A First Trip to Italy (and Europe)

Posted July 19th, 2014 by Tom
First Trip to Italy

The year was 2014, and this was going to be our first big trip to Europe. Originally, the plan was to go to Greece. Athens and the Greek islands sounded very appealing. The idea of warm temperatures and Mediterranean breezes fit nicely with the thought of a relaxing vacation. However, 2014 was a tumultuous time for Greece, with a shaky economy and the threat of widespread strikes. Italy was the closest both geographically and culturally to the Greece idea, offering both the stunning architecture and the great weather. We knew it was just going to be the two of us, and that we wanted to do some sightseeing. Some light hiking was fine, but no Tour de France type activity.

Where to go in Italy?

Most people think of the Roman Colosseum or the Leaning Tower of Pisa when they think of Italy. We watched some videos on YouTube, with Rick Steves being our favorite. I was reading reviews from travel websites on a daily basis. Italy has so many varied locales: Rome, Venice, Florence, Milan, Naples, Sicily, even Tirol. How do you choose? Diane and I are both wine drinkers, so we were more drawn to Tuscany than to Rome. The more we read and watched, the more we were drawn to Tuscany. We were already big fans of the movie “Under the Tuscan Sun” with Diane Lane. That became the focal point for the vacation: Tuscany. Should we try to see more?

Many folks are drawn to the European “blitz” tour – how many cities can you see in a week? Two weeks? That sort of travel sounded overwhelming to my senses, my patience and my lifestyle. We’re sort of laid-back people. I didn’t want Italy thrown at me like water through a firehose and I wanted a feel for the culture in each location we chose to go to and wanted to feel like we had ‘seen’ that particular place as well. We decided that due to job obligations and pets, that we would limit our trip to eleven days. Travel to and from Italy was going to account for full days, leaving a total of nine. Based on what I read, nine days allowed for visiting three areas of Italy for three days each without rushing. So… what three areas? Rome seemed like a no-brainer, followed by Florence. Three days to see Rome. Three days to see Florence. Three days under the Tuscan sun.

My wife was convinced by her friends that any trip to Italy was not complete without seeing the Cinque Terre, also known as the Italian Riviera. After much discussion, I relented and returned to my reference materials to absorb as much as I could about this relatively unknown (to me) part of Italy. It turns out that the Cinque Terre is relatively close to Florence, so it fit nicely with the idea of a Tuscan-centric visit. It meant changing the itinerary, so I considered what might happen on a future Italian trip.

I decided to do the unimaginable and drop Rome, since that future Italian trip would then include Rome along with cannot-be-missed Venice and/or Naples. There were a lot of concerns about pick-pockets lurking the streets of Rome as well. I would probably be better prepared for such once I was more seasoned as a European traveler. The outcome of these adjustments was that the flight would stay to Rome (changing to Florence was outrageously expensive), but Rome would simply be a place to arrive to and depart from.

Change of process – decide definitely where you’re going before booking your flight reservations.

The Time of the year to Visit Italy

General locations are picked out, so what’s the next thing to do? Picking a timeframe, of course! It was January, so I knew I needed at least a couple of months to get some decent reservations. Projected sun and temperatures, mixed with the need to stay away from peak tourist times, gave a range of April to June. The middle of that seemed like a good idea, and thus resulted in an early May choice. May 1st is the Italian Labor Day holiday, so probably not the best day to arrive. Trying to squeeze in a couple of weekends in so as not to completely squander all of my vacation days, the choice was then to leave the USA on May 1st, arriving in Rome on the morning of May 2nd.

How to Travel to Italy

Checking with multiple airlines, Delta appeared to offer the best price for the trip. Round trips were cheapest, and I was eager to get things going. I booked the flight to Rome, as it was by far the least expensive Italian airport. Unfortunately, turned out to be a bit premature, due to…

Our Itinerary to Italy

It made sense to me then, and it still does, to start with the Big City Experience first. The Big City, in my sweeping generality, would be most accustomed to foreign visitors with lots of silly questions and tend to speak English. In this case the Big City would be the capitol of Tuscany. The population of the greater metropolitan area of Florence at the time was roughly 1.5 million people, so that allows for a lot of questions to people who are accustomed to US travelers.

A 2.5 hour drive, according to Google Maps, could get us to the Cinque Terre. When I started checking on hotels in the area, much was already booked. Luckily I was able to secure a beach-front hotel in Monterosso al Mare.

A 3.5 hour drive could then get us from the Cinque Terre to the heart of Tuscany. I had already decided, thanks to Rick Steves, to base this part of the trip in the small but beautiful hillside town of Montepulciano.

Thus the final itinerary for our vacation to Italy was:

  1. Fly into Rome’s Fiumincino International Airport
  2. Rent a car
  3. Drive 3.5 hours to Florence, stay two nights at Hotel Loggiato Dei Serviti
  4. Drive 2.5 hours to the Cinque Terre (Monterosso al Mare), stay two nights at la Spiaggia
  5. Drive 3.5 hours to Montepulciano, stay three nights at Meuble Il Riccio
  6. Drive 2.5 hours to back Rome’s Fiumincino Airport, stay the last night the Airport Hilton Garden Inn

Big Question: Why use a rental car for the entire trip?

Answer: At the time, trains were as foreign to me as traveling via camel – I could hardly imagine it. Of course, an intelligent trip would have allowed for a train from Fiumincino to Florence via Rome. My only response is that I was ignorant about European trains in general, and thought the car would be more comfortable, allowing us to enjoy the countryside views and provide more travel flexibility.

