The United States Virgin Islands (USVI) are a group of Caribbean islands, islets and cays that are an unincorporated and organized territory of the United States; which means if you are an American Citizen, you don’t even need a passport to go enjoy these tropical places and the official language is still English (although they do drive on the opposite side of the road). The USVI includes many islands but the main islands are St. Thomas, St. John, and St. Croix and the capital is Charlotte Amalie on the island of St. Thomas.
The Caribbean is a great place to sail and we have enjoyed sailing in the British Virgin Islands may times, using St Thomas as out transition spot – flying into the Cyril E. King Airport and then taking a ferry into Tortilla. However, this year, due to the Covid-19 pandemic, we were only permitted to sail in US waters and visit islands in the USVI territory, so we took the opportunity to get familiar with the islands of St. Thomas, Great St. James, St. John and Water Island.
There are several different places to charter sailboats on the island of St. Thomas, with or without a captain and chef, depending on your sailing credentials. Since my husband and I both have taken the American Sailing Association (ASA) classes and have previously chartered sailboats, we were able to rent a Beneteau 41 with a charter company located on the west side of the island at Frenchtown Marina, adjacent to Charlotte Amalie.
The magic really begins then, when you are on board, with your provisions and settled in and you can plan your week on the water! The possibilities are endless but leave some room for flexibility because you rarely even stay with your first plan of action!

Some of the epic things about St. Thomas –
- The friendly people
- Magen’s Bay – called one of the world’s top 10 beaches by U.S. News & World Report
- The Views – especially from anyplace high up
- The food – some great restaurants in Frenchtown and Charlotte Amalie
Much of downtown Charlotte Amalie is structured with shopping and restaurants that cater to the cruise boat tourists. There is a grocery store that was helpful for provisioning our boat and we did find some great places to grab a drink and enjoy some local, fresh cuisine. In Frenchtown, there are also a few good restaurants and do not miss the Frenchtown brewery.

I think my favorite thing to do, outside of sailing and eating, was visiting Magen’s Bay on the north (Atlantic) side of the island. The drive to the bay was a highlight as the views were spectacular. The beach itself is a peaceful oasis. There are lifeguards, showers and restrooms, equipment rentals, a shop, and a restaurant. The waters are calm, and the sand is soft and white. There is a small cost per person to go onto the beach but the day that we were there is was uncrowded and tranquil – a perfect day of rest and relaxation; however, I can see that the bay might become less tranquil if there was a cruise ship(s) in for the day so you may want to plan accordingly.


From Frenchtown, St. Thomas we sailed to Christmas Cove at Great St. James Island. The mooring balls here were free and that was the problem – there was barely any room for us to even anchor – but we did and had the weather been less windy, we would taken the dingy over to snorkel at the Calf & Cow rocks, but since it was so windy we snorkeled in Christmas Cove instead and then ordered a pizza at the floating Pizza Pi sailboat- because where else can you pay $30 for a pizza and take your dingy over to pick it up?! Since we could not snag a mooring ball, we decided to sail onto the next cove to overnight. Epic thing about Great St. James? If you love salty pizza then stop by for a pie, otherwise you might choose somewhere better to enjoy your time.

The next place we arrived at was Honeymoon Beach on the island of St. John and it was gorgeous! The mooring balls around the island of St. John belong to the National Park Service, they are white with a blue stripe and are $26 per night. There is a floating dock in most of the bays (or go to the nearest one) where you can dingy up, fill out a form(take a pen), pay for your mooring ball and deposit it into a locked box. Simple. Grab several forms on your first trip and then you can have them all filled out for the next night and location. You can use cash or card.
Honeymoon beach was an epic beach with equipment and chair rentals, a tiki bar and beautiful sand and surf. There is a great trail – Lind Point Trail that connects honeymoon beach to the visitor’s center in Cruz Bay. It ascends upward to a very scenic overlook of Cruz Bay and the Caribbean Sea that is worth the short hike.



