Sample Itinerary for a 7-night USVI Charter

Updated: Mar 14

Visiting St Thomas, St John, and Water Island


Day 1 – Welcome aboard LUNA. We will meet in Charlotte Amalie, St. Thomas. After safety briefing and introduction to the yacht, we are ready to start our sailing adventure!

Just a short sail towards the South East of St Thomas is the idyllic Christmas Cove, a sheltered oasis on Great


St. James Island. Relax aboard or enjoy a nice swim and snorkel; sea turtles and other magnificent marine animals live abundantly in the surrounding waters. Christmas Cove is also home to the famous Pizza Pi, a floating restaurant serving NY style pizza. Jump in the crystal-clear water while we prepare cocktails and hors d’oeuvres, followed by a delicious dinner. Overnight in Christmas Cove.



Day 2 – After breakfast, we will set sail St. John, the smallest of the three main US Virgin Islands. Our first stop will be at Trunk Bay. Home to some of the bluest waters in the Caribbean, Trunk Bay is the crown jewel of the Virgin Islands National Park.

This heart-shaped bay is arguably one of the most beautiful beaches in the world; it is a photogenic paradise! After a nice swim in these beautiful waters and lunch, we will continue to Sir Francis/Maho Bay. This bay is one of our favorites. It is calm and protected and has a long, beautiful white sandy beach. Seagrass beds in this shallow bay provide food for green sea turtles, which are often seen early in the morning and late afternoons. Feel like exploring ashore? Take a stroll on the beach or explore the nearby salt pond. Come back to LUNA for cocktails at sunset and a gourmet dinner. Overnight at Sir Francis Bay.



Day 3 – Wake up to the aroma of coffee and enjoy a delicious breakfast with the freshest of local tropical fruits. After breakfast, we are ready to untie the lines. After a short sail to the

East, we will arrive to Leinster Bay, home to the famous Waterlemon Cay, named one of the top snorkeling spots in the Virgin Islands. This calm and protected bay is also perfect for paddle boarding and kayaking. After some fun in the water and lunch, we are ready to explore ashore. Two-thirds of the island of St John is designated as a national park and is managed by the VI National Park system. There are many well-marked and maintained hiking trails. One of the trails you can check out from Leinster Bay is the Annaberg Historic Trail. This is an easy and beautiful trail, most of the time you are walking right next to the water’s edge. You will get to see the ruins of an 18th and 19th century sugar factory from the Danish plantation era when sugar dominated the island. Also, from the top you can enjoy amazing views of the bay and neighboring islands. If you are lucky you might even spot deer or two along the way. Returning to LUNA, cocktails and nibbles will be prepared on time to see the stunning sunset. Overnight in Leinster Bay.



Day 4 – Ready to take on a new day! After a fresh and energizing breakfast, we are ready to sail to the southeastern side of the island to Coral Bay.

This popular beachside town offers plenty of charm to out of town visitors. It’s off the beaten path; the beaches here are quiet, serene and uncrowded. There are several small and protected bays, it is perfect place to have fun with the water sports while enjoying nice views. We have the option to stay at Salt Pond, Lameshur Bay or Hansen Bay. Those wishing to check out another hiking trail can visit Rams Head or the Reef Bay Trail to take a look at the petroglyphs carved in the rocks by the taino indians living on the island around AD 1080-1500. Explore the amazing scenery while we prepare cocktails and hors d’oeuvres, followed by a delicious dinner. Overnight in Coral Bay area.



Day 5 – Breakfast is followed by a quick look at where we’ve been and where we’re going with a chart briefing from Captain Nim. Today we are off to Caneel Bay and Honeymoon Beach, it’s going to be a beautiful downwind sail along the coast of St John. We are headed to a picture-perfect white sandy beach where you can enjoy a nice swim or snorkel next to the shore and spot stingrays, turtles, lots of sergeant majors, parrot fish, tangs, and other abundant marine critters. After a delicious lunch aboard, we can take you for a dinghy ride to Cruz Bay, the active yet laid back main town on St. John and a good place to check out for souvenirs. Have a great afternoon stroll through the nice shops and bars in this cute village before your dinner is served on board. Overnight in Caneel Bay.


Day 6 – Wake up to another tasty fresh breakfast. Then we set off for beautiful Magens Bay on St Thomas. Magens Bay is a scenic haven of calm waters and secluded shoreline, perfect for getting in the swing of island time. We’ll pick our place for the day and enjoy lunch aboard. Paddle board around the bay, relax on the remote beachfront, or enjoy a famous banana daiquiri in the place where it originated.

Magens Bay is the most popular beach in St. Thomas and one of the top 10 beaches in the world as named by National Geographic. Featuring almost one mile of soft white sand, Magen's Bay is also home to some magnificent mountain views. Back on board for afternoon cocktails and nibbles, followed by dinner, you know you’ll be in for a treat. Overnight in Magens Bay



Day 7 – Today, after a delicious breakfast, we will go on a scenic sailing trip around St Thomas. As we circumvent the island, we will enjoy the beautiful views through the cut of Hans Lollick and Little Hans Lollick and continue our journey sailing West passing by the Savana Passage to our final destination, Water Island. This picturesque island is the smallest of the US Virgin Islands, it is three-quarters of a square mile in size, and was named by the European settlers because it has lots of fresh water, which was lacking on many of the nearby islands. We will anchor in Honeymoon Beach, a white sandy beach with calm waters and palm trees.

You can enjoy a nice swim or snorkel right off the beach. There are coral reefs, sea turtles swimming and iridescent fish summoning you to the water. On a clear day you can see Puerto Rico off on the horizon. Returning to LUNA, cocktails and hors d’oeuvres will be ready to enjoy a magnificent sunset, followed by dinner. Overnight in Water Island.

Day 8- After breakfast, we will set sail to Charlotte Amalie, St. Thomas. This will be the last stop of the trip and where we will say “until we meet again”.


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