Three weeks in Italy
- The Highrise Hostess
- Jun 23, 2020
- 4 min read
When my girlfriend told me she was getting married in Italy I was so excited. Chris and I decided we were going to take a few weeks off and travel right before her wedding and see the country. Neither of us had ever been, so this was the perfect opportunity. Because neither of us had ever been, we wanted to cover a lot of ground and see as much as we could. We decided we would fly into the North and meander our way South.
When we decided we were going, I reached out to several of my Italian friends who live in Milan, Turin and Florence, to get tips on things to do while we were there. Many of them urged us not to come in August because most of the country goes on holiday this month and most things are closed. I did not heed their advice because my best friend was getting married in this month and I wasn't about to ask her to change her date, and secondly because I thought there's no way that EVERYONE leaves in August and takes a holiday. Funny enough, they were right. Many things were closed during our trip, but there were still so many things for us to do.
To say we covered a lot of ground on our trip is an understatement. We visited Venice, Florence, La Spezia, Cinque Terre, Rome, Naples, Sorrento, Positano, and Capri. We flew into Venice then took the train to each city and flew out of Naples. When people ask what my favorite city in Italy was its impossible to answer. They are all so beautiful and unique. I studied Art History in college so the museums, the architecture and the history of each of these cities are so different and magically unique. We loved them all. I will say however, next time we go I will stick to the coasts during the summer and leave the interior cities for the cooler months in the Spring or Fall. It was very hot during the day in Florence and in Rome. That did make for fewer tourists though!
Another thing I will strongly encourage you to do if you plan to visit Italy is to travel with a carry on or a backpack! There are cobble stone streets and oh so many stairs all over Italy. They are not friendly to stiletto shoes or suitcase wheels. If you're bouncing between cities, you want to travel light. We stayed in many beautiful boutique hotels and villas without elevators. Carrying a large heavy suitcase up several flights of stairs may be great exercise to help you work off some of those big plates of pasta and many cones of gelato, but it is not fun.

We both did some impressive packing for this trip. We each went with only a carry-on suitcase and a backpack. Somehow, I managed to squeeze in swimsuits, hiking clothing, an outfit and matching shoes for 10 days, 6 evening dresses, 3 pairs of stilettos, and cosmetics into a carry-on. I don't know how I did it. I credit the AWAY bag. This carry-on suitcase can really take a beating. It was over-stuffed, dragged all over cobblestone streets and carried up and down many flights of stairs without breaking. We really tested its capabilities. The best thing about this bag is that it comes with a battery back charger. We were on our phones constantly looking up restaurants, directions and things to do, so we were always draining our batteries. On the long train rides we could keep our electronics plugged in so we could prep for all the photos and adventuring through the next city.
We did so much walking all over Italy. A few things I regretted backing for this trip were the cute flats that I brought to wear during the day to match my outfits. By the end of the first few days I had horrible blisters from all the walking. Fortunately, I had packed these cute plain white sneakers that went with everything. These saved the trip. Walking around with uncomfortable shoes can really put a damper on the day. Forego being matchy matchy and bring a comfortable pair of shoes that go with everything.
If you plan on traveling in the hot summer months like we did, pack a hat. I had packed a few brimmed hats to wear, but Chris had not. He wound up buying one outside the Pantheon in Rome half way through the trip because he was getting so burnt.
The only things we booked before our trip were the Airbnb's, the hotels and the flights. We also signed up for the rail pass. That has to be shipped to your home address prior to you traveling, so you'll need to make arrangements for that well in advance. Everything else we booked when were there. Without a strict itinerary you can wander around and get to know the city without feeling rushed. This is how we both like to travel. I know it stresses some people out to not have a schedule. This way, however, the city is your oyster and you can experience it as you go. You never have that feeling of rushing to be somewhere or disappointment because something didn't go as planned.

Our Itinerary:
VENICE
FLORENCE
LA SPEZIA
CINQUE TERRE ROME SORRENTO CAPRI POSITANO NAPLES
Subscribe to The Highrise Hostess page to read about each of these amazing cities in upcoming posts.
X,
Jess




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