The best time to charter in the Caribbean and Bahamas is from December through July, with peak season running mid-December to March. That’s when you’ll find the most settled weather and lively island atmospheres—perfect for escaping southern hemisphere winters or northern chills.

If you're looking for quieter anchorages and better value, consider the shoulder season from April to July. Conditions are typically excellent, and there’s less competition for boats and moorings.

We recommend booking at least 6 to 12 months in advance, especially if you're planning to travel over the festive season or school holidays. The best boats and bases fill up quickly—particularly in popular spots like the British Virgin Islands, Bahamas, and St. Lucia.

For late bookings or low-season travel (August to October), we can often find excellent last-minute options, though be aware it's hurricane season. We’ll advise you on that and help plan a flexible itinerary.

Early booking also opens the door to discounts and ensures you get the best boat for your group and budget.

Related FAQs

What sailing qualifications are required to bareboat charter in the Caribbean?

Most Caribbean destinations do not require a formal sailing licence to charter a bareboat. Continue Reading...

Am I responsible for damage to my chartered boat?

From time to time, damage can occur during a yacht charter. Continue Reading...

What do you recommend about boat chartering in the Caribbean?

Chartering a boat in the Caribbean is one of the most rewarding sailing experiences Continue Reading...

What are your favourite Mediterranean sailing spots?

When it comes to sailing in the Mediterranean, we're totally sold! Continue Reading...

When should I book a charter boat in the Mediterranean?

For the Mediterranean It’s best to book 6 to 12 months in advance. Continue Reading...

When is the sailing season in the Mediterranean?

The Mediterranean sailing season generally runs from April to October Continue Reading...

What types of boat can be chartered with skipper or fully crewed?

A wide range of yacht types is available for both skippered and fully crewed charters Continue Reading...

What level of service is provided in a fully crewed luxury yacht charter?

Tis charter type offers the highest level of service available at sea Continue Reading...

What extra level of service is there in a skippered bareboat charter?

With a paid skipper you get more peace of mind and local knowledge Continue Reading...

Is it best to book a Greece sailing holiday through a broker or directly with an operator?

Using a reputable broker is almost always the better choice Continue Reading...