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.

Related FAQs

What are the sailing conditions like in the Virgin Islands ?

The Virgin Islands offer some of the most accessible and enjoyable sailing in the Caribbean, ideal for both first-timers and seasoned sailors. Prevailing trade winds blow consistently from the east at 10–20 knots, short distances between islands mean less time sailing and more time relaxing, the waters are well charted with plenty of sheltered anchorages, minimal tidal range and good marine infrastructure.

What types of boats are available for USVI charter and do they include crewed boats?

In the USVI there is a wide selection of charter boats available, tailored to suit your group size, sailing experience, and holiday preferences. Crewed yacht charters are popular in this destination, offering a stress-free way to enjoy sailing without needing any boating experience. Continue Reading...

Can I sail between the US and British Virgin Islands on a USVI charter?

Yes, you can sail between the US Virgin Islands and British Virgin Islands (BVIs), but there are important legal and logistical considerations. Not all charter boats based in the USVI are licensed to enter BVI waters. Continue Reading...

Do I need a sailing qualification to charter a boat in the US Virgin Islands?

In most cases, you don’t need a formal sailing license or qualification to charter a bareboat in the US Virgin Islands. Continue Reading...

What expenses should I expect during a BVI bareboat charter?

While your bareboat charter includes the yacht itself, there are several additional costs to factor into your holiday budget. These vary depending on your itinerary, provisioning style and personal preferences. Continue Reading...

Should I start a Virgin Islands charter from Tortola (BVI), St. Thomas (USVI) or San Juan (Puerto Rico)?

Your choice of charter base in the Virgin Islands, whether Tortola in the British Virgin Islands (BVI), St. Thomas in the US Virgin Islands (USVI), or San Juan in Puerto Rico, depends on convenience, sailing plans and travel logistics. Continue Reading...

Where can we get away from it all on our BVI charter?

For those who love to explore by sail, the British Virgin Islands offer so much. Beyond the popular moorings you will call at for provisioning and the nightlife, lie peaceful anchorages, untouched beaches and wildlife-rich bays that reward you for going a little further. Continue Reading...

Where is the British Virgin Islands' sailing charter base?

The main sailing charter base in the British Virgin Islands is located at Wickhams Cay II Marina in Road Town, Tortola. This is the central hub for most charter departures and home to several major operators. Continue Reading...

What are the best air connections to the British Virgin Islands from USA and Europe?

Here are some of the best air connections to the British Virgin Islands (BVI) from the USA and Europe (effective June 2025): Continue Reading...