01Choose the island, not just the hotel
Caribbean islands can feel very different. Flight routing, transfer time, beaches, excursions, local culture and hotel style all matter, so start with the experience you want rather than a generic “Caribbean” search.
02Look for memories beyond the pool
In Cuba, I remember the watersports, family experiences and touring the mainland in a classic pink Cadillac. A couple of well-chosen excursions can add a completely different dimension to a beach holiday.
03Check the room and board basis carefully
Family room layouts and meal plans can have a large effect on comfort and total cost. The cheapest headline rate is not always the best-value family option.
04Be realistic about transfer time
After a long-haul flight, the final transfer matters — especially with young children. I can compare the whole journey rather than just the resort itself.