Catamaran Charter St Maarten – Luxury Island-Hopping Adventure in Paradise
Why Choose a Luxury Catamaran Charter in St Maarten?
St Maarten (Sint Maarten) is the quintessential Caribbean paradise – a half-French, half-Dutch island renowned for its eclectic culture and upscale leisure offerings. From sparkling white-sand beaches and duty-free shopping to gourmet dining and vibrant nightlife, “The Friendly Island” truly has it all. With so much to see and explore – including neighboring gems like Anguilla and St Barts – there’s simply no better way to experience this five-star paradise than aboard a private yacht. A luxury catamaran charter in St Maarten immerses you in the island’s glamour and natural beauty, all from the deck of your own floating villa. You’ll enjoy panoramic sea views, gentle trade winds, and the freedom to set your own course. Whether you’re a first-time charterer or a seasoned sailor, a catamaran provides an ideal blend of stability and indulgence for exploring St Maarten in style.
Another reason savvy travelers choose a catamaran rental St Maarten is the sheer variety of vessels and destinations available. Boatcrowd’s extensive fleet offers everything from intimate sailing catamarans perfect for family getaways to crewed mega-catamarans outfitted with chef and crew for an all-inclusive escape. Catamarans are ideal for families and groups because of their stability, space, and comfort – the twin-hull design means less rocking (great for kids or first-timers prone to seasickness) and expansive decks to lounge or play. Thanks to St Maarten’s world-class marinas and the 12-square-mile sheltered Simpson Bay Lagoon bustling with yachts, you have a wide range of catamaran choices at your fingertips. Even more enticing are the amazing destinations you can reach on charters of various lengths. On a 3-day catamaran charter in St Maarten, you might circle the island’s best beaches and even sneak in a day trip to nearby Anguilla or St Barts. Opt for a 5-day catamaran rental, and you can split time between St Martin’s chic French-side ports and the luxurious harbor of St Barts, indulging in French cafés one day and snorkeling remote coves the next. And if you have a full week, get ready for an island-hopping odyssey – a 7-day luxury catamaran rental lets you savor St Maarten, Anguilla, and St Barts all in one trip. Each day brings a new anchorage: one morning you’re paddle-boarding in a calm turquoise bay off St Maarten, the next you’re dining under stars in a secluded Anguilla cove. The ability to craft your own itinerary with Boatcrowd means your charter is as adventurous or relaxed as you desire. It’s your private resort on the water – inquire now to let Boatcrowd help plan the perfect St Maarten catamaran charter tailored to you.
Best Season for Catamaran Charter in St Maarten
St Maarten enjoys warm, tropical weather year-round, making it a viable sailing destination in any season. However, the island – like the rest of the Caribbean – has two distinct sailing seasons to consider. The winter months (December through April) are part of the dry season and widely regarded as the best time for a catamaran charter in St Maarten. During this period, you can expect consistent trade winds of 15–20 knots, plenty of sunshine, and comfortably warm temperatures averaging in the 80s°F (around 27°C). It’s the peak charter season when the weather is at its most pleasant and stable – perfect for smooth sailing and enjoyable evenings on deck. Winter also brings a buzzing social scene: holiday festivities, regattas like the famous Heineken Regatta in March, and fully booked marinas lined with impressive yachts. If you crave a lively atmosphere and premier sailing conditions, December to April is ideal. Keep in mind it’s the busiest season (especially January–March), so securing your catamaran rental St Maarten well in advance is wise. Boatcrowd can assist with early bookings and local insights – start planning now to lock in your preferred yacht and dates.
The summer season (May through August) in St Maarten offers a different but equally appealing experience. These months fall in the Caribbean’s off-peak period, meaning fewer crowds, more secluded anchorages, and often attractive charter rates for the same luxury catamarans. Temperatures are a bit warmer (high 80s°F, ~31°C) with higher humidity, and while it’s the official wet season, rainfall in early summer is typically in short, refreshing bursts. July and August still see plenty of sunshine, and the sea is at its warmest – perfect for snorkeling and swimming. Do note that the Atlantic hurricane season runs from June through November, with the highest storm risk in late summer (especially August and September). Many charter guests successfully sail in summer by sticking to early summer dates or monitoring weather patterns closely. Boatcrowd’s charter specialists can advise you on routing and travel insurance if you plan a summer trip. If you’re flexible and a bit adventurous, a June or July catamaran charter in St Maarten can be magical – picture calm bays all to yourself and vibrant local festivals onshore. Just avoid the peak hurricane window or ensure you have a contingency plan. Whenever you choose to go, St Maarten’s steady trade winds and 80°F waters await. Plan your charter around the season that suits your style, and let Boatcrowd help make it a smooth sailing from start to finish. (After all, the best time for your charter is whenever you’re ready to cast off in paradise – inquire now and we’ll handle the rest!)
