If you are dreaming of turquoise water, white-sand beaches, warm evenings and sailing between tropical islands, a catamaran charter in the Caribbean is hard to beat. But if you have never booked one before, the process can seem complicated. Where should you go? When should you travel? Do you need sailing qualifications? Should you book a bareboat or skippered catamaran? And how do you choose the right boat?
The good news is that booking a Caribbean catamaran charter is much easier than you might think. With a little planning, you can go from having a vague idea of a sailing holiday to having your own catamaran booked and your crew looking forward to the trip.
Choose where you want to sail
The first decision is your destination. The Caribbean is a huge sailing area, and each cruising ground offers something slightly different.
For a first Caribbean catamaran charter, the British Virgin Islands are one of the easiest places to start. The islands are relatively close together, there are numerous sheltered anchorages and much of the sailing is straightforward, making the BVI particularly well suited to families and first-time charterers.
The Bahamas offer a completely different experience, with shallow turquoise water, beautiful beaches and spectacular cruising around the islands and cays.
Further south, Antigua offers access to the Leeward Islands, while Grenada provides a gateway to the Windward Islands and the Grenadines. The latter can be particularly appealing if you want a more adventurous sailing experience, with longer passages, beautiful islands and highlights such as the Tobago Cays.
PlainSailing.com offers catamaran charters from bases in the Bahamas, BVI, Antigua and Grenada, giving you a choice of cruising grounds without having to search multiple charter companies.
Decide when to go
The Caribbean is a year-round destination, but the best time for a sailing holiday depends on your priorities.
The main sailing season generally runs through the winter and spring, when the weather is warm and the trade winds provide reliable sailing conditions. January to March is particularly popular, with excellent weather but also higher demand and higher charter prices.
If you want to balance good weather with better prices and fewer boats in the anchorages, consider the shoulder seasons. May and June can offer excellent conditions in some areas, while November can also be an attractive option as the Caribbean sailing season gets underway.
The main period to approach with caution is the Atlantic hurricane season. August and September are generally best avoided for a Caribbean sailing holiday, and conditions and fleet availability can vary considerably from June onwards.
Christmas and New Year are especially popular, so if you want to charter over the festive period, booking well in advance is sensible.
Choose your catamaran
Once you know where and when you want to go, the fun really starts: choosing your boat.
Catamarans are particularly well suited to Caribbean cruising. They are stable, spacious and have shallow drafts, making it possible to explore many anchorages that would be less accessible to a deeper-keel yacht. They also provide plenty of outdoor living space, which is exactly what you want when the weather is warm and you spend much of your holiday swimming, eating and relaxing outside.
The key is to choose a catamaran that suits the size and needs of your group.
A four-cabin catamaran might be ideal for two families or a group of friends, while a larger five- or six-cabin boat can give everyone more space and privacy. Think about how many people are coming, how many cabins you need and whether anyone requires their own bathroom.
It is also worth looking beyond the number of berths. Consider the age of the boat, the size of the cockpit and saloon, air conditioning, watermakers, generators, refrigeration, water toys and the size of the outside entertaining areas.
Bareboat or skippered?
The next question is whether you want to sail the catamaran yourself.
A bareboat charter means that you take responsibility for the boat and sail it yourself. This is an incredibly rewarding way to experience the Caribbean if you have the necessary sailing experience.
However, you do not have to be an experienced sailor to enjoy a catamaran charter.
A skippered charter puts a professional skipper on board. They take care of the sailing and navigation, while you can concentrate on enjoying the holiday. A skipper can also bring valuable local knowledge, helping you find the best anchorages, restaurants, snorkelling spots and beaches.
This can be an excellent choice for families or groups where only one person has sailing experience – or for experienced sailors who simply want to relax for a week.
PlainSailing.com can help with both bareboat and skippered options, and its Caribbean guide notes that formal qualifications are not necessarily required in every Caribbean destination; sailing experience and evidence such as a skipper’s logbook can also be relevant. The exact requirements depend on the charter and destination, so it is important to check before booking.
Search and compare boats
This is where using a specialist charter company can make the whole process considerably easier.
Rather than visiting dozens of individual charter-company websites, you can search for boats based on your dates and destination, then filter the results according to your requirements.
PlainSailing.com provides live pricing and availability for its Caribbean charters, allowing you to see which yachts and catamarans are available for your dates. You can compare different boats and find one that fits your budget and group rather than simply choosing the first boat you find.
If you are unsure what you need, the bookings team can also help. This is particularly useful if it is your first charter, because a few seemingly small decisions – such as the number of cabins, whether you need a skipper or which base to choose – can make a significant difference to your holiday.
Plan your itinerary
You do not need to have your entire holiday planned before booking the boat.
In fact, one of the great advantages of a Caribbean catamaran charter is the freedom to decide how much or how little you want to do.
In the BVI, for example, you might spend a week sailing between Norman Island, Virgin Gorda, Jost Van Dyke and Anegada. You can snorkel, swim, explore ashore and enjoy a different anchorage each night. In the Grenadines, you might spend longer sailing between islands and make the Tobago Cays one of the highlights of your trip.
The important thing is not to try to see everything. A sailing holiday should be relaxing, and attempting to cover too many miles can turn a dream holiday into a race against the clock.
Your charter company can help you understand realistic sailing distances and suggest an itinerary that suits your experience and the time you have available.
Sort out the extras
Once the boat is booked, there are a few practical details to arrange.
Think about airport transfers, travel insurance, provisioning, fuel, marina fees and any additional equipment you might need. You may also want to arrange an outboard engine for the dinghy, paddleboards, Wi-Fi or additional water toys.
Provisioning is particularly important. You can either shop when you arrive, arrange for provisions to be delivered to the boat or ask your charter company to organise it for you.
PlainSailing.com can help arrange transfers and provisions, which can be particularly useful if your flight arrives late or you simply want to step aboard and start your holiday rather than spending your first afternoon in a supermarket.
Book early – especially for peak dates
Once you have found the right catamaran, do not wait too long if your dates are fixed.
The most popular weeks, particularly Christmas, New Year and the peak winter months, can sell quickly. Booking early gives you the widest choice of boats, cabin layouts and prices.
It is also worth remembering that the cheapest catamaran is not necessarily the best value. A slightly newer or larger boat with a better layout might make a significant difference to your experience, particularly if you are spending a full week on board.
Make the booking and start looking forward to it
Ultimately, booking a Caribbean catamaran charter should be exciting rather than stressful.
Choose your cruising area, pick your dates, decide whether you want to sail yourselves or have a skipper, find a catamaran with the right number of cabins and facilities, and then book it.
The rest can be built around the boat.
Flights can be arranged, transfers organised, provisions ordered and an itinerary created. Before long, the complicated-looking holiday you were considering becomes something very real: a catamaran waiting in a Caribbean marina, a week of warm trade winds ahead of you and a string of beautiful islands waiting to be explored.
And that is perhaps the best thing about booking a Caribbean catamaran charter. You are not just booking accommodation. You are booking the freedom to wake up somewhere different every morning, swim straight from your own boat, sail when you feel like it and spend a week living life at the pace of the Caribbean.
Choose your island group. Find your catamaran. Get your crew together. Then let the Caribbean do the rest.
