Sailing the Virgin Islands

Since I was a little girl I have spent many winters in the US and British Virgin Islands (USVI and BVI). I have seen resorts destroyed from hurricanes and rebuilt by the community. The Islands continue to develop while holding true to the Caribbean culture. I have memories as a little girl sitting on the beach as local women braided my hair. The locals are proud and welcoming to assist tourists with questions and recommendations. Here is my personal guide to sailing the Virgin Islands.

Little me with a pacifier in the islands.

The best time to visit is between February and April, after May the weather gets warmer and hurricane season approaches. My most recent trip was in February 2024, we stayed on a sailboat and sailed from island to island. This is the best way to see more islands and explore less populated beaches. If you want to travel the BVI’s you will need to bring your passport and stop at customs in Road Town. However, if you would prefer to stay in the USVI’s there is plenty to explore in St. John. Sailing gives you the flexibility to decide how long you want to stay in one spot. If you are curious about chartering a sailboat I would look into The Moorings, they are beginner friendly and offer captains for non-experienced sailors.

A sailing trip to the Virgin Islands is full of adventure and sandy beaches. The winds and weather are mild during season making sailing enjoyable. Staying on a sailboat is a unique experience that allows you to see more along the coast. This trip is for those that are looking to go with the flow and soak up the sun.

St. Thomas

We flew into St. Thomas airport and took a shuttle taxi to meet the boat at Yacht Haven Grand. Along the marina dock there are shops and restaurants to explore. Cruise liners come and go in the bay bringing a more touristy crowd of people and restaurants. For the coffee shop lovers like me I recommend getting a latte and pastry at Stir It Up Coffee Shop & Bakery. In Yacht Haven Grand there is a grocery store to gather provisions for the boat. It is the best one in the area, however the prices can sometimes be more expensive. This is one of the best spots to find produce, once you head to smaller islands it can be harder to find a grocery store with a wide selection. From St. Thomas we sailed over to St. John.

Yacht Haven Grand

upSt. John

My favorite spot in St. John is in Caneel Bay. You can find sandy beaches along the coast and sea turtles. There is some good snorkeling along the rocky shore, but more of a place to swim to the beach and get a drink. From here you can dinghy to Cruz Bay where there are many restaurants and shops. For a local BBQ meal go to Uncle Joes Cafe near the customs and border office or The Roti King a couple blocks up the hill. Looking for a coffee shop I recommend stopping at Downtown Sips, where you can find an assortment of teas and coffees along with wines and cocktails. Walking through the streets there are many gift shops, along the water you will find jewelry, clothing, and food. For dinner I recommend getting reservations up the hill at Extra Virgin Bistro. I still think about how wonderful the wild mushroom pappardelle was and recommend giving it a try if you enjoy mushrooms. From Caneel Bay we made our way over to Maho Bay.

Mushroom Pappardelle

Maho Bay is a great spot to snorkel with the turtles. From the shore there are hiking trails and one beach bar. The hiking trails are a mix of walking on the road and gravel paths. I recommend going inland for hiking to see some of the history of the island. There are also car tours that you can schedule from cruz bay to take you around the island. Heading into the BVI’s we made a stop at The Indians to snorkel. This is one of the best places to snorkel and scuba dive, it is a coral reef along boulders north of Norman Island.

The Indians

Jost Van Dyke

This island in the BVI’s is for the party people. It has two well known bars to stop in for a drink and food. Foxy’s has been around since I was a little girl and has a local feel to it with music at night and occasional buffets during the weekend. At Foxy’s you feel the energy of the island. Down the road from Foxy’s are a few restaurants for casual bites.

At White Bay you will find a more refined beach location with some hotels with beach access. Along the beach is Soggy Dollar Bar, this place has great food and drinks to be enjoyed on the beach. You are sure to meet a friend or two to share a drink with on this island. From here we took a day sail to Virgin Gorda.

Foxy’s Bar

Virgin Gorda

As you sail toward Bitter End you will pass Virgin Gorda where Richard Branson has a home. We found a mooring near Saba Rock Resort which has recently been remodeled and a great place to explore. The Bitter End Yacht Club is a classy location with a long sailing history. They have multiple bars and restaurants with a small foods store. The wind blows through these islands making it a popular location for wind surfing and kite surfing.

The islands are a great vacation that is family friendly and culturally rooted. You can find new restaurants every year and stop at all the sandy beaches that have been enjoyed for ages. Let me know if you sail in the virgin islands and what your favorite stops are!

Sunset at Bitter End