My wife and I dreamed about the possibility of traveling to Europe since we were dating, but it always seemed so far out of reach. It remained a bucket list item for “one day” after we had a house and kids, a vague idea for an undetermined time in the future.

Then, one night I was browsing my favorite deal site,, and on the front page was an unbelievable find: round trip tickets for two from New York to Milan, Italy. The price? $900. That’s right, $450 a person for round trip tickets. That’s cheaper than a lot of domestic flights! We’re talking about upwards of a 50% discount off normal airfare rates.

We knew this kind of deal probably wouldn’t come around for a long time, and we knew that the window of opportunity for this kind of trip was realistically only a short number of years until we had kids. We talked about how it wouldn’t be the same if we took the trip with kids, how we’ve wanted this adventure for a long time.

Then, we talked about the more practical details. How much will it all cost? When would we go? How long would we go for? Could we get off work for that long? How far would this set us back on our goal of saving for a house?

We decided to go for it.

Thankfully, we had the cash on hand from saving toward a house and we decided that we would prioritize this trip even if it meant pushing back our house buying goal a bit.

Since my wife is working as a full time substitute teacher this year, getting off work was not a problem like it would have been for a regular employee. We planned for the first week of our trip to be over her Spring Break, so it was technically only a week off. I had carried over 5 vacation days from last year in case the opportunity for a big trip like this should arise.

We got our approval from work the day after we saw the deal, bought the tickets that night, and celebrated the fact that our dream was finally going to be realized. I’m glad we bought them that night, because if we had waited another day, the discounted tickets would have been sold out, leaving only the regularly priced tickets at over $1,900!

That was on January 20th, and our flight was booked for March 27th. This left us with only two months to plan out a two week trip covering Italy and Greece, both of which we knew almost nothing about, other than what we had seen in movies.

Now, it was time to let the preparation and planning commence!

We started off with renewing my wife’s passport because it hadn’t been updated with her new last name since we got married. In case you’re in a similar situation, you have to submit the DS-82 form for passport renewal along with a certified copy of your marriage certificate. The government will happily take $110 for the trouble, too. (If you’re traveling internationally for your honeymoon, however, you’re best off leaving your passport as it is until after you return home from your trip. The important thing is that your passport, driver’s license, and your ticket all match your last name).

After doing a bit of research, we wrote out a barebones itinerary including just the cities we wanted to visit, the days we wanted to stay in each city, and when we’d travel between each one. Packaged tours and down-to-the-minute planned days don’t appeal to us, so we decided to plan the whole trip ourselves. We wanted the freedom to hang out at cafes eating pastries or simply wandering the streets if we wanted, while being able to see the main attractions at our own pace.

With our basic itinerary in hand, we decided the next logical step was to book our major transportation: flights between Italy and Greece, and a ferry ride between islands in Greece and our lodging. The toughest part was organizing everything so that we would end up back in Milan to catch our flight back out to the States!

After several months, we had bulked up our itinerary with sites we wanted to see, restaurants we wanted to visit, hotels we’d stay in, and more. Side note: Google Maps can be used to create a detailed itinerary. You can see each hotel, restaurant, airport, and attraction on your map with each one listed in a panel. This allows you to visualize everything and also to be able to access them easily when you are overseas. Clicking a location from our saved itinerary and getting directions was a breeze while we were there!

Google Maps

In Part 2, I’ll fast forward to the exciting part – the trip itself – and fill in the details and numbers along the way. For our entire trip, we kept track of everything we spent to the best of our ability, so we hope it will be helpful to share for those of you who are looking to plan a similar trip of your own. We couldn’t find anything like this online when we were preparing, so we had to make our best guesses at the smaller expense details. Hopefully, by listing out our expenditures as we go, you’ll be able to better estimate a realistic cost of your own trip. Hang on for Part 2!