Yacht Charter Anguilla: Luxury Adventures in the Caribbean
A yacht charter Anguilla experience provides you with an elite Caribbean vacation opportunity. The island of Anguilla reveals its hidden treasures through private yacht exploration because each day becomes a personalized experience. This guide provides complete information about luxury yacht charters in Anguilla including the island's hidden gems and ideal sailing periods and sample itineraries to St. Martin and St. Barts. Boatcrowd enables you to transform your yachting aspirations into reality whether you want to spend time with family or escape with your partner or explore different islands with friends.
Anguilla as a Hidden Gem Caribbean Destination for Yacht Charters
People consider Anguilla the secret jewel of the Caribbean because this tiny unblemished island provides exceptional luxury and natural wonders. Located between the popular St. Martin and fashionable St. Barts, Anguilla presents an exclusive tranquil destination featuring white sandy beaches and blue waters and peaceful ambiance. The 35-square-mile sanctuary has maintained its position as a well-kept secret for both celebrities and sophisticated travelers who value its unique combination of privacy and relaxing atmosphere. The purposeful peace of Anguilla exists because it lacks cruise ship ports and high-rise buildings and operates a small-aircraft-only airport which keeps the island peaceful. Your arrival by yacht creates the illusion that you have the whole island at your disposal to explore. The uncluttered beaches of Anguilla include Shoal Bay East and Little Bay as well as 33 other pristine shores which remain unvisited by the crowds typical of major islands. The lack of towering resort structures preserves this island's genuine character while creating a private paradise atmosphere. The yacht allows you to find unpopulated beaches where you can snorkel colorful coral reefs while enjoying sunsets that create breathtaking colors in a completely peaceful environment.
Private jet or ferry travel from St. Martin to Anguilla leads to the destination but sailing on your own yacht offers an unparalleled degree of solitude and freedom. Anguilla serves discerning visitors through its combination of relaxed luxurious comfort with exploratory spirit. The destination welcomes all types of visitors including families seeking safety and memories as well as first-time charters and experienced yacht guests looking for new exploration opportunities. The island waters remain perfect for motor yachts and luxury catamarans to glide between attractions because they offer smooth sailing. A powerful motor yacht enables you to reach distant cays and neighboring islands at exceptional speeds but a luxury catamaran offers broad stability and spacious deck space that enables you to moor in shallow pristine bays which most boats cannot access. You have the option to visit hidden bays during the day and enjoy fine dining at beachside restaurants before returning to your yacht's deck to enjoy starry nights. Every moment feels bespoke and intimate.
Anguilla’s brand of luxury is refreshingly unpretentious. The island favors refined authenticity over flashiness – there are no casinos, no cruise ship crowds, just a peaceful upscale vibe. Days on charter often blend adventure and indulgence: one moment you’re paddleboarding over a coral reef or zooming off on a jet-ski, and the next you’re savoring champagne and fresh-grilled lobster on a deserted beach. With a professional crew attending to your needs, even first-time charterers feel completely at ease. Families appreciate the safety and comfort onboard (many yachts come equipped with snorkeling gear, water toys, and modern amenities for all ages), while experienced yacht-goers cherish the freedom to craft a unique itinerary. Anguilla’s crystalline marine parks are a diver’s dream, too – certified divers will discover fascinating undersea sights, as the island’s protected waters hide shipwrecks and coral gardens brimming with marine life (all accessible as memorable dive stops right from your yacht). If you have a special request – perhaps a picnic lunch on a deserted sandbar or a celebration under the stars – your crew will make it happen with effortless grace. These bespoke touches are what elevate a Boatcrowd charter into the realm of once-in-a-lifetime experiences.
For Families: Parents and children alike love the ample space and stability of a catamaran charter. Imagine the kids snorkeling alongside turtles in shallow bays or enjoying the yacht’s collection of water toys, all under the careful watch of a professional crew. Meanwhile, adults can unwind knowing that every meal, activity, and detail is handled – creating stress-free family memories on the water.
