Sailing in the Caribbean: islands, trade winds and hurricane season
as of 07/10/2026 · 6 min read
In short: In the Caribbean you sail from island to island in the steady trade wind from December to April, clear in again in every country and stay clear of the hurricane season.
The Caribbean is a winter cruising ground: from December to April the trade wind blows steadily from northeast to east, usually at 15 to 25 kn. The Lesser Antilles from Grenada to the Virgin Islands lie across it, so island-hopping is a beam reach. June to November is hurricane season, and every country requires its own clearance.
Which cruising areas does the Caribbean have?
The classic route follows the chain of the Lesser Antilles, a good 400 nm as the crow flies from Grenada to Tortola. Most legs between neighbouring islands are 20 to 40 nm long; through the Anegada Passage to the Virgin Islands it is around 80 nm.
| Area | Islands | Harbours and countries (examples) |
|---|---|---|
| Grenada and the Grenadines | Grenada, Carriacou, Union Island, Tobago Cays, Bequia | Port Louis Marina, Port Elizabeth on Bequia; Grenada, St Vincent and the Grenadines |
| St Vincent to Martinique | St Vincent, St Lucia, Martinique | Marina du Marin; St Lucia, Martinique |
| Dominica to Antigua | Dominica, Guadeloupe with Les Saintes, Antigua | Bas-du-Fort, English Harbour, Jolly Harbour; Guadeloupe, Antigua and Barbuda |
| Northern islands | Saint-Martin and Sint Maarten, St Barths, Anguilla | Marina Fort Louis, Gustavia |
| Virgin Islands | British and US Virgin Islands, Puerto Rico | North Latitude Marina, Virgin Gorda Marina, Green Cay Marina; BVI, USVI |
The Grenadines between Grenada and St Vincent are the classic area for anchoring bays over sand and reef, with the Tobago Cays as a marine park. The Virgin Islands lie close together and are the charter area for short day sails in sheltered water.
Further south and west lie Trinidad with Chaguaramas, the ABC islands and the Greater Antilles. To the north come the Bahamas with their shallow banks, for example in Marsh Harbour (Conch Inn Marina), and Bermuda as a stopover on the way to the Azores. To the west the area reaches as far as Panama with the canal and Shelter Bay Marina near Colón.
When is the best time to sail in the Caribbean?
From December to April: dry, with a steady trade wind and outside the hurricane season. Around Christmas and in January the trade wind often blows harder; sailors call these the Christmas Winds. May and June are calmer and hotter. The hurricane season runs from 1 June to 30 November and peaks from August to October.
How does the trade wind blow between the islands?
Mostly from east to northeast at 15 to 25 kn, stronger in the channels between the islands and with bigger seas. In the lee of the high islands it gets light and gusty.
- Along the chain: heading north or south you sail on a beam reach, fast but wet in the channels.
- Heading east: from the Virgin Islands to Antigua, for example, it is against wind and swell, so plan quiet days for it.
- In the lee: on the west coasts of Martinique, Dominica, St Vincent and Guadeloupe, calms alternate with downdraughts from the mountains.
- Squalls: rain squalls bring much more wind for a few minutes. Reef early when a dark cloud approaches, see Gusts and thunderstorms.
The tidal range in the Lesser Antilles is small; more important is the swell that runs into open bays.
What applies in the hurricane season?
Hurricane season runs from 1 June to 30 November, most active from August to October. Many yachts then go ashore or sail south, out of the zone of the most frequent storm tracks.
Many crews use Grenada as a base for the season; whether the island lies within your insurer's hurricane zone depends on the policy. Panama lies south of the storm tracks, and Shelter Bay, Linton Bay, Bocas del Toro and Guna Yala are popular places to spend the season. Insurers usually restrict cover during the season: check your policy before you plan. A Hurricane Watch from the National Hurricane Center (NHC) means hurricane conditions are possible, a Hurricane Warning that they are expected.
How do you clear in in the Caribbean?
