The Rome2Rio Q1 2026 Travel Discoveries report contains a statistic that should interest anyone running a Caribbean destination: 76% of travellers say transport options influence which destinations they choose.
Not price. Not weather. Not marketing. Whether they can work out how to get there.
The same report found the average journey now involves 2.2 transport modes, that nearly 45% of Rome2Rio searches return multimodal routes, and that almost 40% of users have not settled on a destination when they start planning. The figures come from a survey of 3,100+ adults run with Harris QuestDIY and from first-party search data across more than 10 million locations.
Read those together and you get an uncomfortable conclusion. A meaningful share of destination choice is now made by whichever places look easiest to reach and combine at the moment someone opens a planning tool. A destination that is genuinely easy to reach but does not appear to be loses that comparison anyway.
The Caribbean's problem is legibility, not distance
We have written about the 34 territories and the single Caribbean the visitor sees. That piece was about identity. This one is about plumbing.
The islands of the northeastern Caribbean are, physically, close together. Anguilla is a short ferry from Sint Maarten. Saba is a short flight. St. Barthelemy is a morning. In pure distance terms this is one of the more tightly connected archipelagos in the world.
Now try to plan it from Dusseldorf.
The ferry operator publishes a schedule as a PDF, or a photo of a printed timetable, or a Facebook post. The regional carrier's availability is real but thinly represented in the tools most people plan with. Connections between a flight arrival and a ferry departure exist in practice, in the head of someone who has done it, and essentially nowhere a planning engine can read.
The connection is real. The data is not. So the itinerary that would have worked never gets built, because the traveller could not see it.
What "easier" actually means
When a destination says it wants to make multi-destination travel easier, it usually reaches for a marketing campaign or a regional co-operation agreement. Those are not useless, but they do not touch the mechanism.
Easier, in the sense that changes behaviour, means four unglamorous things:
Schedules that exist as data. Not a PDF, not an image, not a phone number. A structured feed that states what runs, when, from where, and what happens to it seasonally. This is the single highest-leverage item on the list and the one most often left undone.
Connections expressed as connections. A flight landing at 13:40 and a ferry leaving at 15:00 are two facts. That they combine into a usable same-day route is a third fact, and it has to be stated somewhere, with an honest minimum transfer time, or nobody planning from abroad will find it.
Requirements stated plainly. Immigration, documentation and entry conditions vary by island and by nationality. Travellers do not skip an island because the requirement is onerous. They skip it because they could not establish what the requirement was and would not risk it.
One version of the truth, kept current. When four sites disagree about a ferry time, the traveller does not investigate which is right. They pick the itinerary where the sources agree.
This is infrastructure, not content
The instinct is to treat this as a content problem and hand it to a marketing team. It is not. It is closer to a data infrastructure problem, and it behaves like one.
It has to be maintained, because a schedule that was right in November is wrong in February. It has to be structured, because the consumers are increasingly not humans reading a page but planning engines, AI assistants and booking tools reading a feed. And it has to be regional, because the thing being described is a connection between two islands and neither island owns it on its own.
That last point is why this rarely gets built. Every island has a tourism authority responsible for its own destination. The connections between them belong to nobody's mandate and therefore nobody's budget.
Why the window is now
Two things are converging. Travellers are building multi-stop itineraries as the default rather than the exception. And the tools they use to build them are shifting from human-read web pages to machine-read structured data, as AI assistants take over more of the "how would I even do this" stage of planning.
An assistant asked to plan five days in the northeastern Caribbean will answer from whatever it can actually parse. Islands whose connections exist as structured data will appear in that answer. Islands whose connections exist as a PDF will not, however good they are.
That is a fairly stark way to lose share, and it happens quietly, because nobody files a complaint about an itinerary that was never suggested to them.
How we do this
This is the layer IIG builds: structured destination data, traveller-facing systems at airports and ports, and the content architecture that makes a region readable to the systems travellers now plan with. That work is Destinito.
It is also the layer Destinito operates against. The same platform that makes the connections legible runs the programmes that use them: multi-island itineraries, guides and transfers, ferry and Winair connections, coordinated on the island.
Two brands, one operation. If you run a destination and the honest answer to "can a planning engine read our connections?" is no, that is the conversation to start. If you are the one trying to build the itinerary, Destinito Groups is where it gets built.