Anguilla Guide: Luxury Yacht Charter in Anguilla

Anguilla is the Caribbean stripped back to its essentials: 33 powder-white beaches on an island just 26 kilometres long and 6 kilometres wide, a coral limestone platform so flat that the highest point barely clears 65 metres, and water so clear that your anchor chain is visible in 10 metres of depth. This British Overseas Territory sits roughly 12 nautical miles north of St Martin, close enough that the green mountains of the larger island form a constant backdrop to the south, yet a world apart in atmosphere. Where St Martin buzzes with dual-nationality energy and St Barts gleams with French sophistication, Anguilla offers something quieter and arguably more precious: genuine, unhurried Caribbean tranquillity paired with some of the finest dining, most pristine beaches and most exclusive resorts in the West Indies.

The dining scene is the island’s great surprise. For a territory of just 15,000 permanent residents, the restaurant quality rivals islands ten times its size. Blanchard’s on Meads Bay has been serving elevated Caribbean cuisine since 1994 and is regularly cited among the finest restaurants in the region. Veya offers global-fusion creativity in a treehouse setting above Sandy Ground. Hibernia, on the east end at Island Harbour, blends Asian and European techniques with fresh local seafood. Jacala delivers French-Caribbean finesse on the sand at Meads Bay. And then there are the beach bars – Elvis’s at Sandy Ground, Smokey’s at Cove Bay (with sunset views stretching to St Martin), and the legendary Scilly Cay, a tiny island off Island Harbour where you wade across turquoise shallows to an open-air kitchen grilling the day’s lobster catch. Anguilla also holds a rare distinction: Caribbean spiny lobster is available year-round here, unlike most of the Caribbean where seasonal restrictions apply.

For yacht charter guests, Anguilla’s appeal goes beyond the beaches. The offshore cays – Sandy Island, Prickly Pear, Dog Island, Scrub Island – provide day-charter destinations with outstanding snorkelling, wreck diving and deserted-island picnics. Seven deliberately sunken wrecks (including the 70-metre MV Sarah off Sandy Ground) create artificial reefs that attract abundant marine life. And the island sits at the northern apex of the Leeward Islands triangle, making it an ideal starting or ending point for a multi-island voyage that takes in St Martin and St Barts. Enquire with Boatcrowd for yacht or catamaran availability and pricing on our Anguilla fleet.

Why Charter a Yacht in Anguilla

33 Beaches, Zero Crowds

Anguilla packs 33 distinct beaches into 26 kilometres of coastline – more beaches per square mile than almost anywhere in the Caribbean. Shoal Bay East, with its mile-long sweep of pinkish-white sand and turquoise shallows, routinely ranks among the world’s best. Meads Bay stretches 1.5 miles of open sand with gentle wave action. Rendezvous Bay offers 2 miles of powder with views of St Martin. Maundays Bay, a half-moon of ivory sand beneath the white Moorish arches of Belmond Cap Juluca, is as beautiful as any beach in the Caribbean. Yet even in peak season, Anguilla’s beaches feel uncrowded. The island receives a fraction of the visitors that descend on larger Caribbean destinations, and many of the best stretches of sand are most easily reached by yacht tender.

Caribbean Dining at Its Finest

Anguilla’s restaurant scene belies its tiny size. Blanchard’s (Meads Bay, since 1994) serves elevated Caribbean cuisine that draws devoted regulars from across the region. Veya (Sandy Ground) offers global fusion with Moroccan influences in a treehouse-style setting with live music. Hibernia (Island Harbour, since 1987) blends French, Asian and Caribbean flavours with ingredients from the chef’s own garden. da’Vida at Crocus Bay delivers five-star ambience rivalling St Barts. And then there’s the lobster: Anguilla is one of the few Caribbean islands where spiny lobster is available year-round, and it appears on virtually every menu – grilled at Scilly Cay, in a club sandwich at Jacala, as a white-wine-and-lemon preparation at The Lobster House, and at the weekly unlimited lobster buffet at Aurora Anguilla. For casual eating, the Blanchard’s Beach Shack, Elvis’s Beach Bar and Smokey’s at Cove Bay are local institutions.

