St Thomas (USVI) Sailing Itinerary

We are no longer operating in St. Thomas, however, our British Virgin Islands base is only a short island hop away.

A St Thomas Crewed yacht charter offers the very best service from your professional captain and chef, as well as the opportunity to experience the very best sights and sounds of two beautiful Caribbean destinations – the US Virgin Islands and the British Virgin Islands. These turquoise waters are just waiting to be explored!

Choose Itinerary

St. Thomas Crewed Charter – Popular 7-Day Itinerary

Day 1

Christmas Cove

Just off the eastern coast of St. Thomas sits Christmas Cove, a sheltered oasis on Great St. James Island. Sea turtles and other magnificent marine animals live abundantly in the surrounding waters. That, combined with the ocean clarity make for the most spectacular snorkeling experiences.

Mooring

Anchoring is only allowed where seagrass and coral are not present. Moorings for a fee are plentiful, but get there early. You can find all the details on mooring and anchoring here: https://www.vinow.com/travel/marinas-anchorage-sites/

Things to do

Float atop the clear blue waves or dive below and swim with sea turtles, stingrays and other majestic marine life. Relax on the secluded shore or take the dinghy to Pizza Pi, a one-of-kind sailboat serving up some of the Caribbean’s best pizza. And if you stick around until sundown, nothing compares to basking in the orange glow of the horizon as the night sky sets in.

Facilities

Restaurants – Resorts

Yacht Haven Grande or Christmas Cove

For 6pm check-in- Overnight at Yacht Haven Grande- AM boat briefing. Unwind at Twistt, Enkai or Navy Beach on premise or head to French Town (5 minutes away by car) for dinner.

*OR* 12pm Check-in & provisioning before setting sail to Christmas Cove. Christmas Cove is a popular stop with a panoramic view of the surrounding island keys. Conveniently located between St. Thomas and St. John, it’s a great introduction to the surrounding areas. It’s also the home of our locally famous “Pizza Pi” boat!

Day 2

Caneel Bay

Located in the Virgin Islands National Park, Caneel Bay is a sandy crescent shaped beach offering a relaxing ambience with upmarket amenities. It is one of the first beaches you come to as you drive up North Shore Road out of St. John’s main port, Cruz Bay.

Mooring

Anchoring is not allowed here. Secure a NPS mooring ball (white ball w/ blue stripe) for $26 cash per night.There are 20 mooring balls available, so get there early if possible. Fee is paid at the floating fee station.

Things to do

Take the dinghy to over and explore Saloman Bay Beach, an excellent snorkeling spot. After a day relaxing, head to Zozo’s, where you can enjoy a luxury setting with restaurant and bar, booking is preferred but not essential.

Facilities

Bar, restaurant, laundry (at Caneel Bay resort) BAR AND LAUNDRY NOT OPEN TO PUBLIC- CANEEL GUESTS ONLY

Christmas Cove to Caneel Bay (Cruz Bay)

Head to Caneel Bay or Honeymoon beach. Honeymoon beach is right around the corner from Cruz Bay. Cruz Bay is the main town of St John and has a couple of supermarkets and everything you would need to stock up. Cruz Bay is also a great place to pick up anyone from the ferry from St Thomas to St John. Feel free to dinghy into Cruz Bay from Caneel Bay for restaurants, shops and bars, including the popular restaurant ZoZos – perfect for sundowner cocktails. There are national park mooring balls here as well.

Day 3

Trunk Bay

Home to some of the bluest waters in the Caribbean, Trunk Bay is the crown jewel of the Virgin Islands National Park. Trunk Bay is a photogenic paradise that even features 650 feet of underwater trails with signs for the most remarkable swimming and snorkeling experiences. This heart-shaped bay is arguably one of the most beautiful beaches in the world.

Within a protective cove, you will find Maho Bay. With long seagrass, Maho Bay is great for seeing turtles whilst snorkelling. North of Maho Bay and less popular (however just as beautiful) is Francis Bay. If you are looking for a more laid back atmosphere Francis Bay is the perfect spot with turquoise blue waters and the breathtaking mountainous backdrop of St John.

Cinnamon Bay Beach is ranked as one of the most beautiful, pristine beaches within the Virgin Islands National Park. Enjoy 1/2 mile long of white sand dotted with stunning coconut palm trees, and plently of cays to explore for snorkellers. You may even spot a turtle or stingray, as well as colourful fish.

Mooring

Anchoring is not allowed here. NPS moorings ($26) are available but not plentiful, so get there early.

Things to do

Enjoy the underwater trails by swimming or snorkeling your way through the breathtaking blue water or bask in the Caribbean sun on the white sand beach.

Snorkelling, swimming ,kitesurfing, paddle boarding, windsurfing, hiking

Facilities

Restaurants – Retail shops – Picnic areas – Restrooms and showers – On-duty lifeguards – Snorkeling gear rentals -taxi

Trunk Bay; Maho Bay & Cinnamon Bay

Next stop the famous Trunk Bay! Trunk Bay has a bar, food truck, and music daily. The white powdery sand on Trunk Bay makes the shoreline top-tier. With a food truck, bar, rental shacks and restrooms available, Trunk Bay is equipped for a family day. With Trunk Cay just off of the beaches shore, the snorkeling experience here is breathtaking during peak seasons for marine life.

