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Anguilla sits 6 nautical miles north of St Martin and 12 nautical miles north of St Barths in the northern Leeward Islands, a 16 mile by 3 mile flat coral island with 33 named beaches and approximately 15,000 residents. A 40m motor yacht working Anguilla in February as part of a Northern Leewards rotation runs $140,000 to $180,000 per week before APA, with Anguilla typically absorbing 1 to 3 days of the rotation. Anguilla holds no superyacht marina; the working overnight anchor is at Sandy Ground on the south coast and the Forest Bay outer anchor on the north. Most charter clients arrive into Anguilla via Princess Juliana airport (SXM) at St Martin with the 25-minute Blowing Point ferry, or via the small Clayton J. Lloyd airport (AXA) on Anguilla itself with regional lift from San Juan and Antigua.
The point of Anguilla on a Caribbean charter week is the beaches and the on-shore product. The Anguilla resort calendar runs the strongest in the Caribbean at the top end with Belmond Cap Juluca at Maundays Bay, Four Seasons Resort Anguilla at Meads Bay (the converted Viceroy property), Aurora Anguilla Resort at Rendezvous Bay (the converted CuisinArt Resort, reopened 2023 after a full rebuild), Malliouhana at Meads Bay, and Zemi Beach House at Shoal Bay East. The restaurant calendar runs Veya at Sandy Ground, the Straw Hat at Frangipani Beach, Tasty's at South Hill, Blanchards at Meads Bay, and the Hibernia at Island Harbour. The yacht is the trip in Anguilla in the sense that the beach product is approached from the water and the working day runs from the Sandy Ground anchor at the morning to a Meads Bay lunch on the beach at the Belmond or Four Seasons, an afternoon swim at Shoal Bay East, and a Veya dinner at Sandy Ground before the overnight.
Anguilla is also the working day-trip destination from St Barths. The 12 nautical mile cross from Gustavia to Sandy Ground runs at 45 minutes on a 40m motor yacht and absorbs cleanly into a St Barths-based charter week. Most charter clients chartering in the Northern Leewards build Anguilla in as a 2 to 3 day window with the boarding and disembarkation at SXM (St Martin).
When to charter Anguilla
December 15 to January 5. Christmas and New Year peak. Water 26 degrees Celsius. Trade winds 15 to 22 knots from the east-southeast. Sandy Ground and Meads Bay at peak utilisation. Resort calendar at peak (Belmond, Four Seasons, Aurora at 95 to 100 percent capacity). Rates at peak; book 9 to 12 months out.
January. Shoulder through January 15 (rates 10 to 15 percent below peak), returns to peak from January 20. Water 26 degrees. The Anguilla day calendar runs at its cleanest in the second half of January with the beach product at moderate density.
February. Peak. Water 26 to 27 degrees. The strongest charter window for Anguilla in combination with St Barths. The Anguilla beach product runs at full strength.
March. Peak through Easter. Water 26 to 27 degrees. The Moonsplash music festival at Dune Preserve on Rendezvous Bay runs in early March (Bankie Banx's annual reggae and roots festival) and absorbs the south coast inventory. The festival reads as a working draw rather than a deterrent for charter clients.
April. Peak through Easter, shoulder from the week after Easter. Water 27 degrees. Trade winds tapering through April 15. The Festival del Mar at Island Harbour runs mid-April (boat races, fishing tournament, fish chowder competition).
May. Shoulder. Rates 25 to 35 percent below peak. Water 28 degrees. The charter fleet begins repositioning. The cleanest non-peak Anguilla window for resort and restaurant inventory.
June to November. Hurricane season. Most crewed charter inventory closes. The Hibernia restaurant typically closes for the summer; resort calendar runs at reduced capacity. Charter weeks at this window run operator-by-operator with weather-window flexibility.
The Anguilla cruising zones
Sandy Ground (Road Bay). The working charter anchor. 12 to 18 metres of holding ground on sand, the customs clearance at the south coast Anguilla port, and the on-shore village product including Veya, the Pumphouse, Elvis Beach Bar, and Roy's Bayside Grill. Sandy Ground absorbs 10 to 25 yachts on February nights with the south coast lee on the trade winds. The cleanest single working anchor in the Northern Leewards.
