Island Hop the U.S. Virgin Islands During Festive Season

Your Caribbean adventure begins as you land at Cyril E. King Airport on St. Thomas, welcomed by warm tropical air and stunning harbor views. Take a short taxi ride to your accommodations—either the Ritz-Carlton overlooking Great Bay or Club Wyndham Elysian Beach Resort on the island’s east end.

Start your island orientation with a visit to Fort Christian, a distinctive red Danish colonial fortress dating to 1680 and designated as a National Historic Landmark. Inside, a museum displays artifacts illustrating the islands’ diverse heritage. From there, stroll along the charming cobblestone alleyway known as 99 Steps (though there are actually 103), built by the Danes using ballast bricks from sailing ships.

For lunch, explore the local dining scene in Charlotte Amalie, where you can sample authentic West Indian cuisine, like conch fritters, curry goat, or patés (savory pastries filled with spiced meat or seafood). After your meal, spend the afternoon browsing the duty-free boutiques along Main Street. (The duty-free allowance for U.S. citizens returning to the mainland is $1,600 per person.)

If your visit coincides with the St. Thomas Carnival season (generally April-May), you might catch evening events like calypso competitions or cultural performances. Consider taking a guided historical tour outside of festival season to discover Charlotte Amalie’s rich past. For dinner, enjoy fresh seafood at one of the waterfront restaurants overlooking the harbor, where you can watch boats returning as the sun sets.

Begin your day by riding up Paradise Point Tramway, which ascends 700 feet above Charlotte Amalie. From this vantage point, enjoy panoramic views of the harbor, neighboring islands, and the Caribbean Sea stretching to the horizon.

Next, head to Sapphire Beach on the east end of St. Thomas for a morning of snorkeling. This crescent-shaped beach with white sand and turquoise waters is home to a vibrant coral reef. Rent snorkeling equipment from the beach concession if you haven’t brought your own and explore the underwater world’s coral formations and shimmering tropical fish.

Try one of the local restaurants serving fresh seafood and Caribbean specialties for lunch. Many offer dishes featuring the catch of the day prepared with island spices and accompaniments like rice and peas, plantains, or johnnycakes (fried bread).

In the afternoon, choose between two marine experiences. Visit Coral World Ocean Park, where you can try SNUBA—a hybrid between snorkeling and scuba that requires no certification—or opt for snorkeling at one of St. Thomas’s protected coves, which offer exceptional underwater viewing opportunities.

If you visit in late March, you might catch the St. Thomas International Regatta, where sailing vessels compete in races visible from various coastal viewpoints. The event includes shoreside activities and celebrations that showcase the island’s maritime culture.

As evening approaches, dine at one of St. Thomas’s restaurants housed in historic buildings. Many spots offer cuisine that blends Caribbean traditions with international influences, accompanied by tropical cocktails featuring local rum. Listen for live music featuring calypso, soca, or reggae rhythms that provide an authentic soundtrack to your night.

Start your day with breakfast at a local café, where you might enjoy tropical fruits, fresh pastries, or traditional island breakfast dishes to fuel your day’s adventures.

If your trip coincides with the St. Thomas Carnival (generally April-May), immerse yourself in one of the Caribbean’s vibrant cultural celebrations. The event features parades with elaborate costumes, steel drum music, and performances that showcase the island’s heritage. Food vendors serve traditional dishes, offering opportunities to sample local specialties like kallaloo (a spinach-like stew), johnnycakes, and fresh seafood.

Outside carnival season, spend your morning exploring other St. Thomas highlights. Consider visiting Mountain Top for spectacular views from the island’s highest accessible point at 2,100 feet. Be sure to sample the famous banana daiquiri. For lunch, stop at one of the casual spots in town for fresh, locally inspired cuisine before preparing for your journey to the next island.

In the afternoon, take a taxi to the Red Hook ferry terminal on St. Thomas’ east end for the scenic 20-minute ferry ride to Cruz Bay, St. John. Watch for seabirds and enjoy views of both islands and smaller cays dotting the seascape.

