As your cruise ship glides into the harbor, the town of Charlotte Amalie stretches around Long Bay. The pastel-colored houses contrast with the lush green hills in the background. So, you cannot wait to step ashore and begin your walking tour of St. Thomas’s vibrant capital.
A historic walking tour of Charlotte Amalie is the best way to experience lively Caribbean life. With downtown just a 30-minute from the terminal, the town is very accessible. Of course, you can get a taxi from the cruise terminal to Vendor’s Plaza to save some time and spend more time in the beautiful port town.
What are the hidden gems and best photo opportunities when strolling the cobblestoned streets of Charlotte Amalie? Based on my experiences and comments on many travelers’ forums, I’ve compiled the ultimate guide to walking Charlotte Amalie on a cruise day.
Check out the other walkable Caribbean cruise ports on cruise itineraries.
Charlotte Amalie Walking Tour Map
Follow this map to explore the must-see locations on your walking tour of Charlotte Amalie.
Charlotte Amalie Walking Tour Route: Step-by-Step Guide with Hidden Gems
Charlotte Amalie is a treasure trove of history, charm, and adventure waiting to be uncovered. This walking tour guides you through centuries-old alleys to colorful colonial buildings and historic landmarks. You’ll get plenty of opportunities to explore bustling markets and pick up some local souvenirs.
Remember to come prepared. Comfortable shoes are a must as you meander along cobblestoned streets and tackle hilly sections like the famous 99 Steps. What can you expect along the way? Panoramic harbor views, Insta-worth shots, and plenty of chances to soak up the island’s rich culture.
Starting Point: Havensight Cruise Pier to Waterfront Promenade
Your adventure begins at the Havensight Cruise Pier, where most major cruise line ships dock. Stepping ashore, you’ll find the terminal area a hub of activity—duty-free shops, local vendors, and cozy cafes. Of course, it’s tempting to linger, but it’s best to leave shopping for your return. Charlotte Amalie is waiting!
Note that some cruise ships dock at the Crown Bay Marina on the other side of the bay. In this case, you’ll need to get a taxi to the first stop, Vendor’s Plaza.
On rare occasions when several ships are in port, the cruise ship tenders in Long Bay. In that case, the tender boats arrive at the downtown harbor, where you can start your walking tour immediately.
Stop 1: Vendors Plaza
Take a taxi or walk 25-30 minutes along Veterans Drive to get to Vendors Plaza in the heart of downtown. Along the way, take snaps of shimmering harbor views with the cruise ship in the background. Note that there’s no shade along the way—so don’t forget your sun hat and stay hydrated.
Vendors Plaza is the heartbeat of local commerce in Charlotte Amalie. This vibrant open-air market is a hub for handmade crafts, colorful sarongs, and souvenirs that capture the island’s spirit. Historically, it was a bustling trading spot for locals, and today, it connects visitors with St. Thomas’s lively culture.
The plaza is the best place to purchase locally made handicrafts. Popular items include dolls, straw hats, and wooden carvings. The street food here is fantastic. it’s a go-to spot for Johnnycakes, a local favorite.
One fellow cruiser told me that it’s an excellent place for souvenirs, and haggling was a fun part of the experience. In my experience, it can get busy around midday. So, it’s best to get there as early as possible. However, the vibe is always fun and lively.
The next stop is right next door, and it’s the oldest building in the U.S. Virgin Islands.
Stop 2: Fort Christian
Danish colonizers built Fort Christian in the late 1600s to protect the island from hostile invaders. The distinctive red building is an iconic landmark at the downtown harbor. Its walls are 3 to 6 ft. thick and made the fortress almost indestructible.
The Dano-Norwegian-built Fort Christian is now a museum with exhibits of period furniture, historic photos, and documents. Displays also showcase the island’s history, from Indigenous people to colonizers, the Dano-Norwegian period, and pirate invasions. You can also walk through eerie dungeons and imagine what being a prisoner was like in the 1700s.
Many tourists highly rate the views from the upper sections of the fort and the gardens. One said that climbing the steps for the views of the plaza and harbor is well worth the $10 admission fee. If you’re a history enthusiast, I’d recommend reading up on the fort’s history first, as the signage could be better in the museum.
For the best photo ops, climb the stairs to the ramparts for spectacular views of the harbor and bay.
Stop 3: Emancipation Garden
Across the street from Fort Christian is the Emancipation Garden. This beautiful park celebrates the emancipation of enslaved people in the Danish West Indies in 1848. Don’t forget to check out the iconic Liberty Bell, the statue of Christian IX of Denmark, and the bronze bust of a formerly enslaved person blowing a conch shell—a poignant reminder of colonial heritage.
The large trees, benches, gazebo, and local refreshment kiosks also provide a welcome break from the Caribbean sun. It’s also a place to people-watch and soak up Caribbean island vibes. If you’re lucky, you may catch a music event or ceremony that frequently takes place throughout the year.