Outstanding Offshore Cays and Marine Parks

Anguilla’s seven designated marine parks protect some of the healthiest reef systems in the Leeward Islands. Sandy Island, 15 minutes offshore from Sandy Ground, sits in impossibly blue water with a beach bar, palm shade and exceptional swimming. The Prickly Pear Cays (east and west) offer vibrant living reef and shallow snorkelling perfect for all abilities. Dog Island, further north, features spectacular drift diving along a rock wall teeming with marine life. Scrub Island, the largest offshore cay, is barely developed and home to 34-plus bird species, emerald lagoons and turtle-rich snorkelling waters. Seven deliberately sunken wrecks (sunk in 1990 to create artificial reefs, at depths of 10–25 metres) add a unique diving dimension – the MV Sarah, at 70 metres, is the largest and most impressive. You can experience it all on a 3-day yacht charter or luxury catamaran if that is your preference.

Heritage, Boat Racing and Island Culture

Anguilla has a cultural depth that rewards curious yacht charter guests. Boat racing is the national sport, a tradition dating back more than a century, and race days are major island events complete with beach picnics and community celebrations. Anguilla Day (30 May) commemorates the 1967 revolution that separated the island from St Kitts and Nevis, and the month-long programme includes the Anguilla Day Boat Race (a circumnavigation of the entire island), choir festivals, quiz competitions and street fairs. Wallblake House (1787), in The Valley, is the oldest surviving plantation house on the island – unique in the Caribbean for retaining its complete complex of main house, kitchen, stables and workers’ quarters. The Road Salt Pond behind Sandy Ground dates to Amerindian salt-harvesting times. And Bankie Banx’s Dune Preserve on Rendezvous Bay – a beach bar built from old boat hulls and driftwood – hosts the annual Moonsplash Music Festival, the oldest independent music festival in the Caribbean (founded 1991), with reggae, soca and roots music beneath the palms.

Key Destinations Near Anguilla

• Sandy Island – A tiny cay 15 minutes offshore from Sandy Ground, surrounded by some of the bluest water you will ever swim in. A beach bar, palm shade and exceptional snorkelling in all directions. The ferry runs hourly from 10 a.m. ($10 per person round trip), but arriving by yacht tender is the way to go.
• Prickly Pear Cays – Twin cays roughly 25 minutes north of Sandy Ground. The western cay is uninhabited and pristine; the eastern cay has two small beach restaurants and a bar. Crystal-clear water, vibrant reef and shallow snorkelling ideal for families. A favourite day-charter destination.
• Dog Island – Uninhabited and rugged, with two primary dive sites (West Cay and Devil’s Wall). Drift diving along the spectacular rock face reveals abundant marine life in current-swept waters. Best suited to experienced snorkellers and divers.
• Scrub Island – The largest offshore cay, minimal development, home to 34-plus bird species, emerald lagoons and turtle-rich snorkelling waters. A genuine Robinson Crusoe experience within a yacht tender distance of Anguilla’s east end.
• Little Bay – A secluded cove on the south-west coast, accessible only by boat or by rope descent from the clifftop. Glass-calm water, excellent snorkelling, and a small sand crescent that feels entirely private. Your crew sets up inflatables and a beach picnic while you swim in silence.
• Shoal Bay East – Anguilla’s signature beach: over a mile of pinkish-white sand with turquoise shallows and a fringing reef for snorkelling. Beach bars (Uncle Ernie’s, Gwen’s Reggae Grill) line the sand. Anchor offshore and swim in for a morning that defines the Caribbean.
• Scilly Cay – A tiny private island off Island Harbour where you wade across turquoise shallows (or take a short tender ride) to an open-air kitchen grilling fresh lobster and ribs. Cold rum punches, sand between your toes, and one of the most memorable lunch spots in the Leeward Islands.

Best Time to Charter a Yacht in Anguilla

Peak Season: December to April

The dry season brings warm, comfortable weather (25–30°C / 77–86°F), steady north-east trade winds that keep the air fresh, and virtually no rain. Water temperatures sit at 26–27°C – perfect for swimming and snorkelling. This is the most popular period for Caribbean charter, and Anguilla’s resorts and restaurants are at their liveliest. February and March are the driest months. Charter rates are at their highest over Christmas and New Year, but January through April offers excellent conditions at slightly softer pricing. Annual rainfall on Anguilla is just 35 inches – significantly drier than most Caribbean islands.

