this harbor than there are good boats! Skinny Legs Bar and Grill is a popular cruiser hangout that is fun to stop in for a drink or two. They have a nice little shop next door, as well. 

Day 4:

A day of sailing, at last! We’re now ready to turn the corner around the eastern end of St. John and begin our lovely downwind sail. The north side of the island is full of beautiful white sand beaches that are made even brighter when sandwiched between vibrant blue water and green mountainside. Waterlemon Cay is a picturesque spot and nicely protected anchorage. There are two ruins to visit here. One is the famous Annaberg Sugar Plantation to the west, and the other is an old manor that sits atop the peninsula northeast of the bay. Both are worth a visit. The hikes are easy and offer great views along the way. You may even find yourself chewing on sugarcane and fresh coconut, gifted by the friendly and knowledgeable gardener at Annaberg. 

After a morning of sailing and hiking, it’s time for lunch and a swim to cool off. Making a loop around the cay offers the best snorkeling. 

Then we’re off to Francis Bay! A short but enjoyable sail through Fungi Passage (my favorite!) brings you to two nextdoor bays: Maho and Francis. Both are breathtaking beaches that offer protection from swell while still getting a nice breeze through the boat. Maho is also one of our best chances to swim with sea turtles! During the day, these beaches can be crowded with tourists, as there are food trucks hidden behind the first row of trees. But come evening, things quiet down and we are left with a peaceful anchorage. 

A slow evening like this is best enjoyed with a happy hour on the bow, some captain-cooked curry, and maybe even a movie night! 

Day 5:

The days are winding down…this will be our last full day on St. John. We’ll start with a lovely morning sail to Lovango Cay. This little island just off the northwest corner of St. John makes a great stop for lunch. The private resort is both high end and low profile. You wouldn’t know it was even there from the water…and that’s their goal! Lovango Resort and Beach Club has a mission of providing a luxury experience without compromising the natural beauty of the island. Treat yourself to a delicious meal in their open-air dining room steps away from the beach.There is good snorkeling around Lovango, as well. They are in the process of a coral restoration and outplanting project with the University of the Virgin Islands. 

A short sail across to St. John brings us to Caneel Bay and Solomon Bay. The Lind Point Trail brings you up and over the lively town of Cruz Bay. Or, you can opt for the dinghy ride around. Cruz Bay has two distinct spots to explore - Mongoose Junction and Wharfside Village. Take the time to wander around both, hitting up the many little shops and art galleries. A stop for vegan ice cream and popsicles at Irie Pops is always on my list. As the afternoon winds down, pick your favorite restaurant that you scoped out while exploring, and sit down for dinner on land. If you’re looking for a night out on the town, this would be the spot. There are many fun bars to hop around and get a taste of the nightlife. 

Day 6:

Sadly, today calls for our sail back to St. Thomas. We’ll first make a stop at another favorite of mine, Christmas Cove, home of the famous Pizza Pi. A nice snorkel around the rock in the middle of the cove will bring us right to the brightly painted pizza boat! Similar to Lime Out, we’ll swim up to a float and grab a menu. Soak up the sun and good island energy here amongst the other anchored sailboats. 

After lunch, we’ll leisurely sail to Charlotte Amalie, anchoring right back in my usual spot behind Hassel Island. Tonight's dinner can be spent either aboard or ashore. We’ll then finish off the trip with a night kayaking adventure! At Frenchman’s Reef (the Westin), we’ll make our way down to the waterfront. Rather than darkness, we’ll be greeted by glow in the dark face paint, glow sticks, and lighted clear-bottom kayaks. As we paddle around with the guides, the lights shining down from each kayak attract sea life. Fish, turtles, and rays glide effortlessly under the kayaks. It’s a magical experience. 

Day 7:

The very last day of your trip all depends on flight times… A walk around downtown Charlotte Amalie, a farewell lunch at Hull Bay, or a simple morning aboard Bella will bring an end to this week-long island adventure. 

So now…are you fully immersed in this island lifestyle? I hope so. Wherever you are and whatever the weather is there, just know that there’s always a good time to be had down here in the Caribbean - only a short flight away!