It’s Time to Up My Game in Planning Favorite Port Repeats

Days 27-30, 2026 Fall Atlantic Sampler

Thursday to Sunday, Oct. 22-25, 2026; Florence, Civitavecchia, Naples and Messina, Italy.

After four straight days of familiar ports, I think I might need a new strategy for port planning.

Not that I haven’t enjoyed myself.

I spent a pleasant few hours in Florence, including seeing famous Italian Renaissance art in the Uffizi Galleries.

I purchased a watercolor of the Ponte Vecchio from artist Susanna Casari at her stall in the Piazzale degli Uffizi. I intended to create a repeat of my 2024 painting of the famous bridge, but struggled in the time I had. So, I erased mine and later in the day replaced it with a simpler sketch of the Duomo di Firenze, which I painted back on the ship.

In Civitavecchia, I squeezed through crowds walking to the city center. It was turnaround day for at least one large ship, and many passengers opted to roll their wheeled suitcases along the narrow rough sidewalks between the train station and the port. My highlight of the day was a charcuterie plate and wine on a sunny terrace.

Naples was a pass for me – by now I was realizing my somewhat aimless wandering wasn’t as satisfying as I had hoped. I enjoyed a ship day, catching up on photo organization, blog writing and other miscellaneous tasks. Strangely, I find such work to be relaxing and rejuvenating at times. And I watched the North Star observation pod lift off the top deck of the Odyssey of the Seas berthed next to us.

For my fourth stop in Sicily over the past year, I once again toured Taormina, a charming but touristy village clinging to a hillside. After a brief early rain, we only had time to wander the shops and have lunch – the pistachio pizza was surprisingly good.

I’ve felt this slight sense of dissatisfaction before on cruises, usually after the initial excitement of a new journey, when the routine of ship life sets in. With so many upcoming ports to research and plan, I usually just skip over the familiar ones. My planning spreadsheet simply reads “explore on my own.”

That’s well and good, but after two or three visits covering the same territory, it no longer feels like a welcome return to a favorite coffee shop, shopping street or café terrace. I know there is more to see and explore, had I only better prepared.

I’m pledging to be inspired by fellow passenger Jeff, who has many more days on Holland America ships than me (and virtually anyone else these days who’s not paid to work on board). He and travel companions Ann and Cathy told me they research and prepare at home before each long journey, supplementing new ideas with side trips inspired by sites that caught their interest on previous cruises.

While I simply wandered familiar streets in these Italian ports, they found guides and drivers to lead their explorations of Pisa and Lucca from Livorno; Tarquinia and Tuscania from Civitavecchia; and Herculaneum from Naples. They visited Taormina just as we did, but had more time and explored farther off Corso Umberto, the main pedestrian street through town. You can follow Jeff’s descriptions and photos of their “amazing voyages.”

I first visited the Mediterranean in 2007 with Mom and my sisters and later again with Mom in 2011.

I’ve been back on longer cruises for the past three years. Last year on repeat back-to-back cruises, we stopped at many new ports, but I still enjoyed the repeats — Rhodes, Mykonos and Malta, to name a few.

Mid-to-late fall is perfect, although it’s becoming harder to miss the crowds as more ships stay here longer before heading to the Caribbean for the winter. The weather is mild and generally sunny, the food and drink are great and I can forget that winter is coming to places where I used to live.

Still, if I keep coming back, I’m committing myself to finding new memories to add from favorite places.