Catamaran Charter Anguilla – Luxury Sailing Adventures in Paradise
Why Choose a Luxury Catamaran Charter in Anguilla?
Anguilla, with its pristine white-sand beaches and turquoise bays, is a dream destination best explored by sea. A luxury catamaran charter in Anguilla offers an exclusive way to experience this Caribbean gem – combining five-star comfort with the thrill of open-water adventure. Unlike crowded tourist hotspots, Anguilla preserves an untouched and laid-back vibe; even in peak season, you’ll never have to jostle for space on its shores. In fact, this tiny island boasts 33 spectacular beaches – each open to the public and often classed among the best in the world. From the deck of your private catamaran, you can wake up to a new idyllic bay every day, snorkel vibrant coral reefs straight off the boat, and step ashore on secluded coves only accessible by yacht. It’s the ultimate blend of luxury and adventure – one moment you’re sipping a cocktail prepared by your personal chef, the next you’re diving into crystal-clear waters alongside tropical fish, all with no crowds in sight.
Catamarans are ideal for both first-time charterers and seasoned yacht guests, especially families. Thanks to their twin hulls, catamarans remain stable and level even in moderate seas – a big plus for those with kids or anyone new to sailing. They also offer expansive decks, multiple cabins, and shallow drafts that let you anchor closer to Anguilla’s powdery beaches, so you can literally hop from yacht to shore in seconds. With Boatcrowd’s curated fleet ranging from elegant sailing catamarans to high-performance power cats, you can choose the vessel that perfectly suits your style and group size. Charter lengths are flexible too: opt for a long weekend catamaran rental in Anguilla to sample a few nearby spots, or indulge in a 5-day or 7-day escape that includes island-hopping to St. Martin and St. Barts. Even a short 3-day charter can whisk you to Anguilla’s must-see gems like Sandy Island or Shoal Bay, while a full week lets you explore the entire Leeward Islands playground. With such enticing possibilities, it’s wise to plan early – inquire now with Boatcrowd to secure your ideal yacht and dates, and get ready to embark on a tailor-made adventure in paradise.
Best Season for Catamaran Charter in Anguilla
Winter Charters (High Season): Anguilla’s tropical climate and steady trade winds make it a viable sailing destination year-round, but the winter months (November to April) are especially popular for luxury charters. This period is the official high season, bringing dry, sunny weather and balmy temperatures around 80 °F (27 °C). The trade winds are consistent and near their peak during winter, providing excellent sailing breezes for your catamaran. Seas are generally calm yet invigorating – perfect for both novice sailors and adventure-seekers. Many travelers prefer winter charters to coincide with the festive atmosphere in the Caribbean. Around the holidays, the region buzzes with activity: St. Barts, for example, hosts chic New Year’s Eve soirées and mega-yacht gatherings, while St. Martin features the world-famous Heineken Regatta in early March. If you crave a lively scene and picture-perfect conditions, winter is the ideal time for a catamaran charter in Anguilla. You’ll enjoy spectacular sailing weather by day and cool, starry tropical nights – all amid the height of Caribbean social season.
Summer Charters (Off-Peak Seasons): Summer charters in Anguilla, roughly May through August, offer a different but equally enticing experience. The crowds thin out after spring, so you’ll enjoy even more tranquility – and often better charter rates – during these months. Late spring and early summer bring especially calm seas and gentler winds, making island-hopping and snorkeling excursions a breeze. It’s an excellent time for families with small children or first-time charterers who prefer smoother waters. You might even plan your trip around unique local events: in mid-May Anguilla hosts its annual sailing Regatta, considered among the best in the Caribbean, and the island’s lively Summer Festival (Carnival) kicks off in late July, reaching its peak around the first Monday in August. Chartering during these festivities can be magical – imagine anchoring in Road Bay while colorful boat races and calypso music animate the shoreline! Do note, however, that summer overlaps with the Atlantic hurricane season (June through November), which peaks in September and October. Many yachts still operate in early summer, but by late August a number of resorts and restaurants start to close for the quiet off-season. If you plan a summer catamaran charter in Anguilla, it’s wise to remain flexible with routes and have a weather contingency. With good planning (and perhaps travel insurance as a safeguard), you can still reap the rewards of a serene, sun-drenched yacht vacation – often feeling like you have the Caribbean all to yourself.