For First-Time Charterers: Anguilla is an ideal starting point for your first yacht adventure. Distances between attractions are short, navigation stays mostly within calm, protected seas, and our experienced crew ensures a smooth journey. You’ll receive five-star service aboard, so you can simply enjoy the ride – no sailing experience needed. It’s like a boutique hotel experience combined with the thrill of exploration, all set against a new ocean backdrop each day.
For Seasoned Yacht Guests: Even veteran charterers find fresh delights in Anguilla’s cruising grounds. The island’s hidden anchorages and the option to hop to neighboring hotspots (like a day in St. Barts or St. Martin) in one itinerary bring plenty of variety. Experienced sailors appreciate the region’s steady trade winds and the chance to indulge in both low-key natural beauty and high-end island society in one trip. Your crew can craft as active or relaxed a schedule as you wish, ensuring each day on board exceeds your expectations.
With Boatcrowd’s charter specialists ready to tailor every detail, your Anguilla yacht charter promises an unforgettable journey – start planning with Boatcrowd today.
Best Season for Yacht Charter in Anguilla
Anguilla enjoys a warm, tropical climate year-round, but the best season for a yacht charter in Anguilla is during the winter and spring months. Many travelers find the shoulder months of November and late April particularly appealing, offering prime weather with slightly thinner crowds. From December through April, the weather is at its most idyllic – expect steady sunshine, gentle trade winds, and low humidity. This period is Anguilla’s high season, when average daytime temperatures hover around 25–28°C (77–82°F) and rain is scarce. Seas are generally calm and crystal-clear, perfect for sailing or motor cruising from one beach to the next. It’s the ideal time for a luxury yacht charter Anguillaadventure, as the island buzzes with a relaxed energy: beach bars and fine dining restaurants are in full swing, and the atmosphere is festive yet never overcrowded.
Summer and early autumn (May through October) constitute Anguilla’s off-season, offering a different but still enticing experience. The temperatures rise slightly into the 30°C range (mid-80s°F), and the ambiance on the island becomes even more peaceful with fewer tourists around. Early summer – especially May and June – features seas so calm they’re like glass, making island-hopping and snorkeling a delight. Yacht charter rates may be more attractive during these months, and you’ll enjoy secluded anchorages all to yourself. Notably, September and October tend to see the most rainfall (and some establishments close for annual breaks), while February and March are typically the driest months. Do keep in mind that the late summer and fall coincide with the Caribbean hurricane season (peaking in September), so itineraries need a bit more flexibility and attentive weather monitoring. Many seasoned guests still choose a summer yacht charter in Anguilla for the chance to experience its tranquil beauty at their own pace – with the bonus of spectacular sunsets and warm, bath-like sea conditions. Anguilla also hosts vibrant events during the so-called off-season – from the annual Anguilla Regatta each May, where sailing enthusiasts gather for friendly races, to the lively Summer Festival Carnival in early August – proving that the island’s spirit shines year-round. Whenever you visit, Anguilla’s gentle trade winds and inviting waters mean there’s truly no bad time to set sail.
Boatcrowd’s charter experts are happy to guide you on the best timing for your voyage, ensuring your Anguilla yacht charter is perfectly aligned with the weather and events that matter to you.
Yacht Day Charter Anguilla – Most Popular Destinations for a Day Trip
In just a single day on the water, a yacht day charter Anguilla can whisk you to a handful of enchanting spots around the island and its neighboring cays. Thanks to Anguilla’s compact size, you can pack in multiple highlights even on a short outing. Whether you choose a nimble motor yacht or a stable luxury catamaran for the day, you’ll have time to see several attractions in one trip. Here are the most popular day-trip destinations not to miss:
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Sandy Island – A tiny ivory-sand cay off Anguilla’s coast offering a true castaway experience. This speck of an island boasts a laid-back beach bar and grill, vibrant reefs for snorkeling, and nothing but crystal-clear water in every direction – perfect for a lazy lunch and sunbathing in total seclusion. (A short 10-minute boat ride from Anguilla’s main island, Sandy Island feels like your own private paradise.)
