
On September 19th, 2023, my partner Michael and I departed from Boston to Rome for a three-month trip to Italy. How did we get to this point in our lives where we could actually drop all responsibility and go? I call this our “semester abroad”. If the college kids can do it, why can’t two adults in their early 60’s?
We started planning our adventure knowing we would both retire six months later, an amazing journey to “jumpstart” our retirement that we will never forget. We flew directly from Boston and picked up a little black French Peugeot in Italy which Mike leased for our three-month journey. The auto had Italian plates, so the entire length of our drive through Europe, we were “Italian”. Mike’s grandparents originally came from Italy and part of our itinerary included exploring his ancestor’s villages. Our plan was to drive the entire boot of Italy up and down along the coast over a period of five weeks on our self-guided tour. Mike planned the first part of our trip in Capri for some sun and much needed R & R.
The first day after our arrival we had phone connection delays due to the time change–we really needed the international service for google maps, google translate (which is amazing), and our reservation confirmations. By the time we straightened it out and drove to from Rome to beautiful Salerno we were behind schedule and there were no more ferries to Capri! That is when Mike’s Italian hand gestures and various words of excitement began. We laughed a lot as we realized we were in a foreign country and really didn’t know what we were getting into! After a very scenic drive along the Amalfi coast and some broken Italian phrases, we found a town where we could catch a ferry before dark. We found a long- term lot on a hill and then carried all our luggage through a tunnel and bumpy cobblestone streets. Mike lost a wheel on the way! Finally, 22 hours after leaving Boston, we arrived at the Hotel Ambassador in Capri.

Day 2
The weather in Capri is gorgeous that time of year and we had a nice terrace view of the water which is spectacular in the morning sun. We start our day with a walk up many steep stairs which I later find out are the Phoenician Steps uniting Capri with Ana Capri. These steps were formed by ancient Greek colonists and are hundreds of feet above the Mediterranean Sea. We are near beautiful Marina Piccola. These steps do not have handrails so good balance is needed. I am thankful that we are fairly able- bodied. As the days go on, we forget what day it is and my legs are really sore, actually they feel like lead. Everything here is hilly, but we feel good and are finally starting to feel relaxed. I do miss family and home knowing I will be away for three months, but Facetime and emails are keeping the connection. I remind myself that this trip is a dream come true and can’t wait to see what awaits us each day.
I am brave and wear a small bikini to the pool. At home I wouldn’t wear one, but I bought one in Capri town along with a beautiful colorful dress which is the fashion there. Everyone wears bikinis no matter their age or size, so “when in Rome” as they say. We have been having breakfast or lunch around 1 or 1 30 pm by the pool and are eating a lot of fish, salads, pasta, olives, tuna, olive oil, bread and a little cheese. Yum, the food here is so good!
The locals are welcoming, and we laugh a lot and have fun. Sometimes it is too much fun. One day I was sitting in a café and accidentally hit the table and knocked over a glass of wine. Within minutes and after some very Italian looks of disgust, three table servers arrived with brooms and cleaning rags. I promptly had a new glass of wine in front of me. I will try not to do that again! People watching is fun as is shopping. However, the shops are very expensive. Needless to say, I didn’t shop much but enjoyed window shopping and did purchase some souvenirs.
Some experiences in Italy are what I call an “Italian car fight”. This starts when you hear a few horn beeps, then escalating beeps, and then some hand gestures. Mike and I tried not to get entangled in them. Prior to arriving in Capri, I went to a convenience store to use the “bagno” when I heard two gentlemen speaking loudly in Italian followed by these hand gestures. I then saw the “poliziotti” arrive and thought I should hide for a minute behind a building until Mike arrived. Finally, Mike pulled up on the other side of the road and I quickly got in our Peugeot. “Phew,” I thought, and this was our first day in Italy.
Some highlights in Capri on our walk back to town after shopping where we found a nice garden restaurant. The waiter gave me a free glass of wine to start our evening and a beautiful wool scarf to keep warm which was lovely in the cool terrace air. On the way home we walked through the cobblestone streets to a local bakery and bought a variety of goodies. We went back and had them on the terrace of our hotel overlooking the sea with me having a limoncello drink. Limoncello is the famous lemon drink in Capri and is sometimes straight Limoncello, or in a spritz with a slice of orange. This drink is light and delicious and will put you right to sleep. A great way to end our dinners in Capri. I talk a lot about the food, but it is really good and fresh here, and the people here take much pride in their food and making sure that we like it.
Another highlight of Capri is the Arco Naturale. On Sunday the shops are closed so there are fewer tourists, which is nice. We took our usual morning walk which then turned into a hike. We found a path and went up many steps, across a small street, more steps, through a tunnel uphill and around a curve we entered the town of Capri after about 25 minutes of leg burning activity. We approached the beautiful Arco Naturale. The walk to get there was breathtaking and so picturesque. Along our way we found a little wine bar which also had a much-needed water bottle. The best part of this stop was I asked the waiter if there was a shorter way to town. He pointed one way for an “hour” and another for “15 minutes” to get back so we took the shorter route as it was a really hot day. The flowers and terraces overlooking the Mediterranean Sea are abundant and breathtaking on the way back to town and worth the hike.
Anna Capri
To get to Anna Capri we took a shuttle to Capri center and then a bus to Anna Capri which is about 25 min from town on the other side of the island. The bus is packed full and we had to stand and hold on to a rail the whole way which usually would be easy, but the road is so narrow that it stopped still many times to let another bus pass and we came within 2-3 inches of it After you get used to the many hair- pin turns up narrow roads you can enjoy the beautiful scenery. The town is quality and has similar shops to Capri but a little less expensive. We hiked toward mountain Anna Capri ski lift to catch the beautiful view.
One highlight of this day was while getting coffee I met a girl from Canada named Caroline who was travelling alone for a wedding. She told me she is rethinking her life; her marketing job has caused high blood pressure and she had gained 40 lbs. I told her about us leaving our jobs and taking this sabbatical. She was inspired and is journaling about her next career. We had a coffee together at the hotel café and had a nice chat. It is good to meet new people during our travels.
Later in the day we toured an old castle of “Villa San Michele” which had was beautiful old sculptures, gardens, and a really old kitchen, living room, library, and bedrooms. The gardens contain the sculpture loggia, and an interesting sphinx sculpture. A walk back in time and very enjoyable.
Anna Maria dinner Capri
I sent some postcards from town and inserted them into a small red mailbox. Mail works differently: stamps are purchased at a smoke shop not at the post office and mailboxes are small and hard to find. I found out they arrived in the US a month later! In the evening, we took a cab to Anna Maria to the hotel La Terrace at the Ceasar Augustus. We had dinner at the Terrazza di Lucullo Restaurant which was absolutely amazing. An old building on a hill overlooking the sea similar to the Newport Mansions. The sunset was absolutely gorgeous, and I wore my new red dress from Italy so felt like a million bucks!

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This Post is republished on Medium.
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Photo credit: Author

Hi Ansje, It was fun to read your blog. I’m so happy you getting to enjoy yourself in this way. I’ll be looking forward to part 2. Day hello to Mike
Reading this made me feel like I was there! What a fun adventure