St John Island is just 9 miles long and over half of the island is taken up by the Virgin Islands National Park. There are loads of trails across the island if you want to stretch your legs after sailing. Some of the trails lead to sugar plantation ruins which are interesting to see. As far as sailing, there is not enough “sailing time” to get from place to place as the bays are close together. However, the island is beautiful, and since we had to stay in US waters on this trip, we made the most of what we had. My thoughts about St. John for sailors is that is worth a stop or two, but options are limited, and it would be a good companion to sailing to the British Virgin Islands or elsewhere in the Caribbean. The bays are quiet and geared to a self-sufficient sailor who is planning to do their own cooking. The islands are not geared to the sailing community as they are in the BVIs. It was difficult to find ice, water, gas, or restaurants near the mooring fields, except for Cruz Bay. Additionally, we received an extremely chilly greeting from Coral Bay residents, who made it clear that they did not welcome tourists.
Epic things about St. John Island –
- Maho Bay and the turtles
- Cruz Bay
- Honeymoon Beach
- The scenery
We kept our boat on its mooring at Honeymoon Beach and took the dinghy to Cruz Bay. We were told that the waters here were off limits to larger vessels and taking your dinghy ashore is your only option to visit Cruz Bay. We had a wonderful meal, did some shopping, and picked up a few things at the local grocery store. It was the most populated area on the island and loads of fun. The ferry dock is also here for those arriving from other islands, as there is no airport on the island of St. John. The people in this bay were lively and friendly and we really enjoyed our short visit at Cruz Bay. The National Park Service Headquarters are located here if you wish to stop in and gather information on the park, tours, things to see and regulations. This is also home to Customs & Immigration for those visiting the island from a foreign port. And there are plenty of place to rent a jeep if you need a day on land to drive and explore.
From Caneel Bay we sailed to Hawksnest Bay and then onto Trunk Bay to snorkel. There are plenty of inlets and beaches to explore as you head southwest via the Durloe Channel but do beware of Johnson Reef, a large reef ½ mile to the north of Trunk Bay. Next up was Cinnamon Bay and then our favorite of all – Maho Bay.
Maho Bay has 28 moorings and adjoining is Frances Bay with 29 more moorings. In Maho Bay, there is a portion of the water, between the mooring field and the shoreline where we saw 50 plus Hawksbill Turtles just swimming around and it was fabulous to have the opportunity to swim near them. Of course, it is against the law to touch them, as they are protected, but you are really close, and the water is clear, and it was one of the highlights of our trip. Make sure to bring a snorkel mask and swim parallel to the shoreline. We also saw a large starfish on the bottom of the sea and tons of other fish. The beach here is beautiful and across the street there is equipment rental and a tiki bar and food truck called Crossroads. (Make sure to bring shoes on land to walk to Crossroads as the road itself and the sand was extremely hot.) It all closed at 4 pm when we were there - so check the times. We spent more than a few hours here in the shade trying delicious sandwiches and cocktails. There is a small gift shop here but no ice or groceries.

The area also has some great hiking trails nearby. We attempted one but gave up quickly in the heat. However, we did walk south along the road and up the hill overlooking the mooring field and water and were rewarded with an amazing view and photo opportunity!

At Leinster Bay you can snorkel at Waterlemon Cay or take a short hike on the Leinster Bay Trail up to the Annaberg sugar planation ruins. It is worth the trek to see the ruins and the view from the top of the hill. Before the USA purchased the island from Denmark in 1917, raising sugar cane, harvesting it, and then transporting it to the mill was the labor of the land. Once at the mill the sugar cane was crushed between rollers and the juice would flow downhill in wooden troughs to the boiling room where slaves would ladle the hot sugar cane liquid from kettle to kettle, gradually concentrating and purifying the boiling liquid. Then it would then be poured into flat pans where it was left to cool and crystallized into sugar. In 1848, the slaves staged an uprising that ushered in the end of slavery and the production of sugar cane.

After sailing around the island, we arrived in Coral Bay. The best thing about this unwelcoming bay was a floating restaurant called “Lime Out”. We anchored the boat and tried to explore ashore but quickly gave up on being on land, although we did manage to get some ice and water before leaving. Instead we drove our dinghy to “Lime Out” and ordered our tacos to go! Although they were probably one of the most expensive tacos you will ever order (at $12 each) they might have been some of the tastiest and they had lobster, shrimp, and fish tacos among the choices.

We had planned to find an overnight mooring in Salt Pond Cay but we warned by several different sources that the bay had been the target of thievery and so we sailed on and picked up an overnight mooring ball in Great Lameshur Bay instead. It was a quiet and pretty bay and had some good snorkeling but there is nothing else there, so make sure you have your dinner provisions on board.

The next morning, we sailed back towards St. Thomas and headed to Water Island. Water Island lies south of St Thomas in the Charlotte Amalie harbor. The island is less than 500 acres and is a residential island. The main attractions are beaches including Honeymoon Beach (not to be confused with the Honeymoon Beach on St. John island), Limestone Bay, the plantation ruins and Fort Segarra.
Honeymoon Beach was our destination. There are no mooring balls available here (any of the ones in the harbor are private only) but it is a secure place to anchor and a great place to spend a beach day. Dinghy’s Beach Bar is the local and visitor hangout and we met lots of fun people! They offer a large menu of drinks and food and there is even a little store. You can rent water equipment, chairs, or enjoy the floating bar or relax in a shaded hammock. They often host live music, and you can play horseshoes, volleyball, or cornhole. If you are bringing the ferry over from St. Thomas, they also offer complimentary shuttles from the ferry dock to the beach. It was a perfect island beach day!

Helpful Hints:
*If you are planning a trip to sail in the USVI or the BVI, I highly recommend picking up a copy of the Cruising Guide by Simon Scott. As the book says – it is a “complete guide for yachtsmen, divers and watersports enthusiasts”. Additionally, it is updated regularly so make sure you get the most current edition.
*Check to make sure that the charter company will provide snorkel masks. Ours provided fins but we had to bring our own masks. The Caribbean is a great place to experience the underwater world so don’t forget to bring a mask. And lots of sunscreen!
*There were a lot of sea urchins in the waters around St. John so make sure you are mindful of where you may be stepping on the sea bottom.
*If you are sailing, make the USVI a small portion of your trip – or make it a shorter trip. A week is more than enough time to see everything and if you are sailing for a week, the majority of your time would be better spent in the BVIs.
Overall – Do not miss out on an opportunity to experience sailing in the Caribbean. The trade winds, warm waters, the amazing snorkeling, and white, sandy beaches make it an epic adventure!