Many cruise passengers love the Emancipation Garden for some respite from the crowds and bustle of the market. One shared online that the trees provide much-needed shade during the midday heat.
Fun fact: The fence around the Emancipation Garden was constructed from cannons and ships’ anchor chains recovered from the harbor.
Stop 4: 99 Steps
To reach the next stop, head up Kongens Gade (King Street) toward Government Hill. Follow the street signs for “99 Steps”—it’s about a 5-minute walk uphill. The staircase is easy to spot, marked by its distinctive brickwork and greenery.
The 99 Steps is one of the most iconic landmarks in Charlotte Amalie. Built in the 18th century, the bricks used to form the staircase were ballasts in the hulls of sailing ships from Denmark. This picturesque staircase is a living reminder of the island’s colonial past. Enjoy the lush shrubs, colorful flowers, and palm trees as you climb.
The steps lead to panoramic views of the town and harbor, making the climb well worth it. Be sure to have comfortable walking shoes. One traveler warned that the bricks can be uneven in places, and it can get crowded on cruise days, so plan your visit early to avoid crowds.
Fun fact: Don’t think you’ve miscounted the number of steps as you climb them—there are actually 103 steps.
Stop 5: Three Queens Statue
At the top of the 99 Steps, take a short 3-minute walk up Blackbeard’s Hill to see the Three Queens Statue. This landmark is a memorial to three courageous women—Queen Mary, Queen Agnes, and Queen Mathilda—who fought for better working conditions on St. Thomas in the 19th century.
In the garden, look for a commemorative plaque detailing the Queens’ bravery and the lasting impact of their uprising across the Caribbean.
Over the whitewashed wall on the other side of the road, you’ll catch a glimpse of Blackbeard’s Castle, which sits on the highest point on Government Hill. Unfortunately, as of 2025, the castle is still closed, and there’s no information on when it will open. Also called Skytsborg, it was initially a defensive tower to keep a lookout for enemy ships.
From the Three Queens Statue, head back down the 99 Steps. To see a stunning colonial building, turn left along Kongens Gade, and in about 350 yards, you’ll see Government House with its red Danish-style guard house. The white building is a stunning example of colonial architecture.
To get to the next stop, head back to the 99 Steps and continue along Kongens Gade to Wimmelskafts Gade.
Hidden gem: 23 Kongens Gade at the bottom of the staircase is a historic parsonage and one of the island’s oldest structures. It was built using Danish stones and bricks, and there is a slave cell in the courtyard.
Optional detour: Head to Norre Gade and walk a few steps east to the Frederick Lutheran Church. It’s said to be the oldest Church in the Americas, being established in 1666. The current building was built in the 18th century, and its sweeping staircases and ramparts above the entrance are impressive from the street. A great photo opportunity.
Stop 6: St. Thomas Reformed Church
Head back along Norre Gade to Nye Gade, where you’ll find St. Thomas Reformed Church on the corner of Krystal.
Built in 1844, the church houses one of the oldest congregations in the Virgin Islands, tracing its roots back to 1660. Its simple yet elegant pale exterior and peaceful interior reflect its Dutch Reformed heritage. Visitors can admire its beautiful interior, but only during services.
Tourists usually comment on the church building’s beautiful facade with its four columns and red doors. One fellow cruiser who attended a service told me that beautifully preserved wooden pews and simple interiors are a quiet escape.
Stop 7: Synagogue of St. Thomas
Not far from the Reformed Church is the St. Thomas Synagogue—the second oldest synagogue in the United States. Like many other other Caribbean synagogues, it has a sand floor. The building is a combination of Greek and Gothic revival styles and Caribbean materials. The mahogany furnishings contrast beautifully with the whitewashed interior.
The Synagogue has a small museum that showcases artifacts, images, documents, and plaques about the history of the Jewish community in St. Thomas. A highlight of the museum’s display is the Memorial Czech Scroll, which was found after World War II and donated to the museum.
Even non-religious tourists say the synagogue is worth visiting. One commented, “The guide was very knowledgeable and shared fascinating stories about the synagogue’s history.” Another said that the “interior is beautiful, and the sand floor is unique and meaningful.”
Stop 8: Main Street (Dronningens Gade)
Head downhill from the Synagogue on Raadets Gade to Dronningens Gade (Main Street). This narrow street is Charlotte Amalie’s vibrant heart. Along the narrow sidewalks are a plethora of boutiques, jewelry stores, duty-free, and souvenir shops. You can also admire the colonial architecture, which blends historic charm with modern conveniences.
Take your time to meander along Main Street, and don’t be afraid to venture into side alleys where you’ll often discover colorful murals, hidden courtyards, and artisan stores. Some cruisers suggest heading down the side streets to escape crowds of tourists.
Here are a few hidden gems I found on Main Street:
Gallery Camille Pissarro: A beautiful art gallery in the same building where the impressionist artist Camille Pissarro once lived. It is an immersive cultural experience and a must for all art lovers.
