So ... little by little, I'm learning about all these great trips smart people put together that include visiting multiple countries in one shot using same amount of miles that it would cost them to go from point A to B and back.
If you could share your best mile redemption you've done with open jaw or multi day stop overs, I think it'll be greatly appreciated by people on this forum.
Something that another person can go right now and book (if available).
Some collect toy cars, others collect stamps ..... I collect miles.
Almost assuredly not what you are looking for, but the wife and I did a standard open jaw on Continental for 30 bday.
Into Paris, out of Rome. Trained/Bus in between over 15 nights. It was the best thing we ever did. Nothing like getting off the plane in Europe and having to restrictions except you better be in Rome in 16 days. Stayed in the smallest apartment ever in Paris (170 sq ft), with Walter in Gimmelwald, with the nuns in Siena among others (no hostels, of course).
Ditto--we also flew into Paris and out of Malpensa (Milan). We took the train (Chunnel) into London, spent a few days there, then did a cruise around the British Isles, took the train (TGV) from London to Brussels, stayed there for a few days, went to Amsterdam for a few days, then did a home-swap in Lake Como for 3 weeks, visited Switzerland for a few days (right over the border from Lake Como), then went on to Rome and Venice, ending in Milan for departure. We had three teens (family) with us, all high-school students, and let me tell you, those kids were wiped out by the end of the trip. (DL codeshare)
My best surprise was 2 years ago. Had booked an 2 business awards (1 with UA miles, 1 with CO miles) open jaw into Bangkok on Thai and out of Phuket on Thai/UA because we were going to make a few stops in between. But then we decided to just drive places from Phuket, and only needed 1 intra-Thailand flight. If purchased separately was looking at a few hundred in additional cost for the BKK-HKT flight. Was able to call back and add the leg for free - and in business class.
I was also able to do something similar a few years ago adding an extra flight between Brazil and Argentina on what was originally an open jaw into Sau Paulo and out of Buenos Aires (adding the leg for free).
Other open jaws (business awards) I have done in the past decade -- most are 2 week trips:
Into Rio and out of Santiago crossing Brazil, Argentina, and Chile in between
Into Warsaw out of Prague with Poland, Budapest, Austria in between
Into Melbourne and out of Auckland seeing Sydney, Brisbane, Cairns, and the south island of New Zealand
Into Rome and out of Palermo driving down the boot and around Sicily
Into Tel Aviv and out of Cairo
Into Paris out of Amsterdam with a fair amount of time in France then up through Brussels
I also travel to St. John's every other year and have been able to do stopovers in Atlanta or DC to see family or Puerto Rico to your around there.
Into St. Petersburg and out of Copenhagen with Moscow and Sweden in between is next this summer.
Yeah, it was a long time ago -- on Pan Am (30k mile ticket).
Fly Bos-Athens. Took a commuter flight to Corfu. Stayed for a week. Took the boat to Brindisi, then the train through Italy, France and Spain and Flew back from Madrid to Boston.
Pan Am left my luggage in NYC for 4 days, so I was stuck at a Greek beach, so I bought a couple of bathing suits and t-shirts. When I filed my report in Madrid, I was upgraded for the return. I received 22k miles on the trip.
Then I received a $500 voucher for the baggage problem.
Programs: AA, BA, UA, US Air, Spirit, Delta, PC Plat, SPG Gold, HHonors Gold, Club Carlson Gold, and more
My example would be useless to you since it can't be replicated, but still.
A few years ago, before AA killed stopovers outside the US, I took an AA flight from JFK to IGU with a 3-day stay in Buenos Aires. From IGU took an overnight bus to Curitiba, then the train down to a beautiful little coastal town (don't remember the name). Then onto the bus to visit Blumenau during Oktoberfest, then a few days in gorgeous Balmenario Camboriu before another bus trip to Porto Allegro and flying back to JFK. That was one of the most exhilarating (and exhausting) trips in my life.
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Programs: US Air Platinum,Delta Platinum,Starwood Platinum,Hilton Diamond,Marriott Silver,Hyatt Platinum
Little complicated. Two years ago, we got Swiss First JFK to Venice outbound and Athens to JFK return (cruise in the middle). Flights both stopped in Zurich. Had some free Hyatt nights and we decided to burn two of them with a stopover in Zurich for two days.
Unfortunately, US Air (whose points I used) allow either a stopover or an open-jaw and since we were already doing the latter, the stopover was not an option. Then I looked into making the return from Zurich and arranging my own transportation from Athens to Zurich. Something like $700+ one way or $450+ RT per person and throwing away the return ticket. Still too much.
Found a very cheap redemption on bmi awards on the same Swiss flight - something like 9,000 total for the two of us (18,000 Business class) but then discovered that there are no transfer partners to bmi. Seemed like a brick wall when I found out I could purchase bmi miles and they were having a 20% bonus on purchases. Cost a total of $375 if I recollect and that made the deal.
Sometimes you need to be creative and not give up!