Upon arrival in St. John, check into the Westin St. John Resort, featuring amenities including multiple pools and beach access on Great Cruz Bay. Once settled, take an orientation walk through Cruz Bay, St. John’s charming main town. Stroll the compact streets and take in the shops, art galleries, and restaurants, many painted vibrant colors and filled with local treasures and tastes. Soak in the more relaxed vibe that distinguishes St. John from its busier neighbor.

For dinner, enjoy a meal at one of Cruz Bay’s restaurants, where Caribbean influence meets international cuisines in a laid-back setting. As darkness falls, the sound of gentle waves and rustling palms welcomes you to your second island experience.

Grab breakfast in Cruz Bay before visiting the Virgin Islands National Park Visitor Center for insight into the protected areas that cover more than two-thirds of St. John. Park rangers can provide information about hiking trails, wildlife, and the island’s ecosystems.

Today’s highlight is Trunk Bay, consistently rated among the world’s most beautiful beaches. Here, you’ll discover the park’s famous Underwater Snorkel Trail, a self-guided route with plaques naming marine life and coral formations. The trail is about 225 yards long, with depths ranging from 3–18 feet, making it accessible for snorkelers of various experience levels.

Facilities at Trunk Bay include changing rooms, restrooms, a snack bar, and equipment rentals. The beach’s white sand and shade from sea grape trees and palms are perfect for relaxing between snorkeling sessions.

In the afternoon, visit the historic Annaberg Sugar Plantation ruins. Learn about the sugar production process and its role in the island’s colonial history. The hillside location offers sweeping views of the British Virgin Islands across the channel.

If your visit coincides with the St. John Celebration (June-July), evening festivities blend Independence Day celebrations with Caribbean cultural traditions, featuring local food vendors, music performances, and cultural displays. St. John Celebration also marks the end of slavery on the islands on July 3, 1848.

For dinner, return to Cruz Bay to dine at one of the town’s restaurants serving farm-to-table cuisine that incorporates fresh island ingredients and seafood.

Today’s adventure takes you to the eastern side of St. John to explore Cinnamon Bay and the quieter community of Coral Bay. Begin with a scenic drive across the island’s mountainous roads, which offer spectacular vistas at every turn.

Within Virgin Islands National Park, Cinnamon Bay offers excellent snorkeling opportunities around its offshore reef, where you might spot various marine life, such as schools of fish and fascinating coral formations. The area also has historical significance—including evidence of Taino settlements and colonial-era structures. The Cinnamon Bay Archaeology Lab and Museum provides context for the area’s rich history.

For lunch, drive to Coral Bay on the island’s eastern side. This smaller, peaceful community offers a glimpse of old St. John. Several open-air restaurants serve Caribbean specialties and fresh seafood in a casual atmosphere.

In the afternoon, head to Maho Bay for exceptional wildlife viewing. Known as a place where visitors can often observe sea turtles feeding on the abundant seagrass beds, this protected cove has calm, shallow waters. The bay’s clarity and sandy bottom create ideal conditions for spotting these creatures as they graze. You might also see stingrays partially buried in the sandy bottom or reef fish along the rocky areas at either end of the bay.

If your visit coincides with a full moon, you can join a Full Moon gathering at one of the island’s establishments. This monthly tradition brings together locals and visitors for music and celebration.

Return to Cruz Bay for dinner at one of the town’s restaurants featuring Caribbean-inspired cuisine. After dinner, appreciate the night sky—with minimal light pollution, St. John offers excellent stargazing opportunities.

Begin your day with a final St. John adventure, perhaps a morning swim or snorkel at one of the north shore beaches. Afterward, return to your accommodation to check out and take the ferry back to St. Thomas.

From there, head to the seaplane terminal for a 30-minute flight to St. Croix on a small plane. You’ll have spectacular aerial views of the islands and the Caribbean Sea before touching down at St. Croix’s Henry E. Rohlsen Airport.

Then, transfer to your St. Croix accommodation, such as the Buccaneer Beach & Golf Resort, a historic property with multiple beaches, a golf course, and tennis courts on its 340-acre grounds.

After settling in, head to Christiansted, one of St. Croix’s main towns, to explore its distinctive Danish colonial architecture and historic sites. Start at Fort Christiansvaern, a well-preserved yellow bastion completed in 1749 that once protected the harbor from pirates and foreign invaders. Part of the Christiansted National Historic Site, the site is a peek into the island’s colonial past under Danish rule.

