TOUR FORT CHRISTIAN

Built in the late 1600s, Fort Christian is the oldest structure still standing in the U.S. Virgin Islands. The eye-catching red fort was built by Danish settlers and has served as a military fort, a police station and a prison over the past 350 years.

Today, the fort is the site of the St. Thomas Museum. Inside the meter-thick walls, tour displays of historical records and photos, a sugarcane press, and period furniture and artifacts. Peek into the cells from the fort’s military past, then climb to the roof for stunning views of the harbor.

CLIMB THE 99 STEPS TO BLACKBEARD’S CASTLE

Next, walk a few blocks over to the 99 Steps. This 18th-century “step-street” was built with stone brought as ballast on Danish ships to the islands. Climb the 103 steps (not actually 99!), surrounded by colorful flowers and shady palm fronds.

At the top, you’ll spot Blackbeard’s Castle, a 1679 Danish watchtower high above the city. Nicknamed after the infamous Caribbean pirate, the tower was used as a lookout for the Danish to spot enemy ships. While the compound’s gates are closed due to hurricane damage, you can still see the tower exterior and enjoy one of the best views on the island.

DISCOVER THE SANDS OF ST. THOMAS SYNAGOGUE

After visiting Blackbeard’s Castle, descend back down to the city to visit St. Thomas Synagogue, the second-oldest synagogue still standing in the Western Hemisphere.

This 1833 landmark combines Jewish tradition and Caribbean architecture, with artifacts like the traditional Ark made of local mahogany. Underfoot, you’ll notice a floor made of sand — a tribute to the Jews of the Spanish Inquisition, who knelt on sand to muffle the sounds of their prayers.

Look around on your own, or take a free 15- to 30-minute tour to learn about the history of this one-of-a-kind synagogue.

TAKE A BREAK IN THE EMANCIPATION GARDEN

On your way to lunch, make a quick stop at Emancipation Garden to rest on a bench under the slow-growing lignum vitae trees. This small park commemorates the 1848 emancipation of the enslaved islanders — a full 15 years before President Abraham Lincoln’s Emancipation Proclamation.

Spot the Freedom statue, a bronze cast representing an enslaved man blowing a conch shell to symbolize the call for freedom. There’s also a replica of the Liberty Bell and a charming white gazebo. You might stumble on a special event here, like a food festival or local concert!

STOP FOR LUNCH

All that walking is sure to work up an appetite. Stop by Amalia Café in the Palm Passage shopping gallery for Spanish tapas on the breezy covered patio. Share small bites like Galician-style octopus, shrimp sauteed in olive oil and garlic, and spicy Spanish chorizo — all paired nicely with a cool Iberian wine.

To sample authentic Caribbean cuisine, visit Gladys’ Cafe in the Royal Dane Mall. Get a table in the historic stone dining room and dig into conch fritters, curry goat and their legendary oxtails. Pick up a bottle of Gladys’ beloved hot sauce for a tasty souvenir.

JOIN THE CREW AT PIRATES TREASURE MUSEUM

After lunch, take a quick cab ride to the Pirates Treasure Museum in east Charlotte Amalie. Learn about legendary scallywags like Blackbeard and Captain Kidd, the most feared pirates in the Caribbean. And get a look at life on the high seas, when any passing vessel could spell your doom.

Examine recovered booty and artifacts, including cannons, sunken cargo and ancient Roman coins. Plus, learn about the technology used today for deep-ocean exploration that helps recover these once-lost treasures.

DO SOME DUTY-FREE SHOPPING ON MAIN STREET

Wander the colorful shops of Main Street (aka Dronningens Gade) for a duty-free shopping spree. Once the Danish warehouses for sugar and rum exports, these historic buildings now house dozens of local shops. Jewelry, watches and precious gems dominate. But you’ll also find island fashions, souvenirs and eye-catching home goods.

Each person can bring up to $1,600 worth of merchandise back to the mainland, duty free! But even if you don’t find anything that speaks to you, Main Street is also a magnet for people watching and soaking up the Charlotte Amalie vibes.

BROWSE THE BOUTIQUES OF PALM PASSAGE

Once a large export warehouse, Palm Passage is now home to an eclectic array of boutiques and shops. Take your time browsing these stores, where the atmosphere is quieter and more relaxed than the bustle of Main Street.

Look for sparkling crystals and locally made gifts at Mystic by the Sea, hand-painted clothing at Just Imagine, and breezy clothing and housewares at Fish Face. All of the shops are arranged around a central courtyard, with shady palm trees and an outdoor bar for a quick happy hour stop.

ENJOY A LEISURELY DINNER

The inviting Stone House Café combines Caribbean, Italian and Asian flavors into one satisfying menu. Try coconut-crusted mahi, conch fra diavolo or spiced rum shrimp kabobs — plus plenty of vegetarian options — in the historic stone dining room. Frequent live music is a bonus!

For an upscale chef’s tasting, visit Blue 11 in the luxurious Yacht Haven Grande marina. Choose a seven-, nine-, or 11-course menu with creative bites like jerk chicken with plantain gnocchi. Watch the masters at work from the chef’s counter, or dine on the patio for a glimpse of the mega-yachts in the marina.

TAKE THE SKYRIDE TO PARADISE POINT

Last stop: An after-dinner cocktail with a truly unmatched view. Climb 700 feet above the island on the Skyride to Paradise Point in an enclosed gondola. From Paradise Point, you can take in the twinkling lights of Charlotte Amalie over the magnificent harbor. You could also plan this as an excursion before dinner to enjoy happy hour drinks and spectacular sunset views.

At the top, sip a cocktail on the double-decker patio of Taste at Paradise Point. Try their signature frozen Bailey’s Bushwhacker — a blend of Bailey’s Irish Cream, Kahlúa, amaretto, crème de cacao and fragrant nutmeg.

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