One Week Catamaran Charter Anguilla – Most Popular Sailing Holiday Itinerary
For those with a full week to spare, a one-week catamaran charter around Anguilla unlocks the best of this region’s islands. Thanks to the short distances between Anguilla, St. Martin, and St. Barts, you can effortlessly explore multiple destinations on a single trip. Below is a sample 7-day luxury catamaran charter Anguilla itinerary – our most popular sailing holiday route – covering the highlights of all three islands. (Of course, every itinerary is customizable to your preferences, whether you want more beach time, cultural excursions, or gourmet dining on shore.)
Day 1: St. Martin (Marigot Bay) or Anguilla (Sandy Ground)
If you are not in Anguilla yet, we recommend starting your catamaran charter from Marigot Bay on the French side of St. Martin, a more convenient embarkation point with an upscale yet charming Caribbean flair. After a welcome aboard your crewed catamaran and a safety briefing, indulge in fresh-baked baguettes or croissants from a local boulangerie – a nod to the island’s French heritage. Spend the afternoon settling in and exploring the picturesque bay. You might take a stroll through Marigot’s boutique-lined streets or visit Fort Louis for panoramic views of the harbor. In the evening, enjoy a gourmet dinner prepared by your onboard chef as the catamaran gently swings at anchor. With the twinkling lights of Marigot in the distance, your Anguilla charter adventure is officially underway in style.
Day 2: Anguilla (Road Bay & Sandy Island)
After breakfast, set sail for Anguilla, which lies just a few miles north of St. Martin. In under two hours, you’ll arrive at Road Bay, Anguilla’s main harbor and port of entry. Road Bay is one of the most beautiful anchorages in the northern Caribbean, featuring a long curve of white sand beach and calm, sheltered waters. Check in with customs here (your Boatcrowd captain will arrange any paperwork), then relish your first taste of Anguilla’s idyllic beauty. You can take the dinghy to shore at Sandy Ground village for a laid-back lunch of barbeque ribs or fresh catch at a beach bar. In the afternoon, a short hop by catamaran brings you to Sandy Island, a tiny deserted cay just off Anguilla’s coast. With its ring of soft sand and vibrant coral reef, Sandy Island is a snorkeler’s paradise – an ideal spot to swim with colorful reef fish and perhaps spot a sea turtle gliding by. Enjoy a private beach picnic or cocktails on the island (the crew can set this up), then return to Road Bay for the evening. As the sun sets, watch pelicans dive for their dinner and marvel at how the entire horizon turns pink and gold. Tonight you might dine on deck under the stars, or venture ashore to one of Anguilla’s casual beach restaurants for live reggae music. The gentle rocking of your catamaran will lull you to sleep, anchored off a truly tranquil shoreline.
Day 3: Anguilla (Prickly Pear Cays & Island Exploration)
This morning, cruise to the nearby Prickly Pear Cays, an uninhabited pair of small islands and a designated marine reserve northwest of Anguilla. The short sail is exhilarating as you head into the open Atlantic, and soon you’ll be rewarded with Prickly Pear’s crystal-clear aquamarine lagoon coming into view. Snorkeling here is a must – the coral gardens are shallow and teeming with marine life, from neon parrotfish to elegant rays. The water is so calm and transparent that even from the deck you can spot fish swimming around. Families love this stop because Prickly Pear’s protected bay has shallow, gentle waters perfect for children to play and swim safely. After a swim, step ashore on the powdery beach where a rustic island bar and grill serves up its famous grilled lobster lunch – a Caribbean delight you won’t want to miss. In the afternoon, your captain can sail around Anguilla’s western tip to show you some of the island’s hidden coves. You might drop anchor at Little Bay, a secluded cove backed by dramatic cliffs, where you can feed tame fish and even spot nesting tropicbirds on the ledges. Or perhaps cruise past Shoal Bay, Anguilla’s most celebrated beach with two miles of gleaming white sand (often voted one of the world’s top beaches). By late afternoon, begin a leisurely sail southward as we prepare to broaden our horizon to new islands. You’ll watch Anguilla’s blue outline fade into the distance, taking with you memories of its peaceful villages and pristine beaches. This evening, anchor off the uninhabited Tintamarre Island at the northeastern edge of St. Martin – a convenient and beautiful stop as you head toward St. Barts tomorrow. Enjoy a quiet night aboard in a calm anchorage, with only the sound of gentle waves and the glow of the moon reflecting on the sea.
