The Caribbean enjoys reliable trade winds and a warm climate year-round, making it one of the most consistent sailing destinations on the planet. That said, the main charter season runs from November to July.

Peak season: Mid-December to March. The best weather and busiest time to charter anywhere in this expansive sailing playground. .

Shoulder season: April to July. Still excellent weather, with fewer crowds and better value charters.

Low season: August to October coincides with the Atlantic hurricane season. While storms are rare and often veer north, it's a time for cautious planning. Rates are lowest and some areas, the Grenadines for instance, remain popular for experienced sailors seeking solitude and savings.

We will you assess weather, crowd levels and pricing to identify the ideal time for your specific trip.

Related FAQs

Can I do a one-way charter in the Caribbean?

Yes, one-way charters are particularly popular in the Caribbean, where they open up possibilities a round trip of the same duration may not. Continue Reading...

Which Caribbean destinations are best for yacht charters?

The Caribbean offers a wide range of charter environments, each with its own character: Continue Reading...

Do I need a sailing qualifications to bareboat charter in the Caribbean?

In most of the Caribbean, you do not need a formal sailing qualification such as an ICC (International Certificate of Competence) or RYA certificate in order to take a bareboat charter. What you do need is to demonstrate sufficient sailing experience and practical knowledge to the charter operator Continue Reading...

Are one-way sailing charters a good option in the Mediterranean?

One-way sailing charters can be a fantastic option in the Mediterranean, especially if looking to experience a greater variety of coastlines and cultures without retracing your route. By starting in one port and finishing in another, you avoid the need to sail back to your original base Continue Reading...

Can Sail Connections match prices I see on other charter websites for the Mediterranean?

Yes, Sail Connections can usually match and often improve on prices listed on large charter booking websites. We access the same global databases and work directly with all major operators across the Mediterranean or any destination. Continue Reading...

Should I choose a bareboat, skippered, or fully crewed charter in the Mediterranean?

Choosing between a bareboat, skippered, or fully crewed charter in the Mediterranean depends on your sailing qualifications, group preferences, and the type of holiday you want. Continue Reading...

How do I book a yacht charter?

Booking a yacht charter with Sail Connections is a simple yet personalised process. Our aim is to match you with the perfect sailing experience for your group of holidaymakers. Continue Reading...

What happens if there’s a problem with the boat during our trip?

Problems on a charter are rare, but should something go wrong, rest assured you're not on your own. At Sail Connections, we only work with established, reputable operators who maintain their fleets to high standards. Continue Reading...

What are some less well known Mediterranean sailing destinations worth exploring?

Beyond the well-patronised waters of Greece, Italy, and Croatia, the Mediterranean offers a host of hidden gems ideal for those seeking a more off-the-beaten-path yacht charter. Continue Reading...

Is the Mediterranean suitable for families taking their first sailing holiday?

Yes, for the most part he Mediterranean is one of the best places in the world for a family-friendly sailing holiday — especially if it’s your first time. Continue Reading...