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Prickly Pear Cays – Two uninhabited islets north of Anguilla famed for their powdery beaches and turquoise lagoons. On a day charter, you can anchor in shallow blue waters, snorkel among colorful fish and corals, and come ashore for a casual beach barbecue (these cays are known for delicious grilled lobster lunches). It’s an idyllic spot to while away an afternoon in paradise.
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Little Bay – A hidden jewel tucked beneath dramatic cliffs on Anguilla’s northern coast, accessible only by boat. Little Bay rewards visitors with utter tranquility – a small beach edged by calm, sheltered waters. Enjoy swimming and spotting sea turtles in this natural sanctuary, or try a gentle cliff jump from the famous rock ledge for a dash of adventure.
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Scilly Cay – A private palm-fringed cay near Anguilla’s east end, renowned for its old-school Caribbean charm. Yachts can stop here on select days when the island’s rustic restaurant is open, serving up its legendary lobster and crayfish lunches. With live music and rum punches in the mix, Scilly Cay offers a memorable slice of local Anguilla flavor combined with the exclusivity of arriving by your own boat.
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Scrub Island – A wild, uninhabited island off Anguilla’s eastern tip that appeals to adventurous souls. Snorkel the site of a hidden shipwreck (and even a sunken airplane wreck), comb the deserted beach for driftwood treasures, or simply relish the utter solitude. Scrub’s rugged beauty showcases just how untouched Anguilla’s outlying cays truly are.
Even on a quick day charter, you can pack in a world of experiences – hopping from one idyllic hideaway to the next. It’s a perfect option for first-time visitors to get a taste of Anguilla’s magic, or as a laid-back outing for those short on time.
3 Day Yacht Charter Anguilla to St. Martin – Sample Itinerary
A 3-day yacht charter from Anguilla to St. Martin is the perfect mini-adventure, blending Anguilla’s tranquility with St. Martin’s vibrant Franco-Dutch culture. Below is a sample itinerary with daily highlights:
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Day 1: Depart Anguilla in the morning aboard your private yacht, cruising south across the channel to St. Martin. (The crossing is typically under 2 hours on a luxury motor yacht, or a bit longer under sail, and if you’re lucky you might be escorted by a pod of dolphins en route.) Arrive on St. Martin’s French side and anchor off Grand Case or Marigot Bay. Spend the afternoon swimming in calm, clear waters with a view of pastel-hued Creole houses ashore. As evening falls, step onto land to explore the charming French-Caribbean ambience – perhaps dining at a waterfront bistro in Grand Case, known as the “gourmet capital” of St. Martin, or browsing the boutiques and cafes around Marigot’s harbor. Savor fine French wine and fresh-caught seafood as the sun sets, then return to your yacht for a peaceful night moored under the stars.
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Day 2: After a leisurely breakfast on deck, your captain charts a course for the natural delights around St. Martin. Start with a short sail to Tintamarre Island, an uninhabited nature reserve just off St. Martin’s coast, where you can snorkel with turtles and explore secluded beaches. Next, hop over to Pinel Island in the calm Cul-de-Sac Bay – a perfect lunch stop with shallow, glassy waters. (You might wade ashore to a casual beach restaurant for grilled fish, or simply enjoy a picnic on the sand prepared by your crew.) In the afternoon, cruise down to the Dutch side of Sint Maarten: anchor in Simpson Bay or off Maho Beach. Here you can enjoy a completely different vibe – thrill at watching airplanes swoop low over Maho’s famous beach, indulge in duty-free shopping, or try your luck at a casino. For dinner, the Dutch side offers lively waterfront venues and beach clubs. Spend the night anchored in Simpson Bay, where gentle tropical breezes and the distant sound of steel-pan music lull you to sleep.
