Airline and hotel mistake deals were the lifeblood of my best travel experiences for a long time. I took plenty of trips I wouldn’t have otherwise taken, and they often pre-empted going places that were ‘on my list’ for places I hadn’t considered and I had really great experiences in the process.

But it’s sure seemed over the past two years that the best mistakes have dried up. Sure, I’ve heard of some glitches that haven’t been all that useful to me, business class fares originating in India or Malaysia that haven’t made sense for me to do or even to blog about since if I’m not finding them useful then it’s unlikely that a substantial portion of my readers will find them all that useful.

I do think that airlines at least have gotten much more careful and have better systems overall for detecting mistakes early on. And certainly there are folks who used to share deals but are now much more wary of doing so for fear that they won’t be honored if too many people get in on them. But in the past the very best ones were most often found by newbies rather than experts, by large numbers of people booking travel and then someone unpredictably stumbling upon a ‘find’. That seems to happen so much less these days, and 2009 feels sort of like when the really great run at this ended. I hope I’m wrong.

Ultimately my approach to deals when they came along was to make a booking, it was up to the travel provider whether or not it would get honored but if it was I certainly wanted to be along for the ride. If not, I didn’t complain, but most of the time luck was on my side.

While I’ve had great deals at places like the Intercontinental Tokyo and the Renaissance Seattle, there are a handful that I consider to be the very best mistake deals of the past 10 years.

Mexicana ~ $55+tax business class fares from their US gateways to Puerta Vallarta (summer 2002). This was the very first mistake fare I jumped on.

British Airways $20+tax World Traveler Plus fare from several US cities to several points in Europe (fall 2002). I missed this one while I was on the beach in Puerta Vallarta.

Conrad Bangkok $51 Presidential Suite (Summer, 2006). American Express travel priced this at $51. They honored it ‘as long as someone didn’t book and pay for the Presidential suite’ in which case they downgraded the booking. The best part is that some folks were able to combine it with…

The Le Meridien $33 Khao Lak Oceanfront Villa (December, 2006). The hotel published its 3 and 4-night discount rate plan in Ugandan Schillings instead of US dollars. That made a ~ $1500 a night 3100 square foot 2-bedroom Oceanfront Resident with Private Pool 60 cents per night. The hotel determined that they wouldn’t honor the rate, but offered $50 per night (with third night free, thus effectively $33.33/night) insead. And the rate included tax and breakfast, the latter normally costing more than the room rate itself. (Currently, a combination of Thailand’s tourism problems, the world economy, promos, and off-season make it possible to secure this room for ~ US$350 per night, which I’d regard as a value.) Some lucky souls timed their Khao Lak Ugandan Schillings trips to coincide with Bangkok travels, combining a an Oceanfront Villa stay with a Conrad Bangkok Presidential Suite stay.

$3 Hilton Tokyo/Osaka (November, 2005) Expedia displayed rooms at the Tokyo and Osaka Hiltons without the last two zeros in yen, so instead of ~ $200 a night for a standard room and $300 a night for an executive rooom (complimentary breakfast, evening cocktails, internet) the rooms became $2 and $3 respectively. Expedia did cancel some bookings but honored a good many as well. This was the first hotel mistake rate I benefited from.

Hilton Moorea Lagoon Resort $120 Overwater Bungalow with Breakfast and Dinner (January, 2009) When Hilton took over management of three French Polynesia properties from Starwood (the former Sheraton Tahiti, Sheraton Moorea, and Bora Bora Nui) I wasn’t surprised that they had currency conversion issues. Bora Bora Nui itself had currency issues when it first went online, creating a famous mistake rahe that wasn’t honored (when the hotel sent a mass email to notify guests of its decision, they failed use the Bcc: filed and violated Starwood’s privacy policies so everyone that booked the rate received 10,000 Starpoints as an apology if I recall correctly). Hilton priced the Moorea property in Congolese Francs (CDF) instead of French Pacific Francs (CFP or XPF). That made a $1000 a night overwater bungalow a bit over $100 with meals included. Initially Hilton refused to honor, but then relented for those willing to convert their cancellable stays into prepaid stays (the prepayment naturally scaring away those not certain to use their reservations).

United Business Class to Auckland via Sydney for $1100+tax (Spring 2007) United loaded a C fare, which means full business class, so availability wasn’t an issue. And it was a weekend, so the fare lasted for days. It was also upgradable to first class for the US-Sydney flights, with onward travel to Auckland on other airlines.

Intercontinental Bali Imperial Villa as a reward night so just 30,000 Priority Club points. (2006) Priority Club long had an issue with hotels loading all room types available for award redemption, and this was certainly one of the very best ones in that overall mistake genre.

Colombo, Sri Lanka to New York JFK one-way for $1100 in business class (Fall 2007) This was a great fare, but tickets departing Colombo were often cheap. What made this an amazing mistake fare was that it lacked any routing or maximum mileage restrictions, which meant that folks could fly on a ton of different airlines, all over the world, as long as they started in Colombo and the ticket concluded in New York. Folks flew well over 20,000 miles one-way.

And the Number One All-time Mistake Fare, Both for Value and for Pure Drama…

Alitalia $33+tax business class fare to Larnaca, Cyprus (April 2006). The fare permitted stopovers in Italy in both directions and required departing from Toronto. The intention was to file a $3300+tax business class fare. Initially Alitalia refused to honor the fare and began cancelling itineraries. They got pushback from some Orbitz lawyers, presumably over the unilateral handling of the situation. They agreed to honor the fare, but reconstructed itineraries to remove stopovers. In some cases travel dates were changed significantly. Then they conceded that was problematic, and began restoring itineraries to their original, but in some cases there was no codeshare availability on the flights between Italy and Cyprus (which were operated by Cyprus Airways) so people were rebooked on different dates, in a different class of service, or found themselves without any flight between Italy and Cyprus at all… Or flying to Cyprus with no way back (such folks were dubbed “the swim team”). This mess was given to one amazing staffer in Alitalia’s New York office named Nicolo to fix. The deal became that these tickets were fully changeable — once. You could change your dates (time of year even). You could change your routing. Add or delete stopovers. The only requirements were that you actually had to fly to Cyprus (a handful of folks circumvented this early on dealing with Alitalia’s Canadian office) and once reissued your ticket became non-changeable.

What other mistake fares deserve to be on this list? When you hit the comments, please be sure not just to list other mistake fares, but make the case for its inclusion — explain the value and why it merits being on the list instead of one of the items I preferred. I considered adding the $28 W Times Square rate or the $2 US Airways fares to Hanover, New Hampshire. But those didn’t seem to quite make the cut. Neither did the $200 first class fares on US Airways to St. Croix. But this is a top ten list, after all!