How to add San Juan, St. Croix, or St. Thomas to your round-trip ticket and pay up to $620 LESS
Host: Come on down, Natasha from Omaha! You’re in the running for a free vacation to the Caribbean.
(Wild studio audience cheering.)
BUT, you need to answer this question first:
(Dramatic music)
Would you like a free vacation?
(Thinking music)
Natasha: Um, yeah…
Host: Correct! Natasha from Omaha! (Ding, ding, ding!) You are our winner! Oh, to heck with that… EVERYONE in our audience is a winner! Free vacations for all of you! (Wild cheering and applause.)
The Stopover Loophole Strategy (SLS) Puts on a Show
Yes, it’s a game-changing strategy that we’ve covered previously to destinations such as Africa, India, and the Middle East.
The Stopover Loophole Strategy takes advantage of airline “stopover allowances.” A stopover is a planned stop of more than four hours for domestic flights and 24 hours for international flights.
But here’s the thing, these stopovers can be for days — or even weeks — if you want. And they are sometimes allowed for free or a very small fee. “Hello vacation” is what we say to that, here in the venerable halls of FCF.
That’s because you can visit an awesome second destination like San Juan, St. Croix, or St. Thomas for no extra cost. Or, would you believe, take a flight to Miami that costs less because you added a stopover? Yes, that’s “less than free” because you’re kind of getting paid to do it. Getting paid to take a vacation? Well, this is the kind of thing that makes life great. This and game shows, of course.
Let’s take a short break — to a tropical paradise!
Free Vacations That Also Save You UP to $620
A San Francisco-Miami round-trip flight in Business Class often costs around $1,577 on American Airlines. However, if you add a stopover to sun-drenched San Juan in the Caribbean, you’d pay $620 LESS! Say what? For just $957, you get two different travel experiences for the price of one. That’s a sidestep that would make a star running back proud.
Or how about this: Instead of traveling round-trip from Dallas to Miami in Business Class for $1,116, you can add a stopover in St. Croix in the U.S. Virgin Islands to bring that price down to $1,081. That’s $35 cheaper — all for adding another vacation destination.
More wild cheering from the audience.
Ladies and gentlemen, please note that you can stop in Miami in either direction, but the cost may be slightly different. For example, on American Airlines, Phoenix-St. Croix-Miami-Phoenix is $948 (a Phoenix-Miami round-trip is $1,347), while Phoenix-Miami-St. Croix-Phoenix is $1,050. A little more, but still a bargain.
Here’s what’s possible with this strategy:
- You can actually get paid to book a side trip to an awesome destination. That is, adding a side trip makes your total booking cost cheaper than the original round-trip booking without the side trip.
- You’ll be able to book a side trip for free – for the same cost as a round-trip booking without the side trip.
- You pay a little bit more to book the side trip, but it’s still considerably cheaper than booking a round-trip to the side-trip destination by itself.
This Strategy Is Ideal for Contestants Such As:
- Leisure travelers who have the flexibility to add in a side trip when visiting friends or family in Miami.
- Business travelers on a budget who still want to sneak in a vacation while on a business trip in Miami.

Where to Use FCF’s Stopover Loophole Strategy to Get Amazing Business Class Travel Deals with American Airlines
Here are some examples of our Stopover Loophole Strategy in action.
The SLS Connection Costs From Various U.S. Cities with an Outbound Side-Trip on American
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The SLS Connection Costs From Various U.S. Cities with an Inbound Side-Trip on American
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Taken for a Loop
Our Stopover Loophole Strategy has proven to be a game-winner for many FCF readers. It’s so counterintuitive — adding a beautiful location and paying less overall. It’s the Upgrade Mindset in action, something I’d love you to consider the next time a vacation calls your name.
See you up front.