The best time to charter in the Virgin Islands depends on your priorities: weather, budget, crowds and sailing conditions. With warm temperatures year-round and steady trade winds, there’s truly no bad time to go. But a few seasonal patterns can help you decide what works best for your group.

Shoulder Seasons: April to June & November

These shoulder months are often overlooked but can be the most rewarding times to charter in the Virgin Islands. In April to early June, the weather is settled, the trade winds are reliable and the islands beautifully uncrowded. November marks the very start of the charter season, with some of the best pricing before the December rush.

December to April: Peak Season

This is the Caribbean’s high season, offering picture-perfect weather with warm sunshine, cooling breezes, and low humidity. It’s the best time if looking to escape northern  winters or enjoy a festive atmosphere around Christmas and New Year’s. Expect lively anchorages, full restaurants, and premium rates during these months, particularly December through March. Book early for the best selection of yachts.

February, April, and May: the Sweet Spot

If you prefer great sailing without peak-season prices or crowds, late February to May is ideal. The winds are still consistent, the sea is warm, and the mood is more relaxed. It's an excellent time for both bareboat and crewed charters, with more boat availability.

June to November: Off-Season and Hurricane Awareness

The official Atlantic hurricane season runs from June 1 to November 30. While major storms are relatively rare and often pass north of the Virgin Islands, the risk increases from August through October. These months offer lower charter rates and quieter cruising grounds, and many experienced sailors enjoy the solitude of the off-season. Travel insurance is strongly advised during this period.

At Sail Connections, we tailor your Virgin Islands sailing holiday to suit your preferred travel window. We take into account not just weather, but your group’s comfort, budget, and interest in local events or quieter waters. Whether it’s a peak-season celebration or a tranquil off-season escape, we’ll guide you to the best time to set sail.

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