One Place, Two Ways: Charlotte Amalie, St. Thomas

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As the largest city in the U.S. Virgin Islands, lively Charlotte Amalie is a hotbed of culture and entertainment, from museums and heritage sites to popular beaches and underwater adventures. 

Whether you prefer to explore the rich history of St. Thomas or hit up the trendiest tourist destinations, these itineraries will help you make the most of your day. 

The History Buff 

Morning

Start your day of discovery with breakfast at Gladys’ Cafe, where stone walls and arches still reflect the building’s shipping warehouse origins. A hearty breakfast of grits and eggs or a lobster and avocado omelet will fuel you up for the journey ahead. Or grab a quick latte, an egg-and-cheese croissant, or a fresh-baked pastry at MBW Cafe and Bakery. This light, friendly cafe is a nonprofit that helps at-risk youth with job training and placement, so you’ll support a good cause. Take your breakfast to go—you can eat on your feet while walking a few blocks to your next destination. 

The 99 Steps on St. Thomas, USVI.

Now that you’re energized, it’s time to climb. Head for the 99 Steps, a special “step-street” designed to make it easier to navigate Charlotte Amalie’s hilly terrain. Each brick was originally imported from Denmark, serving as ballast in empty trade ships before they picked up their cargo on the island. Now, it’s a scenic ascent lined with bright flowers and palm trees for the prettiest workout on the island. (There are technically 103 steps, but the view at the top is worth it.)

Once you catch your breath, you’re just a short walk from the St. Thomas Synagogue. Dedicated in 1833, this is the oldest synagogue building in continuous use in American territory. Inside, the floors are covered in sand to honor the medieval Jews who prayed in secret to avoid exile, forced conversion, or worse. Visit the Weibel Memorial Museum onsite to learn about the island’s Jewish community and spot the Memorial Czech Scroll, rescued from the Holocaust and on “permanent loan” to the synagogue. 

The sandy and historic St. Thomas Synagogue.

Next, take a tour of the St. Thomas Historical Trust Museum. Their docent-led tours dive into the little-known history of USVI with fascinating stories you won’t read in history books. Explore their collection of West Indian antiques and furniture, artifacts from area shipwrecks, and dozens of historic photos. Tours are available by appointment only!

Afternoon

Get a street-side view of some of Charlotte Amalie’s most intriguing architecture with a self-guided walking tour. First, take in the charming green shutters and terraced gardens of Haagensen House, built in the early 1800s by a Danish banker. Next, visit the Frederick Evangelical Lutheran Church, the second-oldest Lutheran church in the Western Hemisphere, completed in 1793. It combines Georgian symmetry with Gothic Revival features like a gable tower added in the 19th century. 

A block away, the beautiful 19th-century Government House holds the offices of the governor of the U.S. Virgin Islands. Spot the intricate ironwork railings, tranquil gardens and a bright red Danish sentry box that has stood guard since 1867 (although the sentries themselves are long gone). Finish your tour at Seven Arches Museum, a Danish colonial townhouse dating back to the 1850s. It’s named for the arches of the distinctive “Welcoming Arms Staircase” leading to the front door. 

After your walking tour, explore Fort Christian—the oldest structure on the island. Built in the 17th century by Danish colonists, it has been a governors’ residence, a military defense post, a place of worship, and a prison. Explore the cells and find historical photos and documents, period furniture, a cane press, and spectacular views from the fort roof. 

Evening

For fine dining in historic surroundings, the Old Stone Farmhouse Restaurant is the place to be. You’ll sit amidst graceful arches, two-foot-thick stone walls, and soaring rafters in this restored 200-year-old plantation fieldhouse. The seasonal menu highlights island fare like local lobster and farm-fresh greens, plus premium dishes like grass-fed filet mignon and New Zealand rack of lamb. 

End your day on a high note at The Dog House Pub in nearby Havensight. Sip local rum and listen to live music as the Caribbean breeze floats through this laid-back bar. It’s been an island mainstay since 1987—and it’s dog friendly! 

The Trendy Tourist 

Morning

Stop by family-owned cafe Sunrise Breakfast N’ Suh for a comfort food breakfast in Crown Bay Center, just steps from the Cruise Port of Charlotte Amalie. Fill up on French toast topped with fruit chutney or chicken and waffles. Don’t let the name fool you—they serve breakfast all day, so feel free to sleep in. 

Relaxing in the cooling waters of Magens Bay.

After you eat, browse the art galleries and charming boutiques of Main Street (also called Dronningens Gade). This cobblestone street is lined with shopping of all kinds, from fine gemstones and watches to premium alcohol and tobacco to unique art and handmade jewelry. You can bring home up to $1,600 worth of goods duty-free, so make some room in that suitcase. 

Not into shopping? Head straight for the beach. Popular Magens Bay Beach is an idyllic spot with white sand beaches and calm blue water. Rent a beach chair and an umbrella to dial up the relaxation. It gets busy when cruise ships dock, so grab your spot early! You can also rent stand-up paddle boards or kayaks. Hit the water and look for sea turtles out on the bay. 

Afternoon

Start your afternoon with a gondola ride to the best view of St. Thomas. The Paradise Point Skyride will hoist you gently into the air, climbing 700 feet in less than ten minutes. As you ascend, a sweeping view of Charlotte Amalie and St. Thomas Harbor will open up below you. On clear days, you can see all the way to Puerto Rico! 

At the top, sit down for lunch at Taste at Paradise Point. Grab a seat by the deck railing so you don’t have to turn your back on that stunning view while you eat. Enjoy local fare like their Caribbean Lobster & Shrimp Roll and Lobster Fritters. Don’t skip their famous Bailey’s Bushwacker—it’s a very adult milkshake made with Baileys, vodka, coconut rum, amaretto, Kahlúa, and cream of coconut. 

After lunch, drive (or catch a cab) to Coral World Ocean Park for an afternoon of water exploration. Their SNUBA® experience lets you explore the coral reefs up close. A raft will carry your air tank at the water’s surface, so there’s no training required. Or spot parrotfish and sea cucumbers as you walk along the sea floor, thanks to a special Sea Trek helmet.

Evening 

Back in Charlotte Amalie, dinner at The Greenhouse Restaurant and Bar comes with sunset views across St. Thomas Harbor. Watch the cruise ships depart from this colorful, beachy spot over Caribbean lobster tail, Angus T-bone steaks or their original Conch Creole—conch sauteed in homemade creole sauce with peppers and onions.

Or take your meal on the water. Dockside Watersports’ sunset dinner cruises combine a luxury catamaran excursion with a locally sourced feast. You’ll spend two hours on St. Thomas Harbor enjoying an open bar and gourmet seasonal dinner. With expert service by a professional crew and some major photo ops, you’ll feel like a serious VIP. 

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