Philipsburg, St. Maarten, is where Dutch Caribbean charm meets coastal beauty, and it’s all just a short walk from your ship. Why spend your cruise day stuck in tour buses or jostling for beach space when you could wander through lively streets, past historic landmarks, and down a sunlit boardwalk? This town was made for walking, with its compact layout and endless opportunities to explore.
A self-guided walking tour lets you soak up Philipsburg’s vibrant energy as soon as you step off the ship. Imagine popping into colorful shops, exploring vibrant markets, sampling local treats, and discovering hidden gems—all at your own pace. And with the famous Great Bay Beach next to the town, you also get to enjoy a relaxing beach day on your cruise. Ready to slip on your comfy walking shoes and find hidden gems in Philipsburg?
Let’s dive into the perfect self-guided walking tour that will make your cruise stop unforgettable.
Best Times to Visit Philipsburg, St. Maarten on a Cruise
The ideal time to visit Philipsburg, Sint Maarten, on a cruise is the dry season—December to April. These months offer warm, sunny weather with minimal rain—ideal for exploring on foot. To avoid crowds, start your walking tour early in the morning before the midday heat.
Visiting the Caribbean island during the shoulder months of May and November can mean fewer crowds and better cruise deals. However, you should pack a poncho or umbrella in a day bag for occasional rain showers. Also, a light jacket is handy in case of brisk Caribbean breezes.
Why Take a Self-Guided Walking Tour of Philipsburg?
Philipsburg is one of the most walkable cruise ports on a Caribbean trip. With the downtown area a leisurely 20-minute walk away or a short water taxi ride, it’s easy to see why some cruise ship passengers decide to avoid shore excursions. So, forget crowded bus tours and rigid schedules, just take your time exploring the unique blend of Caribbean and European influences.
Philipsburg is highly accessible, making it an excellent place for people in wheelchairs or with mobility issues to explore. The city is generally flat, has good sidewalks, and many stores are wheelchair accessible. It is noted that that Great Bay Beach, in the center of town, is accessible for wheelchair users and seniors.
What can you expect from a historic Philipsburg walking tour?
- Distance: 3 miles (5 km) round trip, including the walk from the cruise ship docks
- Walking Time: Around 1 hour to 1 hour 10 minutes if you’re walking steadily without extended stops
- Tour Duration: Expect the full experience to take 2-3 hours or more, depending on how much time you spend exploring attractions
- Terrain: Mostly flat
- Accessibility: Ideal for strollers or people in wheelchairs
Philipsburg Walking Tour Itinerary
I’ve created this Philipsburg walking tour based on my experiences and top-rated reviews by travelers who’ve fallen in love with the Dutch island’s charm.
Dr. A.C. Wathey Cruise Port
Cruise ships dock at Dr. A.C. Wathey Cruise & Cargo Facility Port on the southern side of Sint Maarten (St. Maarten). In the compound, you’ll find the usual tourist traps of souvenir stalls selling duty-free items, Dutch cheeses, and local crafts. Most cruisers arriving in Philipsburg head straight for private buses and taxis or get the water taxi to the downtown area.
So, you have three choices to start your walking tour.
- First, exit the terminal, turn left onto Juancho Yrausquin Blvd, and walk 20 minutes to the first stop.
- Second, you can hop on a water taxi for a scenic ride to the Captain Hodge Pier. The price is $7 for the roundtrip.
- Third, you can catch a regular taxi at the cruise terminal and take the 5-minute ride to Philipsburg—the price is $8.
If you decide to take the water taxi, remember to adjust the tour itinerary as you’ll arrive in the middle of the town.
Stop 1: The Crossroads (Beside the old Guavaberry Emporium)
You’ll find The Crossroads at the start of Front Street—nr. 8, to be precise. This small but meaningful landmark symbolizes the cultural unity of St. Maarten. Located next to the vibrant Old Guavaberry Emporium, it’s an ideal first stop to ease into the charm of Philipsburg.
One cruise passenger shared on Tripadvisor that it’s an excellent place to start a walking tour. They shared that the cultural significance really set the tone for the day. One traveler jokingly commented, “Does anyone come back from Philipsburg without a picture of the Crossroads sign?” However, it’s good to note that it’s easy to miss.
At the Crossroads, take a moment to snap a shot of Philipsburg’s colorful streets before heading to your next stop just a few yards away.
Stop 2: Yoda Guy Movie Exhibit
Located at 19A Front Street, the Yoda Guy Movie Exhibit is one of the quirkiest museumsin the Caribbean. The museum’s founder is Nick Maley—a special effects artist who worked on Star Wars. This small museum is packed with Star Wars props and life-sized models of characters from the film, including Yoda.
If you’re lucky, Nick Maley himself might be there to share behind-the-scenes stories. A fellow cruiser told me that meeting Nick was the highlight of his trip. He said that he’s so down-to-earth and full of amazing stories, and his kids loved it.
Insider tip: Plan to go early or later in the day to avoid crowds, as the place is small and feels cramped when busy.
