Multi-Island Group Programs, Built Around Real Connections
Two or three islands in one program works when it is planned around the sailings and sectors that actually run. Sint Maarten is the hub that makes it possible.
Why Sint Maarten Is the Hub
SXM is the only airport in the northeast Caribbean with both long-haul arrivals and a dense regional network. Anguilla, Saba, Sint Eustatius and Saint-Barthélemy are all reachable from it in under an hour by ferry or by Winair, and for Saba and Statia the Winair sector is effectively the only scheduled link. That is what makes a three-island program possible inside a week without spending half of it in transit.
The Constraint Is Capacity, Not Availability
The planning limit on a multi-island group is almost never hotel rooms. It is seats on the connection. A Twin Otter in standard commuter configuration seats 19, so a larger party is more than one rotation, and the rotations do not land together — which moves the guide, the meal and sometimes the hotel check-in. Ferries carry more per departure but sail to a timetable that thins out in the afternoon. Programs that ignore this look fine on paper and fall apart on day three.
The 19-seat figure is the DHC-6 Twin Otter type certificate maximum (passengers, excluding flight crew), per the Transport Canada type certificate data sheet; operators may configure fewer. Coach and vessel capacities vary by the equipment rostered. As of 19 September 2026 — we confirm the actual equipment for your dates at quoting time.We plan the connection first and build the days around it. For published sailing times and operators see the ferry schedules; this page is about what those schedules mean for a group.
Corridors We Run
- Sint Maarten – Anguilla — the shortest and most frequent crossing, from Marigot and from Blowing Point. Departure tax and immigration apply in both directions and are itemised in the quote.
- Sint Maarten – Saint-Barthélemy — ferry or a short Winair / St Barth Commuter sector. The ferry is cheaper and the flight is far more comfortable in a swell; for groups we normally recommend flying one direction and sailing the other.
- Sint Maarten – Saba and Sint Eustatius — Winair-dependent and the most weather-exposed routing we operate. Saba's approach closes in low visibility and the ferry is sea-state sensitive, so these programs carry a written contingency day.
- Saint Kitts – Nevis — a short, reliable crossing with a water-taxi alternative. Demand here peaks in December rather than January.
- Antigua – Barbuda — a longer crossing best planned as a full day rather than a half day.
- USVI – BVI — St Thomas to Tortola and on to Virgin Gorda, a separate hub from SXM with its own entry formalities.
Season
Planning demand on every one of these corridors runs roughly two to three times higher in January than in September, and Saint Kitts – Nevis peaks instead in December, at roughly five times its August low. Inter-island capacity does not expand to match. If your program falls between December and March, contract it six months out; outside that window three is usually enough.
Seasonality from Destinito's internal northeast-Caribbean route demand study, 16 September 2026. It indexes search demand by month, not passenger counts, so it measures when people plan rather than when they travel.What a Multi-Island Program Includes
- Routing planned around actual sailings and sectors, with connection times that survive a delay
- All inter-island transport booked as group inventory, not individual tickets
- Departure taxes, port fees and entry formalities itemised per island
- A contingency plan for each weather-exposed leg
- One local contact across every island in the program
Planning Two or Three Islands?
Tell us the islands, the group size and the dates. We will tell you whether the connections carry it.
Request a Group ProgramFrequently Asked Questions
How many islands fit in one program?
Two comfortably in a week, three if one of them is Anguilla or Saint-Barthélemy — both are close enough to Sint Maarten to visit without a hotel change. Four in a week means most of the program is transit.
What is the largest group you can move between islands?
On the ferry corridors it depends on the vessel rostered, which we confirm with the operator against your party size before quoting. On the air sectors a Twin Otter in standard commuter configuration seats 19, so anything above that is more than one rotation or a charter, and the routing has to absorb the gap.
What happens if a crossing is cancelled?
Each weather-exposed leg carries a contingency written into the program before departure — an alternative sector, a rearranged day, or a held hotel night. The Saba routing always carries one.
Do guests need to clear immigration between islands?
Yes on most corridors, and departure taxes apply. Anguilla, Saint-Barthélemy, Saba and Statia are separate jurisdictions from Sint Maarten. We itemise the fees and handle the group formalities.