Caribbean Island Hopping by Sailboat
Part 1: The Leeward Islands

Well, for starters:

• Constant warm north-east trade winds;

• Glorious sailing in the long ocean swells between the islands;

• Plenty of sheltered anchorages on the leeward (western) side of the islands. For the more adventurous sailor, shelter from the seas (but not the wind) can sometimes be found behind the reefs on the eastern side of the islands;

• Islands just a daysail apart - didn't I say it was an island-hopping paradise?

• Good yachting services and facilities on the larger islands;

• Memorable beach bars and restaurants ashore varying from haute cuisine to what the rest of us eat;

• Scenic walks ashore to suit all ages and fitness levels. The jewel in the crown here has to be Dominica in the Leeward Islands

• A sailing season throughout which Canadians, North Americans and Europeans would otherwise be having to be dealing with ice, snow, rain and other meteorological unpleasantness;

• Rum;

• Friendly, delightful local people.

Got your attention? Got your up-to-date navigational charts and pilot books to hand?

Right, let's cast off our lines and head south from Anguilla, the northernmost island of the Leeward Islands...

Currency:  Eastern Caribbean Dollars (EC$)

Official Language: English

Port of Entry: Road Bay

The main anchorage is Road Bay, where you'll find the Customs & Immigration Offices near the dinghy dock. 

There are several small but exquisite islands to the north:

• Sandy Island, with a few mooring buoys and a limited anchoring area;

• Dog Island, where solitude is almost guaranteed.

• Prickly Pear Cays, another delightful day anchorage but in northerly swells or unsettled 20kn+ conditions this anchorage is anything but delightful, and is best avoided. Overnighting here is prohibited.

But you must give Scrub Island a miss as there's no suitable anchorage for yachts.

Currency:  Euro (€), plus Dutch Guilder & US$ on Dutch side.

Official Language: English (Dutch side); French (French side)

Ports of Entry: Simpson Bay (Dutch side); Marigot (French side)

The popular anchorage of Simpson Bay Lagoon is similarly shared on a north/south basis, accessed through individual French and Dutch channels.

Some years ago, a stormy night at anchor in Simpson Bay Lagoon demonstrated to me that the holding is distinctly unreliable; the events of that night will stay in my memory for a long time.

Ashore, the night-life is lively - particularly so on the Dutch side!

Currency:  Euro (€)

Official Language: French

Port of Entry: Gustavia

Instead, bash on to Gustavia to complete checking-in procedures which, as in all the islands of the French West Indies, is a breeze.

You'll be hard pressed to find an available dock in the harbour, so anchor outside and dinghy in, tying-up in the dinghy dock close to the Port captain's Office.

Two of the anchorages you won't want to miss are Anse du Colombier and that on the aforementioned Ile Fourchue, both of which offer good snorkelling - and in the case of Ile Fourche, some solitude; there's nothing ashore but a dilapidated hut.

Currency:  US Dollars (US$)

Official Language: Dutch, but English and Spanish are also widely spoken.

Port of Entry: Fort Bay

The two main anchorages are at Well's Bay and Ladder Bay, where you can pick up a mooring if any are available.

The trip around to the harbour at Fort Bay can be something of a challenge in a small dinghy.

There are also four moorings off Fort Bay, but these are likely to be less comfortable unless a northerly swell is running.

Saba is unique, and is another of those destinations where an island tour is an absolute must!

Currency:  Eastern Caribbean Dollars (EC$)

Official Language: English

Ports of Entry: Basseterre (St Kitts); Charlestown (Nevis)

Approaching St Kitts from the north its densely rainforest-covered central mountain range is prominent. This provides a perfect home for the large population of African green vervet monkeys descended from those having arrived via the sail trading vessels of the past.

Approaching St Kitts from the north its densely rainforest-covered central mountain range is prominent.

This provides a perfect habitat for the large population of African green vervet monkeys descended from those having arrived via the sail trading vessels of the past.

The best anchorages in St Kitts are found in the southern end of the island, but all can be uncomfortable - untenable at times - if there is south in the wind.

In such conditions, the Porte Zante Marina at Basseterre provides comfort and safety.

Currency:  Eastern Caribbean Dollars (EC$)

Official Language: English

Port of Entry: Little Bay

With more than half its area designated an exclusion zone you may think that Montserrat would be hardly worth a visit, but nothing could be further from the truth.

Anchor your boat in Little Bay and hire the services of an island tour guide - you'll not be disappointed.

There are numerous hiking trails into the rain forest, where you'll find a multitude of tropical birds and plants. 

Continuing to island hop, you have two choices of destination: northeast to Antigua or southeast to Guadeloupe. Clearly the wind direction will play a part in choosing which one.

Currency:  Eastern Caribbean Dollars (EC$)

Official Language: English

Ports of Entry: English Harbour, Jolly Harbour

Unlikely I know, but if you were restricted to cruising around just one of these islands, then Antigua would be the one to choose.

Antigua has more anchorages than any other in this island chain, some of which will offer total peace and tranquility whilst others such as English harbour and Falmouth Harbour will be crowded with much going on ashore.

The anchorage of Great Bird Island is one of the 'peace and tranquility' locations - it's one of our favourites

There are several locations where you can haul out your boat for the hurricane season, with facilities which will meet the requirements of most yacht insurance companies.

Sadly, Barbuda was hit by hurricane Irma in 2017, when 180mph winds damaged almost every structure on the island, flattening many of them.

The long white sand beach (11 miles of it) was breached by the hurricane allowing dinghy access into the lagoon, where you can visit the once-charming town of Codrington or the world-famous frigate bird colony at the north end of Codrington Lagoon.

Prior to the breach you had to haul your dinghy over the sand spit into the lagoon, or call a water taxi on VHF. Every cloud... 

Most cruisers anchor off the 11 mile beach north of Palmetto Point, the Old Boat Harbour near the Martello Tower or in one of the distinctly reefy spots between Cocoa Point and Spanish Point.

Currency:  Euro (€)

Official Language: French

Ports of Entry: Deshaies, Basse Terre, Pointe a Pitre, Les Saintes and Marie Galante

Deshaies, a picturesque fishing village, is the northernmost anchorage on the east side of Guadeloupe.

Most of the moorings are taken by local boats, but you can normally find a spot to drop the hook somewhere.

Pigeon Island is the next anchorage to the south, where the Cousteau Marine Park is a favourite spot for snorkellers and scuba divers.

Two further anchorages are Anse de la Barque and Marina Riviere Sens which is around a mile south of Basse-Terre.

Les Saintes are a delightful group of islands, where the main anchorage is off Bourge de Saintes on Terre d'en Haut. If you'd prefer a mooring - and many skippers do as these waters are deep and anchoring opportunities limited - you need to arrive early!

It would be a shame not to visit Marie Galante, but it if you set off from Les Saintes it will be hard on the wind. In north-easterlies it is a much easier sail from Pointe-a-Pitre.

Currency:  Eastern Caribbean Dollars (EC$)

Official Language: English

Port of Entry: Portsmouth and Roseau

Rounding the headland you will, in all likelihood, be approached by a local boatman - "Hi Skip, welcome to Dominica!" - who will find you a mooring or a place to anchor, and will be on hand to assist you with anything else during your stay in this charming bay.

He will almost certainly suggest you take an island tour - and without any doubt, you should take him up on it!

Heading south you'll find the next anchorage at Salisbury, followed shortly afterwards by another, off Mero, where you'll see the ruins of the Castaways Beach Hotel.