Favorite Past Mistake Deals: Toronto to Cyprus for $33

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Some of the moments travel enthusiasts live for is finding, and booking, a mistake rate on an airline or at hotel, enabling them to have an amazing experience for a fraction of the price. I’ve missed out on quite a few, but definitely had my fair share of deals. In the coming weeks I’ll be reminiscing about my favorite experiences.

The very first mistake deal I ever booked was in April 2006. $33 + tax business class fare from Toronto to Cyprus on Alitalia. When loading the fare, someone had left out the two zeros that would have made it $3300.

What made this so particularly great, is that the fare booking rules (and Alitalia’s subsequent handling of it) allowed you to have one stopover in each direction, which meant you could spend time in Rome or Milan, or as I did, both. What made it slightly complicated was that you were dealing with paper tickets that had to be Fed-Exed to their office in New York and then sent back.

Half my office wound up going to Cyprus that year. I booked 3 sets of tickets with all the friends who would agree to go, but only wound up taking one of the trips, over Thanksgiving. Our itinerary was Toronto to Rome (staying for 4 nights), Rome to Cyprus (3 nights), Cyprus to Milan (2 nights), then back to Toronto.

I used 20,000 United miles each to get saver awards to Toronto. To make sure weather didn’t affect our flight, we arrived 8 hours early and killed a mind numbing 5 hours watching an art exhibit of floating blocks while waiting for the Alitalia desk to open so we could check in and go through security and get to the lounge.

art exhibit in Toronto Airport

When we boarded, it was nothing special, but it was to me, since this was only my second experience flying international business. I was very excited by the amenity kits that had Bulgari. I was less excited by the somewhat snotty flight attendants who openly criticized my choice of red wine to pair with chicken in a heavy tomato sauce (they were wrong).

We arrived in Rome and took a cab to the 3* hotel I’d pricelined (at that point was still new to Priceline), only to discover that I’d misjudged distances and we were a good 1.5-2 miles from the historic downtown. Ooops. Fortunately there had been a leak on the floor they were going to put us, so they packed us back into the cab (at their expense) and put us up at a 4* very close to the Spanish steps.

We saw all the ruins, piazzas, the Vatican, and there was even time for a day trip to Pompeii.

Vatican ceiling

Keri Heels First Travel Streets of Pompeii

I was less excited about going to Cyprus, but once we were there, I fell in love with it. The people were incredibly friendly and staring at the landscape knowing it had been heavily populated for thousands of years fascinated me.

I’d found a very basic hotel on Orbitz for $26 a night including breakfast. It worked out even though it was only half staffed and closing for the season 2 days after we checked out.

The first full day we joined a tour where we startled everyone when they learned we were only visiting for two full days (we were also the only folks under the age of 50). I also got a kick out of telling them we’d picked Cyprus as our destination because it was the cheapest :).

The tour was fantastic! We saw archaeological sites, uncovering mosaics from thousands of years ago.

Cyprus Archeological Dig

Toured a castle that housed the Knights of the Templar.

Kolossi Castle Alitalia Mistake Fare

And concluded with a very lively wine tasting.

Cyprus Wine Tasting Limassol

The last stop on the trip was Milan, which I wasn’t very excited about. Fortunately, Lake Como was accessible by train, so we went from the flight to the train station and rode up. It was beautiful — the closest I’d ever come to seeing Switzerland (I’ll go one day). The first day was spent wandering around the town of Como and taking the funicular up to the top. (I had way too much fun saying funicular.)

Lake Como Funicular

Next day we took the boat around the lake, getting off for a few hours in the beautiful misty town of Bellagio, before heading back to the train station to overnight in Milan.

Bellagio Lake Como from Ferry

We arrived late and were so tired at that point we didn’t even try to see any sights, just crashed at our hotel near the train station until early the next morning when we headed to the airport to catch our flight.

What I remember most about my time in the Malpensa airport is the Alitalia business lounge was painted pink, and that I was openly mocked for wanting a diet coke at 10AM since I’d already been up for 5+ hours. Sadly I wasn’t in the habit of taking lounge pictures at that point.

The flight back was unremarkable, we landed in Toronto early afternoon and then had a dumb idea. We weren’t flying back to DC until the next day. Maybe we should rent a car and drive to Niagara Falls! So I rented a car and promptly sat in rush hour traffic for 2 1/2 hours as jetlag mercilessly crept in. We had to turn back 30 miles from the Falls because I was afraid I wasn’t going to be able to keep my eyes open for the drive back.

Fortunately the Sheraton Toronto Airport was extremely comfortable, so when we arrived in DC the next day we had almost caught up on our sleep.

Did any one else get in on this deal? Where did you go?


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Living for the little (and big things) that make life so fun, especially mistake deals and crazy last minute weekend mileage runs across the world.


  1. Ren

    October 29, 2013 at 12:41 pm

    Nice! Who’s the dude you are toasting with in the pic? You’d make a nice couple! (unless it’s your cousin or something 😉

    • Keri Anderson

      October 29, 2013 at 1:37 pm

      That’s funny (and fortunately not creepy)! He was my boyfriend at the time.

  2. Heather @ pass the dressing

    October 29, 2013 at 2:29 pm

    Miss the days of ridiculous mistake fares.

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