How the Itinerary to Italy Played Out

The Flight to Italy

: It was wonderful for a long flight. Free movies, lots of food and free wine – what was not to love? Except, perhaps, for the roughly 11 hour flying time. Neither Diane or I are people who can sleep for very long on an airplane, so we were both pretty exhausted on arrival. However, it was thrilling to be addressed in both English and Italian by the flight attendants throughout the flight. The adventure was beginning!

Customs in Rome

: Take a whole bunch of people and shove them through a relatively small funnel, unless you happen to be a citizen of the European Union. I did not get my customs stamp on my passport – instead I had to settle for a sticker on the back.

Renting a Car in Rome

: Unfortunately I did not take the time to learn even basic courtesy words in Italian. My lack of understanding of the Italian language was very apparent as I started the rental car process. Being in the state of mental exhaustion from the flight did not help. Overall, the process was acceptably straight-forward and soon Diane and I were in a cute little Audi A1 diesel with a manual transmission. We had previously read that full insurance on a rental car was prudent. This added about 100% to the cost of the rental care but helped assure that no “surprise” issues would be found with the care upon turn-in.

Driving to Florence in a Rental Car

: Maybe I should have at least learned some basic Italian words for “Exit”, “Entrance” and “Toll”. Gas stations were easy, and I was smart enough to use the right kind of fuel. Entering the toll road was trickier, since it took some staring at the many Italian words on the machine before I realized, with my sleep-deprived brain, that all I need to do was accept a token.

Florence is a bustling, beautiful metropolis. Most of us who are tourists are there to see the old town that resides in the inner city. Unfortunately the inner city is a maze of narrow, one way streets dotted with restricted zones guarded by cameras. Why wasn’t this in any of the videos or books we read about traveling to Italy? It was probably in those somewhere and I had missed it. We spent the better part of three hours driving in circles trying to get to our hotel. I would get close, only to be turned away by a restricted zone or misguided one-way street. Did I mention that I had not slept on the plane, and had not slept in over 30 hours? Finding mopeds and scooters on either side of my car at each stoplight was unnerving as well. Ultimately I gave up – parking my car at the Florence Airport and hiring a taxi. Honestly, at this point I felt kind of brilliant to have thought of this needed solution to our situation. On the drive in, comfortably as a passenger in a taxi, I then discovered that my picturesque hotel was in the very center of a large restricted zone.


: I had read about the Firenza Card, which for one price provided entrance to many of the attractions. It also allowed skipping lines of people waiting to buy attraction tickets. Buying this card was one of the smarter things I did on this trip.
The city was as big and beautiful as you might imagine.

The Drive to Monterosso

: I have driven California Highway 1, which hugs the Pacific in a breathtaking way. I thought this had prepared me for the drive to Monterosso – wrongly. The descent down to the town involved a narrow 1.5 lane road with hairpins, switchbacks and blind curves. At least I was well-rested this time. The views were spectacular, and so was the thrill factor of having to negotiate a blind turn where half of the road was washed away with a sheer drop of 100 feet or more and no guard rail.

Monterosso al Mare

: The Cinque Terre is a wonderful location. The weather was lovely and we enjoyed our balcony overlooking the beach. Don’t miss taking the water taxi to each of the different villages, as they each have an interesting and unique character. Our Audi stayed tucked away on a side street the entire time – this is not a place for private automobiles.

The Drive to Montepulciano

: The only way out of Monterosso was on the same roadway we came in, and it was equally frightening from either direction. Using paper maps, I managed to miss the turn that I planned to use to get to Montepulciano. What should have been a 3.5 hour drive became a 5.5 hour drive. Luckily it was all good viewing and the weather was cooperating. We were able to stop at a rustic winery in Montalcino along the way and taste our first truly Tuscan wine.


: The town is lovely, and our accommodations were rare and wonderful. Having a car came in handy here, as we were able to explore several small towns in the area with ease. Finding that B&B’s particular parking lot was difficult (I may have gone the wrong way down a one-way street) but once we knew the path, it was relatively easy to go explore and return.

The Drive to Fiumincino

: This was a mostly painless drive that included nice views of hill towns such as Orvieto along the way. We did get a little anxiety when we got pulled over by a member of the local polizia stradale (think state highway patrol), who was doing routine vehicle checks. He was standing in the middle of the country road that we were on, waving us off to the side with a hand placard. I rolled down the window and said “Can I help you, Officer?” he visibly sighed. He simply said “Tourist?” is a mildly disdainful way, and when I nodded affirmative he simply waved us on. I had to suppress a chuckle as we happily drove away. Returning the car was no problem, though I could tell they were ready to raise some concerns until they saw that I had bought the insurance. The return “inspection” was abruptly halted at that point.

One advantage of having an early start on the drive back to the airport was that by 2 pm we were at our hotel with our bags stowed, ready for the next day’s flight back to the USA. It was also mildly depressing. Ever adventurous, Diane then had the brilliant idea to catch a bus to the airport and catch the train to Rome. I was still somewhat tentative about the notion of taking a dreaded train, but she was persuasive. It turns out that it was ridiculously easy to buy train tickets and we were able to spend the rest of our day viewing such things as the Colosseum and the Pantheon instead of watching Italian TV in our little room at the Hilton Garden Inn.

Lessons Learned during our Vacation in Italy

Details from Italy… or Living With Your Decisions

Accomodations while in Italy