The Caribbean - Windward Islands

St Lucia, Antigua, St Vincent, Bequia, Grenadines, Tobago Keys, Mayreau, Grenada, Guadeloupe

In a matter of miles you have the most exclusive island of the planet and one of the wildest, like Mustique and the Tobago Keys. Everyone wants to sail the Caribbean and there's plenty to see. Each island is different and all share the same easy going atmosphere: everybody wants to have fun!

Our top 3 SAILPRO anchorages

1. Tobago Keys

2. Petit St Vincent

3. S coast of Grenada

Our Sailing notes

Weather and navigation

All these islands share an unpleasant feature: swell loves to turn around them, and in many anchorages some rolling must be expected, especially under the Pitons and on the E side of St. Vincent and Grenada. Funnily enough, wind is less keen to follow, and you might well find yourself rolling with no wind to speak of once you enter the lee waters. Stay a little farther out before making for your harbour. The trades blow incessantly between the islands, especially around Christmas (Chistmas Winds), when gales are to be accounted for, and nasty seas can increase the ocean 4-ft swell. The crossings between the islands are always lively, never calm and seldom boring. The average trade wind speed is around 20 knots, less at night, more during the day. It's a place where you seldon sail without a reef. 

A nice feature of these waters are the frequent squalls where you can measure your speed in taking a reef or two under a downpour, just to discover that you have to turn your engine on in 5 minutes. There is a good point in the fact that, unless you are blind, you can see them easily. There might be sailors who sail the E windward sides of these islands, certainly beautiful, but never calm. These chaps must be respected and addressed to in French. If you are on holiday, stay on the west side. Westerlies are rare (to say the least)

Hurricane season: between July and November. When, by the way, the weather is stinky hot. 

Temperatures in winter are warm to hot, with fresh nights, hammering sun and daily squalls. Beer weather. Local brews are no cheap but not bad. 

Restaurants and food

If you are used to the Mediterranean, the Caribbean is a desert with few oasis, being these mostly French. These will be mentioned while we sail along. But we can at least start blaming the yanks who, having practically colonized the area, banned, for some strange reason, the meat from Venezuela, among the best on the planet. So you might find yourself in Trinidad, where you can see the Venezuelan grazing cows with a good pair of binoculars, but all you can find is frozen and third choice Iowa tasteless stuff. Good tuna and bonitos. Wonderful, when available, the dolphin fish.


The Caribbean authorities like their paperwork in substantial quantities, especially because most nations find it convenient to pester sailors with taxes. You MUST clear in and out every time and very often custom and immigration are far apart, and their officials not altogether friendly.

Our itinerary

St Lucia

Justly famous for the two huge cone-shaped mountains known as Pitons, where the anchorage is bottomless and one has to be pilfered by locals with mooring buoys, St Lucia has not much more to offer. The only two anchorages are Rodney Bay and Marigot Bay. The former is basically a nice marina where the english speaking sailing community tend to gather and drink beer while the latter is a delightful anchorage but so full of tourist traps ashore that one just wants to escape. Keep in mind that Gros Ilet, by Rodney Bay, hosts the World famous Friday night jump up party, where literally anything can happen. 

St. Vincent and the Grenadines

The first calm stop while you sail south from St.Lucia is Cumberland Bay, a wide and pleasant bight with some local life around the beach. The very near Wallilabu bay, another cove surrounded by lust vegetation and local shacks, reached peaks of fame when they filmed Pirates of the Caribbean, and some sets are still on the place. Alas neither Keira Knightly nor Johnny Depp are often around. Still, many small coves around this area are well worth a stop. 

The main place for boaters to stop in the south and close to the capital Kingston is the small bay, with private moorings, by Young Island. Here you can easily use local boats to desembark and go shopping downtown or eating out in one of the many restaurants. The public markets are well worth a visit, especially the fish one, where the lack of choice (tuna or snapper) is somewhat alleviated by the freshness. The vegetable market provides at least 100 different stall selling exactly the same poor choice. The supermarket and bakery are by the airport and are acceptable. The only frozen meat worth a bite is pork. Things might improve...


