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Italy itinerary help particularly Tuscany and Tuscany itinerary

My wife and I are 69 and early 70's and reasonably fit for travel in late August for 3-4 weeks trip Venice to Rome by way of sail through eastern Adriatic August 2025

I was considering and preferred entering the region by way of Ljubljana for a 3 night stay instead of by way of Milan thereby eliminating the lake regions of Magiorre or Como but the airfare is considerably more expensive from MIA to Ljubjana.

8/20 arrival in Milan MXP
8/20 train to Stresa
8/20-8/21 Stresa, 2 night stay
8/22 train to Venice
8/22 Venice, 1 night stay, brief visit, ready to board Royal Clipper 8/23
8/23 Board Royal Clipper leaving Venice proper 8/23
8/23-8/30 Royal Clipper, 7 nights, tour Dalmatian coast, return Venice 8/30
8/30-9/1 Venice, 3 night stay
9/2 train to Verona, stop in Padova for day
9/2-9/4 Verona, 3 night stay (stay in the loop of the old section or in the Veronetta to the east of core city to enjoy the pedestrian friendly atmosphere) train day trips in Veneto to Vicenza and possibly Padova, Brescia.
9/4 Verona, Arena di Verona, Aida
9/5 train to Bologna
9/5-9/6 Bologna, 2 night stay; day trip by train to Ravenna
9/7 train to Florence (Il Treno Di Dante to Florence, if running 9/7, otherwise slow train to Florence via Brisighella and Marradi
9/7-9/10 Florence, 4 night stay, day trips by train to Luca, ? elsewhere
9/11 rent car Florence (drive through Chianti region from Florence to Siena (through the SR222 Chiantigiana Road. Stop in Greve in Chianti, Radda, or Castellina in Chianti for wine tasting and lunch)
9/11 return car in Siena
9/11-9/13 Sienna, 3 night stay
9/14 Rent a car Siena (from one of the agencies near the Siena train station or just outside the city center (outside the ZTL))
9/14-9/16 Drive Through Southern Tuscany touring Val d’Orcia, Montepulciano, Pienza, and Montalcino, Orvieta (Umbria)

? Where to stay with car on those days and for how long

9/16 drop car Orvieto (Umbria) or Chiusi

This avoids driving into Rome before leaving Tuscany

9/17 Train to Rome from Chiusi of Orvieto
9/17-9/21 Rome, 4 night stay

Suggested stay in Monti neighborhood

9/22 Leave Rome FCO by air to TLV

Posted by
1086 posts

This strikes me as a very busy schedule with the side trips within the places you are staying but if you know your travel style and this works for you then that's fine. Otherwise I would make sure you have enough downtime to really slow down and enjoy the slower pace of life - especially in rural Tuscany where that is part of the experience.

Other notes:
- Your plan for Verona sounds good - I think it is an underrated city in the Veneto and feels much smaller than it's population.
- Brescia has some amazing Roman ruins that continue in the museum - buy the combo ticket. Brescia has a great series of connected piazzas and a castle on top of the hill. I'm apparently alone in this but I preferred Brescia to Padua/Padova.
- Both Padova and Brescia have a fair amount of "everyday life Italy" around their interesting core. I would recommend taking the metro/train from the train station into the city. One stop in Brescia and two stops in Padova rather than walk through it.
- Bologna will support more time than you are giving it with your planned long day trip, but it will give you a taste. I'm not sure where I would steal a night from to add to Bologna - I think the other cities deserve the time they have. If your real goal is to see Ravenna versus Bologna why not just go there instead for 2 nights? People who love the mosaics say it deserves more time than a day trip.
- I would recommend a single stop in southern Tuscany and day trip from there to avoid moving too much and second the wine tasting excursion opinion. Siena is good place to do this from in northern Tuscany with Greve and other small towns around.
- You might think about renting and returning the car in Florence and then traveling to Siena or vice versa after looking at the car drop off penalties. The distances are pretty small to rent and return in Florence and then use public transport to go to Siena. Also compare to the prices of a tour and let some else drive so you can wine taste. Rental cars are more of hassle for short rentals in real life than they are on paper - paperwork, navigation, ZTLs, parking etc - versus letting some else hassle with it.
- Be sure you get an International Drivers License to be able to rent in Italy (I'm sure someone else has said this).
- Orvieto can work for the rental car return but I believe that restricts you to Hertz where Chuisi may have more company choices.

That's probably enough - have a great trip,
=Tod

Posted by
20 posts

I was hoping to rent the car in Florence and drive on through to Orvieto with overnight stays in Siena and Orvieto. Perhaps one night in an agricultural tourism hotel.
Any thoughts?
S

Posted by
7784 posts

Instead of taking the train from Malpensa into Milan and connecting up to Stresa, check if the Alibus times are convenient to just take it directly to Stresa. Another advantage is that their shuttle bus stops at the promenade across from the ferry stop.

While you’re in Verona, another option I really enjoyed was going to Mantova. I stayed there two nights, but you could do a day trip to see the amazing collection & rooms in the Ducal Palazzo. There’s three piazzas in succession for a nice meal.

I’m glad you’re attending the opera at the outdoor Roman Arena venue! Even though it’s Summer, bring a light sweater or jacket for the last hour of the opera. And don’t rush afterwards. Enjoy the night ambiance of Piazza Bra afterwards, even if it’s just walking around.

I have just used public transportation in the Tuscany region or small group day-tour, so I can’t help there. Montepulciano & Pienza were favorites! Montepulciano has orange shuttle buses to go up, up Montepulciano from the parking and bus areas - save your legs! : ). Be sure to wear shoes with good traction soles.

Have a wonderful trip!

Posted by
1696 posts

Check if trains between Ravenna and Florence are running through Faenza and Marradi, as the line was recently damaged in multiple floods and landslides, at present it gets closed as soon as there is danger of heavy rain. For example, today and tomorrow the line will be closed.
In any case, reaching Florence through Castelbolognese and Bologna is always possible.