Cruising in the Caribbean: season, routes and crew
Where most Atlantic crossings end and where winter cruising happens. This page covers season and routes from named sources, links the rallies, and says plainly what it does not cover.
Season
- Typical Winter, from December to February, is the peak season in the Caribbean, and November, March and April are also good. Grenada and Trinidad are common places to spend the hurricane season.Source: Caribbean Compass (bwsailing.com) (article or trade press), seen 1 October 2026.
- Reported The Atlantic hurricane season officially runs from 1 June to 30 November.Source: NOAA (organiser or official source), seen 1 October 2026. Check with NOAA: tropical cyclone climatology before you rely on it.
Typical routes
- Typical The usual cruising ground is the Eastern Caribbean island chain, with boats heading south for the summer.Source: Caribbean Compass (bwsailing.com) (article or trade press), seen 1 October 2026.
Rallies
Each rally has a page with what we have checked, its organiser and the passages tagged for it.
Entry rules to check
- Reported Noonsite says the US Visa Waiver Program does not apply when a person's first arrival is by private yacht, but that a prior arrival by commercial carrier (for example a flight or ferry) works.Source: Noonsite (article or trade press), seen 1 October 2026. Check with US Customs and Border Protection: international visitors before you rely on it.
- Reported A US ESTA is valid for two years. It is an authorisation to travel, not a guarantee of entry.Source: US Customs and Border Protection (organiser or official source), seen 1 October 2026. Check with US Customs and Border Protection: international visitors before you rely on it.
Check your own passport and your own days with the authority before you travel.
What this page does not state
Entry rules differ by island and we have no source for them that meets our standard, so this page states none. Noonsite lists the formalities island by island, and each island's own authority has the last word.
Organisers and authorities to check with:
Last checked 1 October 2026. The facts above come from the sources linked beside each one. We have not opened every source page ourselves; check with the organiser before you rely on it. Dates, fees, deadlines and entry rules change, and only the organiser or the authority can state them.
Open passages
No passage is open here right now. If you are a captain, you can be the first to post one.