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Day 3: This morning, bid farewell to St. Martin and begin the scenic voyage back to Anguilla. On the way, you might detour for one last taste of tropical bliss – for example, stop at the Prickly Pear Cays (just off Anguilla’s coast) for a final snorkel in transparent waters or a quiet beach stroll on an uninhabited shore. Enjoy lunch on board as you soak in views of both Anguilla and St. Martin on the horizon. By mid-afternoon, your yacht glides again into Anguilla’s waters. You might cruise along Anguilla’s coastline for a celebratory swim at Shoal Bay or simply relish the approach into Road Bay’s calm anchorage. Disembark in Anguilla with memories of two distinct islands packed into one enriching getaway – from the serene shores of Anguilla to the colorful culture of St. Martin, all seamlessly experienced via your own charter yacht.
(Note: This itinerary is a suggested outline. With Boatcrowd, you can customize your Anguilla–St. Martin charter – for instance, adding a stop at Orient Bay’s watersport beach, scheduling extra snorkeling time, or enjoying a night in the Dutch capital Philipsburg. Every charter detail is flexible to suit your preferences.)
3 Day Yacht Charter Anguilla to St. Barts – Sample Itinerary
For those drawn to glamour and pristine nature alike, a 3-day yacht charter from Anguilla to St. Barts offers an unforgettable taste of both worlds. Here’s an example of how you might spend three days voyaging to this chic French island and back:
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Day 1: Embark from Anguilla and set course southeast to St. Barts (Saint Barthélemy), a journey of around 2–3 hours across the Caribbean Sea (faster if you’re on a powerful motor yacht). Enjoy panoramic views of the open ocean during the crossing – it’s not uncommon to spot flying fish or seabirds along the way. Arrive by midday to the iconic Gustavia Harbor, where red-roofed colonial buildings and bobbing superyachts create a postcard-perfect scene. After your captain secures a mooring, go ashore to explore Gustavia’s quaint streets lined with designer boutiques, galleries, and cafés. Hike up to Fort Gustav for a panoramic view of the harbor, or take a refreshing dip at Shell Beach, a pretty cove just a short walk from town (named for its shoreline full of tiny shells). In the evening, dine at one of Gustavia’s gourmet restaurants – St. Barts is famed for its blend of French haute cuisine and Creole flair – or enjoy cocktails on the yacht while watching the harbor’s lights twinkle. Your first night is spent in Gustavia’s embrace, with the gentle sway of the yacht and the distant hum of island nightlife reminding you that you’ve arrived in paradise.
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Day 2: Wake up to the aroma of fresh croissants (courtesy of your crew, who can ferry over pastries from a local boulangerie) and plan for a day of beach bliss around St. Barts. Cruise along the coast to Colombier Beach, a secluded bay only reachable by boat or hiking trail. Here, you’ll find unreal turquoise water and a peaceful crescent of sand – an ideal spot for snorkeling or simply lounging on deck in utter privacy. By midday, head to the famous St. Jean Beach, home to upscale beach clubs and the iconic Eden Rock resort. Anchor offshore and tender in to experience St. Barts’ jet-set social scene: sip a cocktail at Nikki Beach or people-watch as small planes land dramatically at the adjacent airstrip. In the afternoon, your yacht can tour more of St. Barts’ scenic coves – perhaps a swim at Gouverneur Beach, known for its powdery sand and clear waters, or a peek at the luxury villas perched above Flamands Beach. As sunset approaches, consider a relaxed evening on board with a gourmet dinner prepared by your chef, or venture out to one of Gustavia’s chic lounges for a taste of the island’s buzzing nightlife. Either way, Day 2 balances leisure and luxury in true St. Barts style.
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Day 3: Enjoy a final stroll through Gustavia in the morning – you might pick up a few duty-free treasures or fresh baguettes for the journey home – then depart St. Barts for the sail back to Anguilla. On the return leg, relish the open ocean views and the salty breeze as you lounge on deck, reminiscing about the past days’ adventures. If time permits, your captain can make a strategic stop en route – for instance, pausing at Tintamarre Island (near St. Martin) or at one of Anguilla’s offshore cays – so you can swim in calm waters and soak up a bit more sun before the trip’s end. By late afternoon, you’ll cruise back into Anguilla’s Road Bay or whichever harbor your charter concludes at. As you disembark, you carry with you the thrill of having enjoyed two very different Caribbean gems: the unhurried, under-the-radar charm of Anguilla and the refined, glamorous excitement of St. Barts – all made possible in just a long weekend on your luxury charter yacht.
