USVI Sailing Vacation

Check Out These Must-Visit Local Hot Spots On Your Next USVI Sailing Vacation

If you’ve started researching where to go on a USVI sailing vacation, you may already have the big picture in mind: celebrated turquoise waters, up-close views of marine life, and exquisite Caribbean cuisine. 

Plus, you likely know this group of islands is a U.S. territory, meaning you can enjoy this side of the Caribbean without your passport, making it effortlessly accessible. But what truly sets a USVI sailing vacation apart?

Speaking from experience as the team at Waypoints Yacht Charters, what makes the U.S. Virgin Islands so special is what you get from visiting Saint Thomas, Saint John, and Saint Croix during a single luxury sailing vacation. 

In addition to what each island is broadly known for – from Saint John’s more natural side to Saint Croix’s historical background and Saint Thomas’s blend of culture and shopping – each has hidden gems, beautiful beaches, and history that turn a regular sailing adventure into something much more special. 

Whether you’re looking to unwind on secluded beaches, indulge in Caribbean cuisine, or experience the local culture, these islands have plenty to offer. Below you’ll find five of our favorite spots to visit from each of these beautiful islands. 

Where To Go In Saint Thomas

Saint Thomas, acclaimed as the shopping capital of the Caribbean, attracts many visitors each year with the promise of duty-free shopping amongst a gorgeous beach-laden backdrop. 

But beyond the glittering storefronts, the island’s laid-back lifestyle and the warm hospitality of its people are the true gems. Saint Thomas blends cosmopolitan allure with tropical splendor, catering to those who seek the finer things in life along with the simplicity of island living, alongside some of those unmistakable island flavors like fish and fungi, callaloo stew, and pates.

The island houses historical treasures such as Fort Christian, built in 1680, the second-oldest synagogue in the Western Hemisphere, and the childhood home of Danish-French Impressionist painter Camille Pissarro.

In addition to a walk through the past, there’s also plenty to do in the here and now on an island known for scuba diving, golf courses, beaches, and nightlife. 

5 Local Spots To See In Saint Thomas

To help you plan your visit, let us guide you to five of Saint Thomas’s best local spots each offering a unique perspective on this lovely island.

  1. Magens Bay

Renowned for its heart-shaped shore and crystalline waters, Magens Bay stands out as one of the world’s most beautiful beaches. Whether you’re here to sunbathe on its white sands or kayak its gentle waves, Magens Bay provides an ideal setting for a day of peaceful indulgence.  

  1. Lindquist Beach

A hidden gem among Saint Thomas’s coastal treasures, Lindquist Beach is celebrated for its unspoiled beauty and quiet atmosphere. The clarity of its turquoise waters makes it perfect for snorkeling or simply enjoying a peaceful swim in a picturesque setting.

  1. Christmas Cove

For the sailing aficionados and marine life enthusiasts, Christmas Cove on Great Saint James Island is a prime spot. Accessible only by boat – and a must-visit for any luxury yacht charter – this anchorage is famous for its snorkeling and underwater life. 

When you finally surface, don’t forget to give Pizza Pi – the Cove’s floating pizza boat – a try! 

  1. Skyride to Paradise Point

Ascend to stunning heights on the Skyride to Paradise Point, a gondola that lifts you 700 feet above the town of Charlotte Amalie. 

At the top, panoramic views of the Caribbean await, alongside a café where you can sip tropical drinks and savor the vista that stretches before you.

  1. Fort Christian

Built in 1680, Fort Christian is the oldest standing structure in the Virgin Islands, offering a glimpse into the island’s colonial history. The fort now houses a museum with artifacts that tell the tale of Saint Thomas through various epochs—from Danish settlers to the present day.

Where To See Saint John’s Natural Beauty

Saint John, the smallest of the U.S. Virgin Islands, boasts some of the most spectacular natural environments in the Caribbean. With more than two-thirds of its land preserved within the Virgin Islands National Park, this island is a sanctuary for flora and fauna, and its protected status maintains the beauty of its landscapes. 

The crystal-clear, turquoise waters around Saint John are not only a snorkeler’s paradise but also a great spot to see sea turtles and rays glide over coral reefs bustling with colorful marine life. 

There’s plenty of adventure to be had on land, too, with over three dozen trails crisscrossing the lush 5,500-acre park. Saint John’s quiet, crowd-free, white-sand beaches are the ideal Caribbean beach experience, one made even more luxurious when you arrive by yacht.

5 Local Places To Enjoy in St John

For those drawn to both relaxation and exploration, let’s take a look at five of Saint John’s must-see local places.

  1. Cruz Bay

Cruz Bay, the gateway to Saint John and its main port, is a bustling hub that offers a variety of fine dining and local shopping, framed by stunning ocean views. 

Its friendly atmosphere is perfect for strolling along beachfront promenades, sipping on your new favorite cocktail, or browsing through locally made crafts and artwork.