Palm Passage: Don’t walk past this unique spot! The narrow side ally is home to boutiques and lovely cafes without the crowds.
Belgian Chocolate Factory: Walk down the narrow lane opposite the end of Nye Gade. Past the boutiques and cafes, you’ll discover one of the best chocolate shops in the Caribbean. It’s a place that not many cruisers know about.
Top shopping tip: Stick to purchasing high-end items like watches and jewelry from trusted stores on Main Street. I’ve heard that many unscrupulous vendors scam cruise passengers by trying to sell them fake goods.
Market Square
At the end of Main Street is Market Square—one of the oldest markets in the Caribbean. In the 18th century, the place had a reputation as one of the busiest slave markets in the Americas. Nowadays, the market is a vibrant hub of activity, with vendors selling fresh produce, handmade crafts, and Caribbean spices.
A tourist shared on a cruise forum, “Market Square is a great place for unique souvenirs and to sample fresh tropical fruits. But bring cash for smaller purchases.” Another warned, “Saturdays are the busiest market days, so expect the place to be crowded.”
After stopping at the Market Square, you have a choice of three options:
- Grab a bite to eat at a local waterfront cafe.
- Take a taxi to explore Frenchtown.
- Travel back to the cruise terminal and take the gondola to Paradise Point.
Optional Stop: Frenchtown
Extend your tour by taking a 10-minute walk to Frenchtown on the shores of Cay Bay. Here, you’ll find quaint cafes, art galleries, and fresh seafood restaurants. The French Heritage Museum gives fascinating insights into French influences on the island. One cruiser commented that it provides a nice escape from the busier parts of Charlotte Amalie.
The taxi ride back to the Havensight Cruise Port is around 15 minutes.
Optional Stop: Paradise Point Lookout
Want to enjoy the best panoramic views of Charlotte Amalie? If so, make the last stop on your walking tour a ride on the Skyline to Paradise Point. From the top, you’ll see downtown Charlotte Amalie and across the Bay to Hassel Island and the Crown Bay Marina. On a clear day, you can see Puerto Rico and St. Croix.
At the top, you can enjoy a Bushwacker cocktail and grab a quick bite to eat at the restaurant.
Must-Try Dishes in Charlotte Amalie
Indulge in the flavors of St. Thomas with iconic dishes like fresh conch fritters, spicy jerk chicken, and buttery Caribbean lobster. Don’t miss local favorites like callaloo, Johnnycakes, and pates filled with savory meats. Pair your meal with a refreshing bush tea or a tropical passionfruit smoothie.
What You’ll Miss If You Only Do a Walking Tour
A 3-hour walking trip of Charlotte Amalie is an immersive experience to connect with the island’s vibrant culture. It’s a beautiful city with historic gems, beautiful Danish colonial architecture, and charming shops. However, you miss out on St. Thomas’s stunning beaches, snorkeling in crystal clear waters, or off-road ATV adventures.
Want the whole St. Thomas experience? In that case, pair a walking tour with a scenic beach visit, snorkeling excursion, or trip to Magens Bay or Water Island. All are within a 20-30-minute taxi ride and offer a relaxing counterpoint to the town’s bustling streets. Coral World Ocean Park is also worth visiting. It has a stunning underwater observatory. Combining these activities ensures you see the island’s best.
Further reading: Top Things to Do in St. Thomas.
Insider Tips for a Better Experience
To ensure your cruise day in St. Thomas is memorable, here are some top tips I’ve found helpful over the years and others I’ve picked up from fellow passengers:
- Start early: Head ashore as early as possible after docking. This way, you beat the heat and crowds and have more time to add activities in the afternoon.
- Wear comfortable shoes: The cobblestone streets and hilly sections can be harsh on your feet. The last thing you want is to hobble back to the ship with blistered feet.
- Stay hydrated: Bring a reusable water bottle. Hydration is key in the tropical heat, and plan stops to rest in shaded places to regain energy.
- Cash is king: Many vendors and small shops prefer cash, so carry smaller bills. The national currency is U.S. dollars.
- Accessibility: Charlotte Amalie is a hilly town with steep slopes and narrow sidewalks. If you’ve got mobility issues, stick to the waterfront area and Main Street.
- Stay safe: Ensure your safety by staying on well-tracked tourist areas and keep valuables out of sight.
Why a Walking Tour of Charlotte Amalie Is Worth It
Walking the streets of Charlotte Amalie lets you experience the island’s cultural heritage, local charm, and Caribbean delicacies. Discover iconic landmarks like Fort Christian and the Emancipation Garden or hidden gems like Frenchtown or street food vendors—all at your own pace. Enjoy your USVI adventure and savor the vibrant atmosphere that makes this port city a popular destination.
Related articles:
- Top Things to Do in St. Thomas on a Cruise Day in Port
- The Ultimate Guide to the Best Beaches in St. Thomas
- Havensight Cruise Port Guide (St. Thomas): Shopping, Dining & Attractions