Better than Free: Enjoy Stopover Vacation Loophole Happiness, San Juan Style

How you can add Puerto Rico to a domestic round-trip on American Airlines and pay up to $280 less.

Keen-eyed FCF readers will know we’ve discussed the Stopover Loophole Strategy (SLS) before. It’s how we maximize the opportunity many airlines offer, called a “stopover allowance.”

A stopover is a planned stop between flight segments on a trip. For international trips, a stop for 24 hours is usually allowed for free, but on domestic flights like those discussed here, it’s usually just 4 hours.

The loophole part is that longer stops are sometimes allowed for free, or for a minimal fee – and sometimes, adding a second destination to your trip can actually lower your original fare.

Like magic.

So rather than thinking of the next trip in terms of a single destination, you can think of that destination as “the stopover,” such as the sandy beach one we’re highlighting this month.

That gives you a chance to score a side vacation (for days or longer) in a gorgeous destination for nothing, or next to it. And in some cases, you can get it for less than the cost of your single-destination trip.

To me, this is the airlines’ way of saying “feel free to stick around in an extra vacation location, and we’ll cover the tab.” But I’m sure they don’t think of it that way.

The San Juan Side-Track

This report features San Juan, Puerto Rico, as the warm, sunny, free, or low-cost stop-over you can add on to your next trip. What a great idea.

For example, you’d normally pay $901 for a Business Class return trip between Los Angeles and Philadelphia to visit Grandma Grace. But with FCF’s stopover loophole strategy, you could sneak in a relaxing few days or longer in the tropics on the way home. I mean, who wouldn’t want to do that after the year that just passed? You can add San Juan, for example, at current fare levels for $280 less. Like magic.

That’s right, you can add a vacation in San Juan and only pay a total of $621 for the entire trip in Business Class. FYI, not all of these add-on trips are “less than free” as we like to call it when you end up paying less and getting more. But in those cases, a couple hundred extra bucks isn’t much to ask to add a great vacation in your life.

A nuance to note: you can stop in San Juan in either direction involving the same cities but the cost may differ. Still good, just different. For example, Cleveland-San Juan-Dallas-Cleveland is $681. (Cleveland-Dallas round-trip is $606), while Cleveland-Dallas-San Juan-Cleveland is $538 .

And here are more:

San Juan Elevator Pitch

Blessed with a rich cultural heritage, golden palm-lined beaches, and a vibrant nightlife, San Juan is a unique Caribbean charmer. Its Spanish colonial history dates back to 1521 and comes alive along the narrow, cobblestone streets of Old San Juan, in the pastel-colored buildings, churches, and convents, and in the iconic centuries-old forts that guard the harbor: Castillo San Felipe del Morro and Castillo San Cristobal.

Beyond its historical authenticity is a modern pulsating city, packed with superb restaurants, cutting-edge galleries, and an exciting nightlife. And you won’t want to miss such signature dishes as pernil (classic roasted pork), mofongo (mashed green plantains), and platanos maduros (fried ripe plantains), washed down with a splash of Bacardi rum, of course. Or better yet, visit the world-renowned Bacardi headquarters itself, the largest premium rum distillery in the world — just 20 minutes from Old San Juan.

For the perfect day trip, head to El Yunque, the only tropical rainforest in the U.S. National Forest Service and the pride of Puerto Rico. Keep your ears tuned for the singsong sounds of Puerto Rico’s tiny coqui frogs, symbols of the island, as they fill the forest with their plaintive calls.