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  • Roam the Historical Beauty of St. Thomas
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    Roam the Historical Beauty of St. Thomas

  • Revel in the Natural Beauty of St. John
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    Revel in the Natural Beauty of St. John

  • Explore the Virgin Islands National Park
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    Explore the Virgin Islands National Park

  • Experience History and Culinary Delights in St. Croix
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    Experience History and Culinary Delights in St. Croix

  • Delve Into European History in Christiansted
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    Delve Into European History in Christiansted

Island-Hopping Through History: A U.S. Virgin Islands Road Trip
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Island-Hopping Through History: A U.S. Virgin Islands Road Trip

By Eric Rosenberg

  • Route distance:
    130.00 km
  • Suggested Time:
    3 days

Pristine beaches, crystal-clear waters and year-long warm weather are just a few of the reasons the U.S. Virgin Islands, an island cluster in the Caribbean Sea, are an ever-popular vacation destination.

Each island has its own unique feel, giving you the perfect excuse to island hop in order to experience the magic of this destination. What to bring: swimwear, plenty of sunscreen and a sense of adventure.

01
Roam the Historical Beauty of St. Thomas
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Roam the Historical Beauty of St. Thomas

Start your trip by flying into the U.S. territory's Cyril E. King International Airport on St. Thomas. There, stroll through the city of Charlotte Amalie, the capital of the U.S. Virgin Islands. The grid of cobblestone alleyways and steep streets lined with brightly colored colonial buildings are a nod to the city's past, when it was founded by the Danish in the 1600s. The bustling shops, busy restaurants and packed bars give you a sense of its present status as the commercial hub of the Islands. 

While in town, be sure to visit the historic St. Thomas Synagogue, the oldest continually operating synagogue in the United States. Or take a guided walk through Blackbeard's Castle, a National Historic Landmark, which opened in 1679. Originally known as Skytsborg Tower, it offered Danish soldiers views far into the sea to spot incoming ships. But no trip to St. Thomas is complete without a visit to Magens Bay. One of the top beach destinations in the world, it's home to soft sand and crystal-clear water, a favorite for water sports like snorkeling and paddle boarding. It's the perfect place to unwind and relax before your trip home.

30 km
0.5 hours by car
02
Revel in the Natural Beauty of St. John
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Revel in the Natural Beauty of St. John

Take the ferry from the Charlotte Amerie Ferry Dock to reach St. John, the smallest of the islands but one packed with plenty of natural beauty. But be warned, driving the island isn't for the faint of heart: Roads cling to the sides of the tree-filled, hilly terrain.

The destinations, however, are truly magical. Case-in-point: Trunk Bay. Considered one of the most beautiful beaches in the world by travel outlets like the Travel Channel and Condé Nast Traveler, Trunk Bay offers white sand and turquoise water as far as the eye can see.  What's more, you can explore the waters with a snorkeling trail — an underwater, self-guided tour where signs guide you to various sites. After soaking up enough sun, head to Annaberg Sugar Plantation. The site is located on a steep hill and features the historic ruins of an 18th-century plantation and sugar mill with a hiking trail throughout the grounds.

11 km
0.5 hours by car
03
Explore the Virgin Islands National Park
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Explore the Virgin Islands National Park

No visit to St. John is complete without a tour of Virgin Islands National Park, which covers 60% of the island and spans more than 2,000 hectares. From Annaberg, head 20 minutes west on the winding North Shore Drive to enter the park through Cruz Bay, the largest city on St. John. You can choose from recommended hikes at the Virgin Islands National Park Visitor Center or visit one of the park's famous scuba diving and snorkeling spots. The park is home to five popular beaches, including Trunk Bay, six major hiking trails that take you through the heart of the island's rainforest and four historic sites.

Walk the Cinnamon Bay Nature Trail to see ruins of the island's historic sugar plantations. Bordeaux Mountain Trail offers a steep path to the top of Bordeaux Mountain, the highest point on the island. The Reef Bay Trail is the most popular hike and offers dense forests, historic petroglyph carvings and a spring-fed waterfall. If you decide to tackle the Reef Bay Trail, you may want to plan for an entire day. The nine-kilometer round-trip is quite tiring, but hikers can also take a guided boat ride back to Cruz Bay if you make it to Reef Bay and want to call it quits.

105 km
0.5 hours by plane
04
Experience History and Culinary Delights in St. Croix
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Experience History and Culinary Delights in St. Croix

Take a ferry ride back to St. Thomas and then a quick flight from Cyril E. King Airport to Henry E. Rohlsen Airport on the island of St. Croix. Since St. Croix is the largest of the islands, it's best to rent a car for your stay. From the airport, drive west on Route 66 to Fort Frederik, a United States Historic Landmark site, built by the Danish in 1752 to protect the deep-water port and defend from pirates. Visitors can delve into this history — and more — with a tour of the site. 

Next, drive north on Centerline Road to Salt River Bay National Historical Park and Ecological Preserve for snorkeling, kayaking, fishing and a gorgeous nature experience. There are also archaeological sites where you can explore 2,000 years of history from the earliest indigenous settlements to clashes with colonial European powers to the present day.

On an island as lush as St. Croix, it's no wonder the farm-to-table movement abounds. The best place to experience this is at Ridge to Reef Farm, which serves a six-course "Slow Down Dinner" that educates guests on the importance of locally grown, organic food.

9 km
0.5 hours by car
05
Delve Into European History in Christiansted
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Delve Into European History in Christiansted

Arrive in Christiansted, one of the larger towns on the island of St. Croix, by taking Route 75 from Salt River Bay. Be sure to stop at Christiansted National Historic Site, a highlight of the city. Offering a taste of European history in the New World, its 18th- and 19th-century buildings, dotted across three hectares, once served as the capital of the Danish West Indies.

This island-hopping itinerary will get you to all the highlights of the U.S. Virgin Islands, but be sure to  check out everything else this destination has to offer.

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Coki Beach and Coral World Aquarium

Destination

St. Thomas

Aerial view of St. John's south side

Destination

St. John

Colorful lion statues on display in Plaza Las Delicias
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Destination

Ponce

A view of Fatumafuti and the Pago Pago Harbor leading to Fagatogo
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Destination

Fagatogo

Overlooking the city and bay from Fort Santa Agueda on Apugan Hill

Destination

Hagatna