With some careful planning, it is possible to take a trip to Europe (perhaps anywhere, but I only have experience with Europe) for around $2000 per person–or less! Here are some basics on how I was able to achieve this:
Select the timing of the trip.
Summer will be more expensive as it is considered “peak season” for tourists. I have found that starting your trip in late February or early March tends to be the least expensive. With this, some sites are not open due to weather. Other sites are not as impressive due to weather. So, if there is some site that you are desperate to see, make sure it is going to be open during your time line before you book anything.
Flights.
Once you know when you would like to travel, and how flexible your schedule can be, it is time to book your flights. If you know when you want to travel, but are unsure of where you would like to travel, my favorite tool is Kayak Explore. Put in your home airport, time frame, and budget and see what’s available. (NOTE: as mentioned on most travel planning sites, Wednesday really is the best day to get deals on flights.)
When planning my most recent trip, I set up email alerts on a couple of websites so that I could keep track of the flight prices without constantly running a search myself. I was able to get round trip tickets from our small airport to Munich for $540! (I could have flown first class round trip for $1200, but opted to fly coach–when I was checking on the flights later, I saw that coach tickets were then going for $1200 or more, so flights are all a matter of timing to get a good deal.)
Another tool many online search sites will allow you to do is look at a graph that will show the least expensive days to fly. When inputting your ideal travel dates, select “+/- 3 days.” If you are a bit more flexible on your time, this could save you a bundle.
Itinerary.
Now that you know what days you will travel, your destination, and the estimated arrival time at your destination, it is time to decide what do do at your destination! How many places do you want to visit? How much time do you want to spend traveling from site to site? Is it cheaper to travel by train, rent a car, or fly?
I am a huge fan of spreadsheets, so I plan multiple itineraries for the trip on a spreadsheet and then decide based on which allows me to see the most things for the least amount of money and using my time efficiently (so as to be able to enjoy the sites and not feel rushed). An example spreadsheet is at the end of this post.
Once I have the skeleton of the spreadsheet worked out, I open a second window (I do prefer using a computer with dual monitors for this–makes it easier to see everything, but it is possible to do on just one screen) with Google Maps. I center on where my flight will be landing and use the map to figure out the most efficient way to get around.
Example: For this trip, I knew I would be wanting a day of skiing, but I didn’t want to go more than 2 or 3 hours from the airport (or previous stop on the itinerary–more on that later). It also had to be within 1 or 2 hours of the next stop on the itinerary. I also had certain people and places I wanted to visit while I was there, so my list looked like this: ski (decided on Obertauern, Austria due to its location and price), Salzburg, Munich, Rothenburg ob der Tauber, Berlin, and Magdeburg. If time: Liechtenstein, Switzerland, Paris, Prague, or Stuttgart.
Now for the fun with spreadsheets! In the column for the details of the day, I entered the different places based on when I thought it would be feasible to get to them. Eventually, Paris, Prague, and Stuttgart all got knocked of the list because of time. Soon, I narrowed the trip down to two possibilities: one with skiing at the beginning of the trip, the other with skiing at the end of the trip. Since a friend was coming along on this trip, I consulted with her to make the final decision. We ended up deciding on the itinerary that had skiing at the beginning of the trip (she doesn’t ski, so she figured it would be a good chance for her to acclimate to the time change).

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