Day 4: St. Martin to St. Barts (Tintamarre & Île Fourchue)
Wake up to a refreshing morning swim off Tintamarre, an unspoiled island nature reserve. Perhaps you’ll spot a sea turtle or two; this island’s reefs are known for them. After breakfast, continue your voyage toward St. Barts. En route, the captain may stop at Île Fourchue(Île Fourche), a deserted islet just north of St. Barts, to break up the sail. The journey from St. Martin/Anguilla to St. Barts is the longest open-water passage of the week, so a pause at Île Fourchue is a welcome adventure. Surrounded by cactus-covered hills and inhabited only by wild goats, Île Fourchue offers excellent snorkeling and a chance to stretch your legs on a short hike. Climb one of the gentle peaks for a panoramic view of the Leeward Islands – you can see St. Maarten, Anguilla, and St. Barts all at once from the top, a breathtaking reward for your efforts. Back on board, enjoy a light lunch as you sail the final stretch into St. Barts. By mid-afternoon, you’ll glide into Gustavia Harbor, one of the most picturesque ports in the Caribbean, dotted with red-roofed buildings and luxury yachts. The moment you arrive, you’ll sense St. Barts’ chic European ambiance. Anchor or dock (subject to reservation) in Gustavia and spend the evening exploring this charming town with its unique blend of French sophistication and laid-back Caribbean warmth. Stroll past designer boutiques and colonial-era buildings, stop by a café for espresso or ice cream, and catch the sunset from atop Fort Gustav for a sweeping harbor view. For dinner, consider going ashore to experience St. Barts’ renowned dining scene – from gourmet French cuisine to créole seafood, the island’s restaurants are world-class. After a lively day of sailing and sightseeing, unwind aboard your catamaran with a nightcap, gazing at the glittering lights of Gustavia and the stars above.
Day 5: St. Barts (Gustavia & Colombier)
Fully immerse yourself in the luxury and allure of St. Barts today. In the morning, enjoy a French pastry and fresh fruit on deck, then head ashore to see more of Gustavia. You can browse high-end boutiques (Louis Vuitton, Cartier, and local designers line the streets) or visit the quaint historical museum to learn about the island’s Swedish colonial past. A hike or short cab ride up to Colombier lookout provides a stunning view of the island’s leeward coast and your next destination: Anse de Colombier, an isolated bay only reachable by boat or hiking trail. Around midday, sail around to Colombier Bay, which many consider the most beautiful anchorage in St. Barts. Here you’ll find a crescent of golden sand accessible only from the sea, ensuring an uncrowded paradise for your group. The bay’s calm, sheltered waters make another great spot for swimming, paddleboarding, or snorkeling with vividly colored fish. Keep an eye out for dolphins – they love to play in Colombier’s bay and often race alongside yachts. In the afternoon, sail back toward Gustavia or to another preferred anchorage. No visit to St. Barts is complete without a bit of indulgence: perhaps arrange an onshore excursion to Shell Beach for sunbathing and to collect unique shells, or relax at a chic beach club. Come evening, Gustavia comes alive with fine dining and nightlife. You might dine ashore at a gourmet harbor-side restaurant, enjoying fresh lobster or a perfectly cooked steak frites paired with French wine. After dinner, stroll the port where mega-yachts are moored, or pop into a trendy lounge for live music. St. Barts is often called the “St. Tropez of the Caribbean,” and its elegant nightlife and cosmopolitan crowd live up to that reputation. You could find yourself dancing under the stars or simply savoring a cognac at a piano bar, rubbing shoulders with the occasional celebrity who frequents this island haven. Tonight, fall asleep in the sheltered harbor, with the gentle buzz of St. Barts in the background and your catamaran, a luxurious sanctuary waiting just for you.