One Week Catamaran Charter St Maarten – Most Popular Sailing Holiday Itinerary
Embarking on a 7-day catamaran charter around St Maarten unlocks a world of tropical adventure. In one unforgettable week, you can explore three enchanting islands – St Maarten, St Barts, and Anguilla – plus hidden coves and islets along the way. The itinerary below is a tried-and-true route beloved by luxury charter guests for its mix of lively ports, pristine beaches, and thrilling open-water sails. It’s the perfect blend of adventure and indulgence, all experienced from the deck of your private catamaran. Keep in mind, this is just one example – Boatcrowd can help customize the journey to your preferences. But if you’re looking for inspiration, here’s our most popular one-week catamaran charter itinerary starting and ending in St Maarten:
Day 1: St Maarten (Simpson Bay) – Welcome Aboard in Paradise
Your Caribbean sailing holiday begins at Simpson Bay, St Maarten’s yachting haven on the Dutch side. After a seamless check-in with Boatcrowd’s local team, step aboard your sleek catamaran – your luxury home for the week. Simpson Bay Lagoon’s calm, 12-square-mile waters are an ideal spot to get acquainted with the yacht and crew. Spend the afternoon provisioning and exploring the bay’s amenities: upscale marina boutiques, beach bars, and maybe a dip in the warm lagoon waters. As the sun sets, toast to the journey ahead with a cold drink on deck. Simpson Bay is known for its lively nightlife and dining, so you might head ashore for a gourmet dinner or stroll the soft sands of Simpson Bay Beach under the stars. (If timing permits, take a quick dinghy ride to nearby Maho Beach to witness the famous spectacle of planes swooping low overhead – an only-in-St Maarten thrill!). Overnight aboard at anchor in Simpson Bay, enjoying gentle swaying and anticipation of the adventure to come. Tomorrow, you set sail for the open sea!
Day 2: St Barts (Gustavia) – Chic Shops and French Caribbean Glamour
After a hearty breakfast on the aft deck, point the bow southward for a 15-nautical-mile sail to St. Barts (Saint Barthélemy). Gustavia, the island’s capital, comes into view by midday with its red-roofed buildings and mega-yachts glistening in the harbor. On a breezy day, the passage can be exhilarating with the tradewinds filling your sails and turquoise waves splashing up – this is what catamaran sailing is all about. Upon arrival, clear into St Barts at Gustavia’s port and prepare to be enchanted. This quaint harbor town offers a perfect blend of French elegance and laid-back Caribbean vibe. Stroll the waterfront streets lined with high-end boutiques and luxury jewelers, or pop into a café for a buttery croissant – you’ll quickly see why Gustavia is often called the Riviera of the Caribbean. History buffs can visit the 17th-century Fort Gustav for panoramic views, while sunseekers might wander to Shell Beach, a pretty cove just a short walk from town (its sands are mixed with tiny shells). Don’t miss trying the “Cheeseburger in Paradise” at Le Select bar – a legendary spot where Jimmy Buffett found inspiration. In the evening, Gustavia comes alive with fine dining and chic lounges. Enjoy fresh Caribbean lobster or French cuisine onshore, then return to your catamaran gently lit by the harbor’s glow. Overnight in Gustavia’s anchorage or moor at the dock (advance reservation recommended in high season). The gentle swaying of your catamaran and the distant hum of nightlife remind you that you’re in one of the Caribbean’s most exclusive ports.
Day 3: St Barts (Anse de Colombier) – Secluded Bay and Snorkeling
Leave the glamour of Gustavia behind for the short sail to Anse de Colombier, a pristine bay at St Barts’ northwestern tip (just 2 miles around the coast). In about 30 minutes, your catamaran glides into a horseshoe-shaped bay so tranquil and unspoiled, it’s only accessible by boat or hiking trail. Often called “Rockefeller’s Beach” (the Rockefeller family once owned the land here), Colombier is a cruiser’s favorite for its natural beauty and calm protection. Grab your snorkel gear – the crystal-clear water is teeming with marine life. You might swim with turtles and colorful reef fish, especially around the rocks on the bay’s edges (part of the St Barts marine reserve). After a snorkel and perhaps a picnic lunch on the sun-warmed trampolines of your catamaran, take the dinghy ashore to the deserted sandy beach. There are no roads or buildings here, just a perfect crescent of sand backed by green hills – the essence of a secluded paradise. Hike the short trail up the hill for a stunning panoramic view of your yacht anchored in the bay’s turquoise waters below. Come evening, Colombier is wonderfully quiet. Enjoy dinner onboard – perhaps fresh fish grilled by your chef or captain – and dine alfresco under the stars. With minimal light pollution, the Milky Way often twinkles brightly above. Overnight in Anse de Colombier, gently rocked by the bay’s calm waters and serenaded by rustling palms onshore. This peaceful night exemplifies the luxury of a catamaran charter: just you, your loved ones, and nature in an idyllic hideaway.
