Planning an Italian vacation

Welcome to the forum!

Just be aware that there really is no shoulder season anymore and May will be crowded
Next year is the Jubilee year so Rome will be slammed.

7-10 days is just enough time for Rome, Florence and Tuscany.
Are you open to renting a car as that would be handy in Tuscany? But you won’t need or want anywhere else.
I don’t see time at all for Sicily as that needs a lot more time not only to visit but to get to.

As far as itinerary you will need to book many things far in advance.
All major venues require that now or you’ll be spending a lot of time in lines

Hotels in the historic centers are mostly all local owned
You will need to have all hotels booked early as well.
The days of going with the flow are past.

Suggested itinerary
Fly into Rome
Train immediately to Florence
Florence 3 nights
Pick up car
Tuscany hill towns 4 nights
Drop car or drive to Rome to drop
Rome 4 nights

Put all your Rome nights at end to avoid a split stay and you will need to be in your departure city night before flight to anyway

Count your trip in NIGHTS
A 3 night stay gives you 2.5 days in location
Each location change takes at least a half day

Get a good guide book
here’s a starting point
https://www.ricksteves.com/europe/italy

How exciting! However, 7-10 days with two major cities (and the surrounding area of Tuscany), as well as Sicily does not equal a laid back trip, imho. Why not focus on Rome and Florence with some day trips to nearby areas like Orvieto, Lucca or Bologna? I’d try to minimize the number of changes in your accommodations and maybe fly into one city and out the other. I’ll be in Italy next month for the 6th time and there are still so many places there I haven’t seen (Venice, Siciliy, Sardinia…), but each time I go, I try to visit a new area while also returning to favorite spots. Italy has so much to experience. Slow down and attempt to immerse yourself in la dolce vita. That’s what it’s all about.

Welcome to the Forum. We were in Italy (Venice, Florence (Tuscany), Rome in May 2023 with the hopes of avoiding the majority of the crowds. It was as crowded as when we visited in June in 2018. Booking hotels and must see sights in advance is highly recommended. We waited in May 2023 to book our hotels 3 months in advance and many of the places we looked at staying were booked.

I agree with ChristineH that 7-10 days is enough time to have a relaxed visit to Rome, Florence, and Tuscany. Sicily alone could take a week to visit on its own.

Since you want to enjoy a relaxed and laid back vacation, I would recommend the following. Note I am assuming a 10 day trip with Day 1 and Day 10 as flight days. If your 10 days don't include your flight days, then. add extra days to Florence or Rome.

• Day 1: Arrive in Rome and take train to Florence
• Day 2-3: Stay in Florence. We stayed in a lovely B&B/aparthotel, you can read the review here: https://community.ricksteves.com/travel-forum/italy-reviews/hotel-review-canto-degli-scali-florence
• Day 4-7: Rent a car and stay in Tuscany (note, if you don't want to drive), then stay in Siena and take day tours from Siena, there are a number of good tour companies. If you want to go at your own pace, then driving a car is recommended. It is hard to really explore Tuscany on public transport.
• Day 8-9: Return car and stay in Rome
• Day 10: Fly home

The RS Italy book is a good guide book to start planning your trip. Once you have a more detailed view of you itinerary, then the come back to the Forum. There are so many kind people here that were enormously helpful to me when I have planned by Italy visits.

You have enough time for Rome and Florence, perhaps including a day in Siena or something. This is pretty straightforward sightseeing with easy transportation via train and absolutely no shortage of sights and experiences. Rome, Florence (and Venice) are Italy’s heavy hitter must-sees and there’s nothing wrong with sticking to them exclusively this time around.

Sicily is, for sightseeing purposes, basically another country. It doesn’t fit easily into your brief visit, and really deserves a trip on its own. At best, you’d get yourself a night or two in Palermo. But this is wasteful. You’d be “robbing (Saint) Peter to pay Paul.”

First of all, ABSOLUTELY FABULOUS that you are working on some Italian for the course of year! That will certainly help you enjoy your time in Italy and it will enrich your encounters with Italians whose English may be as limited as your Italian.

Second, you and your wife should really talk about what you want and if that desire includes a "laid back" time in Italy, please consider the merits of 17 to 30 days, rather than a mere 7-10 day trip. With all that Rome and Florence have to offer, 7 to 10 days even limited to Rome and Florence seems to me like it will be filled with sightseeing, rather than "laid back." (I recognize that others have said the opposite.) COMPARE https://www.ricksteves.com/europe/italy Look at the various RS Italy trips and their itineraries. https://www.ricksteves.com/tours/italy Look at other guidebooks, such as Lonely Planet.

My wife and I have been to Italy three times (2003, 2015 and 2024). Like you, we studied some Italian our first time and that came in handy; I refreshed in the months leading up to 2024. Each of our first two trips were about 17 to 19 days; our most recent was 30.

Our first two trips were Rome and north. 2003: Rome, Florence, Venice, then to Cinque Terre via Florence, Pisa & Lucca, then about 4 days in Tuscany. 2015: Rome (for what we missed the first time), Orvieto, Florence (for what we missed the first time), Venice (for what we missed the first time), Padova, Verona, Lake Como (Bellagio) and Milan. 2024 was for southern Italy, specificaly, Sicily, Puglia & Campania (including Naples and surrounding sights). For 2024, advice from others on this forum was to spend a minimum of two weeks in Sicily, but we slightly shortened that by taking the RS Sicily tour.

FWIW, our 2024 Trip Report discusses the relative merits of the guided RS Sicily tour, a "self-guided" e-bike tour arranged with a local outfit based in Puglia, and finally travelling independently from Puglia to Naples and then in Naples. SEE https://community.ricksteves.com/travel-forum/trip-reports/southern-italy-30-days-three-ways-to-travel