Top 7 Historical Sites in the Virgin Islands by Yacht
- Kayla Anderson
- Nov 14, 2025
- 14 min read
Updated: Dec 22, 2025
Want to mix history with luxury travel? The Virgin Islands offer a treasure trove of colonial landmarks, pirate lore, and maritime history - all best explored by yacht. From centuries-old forts to sugar mill ruins, each site tells a story of the region's past. Here’s a quick overview of the top spots:
Fort Charlotte: A British military stronghold with panoramic views of Road Town.
The Baths at Virgin Gorda: Stunning granite formations with ties to pirate legends.
Norman Island Caves: Rumored pirate hideouts with excellent snorkeling.
Sugar Mill Ruins: Echoes of the sugar trade and plantation life.
Hassel Island: Military batteries and maritime relics in Charlotte Amalie Harbor.
Fort Christian: The oldest structure in the Virgin Islands, now a museum.
Blackbeard’s Castle & 99 Steps: A watchtower with pirate tales and scenic views.
Why by yacht? Many of these sites are tucked away on islands or coves that are hard to reach by land. A yacht provides direct access, privacy, and flexibility to visit multiple destinations at your own pace. Whether it’s navigating the Sir Francis Drake Channel or anchoring near historical landmarks, this mode of travel lets you immerse yourself in the Virgin Islands' heritage while enjoying modern comforts.
Best time to visit: December to April offers calm seas and pleasant weather, but late April or early May is ideal for fewer crowds and local events like Carnival.
Pro tip: Book early, hire a knowledgeable crew, and pack light for shore excursions. Make sure to respect conservation guidelines to help preserve these historical treasures. Ready to set sail? Let the Virgin Islands’ rich past unfold before you, one anchorage at a time.
Episode 17 - Exploring History on USVI's St. Thomas
1. Fort Charlotte
Sitting high above Road Town, Fort Charlotte offers a commanding view of the harbor below. Once a critical British military stronghold, this historic site played a crucial role in guarding Caribbean trade routes and spotting incoming ships. Let’s dive into its rich history and how you can visit it by water.
Historical Significance
Built between 1749 and 1760 during the height of British colonial expansion, Fort Charlotte served as a strategic military outpost. Its primary purpose? To protect British interests against rivals and pirates in the region. Perched on a hilltop, it gave the British forces a perfect vantage point to monitor Road Town and the surrounding waters. This early warning system was essential for defending settlements and ensuring the safety of trade routes. The fort stands as a testament to a transformative era in the Virgin Islands’ colonial history.
Accessibility by Yacht
One of the best parts about visiting Fort Charlotte is how easy it is to include it in a yacht itinerary. If you're sailing through the British Virgin Islands, you can anchor at Road Harbour and either take a short walk or hop in a taxi to reach the site. For those aboard the 105-foot trimaran CUAN LAW, Fort Charlotte is a featured stop on its history tours.
Highlights for Visitors
Fort Charlotte offers more than just history - it’s a visual treat. Visitors can explore the remains of garrison buildings, stone walls, and cannons that have stood the test of time. The panoramic views from the fort are stunning, stretching across Road Town, the harbor, and nearby islands. It’s a perfect spot for photography enthusiasts. Plus, interpretive signs scattered around the site provide fascinating insights into the fort’s defensive role.
A Blend of History and Legend
Fort Charlotte embodies the British Virgin Islands’ colonial past and its role in Caribbean trade and defense. Restoration efforts ensure this historic landmark continues to educate and inspire. Adding to its charm are the tales of pirates like Blackbeard and Sir Francis Drake, which give the fort an air of mystery and adventure. This mix of history and maritime lore makes it a must-visit for anyone exploring the Virgin Islands.
2. The Baths at Virgin Gorda
The Baths at Virgin Gorda stand out as a breathtaking geological marvel. Towering granite boulders create a natural maze of caves, tunnels, and tidal pools. These formations, estimated to be over 70 million years old, showcase nature’s artistry and offer a peek into the island's rich maritime past.
Historical Significance
While their beauty is undeniable, The Baths are also steeped in history. These hidden grottoes once served as storm shelters and lookout points for pirates, making them a key part of the Virgin Islands' seafaring lore. The dramatic landscape we see today was shaped by ancient volcanic activity and the steady hand of erosion over millennia, leaving behind a setting that feels both timeless and mysterious.
