Caribbean and Europe American Airlines AAdvantage
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From Caribbean in Winter + to Europe in Summer for 20,000 American Airlines miles TOTAL

Update: With recent changes, American Airlines no longer allows stopovers on its awards and the following booking is no longer possible. 

American Airlines’ AAdvantage has an amazing stopover rule within North America. It essentially lets you add a segment to anywhere in North America for free. Fortunately, Mexico and the Caribbean are both part of the North American region!

Caribbean and Europe American Airlines AAdvantage
Visit a Caribbean beach and a European city all on one award!

The American Airlines award chart charges 30,000 miles for a one-way flight from North America to Europe in summer. It also charges 17,500 miles to fly to/from the Caribbean in winter. Theoretically, you should be paying 47,500 miles for both segments. But we can do better than that! We can actually do the whole thing for 20,000 miles. It all comes down to finding the right routing.

So… in case you’re thinking about going to Europe this summer, you can think about tacking on a trip to the Caribbean (or anywhere in North America) to make the whole trip 10,000 miles cheaper than just going to Europe.

Overview

In our strategy, we combine two aspects with American Airlines awards:

  • American Airlines allows a free stopover in the North American gateway city on an award between different continents.
  • The AAdvantage award chart only charges only 20,000 miles when flying between North America and Europe during the off-peak period between October 15 and May 15.

A stopover can be created by connecting a segment back from the Caribbean to your home city and then from your home city to Europe. The date of the award is decided by when the award starts. The date you fly to Europe is completely irrelevant; the only restriction is it must be within a year from when the ticket is issued. If you start the award in the Caribbean between October 15 and May 15, the entire award will price at 20,000 AAdvantage miles.

In my example, I will explain how you can fly from Aruba to Los Angeles in February and also from Los Angeles to Berlin in August all for 20,000 miles! Of course, you’ll need more miles to get back, but this is big optimization compared to 47,500 miles.

Free Stopovers in North America

American Airlines allows a free stopover in the North American gateway city on any transcontinental award between North American and another continent. Here, gateway city refers to the city from which you enter or leave the region.

Examples:

1. Miami-NYC-London-Paris: the gateway city is NYC and a free stopover is allowed in NYC only

2. Grand Cayman-Miami-Madrid: the gateway city is Miami and a free stopover is allowed in Miami only

3. Aruba-Dallas-Los Angeles-Berlin-Oslo: the gateway city is Los Angeles and a free stopover is allowed in Los Angeles only

4. London-NYC-Hawaii: the gateway city is New York

Note that all the above routings go through different airports. You are actually not allowed to have a one-way routing that goes through the same airport twice. The idea is that everything on your routing should be (loosely) on the way to your destination and going in a loop means you’re going out of the way.

5. Aruba-Dallas-Los Angeles-Dallas-London: this is not a valid one way-routing as it goes through the same airport twice

Adding free one-way trips within North America

If you are lucky enough to live in a city in North American between which American Airlines or its oneworld partners flies directly to Europe, you can stop over for up to a year from the time your ticket is issued.

For example, if you live in Los Angeles, American Airlines flies directly to Berlin on air berlin. You can even search for award flights on air berlin on AA.com.

If you include the flight from Los Angeles to Berlin in your routing, you can add either before or after a flight anywhere to North America.

Some examples:

1. Aruba – Miami – New York – Berlin is considered a one-way trip from Aruba to Berlin and allows a stop in New York up to a year

American Airlines AAdvantage Caribbean
A route from Aruba to Berlin allows you to stop in New York for up to a year

2. Berlin – Los Angeles – San Francisco is considered a one-way trip from Berlin to San Francisco and also allows a stop in Los Angeles for up to a year

The one caveat is that the overseas carrier must have a published fare that includes your itinerary. I personally have been able to get around this rule by asking enough phone agents to override it and it rarely comes up, but it’s good to be aware of it.

American Airlines off-peak award season: 20,000 miles to Europe

American Airlines AAdvantage award chart has certain off-peak award pricing during their less-busy times on certain routes. Fewer people visit London in December than do in July so it makes perfect sense the awards should cost fewer miles. With Europe, the off-peak period is Oct 15 – May 15.

American Airlines AAdvantage off peak dates
American Airlines AAdvantage off peak dates

While one-way award tickets with American Airlines AAdvantage normally costs 30,000 miles the rest of the year, the award ticket only costs 20,000 between October 15 and May 15.

American Airlines off peak
American Airlines award prices to Europe from North America

If you’re booking a flight from Aruba to Berlin in April, it still only costs 20,000 miles. Aruba is in North America and this is a ticket from North America to Europe.