  1. Caneel Bay

Caneel Bay is an exclusive beach known for its luxurious, low-key vibe and historically significant sugar mill ruins. 

The bay’s clear, calm waters are perfect for snorkeling, with sea turtles and colorful fish frequenting its coral reefs. 

  1. Trunk Bay

Trunk Bay, often listed among the world’s top beaches (and currently ranked #1 on the World’s 50 Best Beaches), is famous for its underwater snorkeling trail and postcard-perfect views. Its well-maintained facilities, including a visitor center and snack bar, make it ideal for families. 

The clear waters and educational snorkel trail provide an engaging way to meet sea turtles, fish, and other marine life as they dart through coral formations that make this bay a jewel of the Caribbean.

  1. Cinnamon Bay

Cinnamon Bay offers an adventurous blend of outdoor activities amidst historical landscapes. The beach is lined with extensive hiking trails that lead to ancient petroglyphs and sugar plantation ruins. 

  1. Coral Bay

Coral Bay, on the eastern side of Saint John, contrasts Cruz Bay with its laid-back charm and slower pace of life. 

This small community is surrounded by rolling hills and coral reefs, offering opportunities for kayaking, sailing, and diving. Local bars and eateries serve up fresh seafood and live music, embodying the spirit of island life away from the more tourist-heavy areas.

Immerse Yourself in The History of Saint Croix

Saint Croix, the largest of the U.S. Virgin Islands, is alive with history. Its layered past is evident in the varied flags it has flown—Spain, The Netherlands, England, France, the Knights of Malta, and Denmark—each leaving an imprint on the island’s culture and architecture. 

The northern shore’s Christiansted, once the capital of the Danish West Indies, is sure to charm with its 18th-century butter-colored buildings topped with red roofs and its stone-paved streets. Meanwhile, its twin city, Frederiksted, features a fort that recalls tales of protection from pirates and rival nations.

Saint Croix is also full of natural beauty, from lush rainforests, serene beaches, and plenty of ways to enjoy them with recreational activities. The ruins of sugar and cattle estates offer a glimpse into the island’s agrarian past, while modern attractions such as resorts, fine dining, casinos, and golf courses provide contemporary luxuries. The arts thrive here, with unique crafts, music, festivals, and cultural events that showcase the island’s rich heritage and community spirit.

5 Great Finds To Visit In Saint Croix

As we explore Saint Croix further, let us guide you to five of its hidden gems.

  1. Cane Bay Beach

Cane Bay Beach is widely recognized for its world-renowned diving opportunities, particularly the famous “Wall,” which plunges over 3,000 feet into deep blue waters just a short swim from shore. 

The beach itself has clear, calm waters perfect for swimming and snorkeling. Onshore, visitors can relax under the shade of sea grape trees or enjoy the local bars and eateries that offer stunning views of the ocean.

  1. Christiansted National Historic Site

Explore the history of Saint Croix at the Christiansted National Historic Site, where colorful Danish colonial buildings line the streets. 

This historic district includes several preserved structures such as Fort Christiansvaern, the Danish West India & Guinea Company Warehouse, and the Steeple Building. The site offers a glimpse into the island’s colonial past and its role in the transatlantic trade.

  1. Frederiksted Pier

Frederiksted Pier is not only a scenic spot for a stroll but also an exceptional location for snorkeling and diving. The pier’s structure hosts a variety of marine life, making it a popular spot for underwater photographers and marine enthusiasts. 

During cruise ship season, the town of Frederiksted comes alive with music, craft markets, and cultural performances.

  1. Estate Whim Plantation Museum

For more of Saint Croix’s history, head to the Estate Whim Plantation Museum, the only sugar plantation museum in the Virgin Islands. 

This preserved estate offers a real look at plantation life with its restored great house, sugar mill, and slave quarters. The museum hosts various cultural events and workshops that celebrate Crucian heritage, providing an educational experience in a historic setting.

  1. Jack and Isaac Bays Preserve

For those seeking tranquility and natural beauty, Jack and Isaac Bays Preserve is home to some of the most undisturbed coral reefs in the Caribbean, providing excellent snorkeling in crystal-clear waters. 

The preserve is also a nesting ground for leatherback, hawksbill, and green turtles, offering a rare opportunity to witness these majestic creatures in their natural habitat.

Book Your Next USVI Sailing Vacation With Waypoints Yacht Charters

From secret anchorages to the finest dining establishments, there is so much to discover in the U.S. Virgin Islands. The best way to experience what these islands have to offer is aboard a luxury yacht charter. At Waypoints Yacht Charters, we provide an unmatched level of elegance and exclusivity that you deserve.

Our fleet features immaculately maintained yachts and we pride ourselves on offering a service where every detail is curated to your comfort. From the moment you are greeted by our professional staff, you will feel the difference that a premium yacht charter company offers. 

Ready to experience everything the USVIs have to offer? Let our Waypoints Yacht Charter Specialists create your personalized itinerary. Contact our team today to get started.