Anew in every country: head straight for a port of entry, fly the Q flag, clear in with customs and immigration, and clear out before moving on. Not within a country: the chain from St Vincent to Union Island counts as one country, as does Guadeloupe with Les Saintes and Marie-Galante.
| Country | Ports of entry (selection) | Special features |
|---|---|---|
| Grenada | Port Louis Marina, Tyrrel Bay on Carriacou | three crew lists, advance notification via SailClear |
| St Vincent and the Grenadines | Kingstown, Port Elizabeth, Clifton on Union Island | Tobago Cays with entrance fee and a charge for a buoy or anchoring |
| St Lucia | Rodney Bay, Marigot Bay, Soufrière | clear in within 24 hours |
| Martinique, Guadeloupe | online or at clearance points such as Le Marin | EU but not Schengen; online clearance since September 2024 |
| Antigua and Barbuda | English Harbour, Jolly Harbour, St John's | advance notification via eSeaClear or SailClear |
| British Virgin Islands | Road Town, Soper's Hole, Great Harbour, Spanish Town | online entry card since 2025 |
| US Virgin Islands | St Thomas, St John, St Croix | with your own boat a B1/B2 visa; ESTA does not apply |
Throughout the region buoyage follows IALA System B: red to starboard when entering from seaward (“red right returning”), the opposite of Europe. Marine parks have their own rules: in the Tobago Cays you anchor only on sand or pick up a buoy, and around Soufrière on St Lucia and in the BVI parks you lie on buoys. More on Schengen, customs and paperwork in Clearing in.
How does Sailseer help in the Caribbean?
On the map you plan between around 810 harbours and anchoring bays from Trinidad to the Bahamas, Bermuda and Panama; bays with mooring fields such as the Tobago Cays or Salt Whistle Bay are included as destinations. Sailseer shows the NHC hurricane warnings with forecast cone, track and the closest approach to your route, the marine forecasts of the NHC and NWS San Juan, Météo-France's Vigilance warnings for the French islands, and the regional model AROME Antilles at 2.5 km alongside GFS and ECMWF. Observations come from NDBC buoys, NOAA and IOC tide gauges and airports. It shows anchorages with their shelter for each wind direction and marine parks with their rules, and the warning alert sends you every new NHC warning for your harbour by email or push. Every country has its own page for formalities, for example Grenada.
Sailseer is a planning aid and not for navigation. Official charts and the forecasts and warnings of the NHC and the weather services always take precedence. Only approach reefs and anchorages in daylight with good light. If you are coming across the Atlantic, you will find passage planning in Atlantic crossing.
Frequently asked questions
When is the best time to sail in the Caribbean?
From December to April. That is the dry season, the trade wind blows steadily from northeast to east and the hurricane season is over. Around Christmas and in January it often blows harder.
When is hurricane season in the Caribbean?
From 1 June to 30 November, peaking from August to October. The forecasts and warnings of the National Hurricane Center (NHC) are authoritative.
Where should I spend the hurricane season with my boat?
Many yachts go ashore or head south, for example to Grenada, Trinidad or Panama, which lies south of the storm tracks. Whether a berth lies outside your insurer's hurricane zone is decided by the policy.
Do you have to clear in on every Caribbean island?
In every country, not on every island. The chain from St Vincent to Union Island counts as one country, as does Guadeloupe with Les Saintes. On Martinique and Guadeloupe clearance has been online since September 2024.
How strong is the trade wind in the Caribbean?
Usually 15 to 25 kn from northeast to east, more in the channels between the islands, less and gusty in the lee of the high islands. Rain squalls bring much more wind for a few minutes.
Do I need a visa for the US Virgin Islands?
Foreign nationals arriving on their own boat need a B1/B2 visa; ESTA does not apply, because a private yacht is not an approved carrier under the Visa Waiver Program. More on the page US Virgin Islands.
Which buoyage system is used in the Caribbean?
IALA System B: entering from seaward, the red buoys are to starboard, the opposite of Europe.