When I moved to St. Maarten after graduating from college in the US, I had never been to an island before and had no idea what to expect. I assumed that everyone lived in homes thatched with palm leaves. I was quite pleasantly surprised as I took the bus that wound through the hills of Dutch St. Maarten from Princess Juliana Airport to Philipsburg. What surprised me most overlooking P'berg from atop the high road leading into the town was the number of white houses with red roofs clustered in the land outside of the town. From there, everything looked pristine and beautiful.
As I disembarked from the taxi bus, paid the driver my $1, and made my way from Back Street to Front Street, I noticed that the roads were littered with trash, potholed, and narrow. I saw very few people as I walked toward the main road through alleys and side streets. I reached Front Street and that’s when I felt like I was in another world. Loads of camera-toting tourists immediately closed in on me, and I quickly understood that most of them were from the cruise ships. The street was lined with jewelry stores and souvenir shops.
If one walks from Front Street toward the bay, they will reach the boardwalk, which really isn't made of boards. No matter. It's a very nice stretch of restaurants and shops. At night, locals gather to sit out on the boardwalk and visit while their children play on the beach. My favorite restaurants are Taloula Mango's, which has happy hour every night from 5-7pm with free tapas. I also like Oualichi's across the Sint Rose Arcade. They have a very cute boutique of women's clothing. Of jewelry stores, I recommend Shiva's. As I have been living in St. Maarten, I have come to know the owners. They are very respectable and sincerely are concerned about the happiness of their customers with their purchases.
Also, don't miss Old Street. There is a lovely French bakery with great sandwiches and pastries. Overall, Philipsburg is a place that looks a little rough around the edges, but underneath it is quite a jewel.