Depart Saint Martin in the morning for an easy first run that sets the tone for a luxury Leeward Islands yacht charter itinerary. Anguilla welcomes you with calm water and a relaxed shoreline feel, ideal for anchoring and starting the week with maximum time in the sea. Anchor off a protected bay for swimming and paddleboarding, then take the tender ashore for a simple beach afternoon if you want a change of pace. Return onboard for a late lunch and an unhurried reset. As the light softens, enjoy sunset cocktails on deck and a refined dinner onboard, keeping the evening quiet and effortless.

Cruise toward Saint Barthélemy with time to arrive in daylight and choose between a marina berth for convenience or an anchorage if you prefer privacy. This is the most polished stop on the route, and it works well for provisioning, shopping, and a livelier evening while still keeping the yacht as your base. Spend the afternoon with a swim off the stern, then step ashore for a short stroll through the harbour and boutiques. Onboard, reset for the evening with cocktails on deck before dinner. Whether you dine ashore or onboard, the day delivers the signature mix of glamour and comfort that defines a luxury Caribbean yacht charter itinerary.

Today is a longer passage that benefits from an early start and a steady cruising rhythm. As you move south, the islands shift in character, with greener silhouettes and a more understated, classic Caribbean feel. Plan a comfortable arrival in the afternoon, choosing a marina berth if you want easy shore access or anchoring if conditions are calm and you prefer a quieter night. Spend the late afternoon unwinding onboard, with time for a swim, a shower, and a long golden hour on deck. Dinner onboard suits this day best, keeping the pace relaxed after time underway and setting you up well for exploring tomorrow.

Depart in the morning and cruise toward Montserrat, an island stop that feels distinct for its wild, dramatic profile. The day is about scenic cruising and anchoring well, with the captain selecting the best shelter based on wind and sea state. Once settled, spend the afternoon with tender exploration and quiet time onboard, letting the landscape do the work. This is a natural day for an onboard focused rhythm, a long lunch, reading on deck, and a slow sunset. Dinner onboard keeps the mood refined and calm, and the evening feels more secluded than the more social harbours earlier in the itinerary.

Make an easy run to Antigua and arrive with time to enjoy the island’s polished charter infrastructure. Antigua is a strong finish for a Leeward Islands yacht charter itinerary, offering marinas, provisioning, and an easy transition to disembarkation plans. Dock if you want straightforward access to shore, or anchor if you prefer one more quiet night with tender flexibility. Spend the afternoon resetting onboard, then enjoy a final evening that feels celebratory but still calm, sunset cocktails, a chef led dinner, and a comfortable night with everything close at hand.

Keep the final day light and uncompressed, starting with a slow breakfast onboard and a last swim if conditions are settled. Use the morning for packing, crew assisted preparation, and a relaxed final lunch onboard if timing allows. Antigua’s marina access makes disembarkation straightforward, while still letting you enjoy a calm, polished finish. This luxury Caribbean yacht charter itinerary closes with an easy handover and the feeling of having moved through multiple island styles in less than a week, chic harbours, quiet anchorages, and sea led days that stayed effortless from start to finish.