Chartering a boat in the Caribbean - including The Bahamas - is one of the most rewarding sailing experiences you can have. We recommend it for its warm climate, steady trade winds, short sailing distances, and abundance of beautiful anchorages. It’s ideal for both first-time charterers and seasoned sailors.

We suggest starting with well-established areas like the British Virgin Islands or the Grenadines—great infrastructure, easy navigation, and plenty of options for provisioning and exploring ashore. For more off-the-beaten-path adventure, consider places like Antigua, Guadeloupe, or Grenada.

Whether you choose a bareboat or a fully crewed yacht, we’ll help you plan an itinerary that balances great sailing with time to relax, snorkel, explore local culture, and enjoy the region’s fantastic cuisine. We work with the best Caribbean operators, so you’ll be in trusted hands.

Let us know your sailing experience, group size, and holiday style, and we’ll recommend the best route and boat for you.

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...

When should I book a charter boat in the Caribbean and Bahamas?

The best time to charter in the Caribbean and Bahamas is from December through July 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...