Caribbean Travel Insurance (2026) — What to Cover + When It’s Worth It
Quick Answer
Travel insurance is usually worth it if:
- your trip is expensive,
- you’re traveling during hurricane season,
- you have nonrefundable bookings,
- or you’re island-hopping (more moving parts = more delays).
If it’s a cheap weekend getaway with flexible cancellation, you may not need it.
What travel insurance should cover for the Caribbean
1) Medical + emergency care
This is the big one. Even minor emergencies can get expensive quickly.
2) Trip cancellation / interruption
Useful if you get sick, a family emergency happens, or something forces you to cut the trip short.
3) Travel delays + missed connections
Huge for island-hopping, ferries, and tight itineraries.
4) Lost/delayed baggage
Nice to have, especially if you need essentials quickly.
5) Weather-related disruptions
Important if you’re traveling in storm-prone months.
When you should definitely buy it
- You’re doing multi-island travel (ferries + flights)
- You booked nonrefundable hotels/resorts
- You’re doing pricey tours (diving, boat charters, biobay tours)
- You’re traveling with kids or older family members
- Your trip cost is “painful to lose”
What to check before you buy (don’t skip)
- Does it include medical evacuation?
- Does it cover pre-existing conditions (if relevant)?
- What are the claim requirements? (receipts, documents, proof)
- What’s the cancellation coverage limit?
- Are weather events covered and under what conditions?
Simple strategy that works
- If you want maximum flexibility: prioritize cancellation + interruption.
- If you want maximum protection: prioritize medical + evacuation + delays.
Common mistakes to avoid
- Buying the cheapest plan without medical coverage limits
- Waiting until the last minute (some benefits require early purchase)
- Assuming “hurricane coverage” means “cancel anytime” (usually not)
- Not reading the exclusions
Quick Spanish Summary (Resumen en Español)
El seguro de viaje vale la pena si tu viaje es caro, tienes reservas no reembolsables, viajas en temporada de huracanes o harás island-hopping.
Busca cobertura médica, cancelación/interrupción, retrasos y equipaje.
FAQ
Do I need insurance for Puerto Rico?
It depends—medical coverage can still matter, and delays/cancellation can still happen.
Is travel insurance worth it for a short trip?
Only if your bookings are nonrefundable or the cost is high.
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