Sailing in the Caribbean: Information for Skippers & Crew

In a Nutshell...

Sailing in the Caribbean is a dream for many, offering a mix of stunning natural beauty, consistent tradewinds, and a vibrant local culture. While the idyllic image of blue seas and constant sunshine is largely accurate, a successful trip requires a good understanding of the sailing season, local weather patterns, and navigation. This guide to sailing in the Caribbean covers everything from preparing for your voyage and managing local formalities to navigating anchorages and getting essential yacht services. It's about being prepared so you can relax and truly enjoy one of the world's most beautiful cruising grounds.

The stuff of dreams...

A Skipper's Introduction to the Islands
Getting to Grips With The Caribbean Sailing Season
Sea & Weather Conditions
Navigation, Charts & Pilotage
Communications Afloat: Staying Connected in the Islands
Yacht Clearance, Customs & Immigration
Anchorages & Moorings
Environmental Stewardship & Marine Life Encounters
Local Culture & Customs
Onboard Safety & Security for Cruisers
Provisioning & Local Delights
Yacht Services & Facilities
Local Currencies & Healthcare
Chartering & Buying a Boat
Summing Up
FAQs

A Skipper's Introduction to the Islands

For most of us fortunate enough to sail these waters, the real gems are the islands to the east of Puerto Rico, known as the Eastern Caribbean. This region is home to the Virgin Islands, a sailor's paradise, as well as the beautiful Leeward & Windward Island nations.

Before you go, it's wise to get hold of the many courtesy ensigns you’ll need for a Caribbean sailing season. Getting your paperwork sorted before you leave is always a good idea.

Getting to Grips with the Caribbean Sailing Season

The official sailing season kicks off in December and begins to fade out around June. If it weren't for the threat of hurricanes, it would be a year-round cruising ground. While meteorologists can provide increasingly reliable forecasts and track predictions, sailing here during the hurricane season, which runs from June to November, is an extremely risky affair.

Some intrepid sailors choose to take advantage of the calmer summer weather and empty anchorages, all while keeping a very keen eye on any tropical depressions tracking across the Atlantic. They figure they have at least three days to make it to a suitable hurricane hole. Even so, it's a huge gamble. By this time, the rest of us have found a suitable boatyard to lay up our boats and scuttled back home to the safety of our homes elsewhere.

Sea & Weather Conditions

Prevailing Winds

The Eastern Caribbean Islands lie in the path of the North East Trade Winds, but these do swing through to the southeast quadrant from time to time. As a general rule, they're stronger and more north-easterly in the winter and veer south-easterly in the summer. Typically, they blow at 10 to 25 knots, but in January or December they can often blow up to 30 knots or more. When they do, we call them 'Christmas winds'.

Squalls

You'll often spot an approaching squall as a menacing, dark cloud on the horizon. Treat it initially as you would a huge oil tanker. It isn't going to stop and probably won't change direction. Will it pass ahead or astern? Can you avoid it by changing your course, ideally passing behind it?

If a squall is heading your way and you can't avoid it, take appropriate action for a lot of wind—sometimes 40 knots or so—and intense rain with a loss of visibility. Prepare to reduce sail, sheet in and take it on the chin. The odds are it won't be as bad as you were expecting and it'll probably be all over in a few minutes, but you need to be ready before it hits.

Sea Conditions

In the lee of the islands, as you might expect, the sea is fairly flat. When you're on passage between the islands, you'll experience the long, Atlantic swells that have swept across several thousand miles of ocean. Combined with the constant, warm tradewinds, this makes for wonderful sailing.

But be prepared for the wind acceleration zones that often occur at the ends of the islands. The wind strength may well increase by at least 10 knots in seconds, kicking up steep short seas. Some locations are notorious for this effect. The northern end of St Vincent is a prime example, where what seems like a gentle run can suddenly become a wild, bumpy ride.

During the winter months, storms well to the north of the islands can produce heavy northerly swells that can make otherwise calm anchorages uncomfortable at best or completely untenable.