Meads Bay. The west coast standing daytime anchor. The 1 mile beach holds the Belmond Cap Juluca (at the western end at Maundays Bay, the converted Cap Juluca Moorish-architecture property reopened 2018 after the Belmond purchase), the Four Seasons Resort Anguilla (the converted Viceroy, rebranded 2017 and now under Four Seasons management), and Malliouhana (the historic 1984 resort, refreshed 2014). The Meads Bay daytime anchor holds the beach calendar with the Blanchards, Jacala, and Straw Hat restaurants on the beachfront.
Rendezvous Bay. The south coast bay between Sandy Ground and Maundays Bay. Aurora Anguilla Resort (the rebuilt CuisinArt property, reopened 2023, the Greg Norman golf course, and the working south coast resort base). The Dune Preserve at the east end of Rendezvous holds the Bankie Banx beach bar (the historic 1990s reggae bar, the working Moonsplash venue).
Shoal Bay East. The standing daytime swim anchor on the northeast coast. 2 mile white-sand beach, the canonical Anguilla swim with the Zemi Beach House at the eastern end, the Madeariman beach bar at the center, and the Uncle Ernie's Beach Bar at the historic shanty. Anchor in 3 to 6 metres of sand. Most charter days build Shoal Bay East in as the afternoon swim stop.
Prickly Pear Cays. 5 nautical miles north of Anguilla. Two small uninhabited cays with the Sunshine Shack (the Garvey Lake beach bar on Prickly Pear East, the working lobster lunch) and the protected anchor between the cays. The canonical daytime offshore Anguilla stop and the working lunch anchor on a Sandy Ground charter day.
Sandy Island. 2 nautical miles north of Sandy Ground. A small 100 metre sandbar with a beach bar (Joash's Sandy Island, the day-rental beach lounger inventory and the casual lobster lunch). The standing morning swim stop on a Sandy Ground-based day.
Forest Bay and the east end. The east coast outer anchor. Less developed than the south or west coasts, holds the Smokey's at the Cove restaurant and the Cap Cap restaurant. The east-end villages of Island Harbour and East End hold the small-scale local product and the Hibernia restaurant on the road between East End and Captain's Bay.
Crocus Bay and Little Bay. The west coast inner bays. Crocus Bay holds da'Vida restaurant on the beachfront; Little Bay (the south side of the Crocus Bay peninsula) is the snorkel anchor accessed only by water with the standing morning stop.
A standard Anguilla 2-day program inside a St Barths charter
| Day | Anchorage | What happens |
|---|---|---|
| Day 1 morning | St Barths to Sandy Ground cross | 12 nautical mile cross from Gustavia, customs clearance at Sandy Ground, morning swim at Sandy Island, overnight Sandy Ground |
| Day 1 afternoon | Sandy Ground | Veya dinner ashore or marina-side at the Pumphouse, overnight Sandy Ground |
| Day 2 morning | Prickly Pear and Shoal Bay | Prickly Pear daytime anchor, lobster lunch at Sunshine Shack, afternoon swim Shoal Bay East, tender ashore Zemi or Madeariman |
| Day 2 afternoon | Meads Bay or Maundays Bay | Beach lunch at Belmond Cap Juluca or Four Seasons, afternoon swim Maundays, overnight Sandy Ground or cross back to St Barths |
This is the canonical Anguilla program. It works as a 2-day window inside a wider St Barths or St Martin charter and absorbs the full Anguilla product without compromising the wider Northern Leewards rotation.
A stand-alone 7-day Anguilla charter is possible but unusual. The Anguilla product alone (Sandy Ground, Prickly Pear, Meads Bay, Shoal Bay) absorbs 3 to 4 days of cruising before the structure starts repeating; the working 7-day charter at Anguilla pairs it with St Barths and St Martin to deliver a Northern Leewards spine.
