Virgin Islands Sailing Itineraries
Virgin Islands sailing itineraries are flexible and tailored to your group’s unique preferences. Whether you dream of lounging on secluded, turquoise-water beaches, exploring vibrant marine life, diving into thrilling water sports, immersing yourself in the rich local culture, or enjoying the perfect mix of it all, we’ll design an unforgettable experience just for you.
Here is a popular itinerary for a glimpse of the adventures that await
Day 1: Exploring Virgin Gorda and The Baths
Explore the giant granite boulders at The Baths - The ancient formations of The Baths, carved by eons of water movement evoke the timelessness of this special place.
Take a moment and enjoy Devil’s Bay Beach.
Enjoy a long walk on the beautiful Valley Trunk Bay Beach or Savannah Bay Beach, depending where you rest for the night.
Snorkel the reef in Savannah Bay Dinner at Coco Maya, or cocktails and dinner onboard your yacht.
Day 2: From the Baths to North Sound, Virgin Gorda
Enjoy the quiet wonder of a yatcht under sail. We will make our way to the protected anchorages of Virgin Gorda’s North Sound. The area offers several island-based nightlife options, including the luxurious Oil Nut Bay, the all-new Saba Rock, and The Bitter End. For younger guests and children, the famous Michael Bean show at Leverick Bay Marina is always a fan favorite.
Enjoy kiteboarding, snorkeling, and epic views from Hog Heaven or, if preferred, the secluded anchorage at Eustatia Island.
Day 3: Anegada Getaway. Sailing, Sand, and Sunset Vibes
In the morning we will set sail to Anegada! Widely considered the best sail of any charter to the Virgin Islands. A reasonable travel distance (about 2 hours) makes for one of the best answers to the question of why to charter a sailing vessel. We will have breakfast underway so we can have as much time to spend exploring the charm of Anegada. Upon arrival in Anegada, we recommend guests rent “Mokes”, a cross between jeeps and golf carts.
The Mokes are the best way to explore and visit the many beaches and bars located along the coast of Anegada. Built up entirely of coral and limestone, Anegada is surrounded by shallow reefs, making for a truly authentic Caribbean experience on shore.
Along with the rare landscapes and a local population of flamingos, you’ll find some of the most eclectic bars the Virgin Islands have to offer! From luxury cabanas at the Anegada Beach Club to the laid-back island style of Tipsy Bar, you’re sure for some fun!
Being the home of the famous Anegada lobster, we strongly recommend guests go ashore for dinner and try this delicacy done right. Afterwards, guests can then move over to Potters by the Sea for some music, dancing, and limbo!
Day 4: Anegada to Sandy Spit/Sandy Cay
Great sail with time to chill in the afternoon
Enjoy the “Robinson Crusoe” feel of Sandy Spit, the beautiful blue water and white sands of the island.
Enjoy a casual evening at Beeline Bar.
Day 5: Sandy Spit to Jost Van Dyke, then to Norman Island
We will head to the world-famous Soggy Dollar bar on Jost Van Dyke. Your troubles will seem worlds away when you take your first sip of a soggy dollar painkiller and look upon the crystal-clear waters and white sand beaches of JVD.
Enjoy the company of the many visitors to this famous spot and even have friends and family back home buy you a drink via their live streaming video channel. Sun, fun, and games are the mainstay of a day on Jost Van Dyke.
Option to move to Norman Island mid afternoon.
Snorkel at The Indians and The Caves — famous underwater caves and coral formations. Party at Willy T’s floating bar (if you dare!)
Beautiful calm anchorage under the stars.
Option for cocktails or dinner at The Bight.
Day 6: Norman Island to Cooper Island and Marina Cay/Scrub Island
Morning sail via Peter Island and a stop at Cooper Island and the famous Rum Bar
Post lunch sail over to Marina Cay /Scrub Island.
Enjoy a snorkel at Diamond Reef or an afternoon at the pool on Scrub Island.
If it’s around the full moon, catch a Trellis Bay Full Moon Party!
Day 7: Farewell from Trellis Bay, Beef Island
After breakfast and the opportunity for one more snorkeling, we will head to Trellis Bay, where our journey ends (this time).
At Trellis Bay, guests will be able to hop a taxi and arrive the Beef Island Airport in 5 minutes.