Day 6: St. Barts to St. Martin (Orient Bay)
Enjoy a leisurely breakfast as your yacht departs St. Barts, bidding adieu to its glamorous shores. Today’s sail will take you back towards St. Martin, giving you a final full day of Caribbean bliss on the water. Depending on conditions and your preferences, you might stop at Île Tintamarre or Îlet Pinel on the French side of St. Martin, if you didn’t visit them earlier in the week. Pinel Island, with its shallow turquoise waters and beach restaurants, is perfect for a relaxed lunch and one more round of snorkeling. Alternatively, sail along St. Martin’s scenic coast to Orient Bay, a famous stretch of white sand beach on the northeast side. Orient Bay offers both bustling beach clubs and quiet corners – you can choose between an active afternoon of windsurfing/kitesurfing or a tranquil swim in the protected waters. As this is your last full day, you may simply opt to stay on board your catamaran for some pure relaxation. Lounge on the sun deck with a book or enjoy the yacht’s water toys – perhaps a last spin on the kayak or stand-up paddleboard around the anchorage. Your crew can surprise you with a special farewell dinner on board tonight: imagine savoring Champagne and freshly caught seafood as the sun sinks below the horizon one final time. It’s the perfect finale to a week of unforgettable moments. Reminisce with your family about your favorite stops – was it Anguilla’s serene beaches, or the chic charm of St. Barts, or perhaps the thrill of sailing itself? – and soak in the ambiance of the Caribbean night.
Day 7: St. Martin or Anguilla (Disembarkation)
This morning, your catamaran returns to the port where your adventure began. Sail into Marigot or another agreed port on St. Martin, or return back to Anguilla if you started from there, arriving with enough time for a last swim or a bit of duty-free shopping on shore. If you have time before your flight or onward travel, consider exploring the Dutch side (Sint Maarten) capital of Philipsburg for souvenirs, or enjoy a coffee and croissant at a Marigot café as you watch the harbor activity. Your crew will assist with luggage and formalities as you prepare to disembark. It’s a bittersweet feeling as you say goodbye to your captain and crew – over just seven days, they’ve likely become friends who catered to your every need. Take one last look at your beautiful catamaran, floating peacefully in the harbor, and savor the accomplishment of all you experienced. In one week, you’ve hopscotched across three enchanting islands, created lifelong family memories, and tasted the freedom that only a yacht charter can provide. As you step back onto land, you’ll surely be plotting your return to these stunning Leeward Islands, because the allure of Anguilla, St. Martin, and St. Barts is one that never fades.
(This sample itinerary is just a glimpse of what you can experience. With Boatcrowd’s expertise, you can customize your route – add extra days in your favorite spot, include additional islands like St. Kitts or Nevis on longer charters, or tailor the activities onboard and onshore to your interests. The goal is a bespoke catamaran charter that exceeds your every expectation.)
Start Planning Your Anguilla Catamaran Charter
Anguilla’s turquoise waters and sun-drenched islands are calling – all that’s missing is you. Whether you are a first-time charterer or a seasoned yacht guest, a bespoke catamaran charter in Anguilla promises the vacation of a lifetime in a truly exclusive setting. Boatcrowd is here to make that experience seamless, from helping you select the perfect yacht and crew to crafting an itinerary tailored to your dreams. Don’t wait – start planning with Boatcrowd and inquire now to turn your Caribbean sailing adventure into reality. Your luxury catamaran escape to Anguilla awaits, and every unforgettable moment begins the instant you step aboard.
