Italian Vacation Diary: Prologue

After a successful Outer Banks trip in 2016, Natalie, Paul, Stephanie and I tossed around the idea of the four of us doing an Italy trip together. The next year both of us couples bought houses and Natalie and Paul were unable to attend the follow up OBX trip so our Italy plans had become unknown. After settling in our new homes we had a chance to talk and we were all in favor of keeping the Italian dream alive. The planning commenced.

We decided that the next spring would be the target time and spreading it over Memorial Day would give us an extra day of vacation to play with. Word soon spread that we were going to Italy so it was expected that we would have some envious outsiders. Paul, Natalie, and myself work at the same company so we had a lot of time to think up ideas at work. Our coworker Mike quickly got word that we were planning this Euro-trip and expressed how he and his wife talked about going to Italy for a honeymoonesque getaway. We accepted Mike and his wife Alaina (who coincidentally works with my mother) into our travel group and began planning the serious details.

One late summer evening the six of us gathered at Paul and Natalie’s house and had a whiteboarding sessions of what and where we wanted to see. I was very ambitious with all the cities and landmarks I wanted to visit since this may be my only visit to Italy. We soon devised a plan to start in the north and work our way south. This was going to take a lot of driving and a lot of time.

As the autumn leaves began to fall our anticipation rose. It was still too soon to act on anything as flights were not available. By the end of the year we had pretty much solidified our plan as follows: Fly to Venice, travel south to Rome, maybe hit Pompeii before making the trek to Sicily. Easy enough right?

Fast forward to New Year’s Eve 2017… we booked our long and expensive transcontinental flight. We were leaving from Pittsburgh, stopping by Atlanta, and landing in Venice the next morning. It was going to be more than 9 hours on a plane, which was about 5 hours more than my longest flight ever. While I was nervous about the flight the once in a lifetime trip excitement conquered all.

After the flights were booked we set our sites on accommodations. We were going to stay in AirBnBs throughout the country as sleeping six in a house was much more affordable than hotels. Mike and Alaina decided that they would parts ways shortly after Rome and spend some time alone before heading back to the states. This was just another cog in our elaborate machine with shuffling of rental cars, hotels, and AirBnBs.

Paul and Natalie are Italy veterans. Not in the sense that they served in the Italian armed forces, but that they’ve vacationed in Italy a few times. They even made the trip all the way to Italy to get married. Paul is the ultimate Italian tour guide as he fluently speaks Italian and has family members living in the country.

We met one last time in March to go over final details and talk about logistics. You could see the excitement building the more we talked. By this time we had all the rooms, cars, and flights booked and I was pretty far into my Italian language app. The only thing we had left to do was pack. Packing for a 15 day trip is very challenging the subject may come up again later.

I want to write down my experience as well as share it with the world as I feel this was a vacation that may not ever be beat. Lots of adventure and great memories to share. Stay tuned.

Read Chapter 1 >