From the Caribbean in Winter and to Europe in Summer for 20,000 miles TOTAL

We now know we can book tickets with American Airlines AAdvantage miles with free stopovers within North America. We also know that between October 15 and May 15, we can fly to Europe for 20,000 miles. So here’s the part that pulls it all together and lets you travel from the Caribbean in winter and to Europe in summer for 20,000 miles total:

If your one way trip in North America starts between October 15 and May 15 and ends in Europe, the price for the entire one-way trip is 20,000 miles!

Now we’re in business. Putting together our Aruba-Los Angeles-Berlin award will only cost 20,000 miles simply because you leave Aruba during the off-peak period.

American Airlines AAdvantage Off-peak
From Aruba to LAX in February and to Berlin in August for 20k miles total!

Booking a ticket with stopover in North America on AA.com

To actually book the ticket on AA.com, you need to go to Plan Travel and then Flights. Under the AAdvantage Award tab, select the Multi-city button and type in your details. Here, I am looking to fly from Aruba to Los Angeles in February and from Los Angeles to Berlin in August.

American Airlines Multi-city award search
American Airlines multi-city award search

Once I click Go, I will get a date selector for the first segment and the second segment. The whole thing is priced as an award from Aruba to Berlin and it also says:

This international award allows a stopover at Los Angeles – LAX for no additional miles. Mileage required for both flights is displayed on the Award Legend for the international flight.

Once I select both dates and flights, the whole award will price to 20,000 American Airlines AAdvantage miles + taxes.

American Airlnes AAdvantage Off-peak award search
Date availability for the flight from Aruba to Los Angeles. It is shown — since this segment costs no additional miles over the transcontinental segment
American Airlines AAdvantage off-peak award search
Date availability for segment from Los Angeles to Berlin. The 20,000 miles shown is the cost of both segments together.

A final note

You don’t even have to come from the Caribbean in Winter. You can start your trip in Hawaii, Mexico, Canada, Los Angeles, Seattle. These all work as long as you find the non-stop flight from your home city to Europe. I just used the Caribbean as an example because it’s where I personally want to go every winter!

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53 Comments

  1. Very helpful. I am hoping to get to Israel in December which is peak for TLV, but now will consider doing it by taking AA to Europe and then perhaps another ticket from somewhere in Europe to TLV. A friend suggested Istanbul to TLV as a cheap way to get there. Anyway, lots of food for thought here. Thanks.

    1. That’s a good idea! Fares to Tel Aviv can run up to $1500 in winter from the West Coast and $1000 from East Coast depending on your dates. Deals do come and go, but hard to rely on. Berlin, by the way, is one of the easier cities to get to with AA miles since Air Berlin flies to Berlin directly from a few US Cities. Air Berlin also has sub-$400 direct fares to TLV for even the most popular days like weekend before Christmas and New Year’s day flights. AA also doesn’t charge any fuel surcharges on air berlin like it does on British Airways. Istanbul may also be worth checking out, but as oneworld doesn’t fly there directly from the states (Turkish Airways is *A), it will probably be an extra connection. Good luck with planning your trip!

  2. Thank you Miles Prof! I’ve seen this discussed in other forums, but never so clearly as you’ve laid out here. I need to start piecing something together for Spring of ’14 from LAX to Europe through Turks & Caicos – any advice for me?

    1. Glad the post was useful! If you want to do a stop in Turks and Caicos on the way to Europe, I believe you are limited to including the British Airways flight to London in your itinerary as no other oneworld partner flies directly between Europe and PLS. This flight is quite infrequent and hard to find award availability with, however. In addition, American Airlines charges fuel surcharges when flying British Airways of a few hundred dollars, but if you can find award space, it may be worth it given how much tickets usually cost from Los Angeles. Providenciales is often voted among the world’s best beaches so I hope your trip works out!

  3. The mile redemption to get to Aruba + from EU to stateside is how much in addition to the 20k for this itinerary? I get 67,500 (17,500[peak] from US to AUA + 30000[peak] from EU to US). While if someone does 2 separate itineraries: US-AUA (35,000) peak + US-EU (60000) peak = 95k

    I think my math is correct.

    1. That’s correct. If you want to get a ticket to the Caribbean and from Europe with American Airlines miles during these peak times, you will pay 17.5k + 30k miles. But, hopefully, you can find better ways to get those other segments than to use miles for one way trips with no stopovers like that :)

      For example, when I flew from Grand Cayman and to Rio with a stopover in New York, I then combined my trip back from Rio in BusinessFirst on United with a roundtrip to Europe. Rather than using 50,000 miles to get back from Rio to New York, I used 80,000 miles to fly BusinessFirst from Rio to New York, Busness from New York to Greece and then economy from Greece to New York. It’s all about maximizing your segments and miles every time.

      So if someone wants to return from Europe with AAdvantage miles, hopefully he has another North America trip in mind and can use his home cities as a “stopover”. Hawaii or the Caribbean again may not be a bad idea!