Experience the dense greenery of Cinnamon Bay. Known for its hiking trails and campgrounds, Cinnamon Bay provide all elements of what an island has to offer. While there, it’s very likely that you may encounter mongoose and deer that have taken up residence on the plush beach. You also have the option of renting water sports equipment and snorkel gear.
Head over to Maho/ Francis Bay where you can pick-up a national park mooring ball for the night. The popular Maho Bay has gained notoriety because of the pristine water. Depending on the season, sightings of ray, starfish and sea turtles are a must! You’re welcome to paddle board or swim to shore where you will find a bar, food truck, and gift shop. When taking your party to shore via dinghy, please use red and green channel markers & blue mooring balls. However, from the swim only zone, you are NOT allowed to dinghy into the beach. There are small blue shallow water mooring balls for dinghy use.

Day 4

Leinster Bay

Snorkeling in the USVI is fairly exceptional overall, but rocky windswept Leinster Bay is the #1 snorkeling spot in St. John. TripAdvisor even named this area, in conjunction with Waterlemon Cay, the #1 St. John attraction for travelers because there’s a little something for everybody.

Mooring

Anchoring is not allowed here. NPS moorings ($26) are available but not plentiful, so get there early.

Things to do

The must-do activity in Leinster Bay is snorkeling because of the abundant marine life and fringing reefs. Sea turtles, rays, and colorful fish are spotted often along with bright and beautiful corals. On land, explore over 30 different trails along Leinster Bay Beach and see the historic Annaberg Sugar Plantation Ruins along the way.

Facilities

No facilities for yachts are available.

Leinster Bay

Feel free to check out Francis Bay (for less traffic and short hiking trail) &/or Whistling Cay (for advance snorkeling) on your way to Leinster Bay which would be our recommendation for an overnight stay. Leinster also has great snorkeling around Watermelon Cay and short hike to Annaberg Plantations ruins.

Day 5

Coral Bay

This popular beachside town offers plenty of charm to out of town visitors, but it is also a haven for many former U.S. residents. Coral Bay is an eclectic community that thrives on the true island living experience. Known by locals as the more quaint and quiet version of Cruz Bay, this is the perfect place if you want something fun to do inland, but don’t require the features of a big city. Not to mention, Coral Bay was ranked number four by The New York Times on their list of best places to go.

Things to do

Head to Drunk Bay Trail for some unbelievable hiking, or hit up Carolina Corral so you can soak up the majestic scenery while horseback riding. When it’s time to eat, choose from a number of unique restaurants such as Skinny Legs, The Tourist Trap, Miss Lucy’s, or Shipwreck Landing. Engage in some island retail therapy because Coral Bay is famous for its funky shops. You can even shop for groceries here if you so choose. You also have the option of snorkelling during your Coral Bay visit. Simply swing by Crabby’s Watersports to rent your gear. The most prominent landmark in Coral Bay is the Emmaus Moravian Church, which is part of the list of registered historical place in the US Virgin Islands. The church is said to be haunted because of the double murder that occurred at the neighbouring Carolina Estate plantation in 1733.

Facilities

Restaurants – Bars – Grocery stores (three) – Shops – Watersports rental – Mall – Mail centre

Day 6

Magens Bay

Located in the north shore of St Thomas, Magens Bay is about one mile long. As this beach is one of the most popular in St Thomas, it does get busy so the best times to visit are morning and late afternoon if you want to avoid the crowds.

If you woud like a break from the beach, you can hike a nature trail. Amongst the mangrove trees, you may spot exotic birds and flowers.

Mooring

Anchoring (left side outside of swim zone)

Things to do

Kayak around the bay, relax on the remote beachfront. For a more active Magens Bay experience, learn about the island’s history while taking in the tropical scenery during a guided walk along tjhe water or an eco tour. Or take a taxi to Estate St. Peter and get your thrills by zooming along the Tree Line Extreme zip line.

Facilities

Public restrooms & showers – Snack stands – Bars – Souvenir shops – Recreational rentals (paddleboards, kayaks, snorkeling gear, floats) – Beach rentals (towels, lounge chairs, lockers); taxi

Magens Bay

Magens Bay is a scenic haven of calm waters and secluded shoreline, perfect for getting in the swing of island time. Kayak around the bay or relax on the remote beachfront. 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 for locals and visitors to enjoy year-round, Magen’s Bay is also home to some magnificent mountain views. This public beach offers calm waters perfect for swimming, as well as on-duty lifeguards, concessions, and paddleboard rentals. The waters are clear, but the sandy ocean bottom is not ideal for snorkeling. For a rejuvenating retreat, escape to the Discovery Nature Trail to explore the coconut grove, mangrove, and arboretum.

Day 7

Druif Bay

Enjoy snorkeling with turtles, relaxing on the beach or grab some drinks and food at Dinghys beach bar. Golf carts are also available for rent to drive around the island. Be sure to eplore the historic fort and enjoy the scenic view.

Mooring

Anchoring is only allowed where seagrass and coral are not present. Moorings for a fee are available.Ask for mooring Ball info at check-in as all mooring balls are private.

Things to do

Select the perfect patch of white sand and temporarily settle into your very own sunbathing sanctuary. Go for a refreshing swim in the surf-free ocean or enjoy snorkeing your way through the clear blue water and colorful coral reefs. With the palm tree scenery and the sparse beach population, take advantage of this incredible photo opportunity.

Facilities

ATM; Restaurant & bars; taxi; Recreation rentals (kayaks, stand-up paddleboards, beach chairs); Dingy’s -Dingy’s offers drinks and nice fresh food (tuna ceviche was a must!)

Druif Bay

Nestled between iconic palm trees and crystalline waters, and lined with quaint palm frond huts, this beach on Water Island just south of St. Thomas is arguably one the most peaceful places in the USVI. For a dose of local history, take the short trip south and visit Fort Segarra, a tunnel-filled underground fort built by the U.S. during World War II.

Back to Top