Shoulder Season: May to July and November

May through July offers warm weather (28–31°C), calmer seas and noticeably fewer visitors. Charter rates drop by 15–25% compared to peak. Anguilla’s restaurants remain open and the beaches are at their emptiest. The Moonsplash Music Festival typically falls in March, and Anguilla Day celebrations run throughout May. November, at the tail end of hurricane season, generally brings settled conditions and warm seas. Both periods suit charter guests who want Anguilla’s best beaches and dining without the peak-season crowds.

Hurricane Season: August to October

The peak hurricane risk window runs from August to October. Anguilla has not experienced a direct major hurricane hit since Hurricane Irma in September 2017 (prior to that, 1995). Most charter yachts reposition out of the hurricane belt during these months. Chartering is possible but limited, and marine insurance requirements may restrict availability. For the best combination of weather, availability and yacht charter value, aim for December through April.

Signature Experiences

• Lobster Lunch at Scilly Cay – Wade across the shallows from Island Harbour (or take your tender) to this tiny private island and sit down to freshly grilled Caribbean spiny lobster, cold rum punches and the kind of barefoot Caribbean afternoon that postcards try and fail to capture.
• Shoal Bay East Morning – Anchor off Anguilla’s most famous beach and swim in before the day trippers arrive. A mile of pinkish-white sand, turquoise shallows and a fringing reef for snorkelling. Your chef has coffee and fresh tropical fruit waiting on the aft deck when you paddle back.
• Sunset at Smokey’s, Cove Bay – Tender ashore to this laid-back beach bar on the west coast for grilled ribs, cold Heinekens and a panoramic sunset view that stretches all the way to St Martin. The vibe is pure Caribbean – reggae on the speakers, sand under your feet, and no rush to be anywhere.
• Wreck Diving the MV Sarah – This 70-metre former cargo vessel, deliberately sunk off Sandy Ground in 1990, sits upright in 10–25 metres of water and is now a thriving artificial reef. Swim through the corridors and cargo holds surrounded by schools of fish, coral encrusted railings and the occasional nurse shark resting in the shadows. Your yacht’s crew can arrange a guided dive.
• Private Beach Picnic at Little Bay – Accessible only by boat, this secluded cove on the south-west coast is glass-calm and utterly private. Your crew sets up inflatables, snorkelling gear and a full beach picnic while you float in water so clear it barely seems to exist.
• Bankie Banx’s Dune Preserve – An evening at the Caribbean’s most legendary beach bar, built from old boat hulls and driftwood on Rendezvous Bay. Live reggae, rum punches, stars above and sand below. If the Moonsplash Music Festival (March) falls during your charter, this is unmissable.
• Cap Juluca Beach Walk – Tender ashore at Maundays Bay and walk the full crescent of this half-moon beach beneath the white Moorish arches of Belmond Cap Juluca. The resort’s Pimms restaurant welcomes yacht guests for a beachside dinner that rivals anything in the Leeward Islands.

Yacht Types Available

• Motor Yachts (55’–99’) – Agile and fast, perfect for exploring Anguilla’s coastline and hopping to the offshore cays. Reach Sandy Island in 15 minutes, the Prickly Pears in 25, and St Martin in under an hour. All-inclusive crewed charters with water toys, chef and full service. Weekly rates start from around $50,000–$120,000 depending on season and yacht.

• Superyachts (100’+) – Road Bay can accommodate vessels up to 60 metres at anchor, and the anchorage offers clear, calm water with good holding in 7–9 metres over sand. A superyacht charter in Anguilla pairs the island’s understated luxury with the privacy and space of a floating five-star resort. Weekly rates from $150,000–$300,000+.

• Luxury Catamarans (55’+) – Stable, spacious and shallow-drafted – ideal for nosing into Anguilla’s reef-protected bays and anchoring close to shore at Little Bay, Sandy Island and the Prickly Pears. The twin-hull design eliminates rolling, making catamarans the most comfortable option for families and guests prone to seasickness. Weekly rates from $25,000–$45,000.