Day 4: Anguilla (Road Bay, Sandy Ground) – Laid-Back British Charm
Rise with the sun for an exciting day’s sail to Anguilla, the third island in your itinerary’s trio. Departing Colombier, you’ll embark on the longest passage of the week – roughly 20–25 nautical miles northwest to Anguilla. Skies of blue and a warm breeze accompany you as the catamaran slices through open water. By mid-afternoon, the low-lying silhouette of Anguilla appears on the horizon. This British overseas territory is famed for its powdery white beaches and relaxed atmosphere, a contrast to bustling St Maarten. Your port of entry is Road Bay, at the village of Sandy Ground, where you’ll drop anchor by a long curve of beach. Clear customs and immigration for Anguilla (Boatcrowd will have prepped you on the simple formalities), then settle in for island time. Road Bay’s shoreline is dotted with charming beach bars and reggae music, exuding an inviting, toes-in-the-sand vibe. After the day’s sail, unwind with a swim in the calm bay or dinghy ashore to sip a rum punch at Elvis’ Beach Bar – a local institution built from an old boat. You’ll notice how undeveloped and peaceful Anguilla feels; even its “busy” beach here is tranquil compared to other islands. In the evening, feast on a beach barbecue or fresh mahi-mahi at a casual eatery with your feet in the sand. The twinkling lights of St Maarten are visible across the channel, but here in Anguilla the stars shine brighter and the night is calm. Overnight at anchor in Road Bay, enjoying the gentle lull of the ocean. With two countries down and one to go, you’re truly cruising the best of the Caribbean.
Day 5: Anguilla’s Hidden Beaches – Snorkeling and Relaxation Day
Today is all about savoring Anguilla’s natural beauty and laid-back pace. After a leisurely breakfast, set sail for one of Anguilla’s picture-perfect beaches or offshore cays. You have options: just north of Road Bay lie the small Prickly Pear Cays, an easy sail away – these uninhabited islands boast vibrant coral reefs and gin-clear shallows ideal for snorkeling. Alternatively, sail a short hop to Sandy Island, a tiny postcard-like spit of sand offshore, where you can snorkel above colorful reef fish and then sunbathe on an empty beach. If you prefer to stick to mainland Anguilla, you might cruise down the coast to Cove Bay or Rendezvous Bay, both offering miles of serene shoreline and turquoise water. (Shoal Bay East, on the northern side, is world-famous – consistently ranked among the top beaches on the planet for its pinkish-white sands and dazzling blue water – though reaching it may require a short taxi from an anchorage.) Whichever spot you choose, this day is your relaxation in paradise. Swim, snorkel, paddleboard or simply lounge on your catamaran’s broad deck with a cold drink and a view of Anguilla’s coast. By now, the crew knows your favorite cocktail and the kids are experts at cannonballing off the stern. Enjoy a laid-back lunch on board – perhaps a spread of tropical fruits and freshly grilled local crayfish (a Caribbean delicacy Anguilla is known for). In the afternoon, consider a sail back toward Road Bay or another secure anchorage like Crocus Bay for the night. As the sun sets in a blaze of orange, reflecting on the calm sea, you’ll feel the unique tranquility that Anguilla imparts. This is the unhurried luxury of a catamaran charter – no schedules, no crowds, just the rhythm of the ocean. Overnight in Anguilla waters, with gentle waves lapping the hulls and the chorus of tree frogs from shore lulling you to sleep.