Stop 3: Old Street
Old Street is a five-minute walk from the Yoda Guy. It’s a picturesque lane with beautiful colonial architecture, a vibrant atmosphere, and plenty of photo ops. Travelers describe it as the perfect spot to slow down, explore unique shops, and soak in the island’s rich history.
Old Street is a great place to browse artisan goods, handmade jewelry, and unique Caribbean and Dutch souvenirs. One traveler noted that the street is a nice break from the hustle and bustle of Front Street, and the boutiques offer beautiful items. Although, one cruiser pointed out that some of the shops are pricey.
Before leaving Old Street, make sure to take photos of the vintage-style lamps against the backdrop of colorful buildings.
Stop 4: St. Martin of Tours Catholic Church
As you continue along Front Street, you’ll come to Sint Maarten of Tours Catholic Church. Take a moment to admire its architecture, which is strongly influenced by Dutch colonial designs. It’s also one of the oldest historical buildings in Philipsburg. Best time to visit? The mornings when there are fewer tourists.
It’s worth a peek inside if the church is open. Visitors describe how beautiful it is inside and how they enjoy the peaceful atmosphere. Even if you’re not religious, it’s a place to enjoy some quiet reflection. There are plenty of photo opportunities, but many visitors take snaps of the beautiful, whitewashed interior or the exterior framed by palm trees.
Insider advice: Women should dress respectfully in Caribbean churches, wearing modest tops, dresses, or slacks.
Stop 5: Philipsburg Courthouse
The most iconic landmark in Philipsburg is the Courthouse on Hendrikstraat. The building dates back to 1793, and its green and white facade and clock tower make it stand out among the other colorful buildings. Over the years, the building has been a fire station, post office, and jail. Look for the pineapple on top of the tower’s belfry—it’s a symbol of Caribbean hospitality.
For the best pictures of the Courthouse, walk to the end of Watney Square toward the shoreline, where you’ll capture the building in its glory, framed by the palm trees lining the street.
Note that the building is still a working court, and there’s not much to see inside. However, it’s a popular stop for cruisers who want to capture some Insta-worthy shots of colonial architecture and palm trees.
Fun fact: Philipsburg Courthouse is one of only two buildings in the world that is featured on a country’s flag.
Stop 6: Philipsburg Market
Walk to the end of Hendrikstraat, where you’ll find a lively marketplace—a collection of 20 stalls lining both sides of the street. At Philipsburg Market, you’ll find a wide range of local crafts, handmade jewelry, souvenirs, and Caribbean-inspired clothing. Take your time to browse the stalls and pick up some mementos to take back home.
Many cruisers comment that the market has the lowest prices for souvenirs—cheaper than the Boardwalk and cruise terminal. One comment on Cruise Critic said that the stalls seemed repetitive, and the sellers get a bit pushy sometimes. However, the overall experience is positive.
Stop 7: Front Street (Shopping District)
After visiting the historical landmarks in Philipsburg, you can take a leisurely stroll along Front Street—the town’s duty-free shopping mecca. Here, you’ll find everything from Guavaberry rum to gold and diamond jewelry, designer clothing, perfume, and high-end watches. Even if you don’t buy anything, the bustling streets and colorful storefronts offer an energetic atmosphere unique to the town.
Visitors often find fantastic deals on designer brands and enjoy sampling Guavaberry liqueurs. However, it can get crowded on cruise days. So, if you want to avoid the crowds, head to Back Street on the Salt Pond side of town.
Stop 8: The Boardwalk (Great Bay Beach)
The Boardwalk along Great Bay Beach is the perfect place to end your walking tour. This lively promenade offers stunning ocean views, beachside dining, and a relaxed Caribbean vibe. It’s time to find a cafe, beach bar, or restaurant to sit back and relax. Usually, on cruise days, you’ll find street performers and live music.
A traveler on Tripadvisor commented, “The Boardwalk was the highlight of our day. We had lunch at the Lazy Lizard restaurant and relaxed on the sand—it was perfect!
Photo tip: Take a panoramic shot of Great Bay with the cruise ships in the distance—a classic Caribbean view.
Option 1: Fort Amsterdam (Optional Adventure)
In my opinion, Fort Amsterdam is well worth a visit when in Philipsburg, and it’s only a short taxi ride from downtown. The 17th-century fortress is perched on a peninsula between the Great Bay and Little Bay. After walking through the Divi Little Bay Resort ground (don’t worry, you’re not trespassing), you can explore the ruins and cannons and imagine a time when locals were defending against invaders.
Fort Amsterdam is one of the best places in St. Maarten to see the island’s national bird, the pelican. Many cruisers agree that you get the best shots on the island, and it’s perfect for history buffs and photography enthusiasts alike.
Here’s a great photo tip from a fellow cruiser: Frame a shot of the old cannons overlooking Great Bay with the cruise ships in the background—it’s a striking blend of history and modern-day travel.
