Anguilla Itineraries: Day Charters and Multi-Day Routes

Anguilla’s compact size and proximity to St Martin and St Barts make it ideal for both day outings and extended island-hopping voyages. The itineraries below are designed to be combined: a guest booking the 3-day and 4-day routes can stitch them together into a comprehensive 7-day Leeward Islands circuit covering three islands, dozens of beaches and three distinct cultures without repeating a single stop. Every itinerary is fully customisable – your captain and Boatcrowd charter specialist will adapt pacing and activities to your group.

Day Charter Routes

Sandy Island and Prickly Pear Cays

Depart Road Bay (Sandy Ground) mid-morning and cruise 15 minutes offshore to Sandy Island – a tiny cay surrounded by impossibly blue water, with a beach bar, palm shade and some of the best swimming in the Leeward Islands. Spend the morning snorkelling, paddleboarding and floating in water so clear you can count the grains of sand from the surface. After a light lunch on the cay or aboard, cruise 20 minutes north to the Prickly Pear Cays for an afternoon of reef snorkelling over vibrant coral in crystal-clear shallows. Return to Road Bay in the golden late-afternoon light.

Shoal Bay East and Scrub Island

Cruise east from Road Bay to Shoal Bay East – roughly 6 nautical miles along the north coast. Anchor off Anguilla’s most famous beach and swim in to a mile of pinkish-white sand with turquoise shallows and a fringing reef. Snorkel the reef, walk the beach, and enjoy a cold drink at Uncle Ernie’s Beach Bar. After lunch on the aft deck, continue east to Scrub Island – the largest offshore cay, barely developed, with emerald lagoons, 34-plus bird species and excellent turtle snorkelling in glass-calm water. Return via the south coast for a different view of the island.

Little Bay and Cove Bay

Head south-west from Road Bay to Little Bay – just 3 nautical miles, a 15-minute cruise. This secluded cove, accessible only by boat, offers glass-calm water, excellent snorkelling and a small sand crescent that feels entirely private. Your crew sets up inflatables and a full beach picnic. After lunch, cruise south to Cove Bay for a late-afternoon swim and sundowners at Smokey’s beach bar – panoramic views of St Martin, grilled ribs, cold beers and a sunset that stretches across the full western horizon.

Multi-Day Itineraries

3-Day Anguilla Yacht Charter Itinerary: Anguilla’s Beaches and Offshore Cays

Day 1: Road Bay, Sandy Island and Sandy Ground

Board your yacht at Road Bay by mid-morning. After a welcome briefing and a champagne toast on the flybridge, cruise 15 minutes to Sandy Island for a morning of swimming and snorkelling in impossibly blue water. The tiny cay’s beach bar serves cold drinks and simple grilled fish, or your chef lays out lunch on the aft deck. Return to Road Bay in the afternoon and explore Sandy Ground on foot – the Road Salt Pond (a remnant of Amerindian salt harvesting), art galleries and local boutiques. Dinner ashore at Veya – creative global fusion in a treehouse-style setting, with live music drifting through the tropical gardens – or at Elvis’s Beach Bar for ribs, rum cocktails and pure Caribbean energy.

Day 2: Prickly Pear Cays and Meads Bay

Depart Road Bay mid-morning and cruise 25 minutes north to the Prickly Pear Cays. Spend the morning snorkelling vibrant reef in crystal-clear shallows – the western cay is uninhabited and pristine, the eastern cay has two small beach restaurants and a bar. Your crew anchors between the cays and sets out water toys. After lunch (on the aft deck or at one of the beach shacks), cruise south to Meads Bay – 1.5 miles of open sand with gentle wave action and some of the island’s finest restaurants just steps from the water. Anchor offshore for a late-afternoon swim, then tender ashore for dinner at Blanchard’s – one of the Caribbean’s most celebrated restaurants, serving elevated Caribbean cuisine in a candlelit beachfront setting since 1994.

Day 3: Shoal Bay East, Scilly Cay and Return to Road Bay

Rise early for a swim at Meads Bay, then cruise east along the north coast to Shoal Bay East – roughly 5 nautical miles. Anchor off Anguilla’s most famous beach and spend the morning snorkelling the fringing reef and walking the mile-long sweep of pinkish-white sand. Continue to Island Harbour and wade across the turquoise shallows to Scilly Cay for a lobster lunch that defines the Caribbean – freshly grilled spiny lobster, cold rum punches, sand between your toes and not a worry in the world. Return to Road Bay by mid-afternoon – time for a final stroll through Sandy Ground and a farewell sundowner on the aft deck.

4-Day Anguilla Yacht Charter Itinerary: St Barts and the Southern Leewards

Day 1: Anguilla to St Martin – Grand Case

Depart Road Bay mid-morning and cruise south to St Martin – roughly 10 nautical miles, under an hour. Anchor off Grand Case on the French north coast, the self-proclaimed Gourmet Capital of the Caribbean. Snorkel Créole Rock (just offshore, teeming with tropical fish) and explore the charming village of colourful Creole houses, galleries and over 80 restaurants packed into a single beachfront strip. Dinner at Le Pressoir – consistently ranked among the finest restaurants in the Caribbean – or Spiga for creative Italian fine dining.

Day 2: St Martin to St Barts – Gustavia and Colombier

Depart Grand Case and cruise south-east to St Barts – 12 nautical miles from St Martin, roughly 45 minutes at cruising speed. Tie up in Gustavia harbour and spend the morning exploring the duty-free boutiques, waterfront bistros and elegant Swedish-colonial architecture of this postcard-perfect port. Provision from La Cave du Port Franc’s extraordinary wine cellar (7,000+ references). After lunch at Bonito overlooking the harbour, cruise north-west to Colombier Bay (3 nautical miles) for an afternoon of snorkelling among turtles and eagle rays in one of the Leeward Islands’ most beautiful anchorages. Dinner on the aft deck beneath the stars, with the hillside village lights twinkling above.

Day 3: Île Fourchue and Anse de Gouverneur

A short cruise from Colombier brings you to Île Fourchue – the uninhabited volcanic island where boulder formations create underwater swim-throughs and the snorkelling is among the best in the eastern Caribbean. Spend the morning exploring, then cruise south to Anse de Gouverneur on St Barts’ south coast – a calm, trade-wind-sheltered bay with undeveloped beach, deep turquoise water and no crowds. Your chef prepares a long lunch on the aft deck while you swim in solitude. Late afternoon, return to Gustavia for a final stroll and dinner ashore – L’Isoletta for handmade pasta, or Maya’s for Creole-French beachfront cooking that has defined St Barts dining since 1984.

Day 4: Return via Anguilla’s South Coast

Depart St Barts early and set course north for Anguilla – roughly 20 nautical miles, arriving in under 90 minutes. Rather than returning directly to Road Bay, cruise along Anguilla’s south coast, stopping at Rendezvous Bay – a 2-mile sweep of powder-white sand with views back to St Martin’s green mountains. Swim, paddleboard and let your crew set up a farewell beach picnic. Continue west to Maundays Bay for a final swim beneath the white arches of Belmond Cap Juluca, then round the island’s western tip and return to Road Bay by early afternoon.

Guests looking for a longer voyage can combine the 3-day Anguilla route with the 4-day St Martin–St Barts route for a comprehensive 7-day Leeward Islands charter covering three islands, three cultures (British, French and Dutch), and dozens of world-class beaches, anchorages and dining experiences – without repeating a single stop.