Navigation, Charts & Pilotage

Tides & Currents

Sailing between the islands, you can normally see the next one before losing sight of the one you've left. However, be aware that your course over the ground will be offset to the west by the Equatorial Current. This flows in a north-westerly direction, varying from almost nothing to a knot or so. It can be even more pronounced around the ends of the islands.

You can take a back-bearing on the island astern to estimate the effect of the current, or just take a look at your chartplotter and compare your course line with the rhumbline. Although the tidal range is only around 0.5 metres, tidal currents do have a localised effect, so always check your charts.

Buoyage

The IALA 'B' (Red-Right-Returning) Buoyage system is in use throughout the Caribbean. Those of you who hail from the US will be familiar with this, but for Europeans where IALA 'A' (Red-Port-Left-In) is used, this can be confusing at first.

You won't see much buoyage other than for marking big-ship channels. Neither are they very reliable as they get moved or entirely removed by hurricanes and it can take time to get them replaced. What you will see plenty of are fishing pot buoys. I'm going to contradict myself by saying that you often won't see them as they're often made of clear plastic bottles or are being dragged below the surface by the current. While I appreciate fishermen have got to make a living, if they made their gear more visible, they'd lose a lot less of it and avoid the wrath of us yachties.

Charts & Pilots

I'm a firm believer in having paper charts even if you've got a chart plotter. The ones I use for the Caribbean are published by NV Charts.

Along with every other cruiser I've met in the Windward and Leeward Islands of the Caribbean, I rely on the cruising guides written by Chris Doyle. They're updated every two years and, in my view, are absolutely indispensable for Caribbean sailing. But not just for sailing. Not only has Chris got thousands of miles of Caribbean sailing under his keel but he's also tramped all over the islands on foot. Consequently, the island trails and shoreside delights are covered in detail too. Quite rightly in my opinion, the 'Chris Doyle Cruising Guides to the Windward & Leeward Islands' are the most popular of all.

Communications Afloat: Staying Connected in the Islands

For many cruisers, staying in touch is a priority. The good news is that local mobile networks are generally reliable and affordable. You can easily pick up a local SIM card in most of the main islands, such as St Martin or Grenada, which will give you decent data coverage. However, the quality can be inconsistent, particularly between islands. For offshore passages and real emergencies, a satellite phone is a much better option. It’s an investment, but one that provides peace of mind far from shore. For everyday communication, the VHF radio is your most important tool, not just for ship-to-shore calls, but also for daily "cruiser nets" where you can get updates on weather, local events, and a heads-up on everything from fresh produce to spare parts.

Yacht Clearance, Customs & Immigration

The Eastern Caribbean is made up of a number of nation states. Some are individual islands, such as St Lucia, or a group of islands, such as St Vincent & the Grenadines. Their entry procedures are different, although they all involve a trip to Customs, Immigration, and sometimes the Police. Always turn up with the passports of all your crew, plus the boat papers. Once you know the system it's all fairly straightforward, but it can be a little tedious in some places.

Always be polite, courteous, and patient, especially if they've got the cricket on TV and the West Indies is batting. You won't be welcome if you're dressed scruffily; as a minimum it's sandals, a presentable T-shirt, and your best shorts. Generally, the French islands (St Martin, St Barts, Guadeloupe, and Martinique) are the most efficient, but other countries are catching up using online processes such as eseaclear.com or sailclear.com.

Anchorages & Moorings

Idyllic anchorages abound throughout these islands. Just take a look at the Chris Doyle Guides and you'll see what I mean. Most are on the west side of the islands in the lee of the prevailing trade winds. For more adventurous types, exquisite anchorages can be found on the eastern side of the islands, in the lee of reefs but open to the wind. Solitude, seldom available on the west side, can be found in these.

Moorings are becoming increasingly available. Too much so in my opinion, because:

They are there to make money for their owners, not to fill a need for cruisers.
They can be very expensive. $35 per night is the norm for the BVIs.

The reason given for their existence is often to 'protect the seagrass', even when the seabed is barren sand.

They're usually cynically placed in the best anchoring spots rather than in deeper water.