Frequently Asked Questions

How much does a yacht charter in Anguilla cost?

Crewed motor yachts (55’–99’) start from around $50,000–$120,000 per week during peak season (December–April). Superyachts (100’+) typically range from $150,000–$300,000+ per week on MYBA terms (plus Advance Provisioning Allowance of 25–35%). Luxury catamarans (55’–80’) start from roughly $25,000–$45,000 per week. Shoulder-season rates (May–July, November) are typically 15–25% lower. Enquire with Boatcrowd for a quote tailored to your dates and group size.

Are luxury catamarans available for charter in Anguilla?

Yes. Boatcrowd’s Caribbean fleet includes premium power catamarans from Sunreef, Lagoon and other leading builders in the 55’–80’ range. These vessels are ideal for Anguilla’s shallow reef-protected waters, with draft shallow enough to anchor close to shore at Little Bay, Sandy Island and the Prickly Pear Cays. Fully crewed with captain, chef and steward/ess, and especially popular with families who value the wide beam, stability and easy swim-platform access.

Can I charter a yacht in Anguilla for a film or TV production?

Yes. Anguilla has served as a filming location for several productions, including episodes of Below Deck, The Bold and the Beautiful, House Hunters International and Love in the Sun. The island’s pristine beaches, clear water and photogenic offshore cays make it a natural fit for luxury lifestyle content, travel programming and yacht-based filming. Boatcrowd can arrange production-friendly charters and coordinate with local authorities for filming permits and logistics.

Is Anguilla a good destination for a proposal, honeymoon or milestone celebration?

Anguilla is one of the most romantic islands in the Caribbean. Your crew can arrange a sunset proposal on the deserted sand of Little Bay (accessible only by your tender, ensuring complete privacy), a honeymoon itinerary that weaves between private beach picnics and candlelit dinners at Blanchard’s, or a milestone birthday celebration with lobster at Scilly Cay and live reggae at the Dune Preserve. The Belmond Cap Juluca, Four Seasons and Malliouhana resorts all welcome yacht guests for special-occasion dining. Let Boatcrowd know the occasion when you enquire and we’ll ensure every detail is handled.

Can I bring the whole family, including grandparents and young children?

Anguilla is exceptionally family-friendly. The island’s calm, shallow bays (Shoal Bay East, Rendezvous Bay, Maundays Bay) are safe for young swimmers, and the Prickly Pear Cays offer protected snorkelling in water shallow enough for children. Catamarans provide the widest, most stable platform for multi-generational groups, with easy swim-platform access and space for everyone. Crews are experienced with guests of all ages and can organise beach treasure hunts, snorkelling safaris and kid-friendly menus. Blanchard’s Beach Shack is consistently voted the island’s best family restaurant.

Can I combine Anguilla with St Martin and St Barts in one charter?

Absolutely, and it’s one of the most popular yacht itineraries in the Caribbean. Anguilla sits roughly 10 nautical miles from St Martin and 20 nautical miles from St Barts. A 5-day charter can comfortably visit all three islands, while a 7-day voyage adds time for the offshore cays and hidden anchorages. The cultural contrast – British Anguilla, French St Barts, and the dual French–Dutch personality of St Martin – makes this one of the most varied short itineraries in the world. Your Boatcrowd charter specialist will design a multi-island route tailored to your group.

What is there to do in Anguilla beyond the beaches?

More than you might expect. Boat racing is the national sport, with community race days throughout the year that are genuine cultural events. Wallblake House (1787) is the Caribbean’s best-preserved plantation complex. The Heritage Collection Museum in The Valley tells the island’s story from Arawak settlement through the 1967 revolution. The Big Spring Cave at Island Harbour contains over 100 Amerindian petroglyphs dating from 600–1200 AD. And the music scene punches well above its weight – Bankie Banx’s Dune Preserve on Rendezvous Bay hosts live reggae year-round and the annual Moonsplash Music Festival (the oldest independent music festival in the Caribbean, founded 1991). For diving enthusiasts, seven deliberately sunken wrecks create a unique underwater heritage trail.