Destination
Puerto Rico
The easiest big trip an American family can take
- No passport needed for U.S. travelers
- Direct flights from the New York area, about 4 hours
- Strongest for: families, long weekends, winter sun
Puerto Rico is my answer to a very common question: “We want a real trip — warm, different, memorable — but we only have a week and one of the passports is expired.” No passport needed, U.S. dollars, your phone plan works, and a direct flight from the New York area has you on a beach by early afternoon.
I plan Puerto Rico from experience — I’ve spent weeks on the island with my own three children, most recently for the better part of a summer. This is the destination where I’ve personally tested the difference between the version in the brochure and the version with a four-year-old in tow.
The shape of a great week
Old San Juan deserves more than a cruise-day stopover. The blue cobblestones, the forts — El Morro’s grassy field full of kites is one of the great free afternoons in the Caribbean — and a food scene that goes far beyond the resort buffet. Two or three nights here at the start of a trip beats a rushed day trip every time.
The rainforest. El Yunque is the only tropical rainforest in the U.S. forest system, and it’s genuinely doable with kids — short trails, waterfall swimming holes, and out by nap time. Access rules and reservations have shifted over the years; this is exactly the kind of detail I keep current so you don’t drive up to a closed gate.
The beach half. Where you base matters more than in most destinations, because the island’s coasts have different personalities — calm, family-friendly water in some stretches, surf in others. And if your crew is up for a small adventure, the islands of Culebra and Vieques hold some of the most beautiful beaches in the Caribbean, plus a bioluminescent bay that children talk about for years.
Why book it through me
Puerto Rico looks simple enough to wing — that’s the trap. The good paradores and resort rooms for school-break weeks go early, rental cars sell out in high season, and the difference between beaches that work for toddlers and beaches that don’t is not in the photos. I’ve done the field research with my own family. You get the version of the island that already has the mistakes taken out.