**There is no scheduled passenger ferry from Europe to either Jamaica or Trinidad. A one-way cruise is the practical sea option**, with dates tied to particular sailings.

- **Jamaica: a confirmed Europe-to-Jamaica itinerary exists.** Phoenix Reisen’s *Amadea* sails from **Bremerhaven, Germany, on 22 October 2027**, finishing in **Montego Bay on 17 November 2027**—26 nights. You could continue overland to Kingston. The advertised package includes a flight back to Frankfurt, so ask Phoenix to confirm arrangements for ending your journey in Jamaica. [Operator’s itinerary and booking details](https://www.phoenixreisen.com/von-bremerhaven-bis-jamaika.html).

- **Trinidad: a crossing to Barbados followed by a regional flight is a workable option to investigate.** For example, P&O’s *Britannia* sails **Southampton–Bridgetown, 30 October–13 November 2026**, taking 14 nights. Caribbean Airlines lists **Bridgetown–Port of Spain** flights. Ask P&O for a cruise-only booking ending in Barbados; the advertised holiday includes a flight to the UK. [P&O crossing](https://www.pocruises.com/find-a-cruise/B626/B626), [Caribbean Airlines routes](https://flights.caribbean-airlines.com/en/sitemap/city-to-city/page-1).

**For an entirely flight-free journey to Port of Spain, I haven’t verified a bookable route.** Its regular passenger ferry connects Trinidad with Tobago. [Trinidad and Tobago ferry service](https://www.ttitferry.com/vessels-and-services/).

Freighter travel is also difficult to arrange: Cargo Ship Voyages’ **5 September 2026 update** says transatlantic passenger voyages are generally unavailable. Older accounts of travelling on cargo ships may therefore be misleading. [Current freighter-travel availability](https://www.cargoshipvoyages.com/).

What month or year are you hoping to travel, and would a short Caribbean flight be acceptable?