They have no third-party certification, and the owner takes no responsibility in the event of their failure.

Generally, they're not maintained. The attitude to routine maintenance is usually 'if it ain't broke don't fix it'. And when it does break, as it inevitably will, it's often 'fixed' to the condition it was in just before it broke.

As may now be apparent, I'm not a fan of local moorings and will avoid them if I can. I have much more faith in my own ground tackle. If you're on a mooring and it breaks, you're instantly adrift. If you're at anchor and it drags, things happen in relatively slow motion. There, rant over!

Environmental Stewardship & Marine Life Encounters

As sailors, we have a privileged front-row seat to the natural beauty of the Caribbean, and with that comes a responsibility to protect it. It’s always best practice to use your holding tank for blackwater and only discharge it well offshore. Many islands, like Grenada, also have official facilities for pumping out your tank. When at anchor, take care to choose a spot with a sandy bottom to avoid damaging fragile coral reefs. While fishing is a great way to provision, be mindful of local regulations on protected species. Finally, proper garbage disposal is a must; always carry your rubbish with you until you find a designated bin ashore. A small effort goes a long way to preserving these islands for future generations.

Local Culture & Customs

One of the great joys of sailing in the Caribbean is experiencing the rich local culture. The islands each have their own unique character, influenced by a mix of African, European, and indigenous traditions. Being a good guest is key. As I've already mentioned, politeness and patience go a long way, especially during clearance procedures. When you're ashore, it's generally best to be respectful of local customs, which might include dressing more modestly when away from the beach. Always greet people with a 'good morning' or 'good afternoon'—a little courtesy goes a long way.

Onboard Safety & Security for Cruisers

While the Caribbean is generally a safe cruising ground, a few sensible precautions can provide peace of mind. When leaving the boat, it's wise to secure your dinghy with a good lock and chain. Onboard, simply locking the companionway and stowing valuables out of sight is often enough to deter opportunistic crime. In my experience, the biggest security comes from being aware of your surroundings and trusting your instincts. If a particular anchorage feels a little 'off,' there's no harm in moving on. A little bit of common sense goes a long way to ensuring your safety and allowing you to relax and enjoy the islands.

Provisioning & Local Delights

While you can find well-stocked supermarkets, I find the real fun of provisioning is in visiting the local markets. The fresh fruit, vegetables, and fish are absolutely fantastic. The waters of the Eastern Caribbean are teeming with fish, and catching them on a trolling line while sailing isn’t too difficult. On board Alacazam, we often dine on the produce of our fishing line. You can expect to catch tuna, wahoo, dorado (Mahi-mahi), Kingfish, and Spanish Mackerel, all of which make excellent eating. You don't need expensive gear. The fish won't object any more strongly about being caught on a simple handline than they will on an expensive rod and reel set-up.

Yacht Services & Facilities

You can get pretty much anything done in the Eastern Caribbean, providing you know where to go and who to contact.

Yacht Services & Facilities	Key Information
Boatyards & Marinas	Wide range of options, from full-service yards to simple moorings.
Chandleries & Fishing Gear	Can be found on most major islands; supplies are often more expensive.
Diesel Mechanics	Generally available, but specialists can be hard to find in a hurry.
Dinghy Repair & Liferaft Services	Specialist services are concentrated around the larger hubs.
Dive Centres & Services	Abundant throughout the islands. Great for tank refills.
Electrical & Electronic Services	Limited but skilled services are available; best to carry spare parts.
Gas Bottle Refills	Available in various formats; check compatibility beforehand.
Hull Painting & Brightwork	Local tradespeople often offer excellent, cost-effective work.
Hull Repair & Gelcoat Specialists	Repairs are possible but can be a little slow.
Laundries for Cruisers	Numerous services for doing laundry are available in most anchorages.
Outboard Motor Servicing & Repairs	Common and essential services available at many marinas.
Refrigeration & A/C Engineers	Key services available, but book well in advance for major work.
Rigging Services	Riggers are available on the larger islands.
Sailmakers, Canvaswork & Upholstery	Sail repair and canvaswork are readily available on most islands.
Shipwrights & Carpenters	Skilled craftsmen can be found, often through word-of-mouth.
Watermaker Services	Essential for blue water cruising; services are available.
Welding & Stainless Steel Fabrication	Specialist welding services are available.
Yacht Management & Guardianage	For those leaving their boat during hurricane season.
Yacht Surveyors	Professional surveyors are available in the major sailing hubs.

