3 Days Exploring the Roads Less Traveled on St. Thomas

Secret Harbour Beach. Photo Courtesy of Taryn Parker.



St. Thomas attracts the largest crowds of all of the U.S. Virgin Islands, with its sparkling beaches and duty-free shopping opportunities. But there’s much more to this island paradise!  

Day trips to the small harbor islands and visits to St. Thomas’ Northside and West End districts can let tourists experience the authentic flavor of this laid-back escape. From local restaurants to scenic ruins, the true beauty of St. Thomas is ready to be discovered.

Day 1: Soak Up the Beach on Water Island

Located within the Harbor of Charlotte Amalie on the south side of St. Thomas, Water Island is a secret jewel of the Caribbean. With fewer than 200 full-time residents and just 491 acres of land, this intimate residential island makes a delightful day trip.

Water Island off St. Thomas, U.S. Virgin Islands. Photo Courtesy of Taryn Parker.

Getting There and Getting Around

To reach Water Island, take the passenger-only ferry from St. Thomas’ Crown Bay Marina. In 10 minutes, you’ll arrive at Providence Point on Water Island’s western shore. 

The island is only 2 ½ miles long from end to end, so you can certainly choose to walk! But to make the most of your time, rent a golf cart when you arrive at the ferry dock so you can zip around the island with ease. 

What To Do on Water Island

Spend the morning on idyllic Honeymoon Beach. With its pristine white sand and picturesque coconut palms, you’d never guess that this beach was essentially man-made back in the 1950s! Rock and gravel were hauled away, and a dredge deposited sand onto the shore to expand a formerly modest stretch of waterfront. Now, it’s postcard-perfect, overlooking the crystal waters of the open sea. 

Dinghy’s Beach Bar on Water Island, St. Thomas, U.S. Virgin Islands. Photo Courtesy of Taryn Parker.

There are no stores on the island, so bring some bottled water, sunscreen, and a towel for your beach day. You can rent beach chairs, snorkel gear, kayaks, and paddleboards from Dinghy’s Beach Bar. And when you get hungry, enjoy a hearty burger or fresh fish tacos with a frozen margarita or their signature passionfruit piña colada. 

After lunch, take your golf cart a mile down the road to explore Fort Segarra. This underground fort was begun during World War II, but it was abandoned unfinished after the war. Walk the subterranean tunnels and rooms built into the hillside. Then climb to the observation deck on the fort’s roof for 360-degree views of Water Island and nearby St. Thomas. 

Where to Stay on Water Island

Many visitors choose to return to St. Thomas at the end of the day. But if you’d like to stay overnight on this quiet island paradise, there are plenty of options. Beachy Rum Point Villa and luxurious Caribview Villa both feature stunning Caribbean views. Or get a true island experience in a wood-and-canvas cottage at Virgin Islands Campground. This eco-friendly site is perched on a hill for fantastic views from each cottage.

Day 2: Hike Hassel Island & Discover Art in Charlotte Amalie 

Even in Charlotte Amalie, the capital city of St. Thomas, there are overlooked delights. Spend a day exploring a few of these hidden gems, and take a short trip to nearby Hassel Island to see the historic sites. 

A plane flies over Hassel Island near St. Thomas, U.S. Virgin Islands. Photo Courtesy of Ramunas Bruzas.

Getting There and Getting Around

Most visitors to St. Thomas choose to rent a car, so they’ll have the flexibility to go anywhere on the island. Taxi services and buses are also available, although the bus routes may not reach everywhere you wish to go. 

To reach Hassel Island, a small passenger-only ferry is available between Crown Bay Marina on St. Thomas and the smaller island. Once you reach Hassel, your best method of transportation is your own two feet!

What to Do on Hassel Island and in Charlotte Amalie

At just 135 acres, tiny Hassel Island is big on charm. Once connected to St. Thomas by a narrow strip of land, it was fully separated from the larger landmass by the Dutch in the 1860s. Today, visitors to the island can enjoy hiking the many trails. Bring water, snacks, and comfortable walking shoes! 

The Historic District ruins on Hassel Island near St. Thomas, U.S. Virgin Islands. Photo Courtesy of Ramunas Bruzas.

To explore the island’s historical sites, schedule a walking tour with the St. Thomas Historical Trust. Their tour includes a visit to three ruins in Fort Willoughby: Prince Frederik’s Battery, a defensive cliffside site that once held Dutch cannons; the Garrison House, with 3-foot walls meant to protect weapons and munitions; and Cowell’s Battery and Signal Station, the highest point on the island. The tour includes a ferry from St. Thomas to the island, making it an easy half-day trip.

Back in Charlotte Amalie, duck into the Camille Pissarro Gallery, often overlooked by the crowds of shoppers on Main Street. Located inside the impressionist painter’s childhood home, the gallery displays some of his original works. 

For dinner, visit Oceana Restaurant & Bistro to enjoy fresh seafood and grass-fed Wagyu beef with fabulous ocean views. 

Where to Stay in Charlotte Amalie

Spend the night away from the crowds at the charming Bellavista Bed & Breakfast. You’ll find lush greenery throughout the property and comfortable island ambiance in every room.

Day 3: Gather with the Locals in Northside and West End 

Most visitors to St. Thomas congregate on the southeastern edge of the island, from Charlotte Amalie to Red Hook. So anyone who wants to escape the tourist crowds can simply travel north and west to see a different side of St. Thomas.

A ferry ride from Red Hook, St. Thomas, U.S. Virgin Islands. Photo Courtesy of Prayitno Photography.

Getting Around Northside/West End of St. Thomas

To reach these further destinations, a rental car may be your best bet. Bus service can be sporadic and may limit your exploration.

Things to Do Away From the Crowds

In St. Thomas’ Northside district, spend a quiet few hours at Hull Bay. Popular with the locals, this calm inlet is home to picturesque fishing boats and friendly residents walking their dogs. Snorkelers should be aware of the rocky seafloor and come prepared with water shoes. But they may be well rewarded with coral, sea turtles, and tropical fish. If you get thirsty, sidle up to the outdoor bar at The Shack at Hull Bay for a couple of greenies (aka Heinekens) or a refreshing Starfruit Margarita. 

As you head to the West End district, stop by Bordeaux Farmers Market to browse the open-air stalls of organic produce, locally-prepared foods, and artisan crafts. The market is only open on the second and fourth Sundays of the month! 

Mermaid’s Chair at the Preserve at Botany Bay. Photo Courtesy of Taryn Parker.

Back on the road, head for the Preserve at Botany Bay. This gated community welcomes visitors to take a 1.5-mile walk to the western edge of the island. At Sandy Bay Beach, you’ll find a private (and undeveloped) bay with expansive vistas of the open sea. You can also walk to the Mermaid’s Chair, a narrow strip of beach that leads to the tiny westernmost tip of St. Thomas.

Either on your way out west or on your return trip to Charlotte Amalie, head up the hill to Sib’s on the Mountain for a feast among the trees. Popular with the locals, Sib’s serves hearty burgers, slow-roasted ribs, and ahi tuna nachos piled high.

Where to Stay on St. Thomas

Get some rest after your adventures at Mafolie Hotel. Perched high above Charlotte Amalie, guests can enjoy scenic views of the town below and the cruise ships in the harbor beyond.

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