MileValue is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Terms apply to American Express benefits and offers. Enrollment may be required for select American Express benefits and offers. Visit to learn more.

Note: Some of the offers mentioned below may have changed or are no longer be available. You can view current offers here.

In my trip report of BA business from Tampa to London, I mentioned offhandedly that a lot of people could find value in AA awards with a stopover in the Caribbean on the way to Europe even after paying the $300 fuel surcharge for flying British Airways on an AA award.

Astute reader Francisco C pointed out that although one example I gave–LAX to Cancun, stopover, Cancun to London (and beyond)–was pricing as a free stopover on, the Caribbean stopover options I had claimed were possible were not booking as free stopovers. I investigated, and Francisco C is absolutely right.

Here’s a successful booking: LAX to Cancun, free stopover, Cancun to London on the direct BA flight.











Since the award is offpeak to Europe in coach, it is only 20,000 miles! Because we are flying BA transatlantic, the fuel surcharge is whopping, and the total out-of-pocket is $289. For many people paying an extra $289 and tacking on a vacation to Cancun would be worth it, so this is an option to consider.

Unfortunately, I also claimed you could have your stopover at one of the Caribbean islands BA services, but’s award booking engine disagrees with me.

Here’s an attempt to replicate an LAX to London award, but this time with a stopover in Nassau, Bahamas.

As you can see, is pricing this as two awards–17.5k to go LAX to NAS and 20k to go NAS-LON for a total of 37.5k. Continuing the dummy booking, this award priced at 37,500 AA miles and $306. So what’s the problem with this award that is pricing it as two awards? Let’s refer to the four rules for stopovers on AA awards.

The four rules with which stopovers on AA awards must comply:

1) Stopovers must occur at the North American International Gateway City. The North American International Gateway City is the last city in North America you fly out of on awards to other regions from North America. On awards from other regions to North America, the North American International Gateway City is the North American city in which you first arrive. North America is defined as the 50 US states, Canada, Mexico, Bermuda, Bahamas, and the Caribbean.

On this award, the last city we finally leave North America from is Nassau, Bahamas. I made sure to find a day with direct availability on the BA flight from NAS-LHR. My full routing was LAX-IAH-MIA-NAS//NAS-LHR. As you can see, we don’t leave AA’s definition of North America until the NAS-LHR leg, so NAS is the North American International Gateway City. No problem here.

2) The stopover must be part of a routing that does not exceed AA’s Maximum Permitted Mileage for your origin and destination by more than 25%. Maximum Permitted Mileage (MPM) is a number of miles that the airline puts on all possible city pairs, and AA awards can exceed it by 25%. MPM is not the direct distance between two cities; it is usually a larger number. You can find the MPM for a city pair on Expert Flyer, the KVS tool, or by asking an AA agent.

I looked up the MPM on AA from LAX-LHR on expertflyer. The MPM is 6,538, so we can fly 25% more than that or 8,172 miles. Our routing is 6,869 miles. No problem here.

3) The airline that operates the flight that connects the two regions must have a published fare for your origin and destination city pair.

BA operates the region connecting flight NAS-LHR, so BA must have a published fare from our origin, LAX, to our destination, LHR. BA has a direct flight from LAX to LHR, so we know BA has a published fare between the two. No problem here.

4) A stopover’s length is limited by the fact that all award travel must be completed within one year of its booking.

In my example, the travel happens in April 2013. No problem here.

There don’t appear to be any problems, and it looks like this itinerary should book as a free stopover in the Bahamas and cost 20,000 miles. But that’s not how treats it.

To figure out the problem, I also attempted bookings of free stopovers in Kingston, St. Lucia, and Providenciales. again tried to charge 37,500 miles for those itineraries instead of pricing them as free stopovers on a 20,000 mile award.

I don’t know exactly why this is happening. The most logical possibility is that AA doesn’t consider those Caribbean islands to be part of North America for International Gateway purposes. But this makes no sense, since they are explicitly part of the definition of North America. Furthermore, NAS-LHR prices at 20,000 miles, the North America price.

That leads me to believe, as my analysis suggests, that these are perfectly legal routings and should price at 20k miles, but is making a mistake. If I were in the US, I would call AA to see what a phone booking priced at. If the agent told me the price was anything other than 20k, I would politely inquire why and contend that it should price at 20k.

For me it’s a mystery. If I uncover why these awards with Caribbean stopovers are not pricing as free stopovers, I’ll let everyone know. And if you have any suggestions why they are pricing as they are, let us know in the comments.

Earn 60,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening.

Just getting started in the world of points and miles? The Chase Sapphire Preferred is the best card for you to start with.

With a bonus of 75,000 points after $4,000 spend in the first 3 months, 5x points on travel booked through the Chase Travel Portal and 3x points on restaurants, streaming services, and online groceries (excluding Target, Walmart, and wholesale clubs), this card truly cannot be beat for getting started!

Editorial Disclaimer: The editorial content is not provided or commissioned by the credit card issuers. Opinions expressed here are the author’s alone, not those of the credit card issuers, and have not been reviewed, approved or otherwise endorsed by the credit card issuers.

The comments section below is not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved, or otherwise endorsed by the bank advertiser. It is not the bank advertiser’s responsibility to ensure all questions are answered.