Hidden gem: If you have time, take the hiking trail to the top of Fort Willem to enjoy sweeping views of Philipsburg and the surrounding lush countryside.
Option 2: Great Bay Beach
Want a more relaxing end to your walking tour? In that case, why not enjoy a Caribbean beach day? This pristine stretch of soft, white sand and crystal-clear waters make it one of the best beaches in St. Maarten. It’s the perfect spot for relaxation, exploration, or water sports. Also, you’re spoiled for choice in terms of lively beach bars and cafes.
Thrill-seekers can enjoy jet skiing, parasailing, or banana boat rides, while paddleboarding and kayaking offer a more serene experience. The calm, shallow waters are perfect for swimming and snorkeling near the shore, making this beach an ideal spot for travelers of all ages.
After having fun on the water, lie back on a beach chair, order a cocktail, and soak in the laid-back vibe that is so unique to the Caribbean.
Whether you’re seeking a peaceful retreat or action-packed fun, Great Bay Beach is the perfect end to your Philipsburg walking tour.
Must-Try Dishes in Philipsburg
I’ve found the cuisine in St. Maarten to be some of the most diverse on my travels. Local dishes are an unforgettable fusion of Dutch, French, and Caribbean flavors. From Creole specialties like conch fritters and dumplings to island staples like Johnny Cakes and fresh grilled lobster, there’s no shortage of authentic flavors to explore. And, of course, you can’t leave without sipping on a Guavaberry Colada, St. Maarten’s signature cocktail.
Here are a few restaurants that consistently get rave reviews from cruise passengers.
Lazy Lizard Beach Bar & Grill: With a rating of 5/5 from over 1,600 reviews, it’s the stand-out restaurant on the island. Cruisers rave about the delicious voodoo shrimp, jerk chicken, and Johnny cakes. One commented, “The Creole shrimp was to die for, and the rum punch was the best we had on the island!”
Chesterfield’s: Located near the cruise terminal, it seems to be the go-to place for fresh fish and conch fritters. One couple shared on Tripadvisor that the local lobster and seafood were “absolutely delicious!” Another added that the coconut shrimp was terrific, the portions huge, and the prices reasonable.
Bold Buddha Caribbean Fusion: Located on Front Street, this restaurant gets top marks for its Asian-Caribbean fusion dishes like coconut curry shrimp and chicken tacos. One cruiser shared, “The jerk chicken tacos were bursting with flavor, and the coconut curry shrimp was absolutely delicious. It’s clear they put a lot of thought into their menu.”
Hidden Gems and Local Experiences
Philipsburg offers more than its iconic boardwalk and lively shopping streets—it’s a treasure trove of unique experiences waiting to be discovered. Here are a few lesser-known attractions to include on your cruise day.
Amsterdam Cheese and Liquor Store: Get a taste of the Netherlands in the heart of Philipsburg, with its wide selection of Dutch cheeses and premium liquors. Try some creamy Gouda cheese, Advocaat, or Dutch gin. Just check beforehand what you can bring back on board if you want to purchase anything.
Juggie’s Place: Looking for a quirky and laid-back dive bar where the drinks are strong, the atmosphere is casual, and the stories are unforgettable? Head to Juggie’s before returning to the ship. One cruiser shared, “Juggie is a legend! This place feels like home with its relaxed vibe and great drinks.”
St. Maarten National Heritage Museum: If you have some time to kill at the end of your day, this museum gives a fascinating glimpse into St. Maarten’s history. Located at the start of Front Street, it tells the island’s story from the Arawak people to colonial times. The museum offers self-guided tours, and admission is free.
Sea Trek Underwater Adventure: Here, you can experience the thrill of walking along the ocean floor with Sea Trek—no scuba training required. It’s an underwater adventure that’s as unique as it is unforgettable. Using specially designed helmets, you can breathe freely and explore a vibrant marine world. It’s close to the cruise port.
Essentials for the Walking Around Philipsburg
Prepare for a comfortable and enjoyable day exploring Philipsburg with these essentials. From practical items to handy tips, this list will ensure you’re ready to make the most of your visit.
- Comfortable shoes for walking 1 to 3 hours
- Lightweight clothing with breathable fabrics to stay cool in the Caribbean heat
- Sunscreen and a hat to protect yourself from the intense tropical sun
- Reusable water bottle to stay hydrated—many shops and cafes offer refills, and tap water in St. Maarten is generally safe to drink
- Cash (U.S. dollars are preferred)
- Island map or download offline maps to your phone
- Swimwear and quick-dry towel for spending time at Great Bay Beach
Philipsburg Awaits — Happy Cruising
Philipsburg offers the perfect blend of history, culture, and relaxation, making it an unforgettable stop on your cruise. Walking around the town is the best way to soak up the lively Caribbean vibes, savor unique cuisine, and explore local landmarks. Don’t forget to try the island’s drink—Guavaberry rum. So, take your time, savor the vibrant atmosphere, and let Philipsburg’s charm create memories to treasure long after your cruise ends.
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