Anguilla yacht size guidance
20m to 40m. The clean fit. Sandy Ground anchor at the inner line, Prickly Pear inside the cays, Meads Bay direct at standoff. The tender absorbs the on-shore product at Shoal Bay East and Maundays Bay without compromise.
40m to 60m. Workable. Sandy Ground at the outer anchor line, Forest Bay as the alternative overnight anchor at standoff. Meads Bay daytime anchor at deep water with the tender absorbing the beach product.
60m to 80m. Sandy Ground outer anchor at standoff, Forest Bay outer anchor. Prickly Pear at the outer standoff position. Meads Bay and Maundays Bay at the deep-water line with the tender absorbing the on-shore product. Above 60m the working overnight is typically at St Barths (Gustavia outer harbor) or St Martin (Simpson Bay outer anchor) with the daytime cross to Anguilla.
80m and above. Anguilla is a daytime anchor. The working overnight returns to St Barths or St Martin. The 80m+ yacht runs the morning cross to Anguilla, anchors at Sandy Ground or Forest Bay outer, runs the on-shore product via tender for the day, and returns to the overnight base in the evening.
Anguilla charter cost math
Anguilla is typically a 2 to 3 day window inside a Northern Leewards rotation. The following figures show the incremental Anguilla cost on a 40m motor yacht charter week priced at $160K before APA, with Anguilla absorbing 2 days of the rotation.
| Line item | Range (40m motor yacht, February peak, 2-day Anguilla window) |
|---|---|
| Pro-rata weekly rate (2 of 7 days) | $46K of $160K total |
| APA pro-rata (28% to 32%) | $13K of $45K total |
| Anguilla cruising permit (per yacht, 7 days) | $0.5K to $1K |
| Anguilla port and customs (Sandy Ground) | $0.2K to $0.5K |
| Restaurant ashore at Veya, Blanchards, Hibernia, or Belmond beach (per visit) | $0.5K to $1.5K |
| Beach club access at Belmond Cap Juluca, Four Seasons, or Aurora (per person) | $0.15K to $0.4K |
| Gratuity pro-rata (10% to 15%) | $5K of $20K total |
| Anguilla incremental check | $14K to $20K above the pro-rata charter base |
The Anguilla cruising permit applies on a per-yacht basis for the charter window. APA pro-rata on a 2-day Anguilla window covers the inbound and outbound passages plus the on-shore tender operations.
What we passed on
We pass on the Cap Juluca as the working overnight anchor base. The Belmond Cap Juluca sits at Maundays Bay on the southwest coast with the swell on the south coast running cleaner at Sandy Ground and the on-shore restaurant and bar calendar at Sandy Ground absorbing the dinner product. Cap Juluca is the working beach lunch and afternoon swim destination, not the overnight base.
We pass on Anguilla as a stand-alone 7-day charter destination. The full Anguilla product (Sandy Ground, Prickly Pear, Meads Bay, Shoal Bay, Rendezvous, Forest Bay) absorbs 3 to 4 days of cruising before the structure starts repeating. The cleanest answer is a Northern Leewards rotation across St Barths, Anguilla, and St Martin (or St Kitts) with Anguilla absorbing 2 to 3 days of the week.
We pass on Crocus Bay and Little Bay as primary daytime anchors on a high-density February peak week. The bays are smaller-scale with fewer than 4 yachts at anchor at peak and the on-shore product (da'Vida at Crocus Bay) absorbs the lunch calendar but the swim itself runs cleaner at Shoal Bay East and at Prickly Pear. Make Crocus a lunch stop, not a swim anchor.
We pass on the historic Smokey's at the Cove on the dinner rotation. The east-end beach bar runs the working lunch calendar at the Cove Beach but the working dinner anchor for a charter night is Sandy Ground with Veya, the Pumphouse, or Roy's Bayside, not the east-end Smokey's. Smokey's is a daytime stop, not an overnight destination.