Day 6: St Maarten (Tintamarre Island & Grand Case) – Wilderness to Gourmet Delights
Bid farewell to Anguilla this morning as you set sail back toward St Maarten. Day 6 is a feast for the senses, combining untouched nature with French-Caribbean gastronomy. First stop: Tintamarre Island, a small uninhabited islet off St Maarten’s northeast coast (part of the St Martin Nature Reserve). Arrive by late morning to find Tintamarre’s deserted beaches and crystal-clear reefs awaiting you. Dive in for some of the best snorkeling of your trip – Tintamarre’s waters are teeming with reef fish and you have a good chance of spotting graceful sea turtles gliding through the seagrass. You can also explore the island’s shoreline; there’s a bit of history here, from an old 1940s airstrip to natural clay mud baths tucked in the interior. After enjoying this Robinson Crusoe escape, it’s time to head to Grand Case on St Martin’s French side, just a short sail across the channel. Grand Case Bay welcomes you with calm, shallow waters and a long stretch of beach lined with colorful buildings. This charming village is famed as the “Gourmet Capital of the Caribbean”, and for good reason. As you anchor, you might catch the aroma of grilled lobster and French pastries wafting from shore. In the afternoon, swim or float around the catamaran in the bath-warm bay, or take the dinghy to Creole Rock (a nearby small rock island) for one more snorkel session – its coral gardens are among St Maarten’s best. Come evening, indulge in Grand Case’s offerings: dozens of five-star restaurants and local lolos (BBQ shacks) await just steps from the beach. Savor some French-Caribbean fusion cuisine – perhaps curry conch or classic escargots and a fine Bordeaux, all while your toes dig into sand. After dinner, enjoy a casual stroll down the beach road, maybe stopping for artisanal ice cream or to listen to live zouk music. Overnight at anchor in Grand Case. The gentle sounds of distant laughter and lapping waves set a mellow scene as you spend your final night aboard in a bay that perfectly encapsulates St Martin’s charm – natural beauty meets culinary excellence.
Day 7: St Maarten (Return to Simpson Bay) – Farewell to the Islands
Your final morning on board starts with the sun peeking over the green hills of St Martin. Take a last refreshing dip off the stern or sip coffee while gazing at Grand Case’s idyllic shoreline – try to commit the scene to memory. It’s a short sail (around 8 nautical miles) back to Simpson Bay, so there’s no rush. Along the way, you might hug the coast, passing Marigot’s picturesque harbor and the iconic outline of Fort Louis on the bluff. Arrive back at Simpson Bay by early afternoon. Before heading into port, you could pause outside the bay for one more swim in the open sea or simply relish the feeling of the wind in your hair as your catamaran glides effortlessly through the water. Entering Simpson Bay Lagoon, you’ll radio the bridge operator to open the Simpson Bay Bridge – a final little thrill as you pass through alongside sleek mega-yachts returning from their adventures. Once docked, it’s time to reluctantly disembark and bid farewell to your captain, crew, and the beautiful vessel that has been your home. Yet the journey isn’t over just yet – celebrate your incredible week with a final evening in St Maarten. Simpson Bay offers plenty of options: perhaps a sunset dinner at a marina-front restaurant or one last night out experiencing the local calypso beats and hospitality. Reflect on all you’ve experienced in seven days: three distinct islands, countless beaches, new skills at the helm, and memories of laughter, sunsets, and starry nights at sea. This one-week catamaran charter St Maarten itinerary has been a luxurious whirlwind of adventure – from the chic boutiques of Gustavia to the tranquil sands of Anguilla and the lively flavors of St Martin. As you say goodbye, you’re already dreaming of the next voyage. After all, the Caribbean has many islands and Boatcrowd is ready to welcome you back when the sea calls again.
(This sample itinerary showcases just a taste of what’s possible. You can mix and match islands, spend extra days where you wish, or even extend your journey – the beauty of a private charter is its flexibility. Start planning with Boatcrowd to design a bespoke St Maarten catamaran route that fulfills your tropical dreams.)
Start Planning your Catamaran Charter in St Maarten
A luxury catamaran charter in St Maarten is more than a vacation – it’s an all-encompassing Caribbean experience that blends adventure, relaxation, and five-star service in one. You’ve seen how a week on board can carry you to multiple islands, each with its own flavor, all while enjoying the comforts of a floating villa. Whether it’s a family seeking bonding time in paradise, a couple celebrating a special occasion, or a group of friends chasing the thrill of island-hopping, St Maarten’s catamaran charters offer something magical for everyone. The freedom to explore secluded beaches, world-class snorkeling spots, and vibrant cultural hubs at your own pace is a privilege only a private yacht vacation can provide. And with Boatcrowd’s commitment to personalized service, you’ll sail with confidence knowing every detail is handled – from choosing the perfect catamaran rental St Martin/St Maarten to crafting an itinerary filled with your bucket-list experiences. Don’t just daydream about turquoise waters and golden sunsets – make it your reality. The islands are calling, and your crewed catamaran is ready to embark. Start planning with Boatcrowd today and let us turn your St Maarten catamaran charter into the trip of a lifetime. Adventure and indulgence await on the horizon – all that’s left is to cast off and answer the call of the Caribbean. Bon voyage!
