Get two trips — plus two side trips — for the price of one round-trip
Imagine you’re headed to Miami for business or leisure, but instead of just visiting Miami, the airline ticket you have includes a stop in the Caribbean – for a few days or more — at no extra cost.
In fact, with FCF’s Stopover Loophole Strategy (SLS), you could end up paying less than you would for a simple round-trip ticket.
Or suppose you’re headed to Los Angeles, but instead of just going to California, your ticket includes a free — or less than free — trip to Mexico to start or end your trip.
Let’s delve into my SLS, a travel strategy that turns ordinary trips into extraordinary experiences without breaking the bank.
In The Upgrade Process, we always start with our baseline. It’s our starting point. Starting points, assumptions, or default states shape everything we experience, perceive, and choose. It’s like a lens we don’t always notice we’re looking through, yet it colors the whole picture.
Let’s start with a snapshot of how good this strategy can be for our initial perspective. Then let’s look at who might desire to use the strategy, the range of potential itinerary options, and the questions to consider for making a decision.
SLS Sample Savings
Los Angeles-Miami round-trip is currently going for $1,942 in Business Class (for non-red-eye or 6:00 AM flights) on American Airlines. Add on San Juan, Puerto Rico, to your trip, and the fare can drop to $960 — that’s $982, or 51% less, plus the bonus Caribbean win.
Typical American Fare on AA.com Los Angeles - Miami Round-Trip

Typical American Fare on AA.com Los Angeles - Miami - San Juan - Los Angeles Using FCF’s Stopover Loophole Strategy (SLS)

Full disclosure: Not all options are this good; the strategy is hit and miss. And it works better with American at the moment. But there are many options that can get you a free or cheap upgrade. More analysis on the options in a minute.
Already Flying Business Class?
Here’s Your SLS Perspective:
Cramped in Coach Class?
Here’s Your SLS Upgrade Perspective:
*Bonus: Earn More Elite Credit and Miles with SLS Extra Flights
Considering Premium Economy? Here’s Your SLS Upgrade Perspective:
51% savings?
That means two trips — plus two side trips — for the price of one round-trip.
Baseline: Upgrade Mindset Pro-Tip
What’s your baseline? Just like our lives aren’t always just shaped by big choices, but more impacted by the quiet, often unnoticed foundation we’re already working from, neither are our travel choices.
Your baseline frames your life. It’s a lens you don’t always notice you’re looking through, yet it colors the whole picture. It’s not just “you are what you eat” — it’s “you see what you stand on.”
My desire is that after reading this special report, you’ll shift your thinking and the baseline from which you make travel (and any other upgrade) decisions will improve. Exploring new options can crack open otherwise hidden desires.
Now that we have a deeper understanding of the FCF Stopover Loophole Strategy baseline, let’s build on the potential and perspective.
The strategy doesn’t work everywhere all the time. Within North American, it works occasionally with Delta and United at the moment, and best in conjunction with American’s hubs – Charlotte, Chicago, Dallas-Fort Worth, Los Angeles, Miami, New York, Philadelphia, Phoenix, and Washington, D.C. – as origins, destinations, or side trips. More on the many options in a moment.
Why does SLS work?
After publishing the longest running newsletter in the history of the air travel industry, I’d love to be smug and tell you I knew exactly why, and I kinda do. It essentially has to do with complex airline pricing structures, and how they sometimes work with stopovers, and sometimes don’t.
In the world of air travel, a stopover is typically a layover lasting more than four hours domestically, often stretching into days or weeks for LESS or little to no additional cost. With SLS, you’re not just traveling from point A to point B, with a stop of a few hours, however. You’re turning a layover into a multi-destination feast.
That’s because the stopover can be turned into a vacation if you’re on a business trip or a second vacation if you’re already traveling for pleasure or visiting grandma.
Now that we have an improved, upgraded starting point, let’s look at the desires for various types of travelers and scenarios.
UPGRADE PROCESS Step #2: Desires
What do you want?