(Note: This itinerary is just one possibility. You can personalize your Anguilla–St. Barts adventure – whether that means spending an extra day anchored off a quiet bay, arranging a visit to St. Barts’ designer boutiques, or focusing more on snorkeling and water sports. Boatcrowd will craft the journey to match your interests.)
Anguilla vs. St. Martin vs. St. Barts – A Concise Comparison
Choosing between Anguilla, St. Martin, and St. Barts for a yacht charter can be a delightful dilemma – each offers a unique slice of Caribbean paradise. Here’s a quick comparison to guide you:
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Anguilla: A secluded haven of tranquility and barefoot luxury. Best known for its uncrowded beaches (33 postcard-perfect strands) and low-key exclusivity, Anguilla is ideal for relaxation and intimate family time. As a British overseas territory, it’s also known for friendly local hospitality and a safe, welcoming atmosphere. Nightlife is quiet and upscale, centered on beachside dining and mellow live music rather than clubs or casinos. Chartering here means immersing yourself in unspoiled nature and enjoying a truly private yacht ambience – it’s the epitome of calm and personalized indulgence. (Anguilla has no big marinas, so charter yachts typically anchor off the coast, enhancing the feeling of escape in nature.)
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St. Martin (Sint Maarten): A vibrant, cosmopolitan island split into French (St. Martin) and Dutch (Sint Maarten) sides, blending two rich cultures and offering the best of both worlds. St. Martin buzzes with activity: gourmet restaurants, shopping boutiques, lively beach bars, and even a few casinos on the Dutch side. It’s more developed than Anguilla, with multiple full-service ports, bustling marinas, and a sociable yachting scene. St. Martin is perfect for travelers who crave variety and a bit of nightlife alongside stunning beaches. The island’s diverse attractions – from the chic cafés of Marigot to the party atmosphere of Orient Bay – make it a dynamic yachting destination and an ideal charter base (its international airport and full-service marinas make logistics easy).
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St. Barts: A glamorous retreat famed for its exclusivity and jet-set appeal. St. Barts truly shines during the winter holidays, when Gustavia’s harbor fills with superyachts for legendary New Year’s celebrations. St. Barts (Saint Barth) is the crown jewel of luxury in the region – expect mega-yachts in the harbor, designer shops, and celebrity sightings, especially in peak season. Despite its high-end reputation, the island remains authentically charming, with pristine beaches like Colombier and Saline offering natural beauty away from the scene. Yacht charter guests in St. Barts indulge in upscale dining, chic beach clubs, and impeccable service at every turn. It’s the go-to for those seeking a sophisticated escape with a French Riviera flair in the Caribbean. (It’s decidedly French in character – you’ll hear français spoken everywhere and the Euro is the currency – imparting an undeniably European ambiance amid the palms.)
In essence, Anguilla promises serene exclusivity, St. Martin offers cultural vibrancy and convenience, and St. Barts delivers deluxe indulgence in a picture-perfect setting. The good news is you don’t really have to choose just one – these islands lie close together (Anguilla and St. Martin are only about 5 miles apart, and St. Barts just a short hop farther), so your private yacht can seamlessly combine all three in one journey. Let our team at Boatcrowd help design a bespoke route that captures the highlights of each locale. For those used to five-star resorts, a private yacht offers something even more exclusive – a floating villa that brings you to a new stunning view each day without the need to ever repack. From Anguilla’s tranquil bays to St. Martin’s lively ports and St. Barts’ high-fashion beaches, your adventure will be tailored to your desires. Inquire now to start planning with Boatcrowd – and get ready to embark on the luxury yacht experience of a lifetime. For those who crave freedom, privacy, and unparalleled luxury, a yacht charter in Anguilla is more than a vacation – it’s a voyage you’ll treasure forever.