Accessibility by Yacht
Reaching The Baths by yacht is straightforward, making it a must-visit stop on many charter itineraries. Nearby anchorages and mooring buoys accommodate vessels of various sizes, allowing visitors to step directly from their boats into this natural wonderland. Charter services like LuxcharterYacht provide tailored itineraries and expert advice to help guests make the most of their visit. Arriving early to secure a mooring buoy is recommended, ensuring you have plenty of time to explore without the crowds.
Unique Features and Attractions
The Baths are an adventurer’s paradise. You can wade through crystal-clear pools, navigate tunnels carved by ancient boulders, and uncover hidden grottoes that spark the imagination. The snorkeling here is top-notch, with vibrant marine life adding to the area’s appeal.
Cultural and Maritime Heritage
Beyond their natural allure, The Baths hold a special place in the local maritime and cultural heritage. Their ties to pirate legends and seafaring traditions are celebrated through local festivals and educational tours. Protected as a national park spanning about 7 acres of coastline, this iconic site remains accessible to visitors. Entry fees are typically around $3.00 USD per person, making it an affordable way to experience the magic of the Virgin Islands.
3. Norman Island Caves
The Norman Island Caves are steeped in pirate lore, once serving as secret hideouts where treasure was hidden during the colonial era. These shallow caves, carved into the island’s rugged coastline, provided natural shelters and strategic lookout points for pirates. Visiting this site adds another layer to the rich maritime history of the Virgin Islands, offering a glimpse into its storied past.
Historical Significance
These caves are entwined with tales of infamous pirates like Blackbeard and Sir Francis Drake. Local legends tell of buccaneers stashing their loot within these chambers and using them as safe havens. Nearby, an 18th-century great house with coral-carved steps serves as a reminder of the region’s plantation history, further connecting visitors to the island’s layered past.
Accessibility by Yacht
Reaching the Norman Island Caves is an adventure in itself, as they are accessible only by yacht through the calm waters of the Sir Francis Drake Channel. This route offers clear navigation and safe anchorages like The Bight. Chartering a yacht with LuxcharterYacht ensures a smooth journey, combining convenience with luxury as you explore this historic destination.
Unique Features and Attractions
The caves are a haven for SCUBA divers and snorkelers, with dramatic rock formations and hidden grottoes waiting to be discovered beneath the surface. For those who prefer land-based exploration, gravel paths lead to the ruins of a plantation great house, offering a mix of maritime and historical intrigue. Nearby snorkel spots, such as "The Indians", add to the area’s allure, making it a favorite among visitors to the British Virgin Islands.
Cultural and Maritime Heritage
Beyond their natural beauty, the Norman Island Caves play a key role in the Virgin Islands’ cultural narrative. They weave together stories of pirate escapades and plantation-era history, showcasing how the region’s geography shaped both commerce and piracy. Conservation efforts are actively preserving these fragile ecosystems, ensuring that future generations can continue to experience this vibrant piece of Caribbean history.
4. Sugar Mill Ruins
Scattered across the Virgin Islands, the Sugar Mill Ruins stand as powerful reminders of the colonial sugar era of the 18th and 19th centuries. A standout among these is the Annaberg Sugar Plantation on St. John, which operated from the late 1700s to the late 1800s, producing sugar, molasses, and rum for international trade. These ruins tell a story of resilience, labor, and transformation.
Historical Significance
These ruins include remains of factories, windmills, and slave quarters, offering a window into the realities of plantation life and sugar production. They also capture the pivotal shift from enslaved labor to a workforce of free individuals, marking a significant chapter in the history of the Virgin Islands.
Accessibility by Yacht
For those exploring by yacht, many of these ruins, especially on St. John and Tortola, are conveniently accessible. The Annaberg Sugar Mill Ruins, for instance, can be reached with a short dinghy ride followed by an easy hike. LuxcharterYacht itineraries often include stops at these historic landmarks, making them an ideal addition to any maritime adventure.
Unique Features and Attractions
Visitors can wander through well-preserved windmills, boiling houses, and factory ruins, following interpretive trails that shed light on the sugar production process and daily life on the plantations. The Annaberg site offers stunning panoramic views, while locations like Cinnamon Bay feature wheelchair-accessible boardwalks, ensuring that these historical treasures are open to all.
