Caribbean sailing holidays

Why is the Caribbean so great for sailing? It all starts with the trade winds. These warm winds, which once brought colonisers across the Atlantic in search of spice, sugar and rum, mean there’s nearly always a reliable, steady breeze here. Then there’s the sheltered, easy ‘line of sight’ sailing, where you’re protected from the waves by barrier reefs and islands. There’s blue water sailing – more challenging sailing in the open water – for those who seek it, but there’s also easy mooring, predictable weather and no fiddly tide tables.
You might think the Caribbean has been carved up between exclusive resorts, but sailing boats give you access to hidden beaches, no pay-per-sit sun loungers in sight.
The trade winds bring something else with them, too: the sense that history is always pressing at your back. As you hop between tropical coves, you’ll feel as though you’re sailing over a 16th century treasure map. Anchored up with a cold bottle of Carib, your swimsuit drying on the guard rail, you have to agree – there’s no more perfect place to sail than the Caribbean.

Types of Caribbean sailing holiday

Flotilla sailing

Flotilla sailing in the Caribbean is great if you want to sail fairly independently but you don’t want to do any of the planning yourself. Flotillas are groups of vessels led by a lead boat. You’ll sail your own boat if you have experienced sailors in your party (they will need to have a RYA Day Skipper qualification or the ICC – International Certificate of Competence), or you can arrange to have a skipper accompany you on board. During the day you can do as you please and there’s a chance to be social with the other crews in the evenings. The flotilla leaders are often local and can provide you with assured regional knowledge. The Caribbean has quite difficult sailing, but some areas, like the BVIs and the Bahamas, are suitable for flotillas.

Bareboating holidays

Many Caribbean sailing holidays are bareboating holidays. This means that you essentially hire the boat and the boat alone. You’ll need to book your moorings and your restaurant reservations at night, and plot out your route every day. Go bareboating alone if you have an experienced sailor in your party – but, again, you can always hire a skipper to accompany you. Bareboating is as about as free as sailing in the Caribbean gets. It means you don’t have to anchor en-masse and can patronise even out-of-reach places.

Small group sailing trips

You can also sail as part of a small group, with a designated on-board crew to show you the ropes. You’ll live at close quarters with other people, all mucking in to sail the boat, cook and keep her ship-shape. This kind of trip is great if you want to socialise whilst learning to sail. You can venture to destinations that you’d be unlikely to tackle solo, and even take on activities like scuba diving and fishing, under the supervision of trained instructors. There’s usually a minimum age to join these trips, so check with your operator.

Our top Caribbean sailing Holiday

British Virgin Islands flotilla sailing holiday

British Virgin Islands flotilla sailing holiday

Sail around the stunning British Virgin Islands

From £1740 to £14798 7 days ex flights
Tailor made:
This trip can be booked all year round except September
Travel Team
If you'd like to chat about Caribbean sailing or need help finding a holiday to suit you we're very happy to help.

What do Caribbean sailing holidays entail?

Your floating home

If you’re sailing in a flotilla or bareboating, a modern fibreglass boat will be your home for the week. Boats are normally between 32 and 51 feet long, with a capacity of between two and 11 people across one to four cabins. Take a catamaran for a little extra space. You could also split your party between multiple boats on a single flotilla. If you’re on a small group trip, you’ll share the boat with others. Usually, there’s a small galley and communal area downstairs, and marine ‘heads’ (toilets, which you need to pump to flush).

If you’re in a flotilla there’s usually a lead boat with a hostess, skipper and engineer – this boat stays in radio contact, and every day there’s an onshore ‘skippers’ briefing’ where you’ll get a detailed weather report and a map of where to go. On arrival you’ll be given a familiarisation with the boat whilst it’s sitting in the marina. You’ll learn about the navigation equipment, tanks, electrics and essential safety stuff. Flotilla and bareboat boats are robust, safe and easy to sail – with a mainsail and jib to play with, and a tender for runs ashore.

Pro-level provisioning

Before you set off, it’s provisioning time. If you’re on a bareboat or flotilla, your hosts can point you towards the nearest shops. Supermarkets in the Caribbean aren’t always cheap as lots of foods have to be imported, but look out for enormous mangoes, creamy green-skinned avocadoes and local chicken. Make sure you get your hands on a bottle of rum and some plantain chips, but don’t forget lots of drinking water, too. Some sailing holidays offer provisioning before you arrive, in which case your boat will be stocked from local shops, so you can come on board to cold beer in the fridge.

