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I get almost as much enjoyment from booking travel as actually being on a trip. It's exciting to look at a map of the world and imagine the places I want to go. Unfortunately, sometimes when you plug in those exotic destinations, the browser doesn't always show the prices or routes you want to see. Such was the case last week when I started trying to book a flight to Europe.

During one of Norwegian Cruise Line's recent "book by midnight" deals, I found a great rate on a cruise sailing from Venice to Barcelona. Already reasonably priced, the cruise came with an added upscale dining package and unlimited drink package as free perks, making the deal even sweeter. I booked the cruise and figured I'd worry about getting to Europe later. Big mistake. The main problem? I had to get to Venice and then home from Barcelona, and those "open jaw" trips can be more expensive than a round trip ticket to the same city. Skyscanner has been a pretty good search engine for me, but the best deal I could find with this itinerary cost nearly $1200 from Houston.

I've been to Europe a lot, and I usually never pay anywhere near $1200 to get there. My go-to airline is usually Turkish Airlines, which offers great service, a fun stopover in Istanbul, and a price that's usually hundreds of dollars cheaper than the other carriers. This time, however, that wasn't the case. I was pretty sure I had seen a $750 deal on Expedia with Turkish, but by the time I was ready to book, the price had increased by $500. And while I thought I'd enjoy a day in Istanbul, I was chagrined to find they were charging $100 more for that perk this time. I tried multiple sites at random times over the course of several days thinking I might have just picked the wrong day to book, but no matter where I looked, I couldn't replicate that price.

Not wanting to pay more than $700 for flights, I decided to get creative and find a way to get them cheaper. Skyscanner has a feature that allows you to plug in the departure city and the dates you're traveling while allowing you to leave the destination blank. Munich popped up as the cheapest destination in Europe; I found I could get there for around $750. That was more reasonable than $1200, but that meant I still had to get to Italy and back from Spain.

It's about an eight-hour drive from Munich to Venice so I hoped to take a train or rent a car. Alas, overnight train tickets were over $200—more than a plane ticket! Driving a car from Munich to Venice meant a $650 drop-off charge. A flight with Ryanair, the cheapest airline in Europe, was inexpensive, but added baggage fees and a return trip from Barcelona actually saved very little money. Frankfurt appeared to be a better option since the fares were just slightly higher, but it had long stopovers. Paris was too expensive, period. Barcelona was a possibility, but the flight had two stops including one in Morocco—an entire extra day would be wasted—and it wasn't even a long enough stop to leave the airport.

I had flown to Europe in April with Wow Airlines and the prices were ridiculously low. Unfortunately, to get those low fares, you have to leave from Boston and stop in Iceland, and, in any case, they weren't flying on to where I needed to go. My trip to Boston had worked out nicely before when I went to Amsterdam with Wow, however, and I was still open to doing the same thing again in another city. If I could get to New York, maybe I could get a cheap trans-Atlantic flight to London or Paris and then get to Venice with Ryanair. It turned out that New York wasn't any cheaper, nor was Baltimore or Boston. It was a futile battle. I started thinking about other popular departure cities. What about Miami?

When I plugged Miami into the search engine, I couldn't believe what I found. A flight to Venice and back from Barcelona for $525! I had to sort through the flights that had long layovers or weird connections, but a Portuguese airline called TAP Airlines was offering flights for less than half and with only a two-hour layover in Portugal. It was perfect.

Norwegian Airlines was the carrier back to Miami so I decided it might be smart to look at the baggage allowances. I don't normally check my luggage, but with a two-week cruise, you really have to consider a little baggage unless you want to look like a stowaway on the ship. Norwegian Air charged $180 to check two bags. Sneaky devils! You've got to read the fine print or you'll be pulling out your credit card at the airport. TAP's policy, on the other hand, included one bag for no extra fee. I looked through my list a few more times until I found a flight with the same airline and at the same price as its Norwegian counterpart. This one stopped in London for three-and-a-half hours—just enough time to go grab some fish and ships and a pint of Bass Ale. I jumped on the flight as soon as I had triple-checked my dates, names and everything else, and was pleasantly surprised to find no hidden fees at the end. I booked it through eDreams, which had some tricky charges when I had tried to book with them before. They've obviously cleaned up their act since then, and ended up being the cheapest website to book my itinerary by at least $50.

Now I had to get to and from Miami. I found a flight to Miami with United Airlines for $50. Unfortunately, coming back was $160. I grabbed the cheap one-way and decided I would try to find a less expensive way of getting back. I tried for several days, but I could find nothing less than the fare that was over triple of what I paid to get there. It was Thanksgiving week, so prices were higher. I knew I was going to be renting a car because I would have to fly back the following day and I wouldn't be happy waiting around in an airport. If I had a car, perhaps I could drive to Orlando or Tampa and save some money. Spirit was having a sale on Tampa it seems and I found the flight back for $40 plus $21 for luggage.

It's a four-hour drive to Tampa, but I saved $200 on two tickets. Besides, The Dali Museum in St. Petersburg has long been on my bucket list and the way I figured there was a whole day to drive there, visit friends, and see some weird paintings.
I added it all up and I got everything for under $700. Mission accomplished! I get to stop in England and run around for a couple of hours, and I also get to Venice a day earlier than the Turkish Airline flight, leaving me an extra day to drive to Florence and see David and a couple other things on my list I missed last time.

The moral of the story is to take your time and find a good deal. You'll learn a lot about travel by trying different sites and experimenting with different departures and stopovers. Don't be a prisoner of your own city's airline deals. Don't limit yourself to flying into the closest airport. The money you save can pay for another trip. Just like this one. Two tickets for the price of one! Book your travel outside the box.

As I write this, I'm looking at a trip to Suriname in a few months. From Miami, it's $355. From Houston, $6000! Yeah, that's a big difference.

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