Cultural and Maritime Heritage Relevance
The Sugar Mill Ruins are deeply tied to the Virgin Islands' identity, showcasing the critical role of maritime trade and agriculture during the colonial period. Sugar, molasses, and rum were exported to Europe and North America, with unique local vessels like the "Tortola Boat" playing a key role in this trade. Today, these ruins are not just historical sites - they're venues for heritage festivals and educational programs that celebrate the islands' rich history. They offer a perfect blend of industrial and cultural heritage, complementing other maritime landmarks in the region.
5. Hassel Island
Hassel Island, tucked within Charlotte Amalie Harbor and spanning 135 acres, offers a fascinating glimpse into centuries of military and maritime history.
Historical Significance
Hassel Island became an island in 1860 when the Danish separated it from the St. Thomas mainland to improve harbor navigation. Its strategic importance is highlighted by structures like Prince Frederick's Battery, Bowell's Battery, and a Signal Station. During the Napoleonic Wars, the Garrison House served as a residence for British officers, emphasizing its role in international defense efforts.
Accessibility by Yacht
Located conveniently in the harbor, Hassel Island is easily accessible by yacht. Visitors can anchor in the calm waters and use tenders to reach designated landing spots. It's a popular stop for LuxcharterYacht itineraries, offering seamless access to the island's historical and natural attractions.
Unique Features and Attractions
Hassel Island is home to several notable landmarks, including the Garrison House, Prince Frederick's Battery, and Bowell's Battery with its Signal Station, all showcasing its rich defense history. Visitors can also see the remnants of the Creque Marine Railway, one of the oldest steam-powered marine railways in the Western Hemisphere. For nature lovers, hiking trails provide stunning views of Charlotte Amalie Harbor and St. Thomas.
Cultural and Maritime Heritage
As part of the Virgin Islands National Park, Hassel Island serves as a living testament to the Caribbean's maritime past. Its batteries and signal stations once safeguarded harbor traffic and facilitated colonial communication. Today, ongoing restoration efforts by local groups and the National Park Service aim to preserve these historic sites and maintain the interpretive trails for future generations to explore and appreciate.
6. Fort Christian
Fort Christian, the oldest structure in the Virgin Islands, has stood since 1672, built by the Danish West India Company. This red brick fortress has borne witness to centuries of Caribbean history, making it a must-see for visitors to St. Thomas.
Historical Significance
Fort Christian holds a prominent place in the colonial history of the Virgin Islands. Built at the dawn of Danish rule, it served multiple roles over the years - military stronghold, government center, prison, post office, and administrative hub. Its construction symbolized Denmark's determination to establish a lasting foothold in the Caribbean, shaping the development of St. Thomas.
The fort’s strategic location overlooking Charlotte Amalie Harbor was crucial during conflicts with rival colonial powers and pirates. From its vantage point, Danish forces could monitor maritime activity, safeguarding merchant ships and the growing settlement below.
Accessibility by Yacht
Charlotte Amalie’s deep-water harbor makes it a favorite destination for yacht travelers. Visitors arriving by yacht can anchor in the harbor's protected waters or use nearby marina facilities. From there, Fort Christian is an easy walk through the historic district, blending modern convenience with a glimpse into the past.
LuxcharterYacht frequently includes Charlotte Amalie in its Virgin Islands itineraries, giving guests the chance to pair luxury yacht travel with an enriching historical visit to Fort Christian.
Highlights and Visitor Experience
Fort Christian offers a well-rounded historical experience in a conveniently accessible location. Today, it houses the Virgin Islands Museum, where visitors can explore the fort’s red brick design, iconic clock tower, and enjoy sweeping views of Charlotte Amalie Harbor. Guided tours are available Monday through Friday from 9:00 AM to 4:00 PM, with an entry fee of about $10 per adult.
The site also features visitor amenities, including restrooms and educational displays, which help bring the colonial era to life.
Maritime and Colonial Legacy
Designated as a National Historic Landmark, Fort Christian embodies the Virgin Islands’ maritime and colonial heritage. It once served as a critical defense against pirates and enemy fleets, protecting the bustling harbor that became central to Caribbean trade.