Some boats have a barbecue at the stern, so you can cook up fish bought on a whim from passing fishermen. You’ll be able to eat on shore in the evenings, too. Caribbean dining ranges from the fancy (hotel restaurants) to the casual (jerk-seasoned barbecues, meat patties, fish fries). Try Caribbean lobster – it’s clawless, but delicious.

Setting sail

When you’re on flotilla or bareboating, you can decide how much you want to sail. Some people in your flotilla might just ‘cheat’ and use their motor all week, but you’re here for the sailing! Haul up the mainsail instead, and you’ll save fuel (which you’ll pay for at the end of the week) and cause less noise and air pollution.

The best thing about sailing is the freedom it gives you to explore, but with great freedom, comes responsibility. It’s up to you to keep your rubbish stowed safely on board, to keep noise pollution to a minimum, and to travel with a light touch. Unfortunately, most boats have to pump their waste out at sea. There are strict stipulations about the distance from shore and the depth of the water at which you can let out your ‘black water’ tanks. You can, at an extra cost, look for marinas with pumping out facilities.

Stopping for lunch

As you’re sailing, remember, you can’t just anchor anywhere – there are strict rules in marine parks, and you wouldn’t want to plonk your anchor through protected coral. However, mooring in the Caribbean is generally very easy as these are well-trodden routes. Tying onto a mooring buoy is one of the easiest ways to stay put if you want to stop for lunch. Once you’ve attached your line to this floating buoy, itself attached to a sunken chunk of concrete, you aren’t going anywhere. Remember, by paying your marina and mooring fees you’re bringing income to island communities.

Once you’ve found the perfect lunch spot, enjoy using the boat as a floating playground. Dive in off the back, grope your way down the anchor chain and snorkel from the boat over nearby reefs. Despite lots of tourism and development, the Caribbean is still great for wildlife spotting. Look up for turtles casually popping up for a breather. You can even combine sailing with scuba diving.

What to bring for sailing in the Caribbean

A soft-sided bag is essential, whatever boat you’re boarding, as these can be stuffed away easily in the often uniquely-shaped cupboards below deck. Sun protection is essential. No one tans quicker than a sailor in the Caribbean. The reflected light off the water and the deceptive coolness of the wind when you’re underway can mean you can get very brown very quick if you’re not careful. A reef-friendly sun cream that doesn’t contain Oxybenzone and Octinoxate, plus a tightly-fitting hat are both worth their space in your case. Polarising sunglasses are great for sailors, as they help cut down the amount of reflection you’ll get off the water surface, so you can better see possible underwater hazards as you anchor. You might need a coat for sudden rain showers; it does rain in the Caribbean, but it’s often over as quickly as it begins. Lastly, remember that bareboat doesn’t mean barefoot. There are plenty of ways to stub your toe on deck, so boaties really like their deck shoes – rubber soled, so they don’t leave scuff marks, easy to slip on and off, and quick-drying.

Best time to go sailing in the Caribbean

The Caribbean is a year-round destination for sailing. Prevailing easterly winds blow constantly across the islands at between 10 and 15 knots all year, and the temperature sits firmly in the high twenties. Many people opt to go between December and March– as much to escape bad weather elsewhere as to enjoy the balmy temperatures over here. It’s also when the biggest regattas occur: Grenada Sailing Week, the BVI Spring Regatta and Antigua Sailing Week. Hurricane season officially begins in June and lasts ‘til October. You’ll notice that sailing trips run throughout the year for many destinations – quiz your holiday provider if you’re worried about bad weather.

British Virgin Islands Weather Chart

 
MIN °C
MAX °C
RAIN (mm)
JAN
21
28
68
FEB
21
28
54
MAR
21
28
57
APR
22
29
88
MAY
23
29
129
JUN
24
30
73
JUL
24
30
85
AUG
24
31
124
SEP
24
31
143
OCT
24
30
161
NOV
23
29
161
DEC
22
28
119
Written by Eloise Barker
Photo credits: [Page banner: SMFS1947] [Flotilla sailing: _dChris] [Your floating home: _dChris] [Stopping for lunch: _dChris] [Best time to go: _dChris]
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