The U.S. Virgin Islands' Biggest City Feels Part Old Europe, Part Caribbean Daydream

You've likely seen images of this tropical paradise a hundred times: A bright blue harbor dotted with sailboats and yachts, flanked by gentle mountains and terra cotta red rooftops. This picturesque scene can be found on many Caribbean islands, but St. Thomas in the U.S. Virgin Islands has a particular blend of charms. The first Europeans arrived in 1493, but that group didn't hang around long. Plundering pirates had a rollicking time until the Danish West India Company arrived in the 1670s. Then, the town around the scenic harbor was renamed Charlotte Amalie in honor of the wife of the Danish king, and it was transformed into a thriving trade center by 1724.

Today, St. Thomas is regarded as a Caribbean destination that should be on your travel radar, and Charlotte Amalie is the largest city on the island. With a current population of around 13,000, the city boasts an abundance of activities for history lovers and beach bums alike. 

St. Thomas was purchased by the United States in 1917. Post-World War II growth in pleasure cruises boosted the island's economy and transformed Charlotte Amalie into a major cruise ship hub, which now welcomes nearly 1.8 million annual visitors on cruise ships alone. Despite the increasing popularity of cruise holidays, especially among younger people, the beauty and historic appeal of Charlotte Amalie draw hundreds of thousands of non-cruise travelers per year, with frequent direct flights to Cyril E. King Airport from major cities, such as New York, Boston, Houston, Orlando, Miami, and Washington, D.C.

The blending of Euro flair and a laid-back Caribbean lifestyle endows Charlotte Amalie with an idiosyncratic appeal. The historic district features sites listed on the National Register of Historic Places, showcasing the island's rich history and architecture. Painted a dazzling red, Fort Christian was built by Danish settlers in the late 17th century, serving as a prison and a military base. Here, you can browse the museum before ascending to the roof for a panoramic view. 

Speaking of ascending, gather some extra energy for the 99 Steps — which is really 103, if you're counting. The heart-pumping climb pays dividends with stunning vistas and Blackbeard's Castle. A Danish watchtower built in 1679, the castle was named after the notorious pirate Edward Teach, aka Blackbeard. More buccaneer roguery awaits at the Pirates' Treasure Museum. Take a breather with an aerial view of the city, minus the aerobics, on the Skyride to Paradise Point, a cable car that climbs 700 feet in 10 minutes. You can spot St. Croix in the distance and enjoy refreshments at the bistro with views of the sunset.

With so many visitors, Charlotte Amalie has its share of souvenir stalls, but it's more diverse than that. Turn into one of the brick alleyways and you'll find charming cafes and boutiques. Just minutes from the waterfront and originally constructed in the 19th century as warehouses, Palm Passage is now a shaded alley of artisan boutiques that perfectly capture the Caribbean's enchanting fusion of European appeal and chill island vibes. The original stone archways are still intact and welcome visitors to mingle with local artists. The lively shopping district around Main Street is a bustling thoroughfare teeming with looky-loos and serious shoppers on the prowl for duty-free bargains.

No need to pretend you didn't come to St. Thomas for the beaches. Considered one of the best beaches in the Caribbean, Magens Bay Beach is a long stretch of pebble-free, pearly white sand caressed by sloping mountains and pristine turquoise water, 3.5 miles north of Charlotte Amalie.  Often featured in travel photos of the island, it's easily accessible by car, taxi, or public transit.  The protected bay offers calm, shallow water ideal for all ages, and it's especially popular among cruise ship passengers. You can even enjoy a hiking or fitness trail, or rent a pavilion with a barbecue grill for a picnic. All the amenities necessary for a comfortable day are on hand, including lounge chairs and watersports equipment rentals, showers, and beachside snack bars and restaurants. It's known to get crowded, so check in advance if a cruise ship is in port if that's a concern.

On the eastern edge of the island, Sapphire Beach offers a more tranquil ambiance with breathtaking views of St. John. A protected bay with calm waters, online reviews praise the bright blue water, great snorkeling, and varied dining options, such as Beach Buzz for coffee and smoothies, and Sapphire Beach Bar & Grill for fish tacos, frozen cocktails, and happy hour with live music.

Also on the island's east side is Smith Bay Beach (formerly Lindquist Beach). About 6 miles from Charlotte Amalie, this is where things feel secluded, and you can play castaway, at least for an afternoon. It's part of a protected, 21-acre preserve, and there are no restaurants, so prepare a picnic. It truly is a Caribbean daydream that's off the beaten path, yet close enough that when you wake, civilization is just a 20-minute taxi ride away.