Colorful, cosmopolitan and endlessly captivating, Philipsburg is your gateway to all the best of St. Maarten. From the moment your ship docks, you're just steps away from soft white sands, world-class shopping, and the unique blend of Dutch and French cultures that make this island so special. Whether you’re seeking adventure, culture, or pure relaxation, St. Maarten delivers with warm tropical weather year-round and a laid-back vibe that invites you to explore at your own pace. Here's everything you need to know before stepping ashore.
There is much to see and do in St. Maarten, from exciting sailing adventures to spectacular shopping to beautiful beaches. All while enjoying world-class dining, luxurious accommodations and incredible shoreside experiences.
Get ready to create memories that will last a lifetime on these guest-favorite excursions.
Ideal for sunseekers and those craving a laid-back island vibe. Your afternoon begins with a chilled rum punch at La Playa, a beachfront resort known for its relaxed atmosphere and postcard-worthy views. Then, it’s two blissful hours to enjoy Orient Beach at your own pace. Walk the shoreline as gentle waves roll in, take a dip in the calm, protected bay or simply unwind in a complimentary lounge chair with the sun on your skin and a cool breeze in the air. Prefer some shade? Coconut palms and rental umbrellas offer a perfect retreat. You’ll also find local restaurants and beach bars nearby for drinks or a casual bite.
Glide smoothly up the mountainside on the Pirate Sky Ride, a scenic open-air chairlift that ascends to the Crow’s Nest atop Sentry Hill — one of St. Maarten’s highest peaks at 1,125 feet. The 30-minute ride is peaceful and packed with photo ops and panoramic views that stretch across the island and out to nearby Saba, St. Barts, Anguilla, and even St. Kitts on clear days. At the summit, wraparound viewing decks let you take it all in at your own pace. When you're ready, descend just as gently to explore Rockland Estate, a restored 18th-century plantation that tells the story of Trace Wilson and island life during that era. Cap off your visit with a taste of local flavor at the estate’s open-air restaurant before heading back to the ship.
This relaxed coach tour crosses both the Dutch and French sides of the island. Along the way, take in postcard-perfect views from elevated lookouts above Orient Bay and Simpson Bay, where mega-yachts glitter in the sun. If the skies are clear, you might even spot neighboring islands across the sea. In Marigot, the chic French capital, you’ll have free time to explore at your own pace. Browse boutiques for duty-free perfumes and designer goods, sample spicy cod fritters at a café or admire the colonial architecture along Rue de la République. History buffs might stop into the Saint Martin Museum, while shoppers and foodies will find plenty to love. Your return includes optional time in Philipsburg on the Dutch side before heading back to the pier.
Step aboard an actual yacht from the legendary America’s Cup and experience the adrenaline of head-to-head racing in the Caribbean breeze. After a short tender ride from the pier, you’ll join the crew on Stars & Stripes, Canada II or True North I — real contenders from the world’s most prestigious sailing competition. No experience? No problem. You’ll get a quick briefing, then choose your level of involvement. Take the helm, grind a winch, trim the sails or just sit back, enjoy the ride, and cheer from the rail. As your crew navigates the course, you’ll feel every tack, jibe and burst of speed across St. Maarten’s turquoise waters. After the race, celebrate your finish with a complimentary rum punch and some time to browse for souvenirs at the 12 Metre shop before returning to shore.
You can reserve your shore excursions in Philipsburg online 180 days before your Regent voyage. However, if you are sailing in a Concierge-level Suite or above (or are a Silver-level Seven Seas Society member or above), you enjoy the perk of priority reservations and may begin booking shore excursions 210 days before sailing.
Browse Regent's all-inclusive cruises to Philipsburg, St. Maarten and get ready to experience the wonders of this captivating destination firsthand.
Regent Seven Seas Cruises® has consistently delivered ultra-luxury travel experiences with the very best value for over thirty years. Aboard The World’s Most Luxurious Fleet®, enjoy unrivaled onboard space, unforgettable shoreside excursions, incomparable culinary experiences, and exceptional Heartfelt Hospitality™.
Our exceptional service begins long before you step aboard. A member of our Reservations Team or your Travel Agent will assist you in planning your next unforgettable luxury cruise.