Continue your historical exploration along the Christiansted boardwalk and through the town’s distinctive arcaded sidewalks, where yellow brick buildings with red roofs create an architectural landscape unlike anywhere else in the Caribbean.

If your timing aligns with one of St. Croix’s quarterly Jump Up celebrations (held in February, May, July, and November), you’ll experience a street festival with local vendors, cultural performances, and musicians.

For dinner, enjoy a meal at one of Christiansted’s restaurants, many housed in historic buildings that combine architectural charm with culinary excellence. The menus often feature fresh seafood and locally sourced ingredients prepared with traditional and contemporary techniques, reflecting St. Croix’s diverse cultural influences.

After breakfast at your resort, embark on a tour boat from Christiansted harbor to Buck Island Reef National Monument. Presidential proclamation established this protected marine sanctuary in 1961. Found on a small uninhabited island about 1.5 miles off St. Croix’s northeast coast, it was expanded in 2001 to preserve “one of the finest marine gardens in the Caribbean Sea.”

The monument features a marked underwater trail where you can follow plaques that guide you through the elkhorn coral barrier reef, home to over 250 fish species, from vibrant parrotfish to graceful spotted eagle rays. The clear waters provide exceptional visibility as you explore this protected area’s coral formations, sandy channels, and thriving marine ecosystem.

After the reef, head to Turtle Beach, a pristine white-sand shoreline on Buck Island’s western side. Tour operators typically provide a picnic lunch before returning to St. Croix’s main island.

In the afternoon, experience authentic local cuisine at one of St. Croix’s traditional restaurants. The island’s culinary scene reflects its diverse cultural heritage, with dishes that incorporate African, European, and Indigenous Caribbean influences.

Your afternoon activities might include festival events, depending on when you visit. December and January feature Crucian Christmas Festival events; in February, AgriFest (an agricultural fair highlighting local farming traditions) takes place; and the Taste of St. Croix food festival happens each April.

As evening approaches, enjoy the sunset from a waterfront establishment in Christiansted, where you can sample locally produced rum while watching boats return to the harbor. For dinner, dine at one of St. Croix’s restaurants that celebrate island cuisine through farm-to-table practices and traditional recipes with a contemporary twist.

For your final day in the USVI, rise early to greet the day at Point Udall on St. Croix’s eastern tip, the easternmost point of the United States and its territories. This scenic spot offers spectacular sunrise views over the Caribbean Sea and features a giant sundial called the Millennium Monument.

From Point Udall, consider checking out a nearby nature area with beaches and hiking trails. Several protected areas on St. Croix’s east end—Cas Cay /Mangrove Lagoon, Great St. James, and the Compass Point Salt Pond—offer opportunities to experience the island’s diverse ecosystems, from dry forests to coastlines with distinctive geological features.

For lunch, visit one of the local places serving authentic Crucian cuisine—dishes that reflect the island’s multicultural heritage and agricultural traditions.

In the afternoon, you might tour one of St. Croix’s historic rum distilleries (Cruzan Rum or Captain Morgan) to learn about the production process of this spirit that has deep connections to Caribbean heritage. Tours typically include tastings of various rum expressions and explanations of how production has evolved from colonial times to today’s operations.

As the perfect finale to your USVI adventure, arrange an evening bioluminescent kayak tour at Salt River Bay National Historical Park and Ecological Preserve. Salt River Bay is home to microscopic dinoflagellates that emit blue-green light when disturbed, a natural phenomenon that occurs in only a handful of locations worldwide.

Several companies offer guided tours, with some providing clear-bottom or transparent kayaks. As darkness falls, paddle through the calm waters, where each stroke creates trails of glowing blue light. Fish swimming beneath your kayak appear as shooting stars in the dark waters, while the absence of light pollution allows for spectacular stargazing above.

For your farewell dinner, enjoy a final meal at one of St. Croix’s restaurants, perhaps selecting a spot with water views where you can reflect on your journey through three distinct islands, each with its own character but collectively embodying the spirit of the U.S. Virgin Islands.