How crew plan the seasonal repositioning between the Mediterranean and Caribbean: crossing under own power or by transport ship, timing and routes.
Twice a year the charter fleet changes ocean. Westbound in the autumn, once the Mediterranean season ends and before the Caribbean opens; eastbound in the spring, in time for the Riviera. It is the least visible part of the charter year and the one that most shapes it, because everything else — the yard period, the crew leave, the first charter of the new season — hangs off when and how the yacht crosses.
This guide covers the two ways to do it, the timing, and how crews plan the year around it. It is written for the operational conversation rather than as passage-planning guidance, which belongs with the captain and the yacht's own procedures.
A yacht can cross under its own power or ride across on a transport ship, and the choice is less about size than about range, crew and calendar.
Typical route. Gibraltar, Canaries, sometimes Cape Verde, then the trade wind route west. Loading in Genoa, Palma or Tivat; discharge at St Thomas or Le Marin. Timing. Departures from late October; the classic window opens once the hurricane season closes. Scheduled sailings, typically October and November westbound. Crew. Full watchkeeping crew for the passage; sea time and experience gained. Skeleton crew or none aboard; most of the crew fly. Wear and risk. Miles on the yacht, fuel burn, weather exposure, the possibility of damage. Minimal sea miles; the cargo risk sits with the transport operator. Cost shape. Fuel, crew, provisions, insurance loading for the passage. A freight rate, plus flights and the delivery legs to and from the load port. Best for. Yachts with the range and a crew who want the passage; sailing yachts. Yachts short on range, tight calendars, or owners who prefer no ocean miles
The transport option has a firmer shape than crews sometimes expect. The Mediterranean loading ports in common use are Genoa, Palma de Mallorca and Tivat, with Caribbean discharge at St Thomas in the US Virgin Islands and Le Marin in Martinique. Westbound sailings cluster in October and November; eastbound returns run from March through May. Published dates are approximate and not guaranteed, which is the single most important thing to build into the plan.
1. Work backwards from the first charter of the new season
The fixed point is not the crossing; it is the first booked charter on the other side. Work back from that: the yacht needs to arrive, clear in, provision, complete any post-passage maintenance, and be presentable with the crew rested. That is rarely less than two weeks and often more. A crossing planned to arrive the week before a New Year charter has no slack in it at all, and the festive season is exactly when slack is most needed.
2. Put the yard period on the right side of the ocean
Most yachts take their maintenance window at the season change, and where it happens shapes everything. A European yard period after the Med season means the yacht crosses late and arrives into the Caribbean with less margin; a Caribbean or US yard period means crossing early and doing the work on arrival. Neither is wrong, but the choice has to be made early because yard slots and transport sailings are both booked well ahead and both are hard to move.
3. Decide the crew plan before the route
The crossing is where crew turnover happens, and it is better managed than discovered. Under own power the yacht needs a full watchkeeping complement for two to three weeks, which may mean bringing on delivery crew; on a transport ship most of the crew fly and someone has to organise flights, visas and accommodation at both ends. Either way it is the natural point in the year for leave, for handovers, and for the crew who are not continuing to the next season to go. Plan it as a crew event rather than a logistics one.
4. Handle the paperwork the season change triggers
A change of ocean is a change of regime. Temporary admission clocks for non-EU flagged yachts in the EU, cruising permits and charter licences in the new region, insurance navigational limits and the named-windstorm position, crew visas — the Caribbean season in particular has US and BVI requirements that need to be current before the first charter, not after. Several of these have lead times measured in weeks. The management company owns most of it, but the crew feel it if it is late.
In Guest Trip: the season's clearances, permits and licence renewals can sit as fixed points on the calendar, so nothing that has a lead time is discovered at short notice.
5. Use the crossing for the work that needs sea days
An ocean passage is the longest uninterrupted block of time the yacht gets all year, and the boats that use it well arrive ready. Deep cleans that cannot be done between charters, inventory and stocktake, refreshing the guest information and photography, retraining on emergency procedures, and rewriting the itinerary templates for the new region all fit naturally into a passage. So does the honest post-season debrief that never happens during the season itself.
6. Build the new season's itineraries before you arrive
Arriving in the Caribbean in late November with no itineraries prepared is how the first charters of the season end up rushed. The crossing, or the weeks around a transport loading, is when to draft the standard weeks for the new ground: the Leewards week, the BVI week, the Exumas week, with the anchorages, clearances and fees already researched. It is also when to update the guest-facing material, which is usually still showing Mediterranean photography.
In Guest Trip: duplicate the yacht's full setup for the new season and save the standard weeks for the new cruising ground as templates, so the first charter starts at eighty percent complete.
Westbound crossings run from late October through November, after the Mediterranean season ends and once the Atlantic hurricane season is closing. Transport ship sailings from Genoa, Palma and Tivat cluster in the same window, with discharge at St Thomas or Le Marin.
It depends on range, crew and calendar rather than size. Crossing under own power suits yachts with the range and a crew who want the passage; transport suits yachts short on range, tight calendars, or owners who prefer the yacht not to accumulate ocean miles. Transport also removes most of the weather risk but adds delivery legs at both ends.
Under own power, the trade wind route west typically takes two to three weeks depending on the yacht and the routing via the Canaries and Cape Verde. Transport ship transits vary by service and are quoted per sailing; published dates are approximate and should be treated as such.
Use it as the longest uninterrupted work block of the year: deep cleans, stocktake, retraining, the post-season debrief, and drafting the new region's itineraries and guest material so the first charter of the new season is not rushed.