Local Currencies & Healthcare

Local Currencies

You'll encounter three currencies here: US Dollars, Euros and the Eastern Caribbean Dollar.

Throughout the Virgin Islands (both US and British), the local currency is the American Dollar ($US).

For the French (St Martin, St Bartholomew, Guadeloupe, Marie Galante, Les Saintes and Martinique) and Dutch (Sint Maarten) islands, it's the Euro (€).

For all the others, it's the Eastern Caribbean Dollar ($EC). The exchange rate is fixed at $US1 = $EC2.70.

Vaccinations

Just what vaccinations do you need for Caribbean sailing? My GP recommended the following:

Tetanus
Polio
Hepatitis A
Hepatitis B
Typhoid

Apparently, this will provide adequate protection wherever you go in the Eastern Caribbean, but for a more focused and up-to-date recommendation, I'd suggest you check a travel health service website.

Travel Insurance & Medical Cover

However fit and healthy you are, things can go wrong very quickly. A serious illness or injury could mean that you need to be medivac'ed to the US for urgent medical treatment. Without insurance, this could blow away your entire cruising fund in the first day or two of treatment.

Good insurance doesn't come cheap, so it's absolutely vital to check the terms and conditions in great detail. Ask your prospective insurer as many 'what if...' questions as you can think of. In my experience, insurance offered by companies that are not used to catering for cruising sailors won't meet your requirements. For example, I was once offered what appeared to be a very attractive policy by my bank. On checking, it proved to be useless. If I strayed outside territorial waters into international waters, the whole policy became immediately invalid.

Chartering & Buying a Boat

If you're not greatly enthused by the long ocean passage required to get to the Caribbean, there's one very good option available to you: buy a boat already there. The logistics of doing so can be a little complicated, and the travel costs need to be carefully considered, but you might just pick up a bargain.

Unless you're a long-term cruiser, a 'snowbird' who keeps your boat in the Caribbean, or a liveaboard, then chartering a boat is the way to go to experience the sheer delight of Caribbean sailing.

Summing Up

Sailing in the Caribbean is an unforgettable experience that combines world-class sailing with vibrant cultures and incredible natural beauty. While the islands can feel like a paradise, a bit of forward planning and a respectful approach to local customs will ensure your trip goes smoothly. From navigating the winds and currents to handling the paperwork, knowing what to expect is half the battle. So, do your homework, pack your best shorts, and get ready for the sailing adventure of a lifetime.

FAQs

What is the best time of year to go sailing in the Caribbean?

The best time for sailing is during the official season from December to June. This period offers consistent tradewinds, low humidity, and is outside of the official hurricane season.

Is it safe to sail in the Caribbean during hurricane season?

Sailing during the hurricane season (June to November) is extremely risky. While some sailors do, the risk of a dangerous storm is high, even with modern weather forecasting. Most cruisers either leave the region or lay their boat up in a designated hurricane hole for the season.

How do I handle customs & immigration when island hopping?

Each island nation has its own set of rules. Generally, you must clear in and out with Customs, Immigration, and sometimes the Police. Always have your crew's passports and all your boat papers ready. Be prepared to be patient and always be polite.

What is the IALA 'B' buoyage system?

The IALA 'B' system is a marine buoyage system where green buoys mark the port side of a channel when "returning" from seaward, and red buoys mark the starboard side. This is the opposite of the IALA 'A' system used in Europe.

Do I need a sailing licence or certification to charter a yacht?

Most charter companies require a skipper to hold a recognised certification or demonstrate significant experience. Qualifications like the RYA Yachtmaster Offshore or an equivalent are often accepted.