Today, the fort continues to connect visitors and locals to its storied past through exhibits and programs. These initiatives highlight its role in maritime defense while celebrating the island’s rich cultural identity, offering a deeper appreciation for this historic treasure.
7. Blackbeard's Castle and the 99 Steps
Sitting high on Government Hill in Charlotte Amalie, Blackbeard's Castle is one of St. Thomas's three National Historic Landmarks. This iconic site, paired with the legendary 99 Steps, offers visitors a mix of pirate tales, colonial history, and sweeping views of the harbor. It's a must-see for anyone looking to dive into the island's rich past.
Historical Significance
Blackbeard's Castle was originally built in 1679 by the Danes as a watchtower. Its primary purpose was to help the colonial administration keep an eye on enemy ships approaching Charlotte Amalie Harbor. While its pirate connections are more legend than fact, the tower remains a fascinating piece of history.
The 99 Steps, constructed in the 18th century using bricks brought over on Danish ships, are another testament to the ingenuity of early settlers. Fun fact: despite their name, there are actually 103 steps - a quirky detail that adds to their charm.
Accessibility by Yacht
Charlotte Amalie Harbor provides excellent anchorage for yacht travelers eager to explore this historical gem. From the harbor, visitors can ascend the flower-adorned 99 Steps to reach the castle. LuxcharterYacht often includes Charlotte Amalie in its Virgin Islands itineraries, blending the luxury of yacht travel with the excitement of historical exploration.
Unique Features and Attractions
Anchoring at Charlotte Amalie Harbor offers easy access to this historic site. The climb up the 99 Steps, lined with vibrant flowers and swaying palm trees, is a memorable experience in itself. At the top, the 17th-century watchtower awaits, offering breathtaking views of the harbor and beyond. The surrounding gardens and statues of Blackbeard and other pirates make for great photo opportunities, especially for maritime history buffs. While the climb requires moderate effort, the rewards are well worth it - both for the views and the historical insights.
Important: The castle has been restored following hurricane damage and now charges a $10 USD entry fee. Be sure to check the latest opening hours and conditions before planning your visit.
Cultural and Maritime Heritage
Blackbeard's Castle and the 99 Steps are more than just tourist attractions - they're a window into the islands' colonial and maritime history. The Danish bricks used in the steps reflect the area's maritime trade connections, while the site as a whole ties together the practicalities of colonial defense with the mystique of pirate legends. For yacht visitors, this landmark offers a tangible link to the stories that have shaped St. Thomas over the centuries.
How to Plan Your Historical Yacht Charter
Planning a historical yacht charter in the Virgin Islands involves understanding the seasons, tapping into local expertise, and booking early to ensure a smooth and enriching experience.
Choosing the Best Time for Exploration
The dry season, from December to April, is ideal for historical yacht charters. Expect sunny weather, temperatures between the mid-70s and mid-80s °F, and a low risk of hurricanes. This is the perfect time to visit outdoor landmarks like Fort Charlotte and the 99 Steps, while calm seas make remote locations like the Norman Island Caves more accessible.
However, keep in mind that peak season comes with higher costs and more crowds. For a mix of pleasant weather and fewer visitors, late April or early May is a great option. This period also coincides with local events like Carnival in St. Thomas, which adds vibrant parades and heritage celebrations to your itinerary. Just remember, these events can increase demand for charters.
The Value of Professional Crews
A skilled crew can elevate your historical charter experience by providing local insights and handling logistics. Experienced captains know the best routes between sites, prime anchorages near landmarks, and the right times to avoid crowds. They also manage docking at locations with limited facilities, ensuring a hassle-free journey.
Crews often take care of shore excursions and guided tours. For example, they can arrange visits to places like the Old Government House Museum in Road Town or the Virgin Islands Maritime Museum (open Monday–Friday, 8:30 am to 4:30 pm). They can also suggest efficient itineraries, such as dedicating Day 1 to St. Thomas landmarks (Fort Christian and Blackbeard’s Castle), Day 2 to Hassel Island, and Days 3–4 to Tortola’s Fort Charlotte and Sugar Mill Ruins.