Port Elisabeth is possibly the busiest sailors' crossroad in the southern Caribbean. The wide bay hosts easily 200 yachts riding at anchor. Choose your spot inside if you want to be close to the lively bars or by the beaches if you happen to like white sand and tranquillity. Although popular, the wind often whistles loudly here and the holding ground is not the best. When the wind picks up in the late morning it's funny to look the boats loosing the holding and moving backwards among the phlegmatic comments of the others ('Hey dude, it's either you going backwards or all of us moving forward...'). Water and diesel are sold by rafts at 'slightly' increased prices, but there is not much of a choice. 


Not very sailor friendly. Waiting for reasons to go there and pay the outrageuos mooring fee just to see the hedges of Mick Jagger's place.

Mayreau and the Tobago Cays

Mayreau boasts some stunning (and very popular) bays. Salt Whistle Bay in the NW, Saline Bay (wider and calmer) in the W, and Saline Bay, sheltered by the reefs in the SE. Most of the reefs of the Antilles are concentrated in this unique and magnificent place that truly deserves its fame and popularity. First of all we strongly recommend to watch your course because reefs are stronger than hulls, but especially wider. Use the well travelled access channels, keep an eye around and avoid shortcuts (the shortest way to run aground) especially in poor visibility. It's tough to see the reef in the glare of the low sun and in the greyness of squalls. 

Union Island provides a rare combination of beauty and services at Clifton Harbour. The round reef around it shelters a wide expanse or water and the base of one of the most famous 'restaurants' in the region: I am talking about the shack partly floating right on the entrance reef, where the best local lobsters are served in a real Caribbean atmosphere. Then Union has a well connect ed airport and a real rarity: a serious, efficient and well stocked workshop/chandlery, where they can solve many problems. It's managed by a French chap who knows his business. The main problem of Clifton is its dreadful holding ground. SET your anchor well and let go PLENTY of chain. A danforth is better then a CQR.

Just S of Union Island lies Petite Saint Vincent (PSV). A long reef lies W of it, forming the two famous tiny and sandy Islet of Pinion and Punaise. If you sail around at night it's mathematically certain that you hit them. During the day a local wisely put a very nice umbrella on top of Pinion. PSV is connected to Petite Martinique by a reef that blocks the entrance to both, boats and waves, thus forming a calm bay of turquoise waters and perfect peace. This is a favourite spot, but definitely less busy than the Cays. Also the beach of PSV is a magical place. And it's the writer's favourite anchorage, combining calm waters, good company and nice beaches. Another advantage of PSV is its close proximity with Petite Martinique, not an inviting place in itself, but possessing that precious feature of being in another nation, Grenada. Where food but especially liquor and wine are definitely less expensive. Do not be surprised to see fast dinghies racing at night between here and Union. It's the supermarket owners buying things where they cost less. Or, in other words, smuggling.

Our cruise S passes by Carriacou, already in Granada's waters. The SE beaches and bays have been reported worth a stop, while Tyrrel Bay gains its fame more for the efficient shipyard in the inner bay and for the liveliness of a couple of bars than for its scenery. 

The crossing between the Grenadines and Grenada is enlivened by a small group of uninhabited and wild islands on of which, Ronde Island, offers a good anchorage in Corn Store Bay. If there is a place where you can feel the urge to shove around for treasures, this is it. There is also a submarine volcano in activity around this group, funnily named Kick'em Jenny, and sailors are advised to sail far aways when it... kicks.

The beautiful Island of Grenada is surely the most imposing and spectacular of the area, with lush green forests, waterfalls, peaks and volcanoes, enchanted valleys and wonderful bays. The latter, though, are certainly not abundant in the north of the island. That means that you have to sail all the way to St.George, the capital nearly at the S end, to find shelter from the swell. With its nicely kept houses and streets on the hills aroung a well sheltered bay, the clean alleys and wooden curches, the small villas and European aura, the capital of Grenada is undoubtely the most pictoresque town in the whole region. 

The Grenada Yacht Club lies in the lagoon, a very well sheltered bay just S of the town. The anchorage is 

The south coast of Grenada is deeply indented by a series of inlets, like Port Egmont and Prickly Bay, providing excellent shelter, good bars and restaurands, wide green lagoons, peaceful and beautiful surroundings. You can also clear in and out from here.

South of Grenada there is just Trinidad and Tobago, more of a technical than a tourist destination. They say it's out of the hurricanes path. They said the same in Grenada too.


For more info download the .pdf

The Caribbean - Windward Islands :: leave here your cruise review