Amici in Italia

A few weeks ago, a friend and I were out enjoying drinks and chatting when the topic of travel came up. We quickly realized we were each hoping for an opportunity to take an autumn trip. Amazingly, independently we had each been thinking about visiting Sicily, a place neither of us had ever been before. We pulled out calendars to compare and, incredibly, we discovered that we had a decent amount of available time that aligned perfectly to allow for a trip of 12 days or so.

I immediately began looking at flights and fares.

As I considered the options, I also gathered some additional information. I knew that some friends of mine were going to be in Italy in November…maybe we could meet up with them? A group chat followed and I learned that we were going to be in the country at the very same time, although they were based in Florence, not Sicily. Hmmm.

Maybe we could overlap for a bit there, a city that I’ve enjoyed visiting, particularly in recent years since I’ve made a couple of friends who live in Florence?

I quickly put the big pieces in place – we could fly into Catania (direct from JFK), spend a week checking out some of the island before flying from Palermo to Bologna where we would grab a train to Florence and meet up with my friends. I reached out to my friend, Gabriel, who rents out two bedrooms in his Porta Romana flat to guests, and locked down our accommodations for three nights.

Things were coming together beautifully.

Our return flights (on different dates since I could stay away longer) to NY were out of Rome, which naturally meant we should spend a couple of nights there, too. And since this second week of ours in Italy coincided with Thanksgiving, we would be celebrating it twice – once in Florence on the actual day of the holiday and for the second time in Rome at a friend’s* annual Friendsgiving dinner party.

Wow – this was beginning to look like an epic holiday in every sense of the word.

Retirement is a funny thing. Trying to find a balance between being fiscally prudent and acknowledging that the ability to be an active explorer is finite, isn’t always an easy place to land. But, when a single trip can take one to both new places, and familiar ones, to enjoy with more than a half dozen dear friends? You spend the money and buy the tickets and you go.

I’ve still got another 10 days to figure out, a “problem” with which I’m happy to have to deal, but here’s how things are looking as of now: Siracusa/Ortigia for 2 nights, Catania and Mt Etna for 2 nights, 3 nights in Palermo, 3 nights in Florence with a day trip to Sienna, 4 nights in Rome, 2 or 3 nights in Naples and then a week or so tbd. I’m interested in seeing some place new to me and my wildly well traveled friend in Rome happens to have a long weekend to join me for an adventure – another happy alignment of circumstances. Wherever we go, I’m sure there will be great food and wine and lots of laughter.

Maybe you have some ideas for my trip? Have you visited Sicily or Sienna? Where would you consider spending 3 or 4 nights if you were starting from Rome or maybe Naples? I’d love to hear your suggestions! Bonus points awarded if the destination features natural hot mineral waters.

*This friend incidentally knows 2 of the 4 friends with whom I’d be traveling/hanging out.