For those seeking a more tailored experience, LuxcharterYacht’s concierge service can book private guides, arrange special access to historical sites, and coordinate educational stops at locations like the Virgin Islands Maritime Museum.
Planning Essentials
Once you’ve chosen your dates and secured a professional crew, it’s time to finalize the details. Book your yacht several months in advance, especially if you’re planning for the busy December–April season, to lock in your preferred vessel and itinerary.
Charter Duration | Price Range | Best For Historical Tours |
Day Charter | $2,500/day | Focused exploration of 2–3 sites |
Weekend Charter | $6,800/2–3 days | Multi-island visits covering 4–5 sites |
Weekly Charter | $18,500/week | Comprehensive tour of all 7 key sites |
Pack wisely for both onboard relaxation and onshore adventures. Lightweight clothing, sturdy walking shoes, sun protection, and waterproof bags for valuables are must-haves. Some locations, like the 99 Steps, involve moderate physical exertion, so inform your crew of any mobility concerns in advance.
Exploring Responsibly
Historical charters often partner with conservation groups to protect the region’s heritage. Do your part by respecting posted guidelines, avoiding contact with artifacts, and sticking to designated paths to preserve fragile ruins. Anchoring restrictions and special permits may apply in certain areas to protect the environment, but your crew will handle these requirements, ensuring your exploration remains responsible and sustainable.
Conclusion
Discovering the Virgin Islands' historical gems by yacht offers a seamless blend of luxury and heritage. With a yacht charter, you gain exclusive access to remarkable sites like the Norman Island Caves and Hassel Island - places that ferries simply can’t reach.
Picture this: snorkeling through legendary pirate caves in the morning, hiking up to colonial forts in the afternoon, and diving into the islands' rich history with insights from knowledgeable crew members. All of this is paired with gourmet meals and top-tier amenities onboard, creating a truly unforgettable experience.
LuxcharterYacht elevates this journey with expert crews and personalized concierge services that guide you to hidden treasures and secure the best anchorages. Whether you're climbing the 103 steps of Blackbeard's Castle or exploring the military history of Fort Charlotte, every detail is thoughtfully planned.
Yacht charters also contribute to sustainable tourism by partnering with local conservation efforts, helping to protect these historical sites for future generations. By choosing this unique way to travel, you’re not just indulging in an extraordinary vacation - you’re playing a part in preserving the Virgin Islands' cultural heritage.
The islands’ historical sites tell stories of colonial times, pirate adventures, and plantation life. Sailing through the same waters that once carried explorers and traders offers a rare connection to this fascinating past, all while enjoying the ultimate in modern comfort and convenience.
FAQs
What makes exploring historical sites in the Virgin Islands by yacht a better experience than other travel options?
Exploring the Virgin Islands' historical sites by yacht blends luxury, ease, and a touch of exclusivity. Unlike traditional travel options, a yacht lets you glide straight to secluded landmarks and hidden treasures, bypassing busy roads and rigid ferry timetables.
With expert crews, fine dining experiences, and tailored concierge services, a yacht charter transforms your journey into pure relaxation. Add to that the onboard perks - like water sports gear and expansive decks - and your adventure becomes as memorable as the destinations themselves.
What are the best ways to visit historical sites in the Virgin Islands responsibly?
When exploring historical sites in the Virgin Islands, it’s important to tread lightly and respect the surroundings. Be mindful of the environment by avoiding any disruption to wildlife, properly disposing of trash, and taking care not to harm fragile ecosystems. Pay attention to posted rules or guidelines at each site - they’re there to help protect both the natural beauty and the historical significance of these places. Additionally, consider supporting local businesses and communities during your trip. It’s a meaningful way to contribute while immersing yourself in the rich heritage of the islands.
What should I keep in mind when planning a yacht charter to explore historical sites in the Virgin Islands?
When organizing your yacht charter, aim for an itinerary that blends historical adventure with moments of pure relaxation. Pay attention to travel times between destinations - some landmarks may need extra planning to ensure you can fully immerse yourself in the experience without feeling pressed for time.
Make the most of the personalized services available. With skilled crews, gourmet meals, and access to water sports gear, you can effortlessly pair cultural exploration with the comfort of onboard luxury. Share your preferences and interests ahead of time to ensure every detail of your trip aligns with your vision.
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