We pass on the May to November shoulder window as a primary Anguilla charter destination outside a Caribbean-summer-only rotation. The resort calendar runs at reduced capacity through summer (Hibernia closes, the Belmond beach club runs at reduced service) and the working Anguilla product through summer absorbs only the Sandy Ground and Meads Bay anchors at full strength. The strongest Anguilla product runs December to April.
Multi-region pairings
The St Barths-Anguilla-St Martin Northern Leewards 7-day charter is the canonical Anguilla structure. Board at St Barths (Gustavia, fly into SBH from SXM via the 15-minute hop), 3 days St Barths, 2 days Anguilla, 2 days St Martin (Simpson Bay or Marigot), disembark at SXM. The structure absorbs Anguilla cleanly into the wider rotation. We cover the St Barths side on the St Barths page and the St Martin side on the St Martin page.
The BVI-Anguilla-St Barths 10-day rotation absorbs Anguilla as a single overnight inside the wider down-island Caribbean charter. Board at Tortola (BVI), run 5 to 6 days BVI rotation, cross 75 nautical miles to Anguilla overnight, 1 day Anguilla, 2 days St Barths, disembark SBH or SXM. We cover the BVI side on the BVI page.
The Anguilla-St Barths repositioning week (December and April) absorbs the inter-resort and inter-island traffic at the charter ends.
The cross-pillar question (villa or charter)
The Anguilla villa inventory at Meads Bay, Shoal Bay East, Rendezvous Bay, and the West End holds the deepest villa product in the Northern Leewards at $5K to $80K per week with the high end at the Long Bay private villas and the Tequila Sunrise estate. For clients prioritising Anguilla as the destination rather than the wider Northern Leewards rotation, the villa is the cleaner answer. A villa stay at Meads Bay or Shoal Bay East plus day charters from Sandy Ground to Prickly Pear, Sandy Island, and St Barths works at $2K to $8K per day. The charter is the cleaner answer when the brief is the Northern Leewards spine across multiple islands; the villa is the cleaner answer when the brief is the Anguilla beach product alone.
The rest of the trip
VillasForKings covers the Meads Bay villas, the Shoal Bay East estates, the Long Bay villas, and the Tequila Sunrise property. HotelsForKings covers the Belmond Cap Juluca, the Four Seasons Resort Anguilla, the Aurora Anguilla Resort, the Malliouhana, and the Zemi Beach House. RestaurantsForKings covers Veya at Sandy Ground, Blanchards and Jacala at Meads Bay, the Hibernia between East End and Captain's Bay, the Straw Hat at Frangipani, and the Pumphouse. BarsForKings covers the Dune Preserve at Rendezvous, the Elvis Beach Bar at Sandy Ground, the Sunshine Shack at Prickly Pear, and the Bankie Banx Moonsplash calendar.
FAQ
What size yacht works best at Anguilla? 30m to 60m motor yacht. Sandy Ground and Forest Bay anchors absorb cleanly, the tender absorbs the on-shore product, and the 12 nautical mile St Barths cross runs at 45 minutes. Above 80m the working overnight returns to St Barths or St Martin with Anguilla as a daytime anchor.
When is Anguilla at its best? The second half of February through Easter. Water 26 to 27 degrees, full resort and restaurant calendar, low cold-front risk, and the Anguilla beach product at moderate rather than peak density.
Is Anguilla a base or a stop? A stop. Anguilla holds no full-service superyacht marina and the working charter structure is a 2 to 3 day Anguilla window inside a Northern Leewards rotation that boards at SXM (St Martin) or SBH (St Barths).
How does the cross to St Barths work? 12 nautical miles from Sandy Ground to Gustavia, 45 minutes at 16 knots on a 40m motor yacht. The captain handles the French Saint Barthélemy customs clearance at Gustavia. The cross absorbs cleanly into a 2-day Anguilla program.
What is the working anchor at Anguilla? Sandy Ground (Road Bay) on the south coast. The cleanest single overnight anchor in the Northern Leewards with the customs clearance, the on-shore village dinner product, and 12 to 18 metres of holding ground on sand.