Universal Upgrade Process–Pro-Tip: While the process has five steps, in reality, you don’t always follow them sequentially. For example, an opportunity might just appear out of left field. Take the SLS for example in this special report's baseline. When you start with an opportunity, or an option, that’s great, just go back to step 1, or at least to step 2 (Desires), and ask yourself upgrade or improvement questions. Let’s give it a try now.
Can you identify with any of the following?
Who Can Benefit from SLS?
Before you commit to a desire, pause to explore your desire options. What you want on the surface — a trip, perhaps — might mask a deeper longing: to rest, to wander, to break free. The more options you consider, the more you uncover about what truly moves you. How often have you chased a want only to find, through exploration, it wasn’t what you originally thought—or you stumbled upon something better later on?
Where does SLS work best within North America?
American
Works best with low-cost add-on destinations:
- Cancun, Corn Islands, La Romana, Managua, Mexico City, Montego Bay, Nassau, Puerto Vallarta, Rincon, San Juan, U.S Virgin Islands
- When ordinarily flying TO American’s hubs: Miami, Charlotte, Dallas, Phoenix
- With transcons to low-cost add-on destinations:
- From Los Angeles and San Francisco to New York and Miami
- From New York to San Francisco or Los Angeles
Delta
Works best with lowcost add-on destinations:
- Cancun, Punta Cana, Montego Bay, San Juan
- When ordinarily flying TO Delta’s hubs: Los Angeles (LAX) and Atlanta (ATL) to destinations like New York (JFK) and Atlanta (ATL)
- With transcons to low-cost add-on destinations:
- From Los Angeles to New York (JFK) and Atlanta
- From Atlanta to Los Angeles
United
Works best with low-cost add-on destinations:
- Cancun, Mexico City, Punta Cana, La Romana, Montego Bay, Guatemala City
- When ordinarily flying TO United’s hubs: Los Angeles (LAX) and San Francisco (SFO) to destinations like Boston (BOS) and New York (JFK)
- With transcons to low-cost add-on destinations:
- From Los Angeles to Boston and New York (JFK)
- From San Francisco to Boston
Samples of Where the SLS Works Best – To Miami on American
Other Sample American Deals
Transcon Opportunities On American
Delta Deals
United Deals
Cracking the Elite Curse & The Upgrade Mindset
Your mindset on airline loyalty elite status programs frame your travel life. It filters what you want and what you think you can have. Elite status expectations shape much of what many experience, perceive, and choose in the world of flying.
Be honest with yourself. The loyalty you’re giving to American, Delta, and United isn’t being reciprocated, is it? Elite travelers know the drill too well — those glossy benefits dangling free upgrades like a carrot on a stick, but the line’s so long you’re left chewing on coach.
It’s a promise whispered by a con artist, or a lottery ticket that never cashes in. You’re stuck in the crucible: pay for First Class and feel robbed of your status, or roll the dice in economy and curse the odds.
Different airlines offer different deals and schedules with the Stopover Loophole Strategy - so locking yourself into loyalty to one airline locks yourself out of options. That’s as true with SLS as any other. That’s why I’ve been advocating for loyalty-free agency for decades.
Closing Arguments
You’ve already done the grunt work: packed the suitcase, lined up the dog sitter, done all the preparations to leave home. So why let that effort sputter out on a one-stop trip when you could tack on a detour that turns a routine trip into a jackpot?
SLS is the poster child for getting more for less. Have to visit a client in Dallas? Why not add on the Miami Grand Prix — and perhaps write off the flight? Facing a ridiculously high First Class fare? Why not cut it in half — in effect having the airlines pay for your trip to the beach. Your hotel and dinner can be financed by the airlines if you’re opportunistic.
If you did this as a lifestyle, you’d go to twice as many places, your experience wealth would double. Best of all, with The Upgrade Process and Mindset, it can even cost you less.
Stay tuned for next month’s SLS Part 2.
Until then, see you up front.
P.S. A friendly reminder to provide feedback on our weaving in The Universal Upgrade Process and Mindset into the travel strategy. We’re about to re-launch The Upgrade Formula and would love your input along the way.