      1. Makes sense if you have ideas in mind. I mean you could potentially nest trips w/in trips w/in trips forever and ever…as long as you got the mileage for it, of course.

  4. Thanks for the info, I never knew!.
    Do you know if this 1 stopover rule applies to AA partner airlines. For example I have redeemed an Etihad Airways ticket using my AA miles from AUH-JFK. Could I have made a stopover in Europe for instance?

    1. You can use any airline in your routing, but the stopover can only be in the North American gateway city. Since I assume you are flying to JFK directly on Etihad, there are no North American gateway cities along the way. You could have added another one way trip from JFK to anywhere in North America, however, absolutely for free!

  5. Ok so I’m still relatively new to this–what do you suggest to do about the return trip? Or can you just do another one way for 20,000 but going the opposite way?

    1. Welcome to the miles game :) If you are returning from Europe between Oct 15 and may 15, then it’s 20,000 AA miles to return. Otherwise, it is 30,000 AA miles. This is just if you want a one-way trip from Europe to North America.

      But, again, you can try to think a trip or two ahead and combine that with a free one-way in North America, essentially doing what I said in reverse with AA miles.

      Or you can use United miles to return from Europe to North America and combine that with a roundtrip to the Caribbean or Hawaii. A one way trip from Europe to North America combined with a trip to the Caribbean is 47.5k United miles total or 50k United miles total for Hawaii.

  6. Using JFK and only AA can you route one trip to Rio or BA from either JFK or Miami and later an JFK to Europe (Madrid). We live on the east coast so we would use JFK as our stop over.

    1. That won’t work, unfortunately. Your route must follow (North American City – JFK – City on another continent) or the reverse. e.g. Miami – JFK (stop) – Madrid is ok, for example. You must start or end in North America. You can only have one non-North American destination on a single one way award if you want to use the free stopover.

  7. Ok I’m brand new to all of this so forgive me if these are stupid questions. I’m a little confused on the whole concept. I live in St. Louis and want to travel to Spain next summer. If I am understanding correctly I could purchase a one way ticket from stl to a gateway city (this is any city that flies directly to my abroad destination correct?)and then from that gateway city to Spain at a completelt later time at the same price as if I went from stl to gateway city to Spain all at the same time? So you then would need airfare from gateway city back to stl and then back to gateway city plus you need a way home from Spain. Would you buy a round trip ticket from gateway-stl-gateway and then just a one way ticket back from Spain? Again sorry if these are dumb questions and/or don’t make sense. Just trying to wrap my head around everything. Loving your site so far! Thanks

    1. When you say next summer, I assume you mean Summer 2014. If you are trying to take advantage of off-peak pricing, you can then do the following:
      1. STL – Gateway City between Oct 15 – May 15
      2. Gateway City – Spain in Summer
      The above ticket costs 20k miles as opposed to 30k if you start the whole thing in summer.

      You would then need a round trip ticket between STL and gateway city as well as a ticket back from Spain, as you said. You would spend 10k miles less, but you will be spending more miles or money on a round trip ticket to the gateway city, which may eat up the 10k miles savings cost unless you were planning to visit the gateway city anyway.

      Since you’re in STL, a good option may be for you to use ORD as a gateway city and plan a weekend trip to Chicago this winter. I know Amtrak routes between STL and Chicago are $50-$70 round trip, though it is a fairly lengthy train ride. Iberia flies to Madrid directly from Chicago, though you can’t search for Iberia award availability on the AA website (I’ll need to write a separate post for how to book flights on Iberia with AA miles!). You’ll need to search on the Qantas website for Iberia availability and then call AA and give them all the flight numbers to book your itinerary. AA also flies from Chicago to London and you can continue to Spain from there on British Airways or Iberia, both partners of AA. Summer award availability is a bit tough, but I usually do quite well when searching 11 months in advance. If I understood correctly and your trip is in 2014, best go plan in advance and grab seats as soon as they become available! :)

  8. Obsessed with your website and your detailed advice. Since I live near SFO, is there anything I can do from here or do I have to fly to LAX? I’m going to Romania in October (ideally, off-peak) and would love to stop by Hawaii in December. Does this mean that I will have to fly back to LAX to to go to HI?

    Thanks, you’re the best!!

    1. Glad you find the info here useful! :) Unfortunately, the only oneworld airline that flies from San Francisco to Europe directly is British Airways and they impose high fuel surcharges of hundreds of dollars so it’s really not worth it, in my opinion. To make the stopover work, you do have to use a gateway city and, in your case, the closest and easiest is probably LA. You can travel between LA and San Francisco for 4,500 British Airways Avios each way (though tickets tend to be not that expensive), but you can also travel to Hawaii from the Bay Area for 12,500 British Airways Avios miles each way if you can find a direct flight on Alaska Airlines. It may be worth it to spend 12,500 Avios miles rather than buying a ticket to LA given you can then go to Hawaii with no stop and that’s so much more convenient. Hope this helps! By the way, air berlin does fly to Bucharest so you can use your AA miles all the way to Romania.

  9. This is exactly what I did earlier this yr! I booked CUN-MIA in early May and MIA-MUC in Sept for Oktoberfest for 20k.
    There was some positioning I had to do from IAH to MIA but this saved me soo much money! Next yr I would love to do Aruba too. Just gotta figure out where in Europe I want to go :)

  10. If we’re not sure about the exact date of the GATEWAY->EUROPE segment, is it possible to change the date after booking, without incurring a penalty or having to pay extra points?

    I.e. if I want to fly PAP-LAX-LHR, and I know when I’ll fly PAP-LAX, but not LAX-LHR, and so pick a random date for the LAX-LHR segment, can I change that date later on?

    Awesome blog!

    1. Thanks for the blog compliments! As long as you keep the same carrier, AA will not charge you a change fee to change dates unless your new changed itinerary is within 21 days. I need to check whether it’s possible to change dates without an additional miles charge (I am not sure whether what I wrote about in this post may be some unintended online glitch that disappears once you start changing things over the phone); I do have an itinerary to Rio booked using a similar trick and I’ll see if I can change dates on it but keep the same miles level… probably tomorrow as I just got back from a vacation :)

        1. Thanks for the reminder! Things sometimes get a little out of hand when I get back from vacation. I actually just called and rescheduled that Rio award over the phone. Same 20k miles as long as you start in the off-peak period and no date change fees :)

          1. Great info! Thx for your post TMP!

            A quick question: if just change the date of the ticket, you won’t be charged as long as 21 days in advance of departure date?

  11. I am not following the part where I have to come back from Europe back to USA. At that time it will be in summer one way ticket which is almost same as full fair. Or which there is some cheaper options to get back from Europe back to some city in USA.

    1. You can use any other method to get back and, yes, 30,000 AA miles is one of them. I am only pointing out the potential savings on the direction there… which is extremely useful if you had already been planning a trip to Europe and can combine with prior trips for big savings :)

  12. If I’m reading the chart correctly this reduced mileage for Off Peak only applies to Economy Class, correct?

  13. Hi Miles Professor,
    What would you say is the routing for redeeming a free stopover if you are based in London?
    Places of interest are LAX, NYC, HNL, CUN

    Thanks!

  14. Thx! One more question though..

    If you have lax-jfk in January and jfk-cdg in June, can you change the dates of itinerary to CDG once travel has commenced? I guess UA allows so but not sure about AA.

  15. I’m looking to do a free one way in Jan 2014 from STL-NYC (JFK or LGA) stop over then fly to visot family in Dublin in summer 2014. Can’t I book a roundtrip initerary with the stopover in NY and still on spend 40k? Ex. STL-(LGA or JFK) stop over JFK-DUB-JFK? I need to get there and back for my family of 3 as cheaply as possible. Any advice?

  16. This is great! I’m still trying to grasp this and the “open jaw” concepts. We are flying to China in April. I tried to do something from Aruba to IAD/Dulles to China, but it didn’t work. Does this only work for trips to Europe? Is AA the best program for a China trip?

  17. Thanks for the post – we wanted to go to Greece with a spring break trip to carribean- maybe in summer 2015 (going to maui this summer – thanks for all of the tips/reviews!). It looks like only british airways and etihad are the only gateway cities in my area (DCA, IAD, or BWI)? is that correct? if so, how do i search award space? AA.com only seems to include AA and US Air flights?

      1. Do you know if this explanation still works. I am having a hard time getting it to work with 20,000 miles. I am trying to do a trip from Chicago to Europe in July and the free one stop in the Caribbean. Thanks

  18. I have Alaska miles, with American as a partner, of course. I see that I can go from Germany to Seattle, with a free flight to Maui (per your instructions) on the aa.com site. But I don’t see this option using Alaska’s site to book the rewards. Is it possible to book via the aa.com site using Alaska mileage number? Can I do it on the phone? Is that even possible?

    1. Hi! Maui is great! I was just there in December and had an awesome time! American Airlines and Alaska Airlines are completely separate programs with different stopover rules and you can’t use Alaska Airlines on the American Airlines website. Alaska Airlines also allows a stopover on international one-way awards, but then you must completely be able to book the itinerary on Alaska Airlines partners; as Alaska Airlines is not a member of oneworld, you can use American Airlines, but not air berlin for example.

  19. Thanks for putting the update on the top. Many other active bloggers don’t spend time to update or remove the information which could confuse or mislead unexperienced traveller.

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