Rome + Tuscan Villa + Florence + <????>

There are truly endless possibilities in Italy. Tell us about your preferences (scenery, museums, churches, other historic sights, mountains, food, larger cities, small towns, etc.) to get more helpful suggestions.

In the meantime, I suggest checking airfares from your origin into Rome and out of the logical northern-Italian airports (Florence, Pisa, Milan, Venice) so you'll know whether heading in one direction vs. another comes with a $$$ fare penalty.

I think it's a good idea to focus on the north since I'm pretty sure you're going to feel like you left Rome too soon after just one full day. The next trip can be a repeat visit to Rome, Naples, the Amalfi area, etc.

Thanks for the reply. We prefer small and charming versus big cities but I truly believe good stuff can be found in any destination. Ideally, I would like a healthy mix of everything over the 5 days. I like museums, interesting architecture, walled cities, narrow cobblestone pathways, beautiful landscapes, etc. I would be good sleeping in 2-3 locations so would prefer suggestions of places that have a uniqueness about them. Good point about the flights, I will do some number crunching.

Three locations in your last five days is just dashing from place to place. Suggest you limit yourself to two and enjoy them.

Perhaps Lucca and CT?

I second Joe's suggestion. Lucca is a charming small city, and although the CT villages will be crowded, by staying there you can enjoy the quieter early mornings and evenings.

I do gave a question, are you renting a car to drive to and for your stay in Montepulciano? Transportation is very limited in this area.

For you 5 day stay after, I would spend 2 or 3 more in Florence.
Plenty of easy day trips from there.
Bologna, Siena, Pistoia Lucca all at about an hour or less by bus or train.
Then pack up and spend 2 nites in the Chinque Terre. Train to Rome to fly home.

Hi- for the stay in Montepulciano, my sister is planning all of that. There will be six of us and I don’t think any of us are keen on driving. I believe she was looking into planning day trips with a driver.

Looking at flights, it will be a lower cost to go in and out of Rome. Considering that, I am now thinking to save Cinque Terre for the next trip when hopefully we can come during a cooler and less crowded time. Instead, I am thinking to stay 2 additional nights in Florence, with the option of day trips to places like Lucca, and three nights in Rome with the intention of seeing anything we feel we missed at the beginning of the trip, and possibly a day trip to Tivoli Gardens or a small charming village. Plus then we will be closer to the airport.

Or perhaps we go to Sorrento for 4 nights and spend the last night close to the Rome airport.

We stayed in Santa Margherita at a lovely argriturismo and visit the CT and surrounding countryside but I'm not sure I'd spend more the 3 nights there. I would consider adding a couple night in Florence.

You could fly out of Bologna - we flew into Bologna to start of last visit but only because we were supposed to fly into Florence. I would totally recommend flying out of Bologna if you end up spending extra time in Florence. We spent 2 days in Bologna with food tours including a balsamic vinegar tour and tours of Ferrari & Lamborghini (which I thought would be boring but turned out to be fun).

If Rome is your first stop I would not head to the AC after Florence. You could also head to the Lake District which is my favorite part of Italy and fly out of Milan

Or perhaps we go to Sorrento for 4 nights and spend the last night close to the Rome airport.

CT would be less train time and backtracking, but, I would be happy to do that. (Sorrento). Had only 2 nights in Sorrento and would have enjoyed more time there.

Thanks for the information Donna! I am still trying to consider all of my options. I have considered/am considering departure points other than Rome but these all come with an extra flight/layover. All other things being equal, I would rather spend 4 hours on a train vs. 4 hours on a connecting flight and layover - trains are just so relaxing! I really need to get my act together and figure out what we really want to see this trip and what we can save for next trip and what makes the most sense from a logistical perspective.

@Joe

-> I would be happy to do that. (Sorrento). Had only 2 nights in Sorrento and would have enjoyed more time there.

One of my friends went on a giant tour of Italy and when I asked her what NOT to miss, the only place she said was Sorrento. ;-)

With respect to train vs. plane:

I, too, much prefer trains. But when you're talking about a return flight to the US, a decision to get back to the departure airport via a long train ride comes with the imperative to build in a lot of extra time. In my case, I'd be going to the departure city the afternoon before my flight, because the cost of missing that transatlantic flight is far more than I'm willing to risk. If you book a connecting flight, it's on the airline to get you home without extra charge. I don't find a somewhat longer flight home particularly burdensome, physically, because I'm not losing a night's sleep.

I admit to being retired, so I don't have to be concerned with whether a missed connection might affect my ability to get back to work on time.

After doing a bit more research on flights and considering the weather for mid-June, I am now thinking of flying home from Milan and heading north from Florence. We'd save the Amalfi Coast and CT for trips when the weather will be a bit cooler. That being said, I would appreciate your thoughts on the following towns/cities.

I do have Rick's book so have his information, including his thoughts on Bologna.

• Bologna
• Padua
• Verona
• Vincenza
• Milan

With those cities in mind, do Florence-Bologna as a day trip, with an evening train to Verona. Spend one night. Then the next day a mid afternoon train to Padua. Spend 2 nights. From here day trips to Vicenze and Venezia.

Fly out of Venice. 48 min train/bus ride from Padua to VCE. Try for a mid-late morning flight back home.

@ Gerri
Thanks for your reply. It does look like flying out of Venice would be around the same price as flying out of Milan. A couple questions:

1. I had Bologna as a stop on the itinerary as it was on the way North and we literally need to go right through it. You suggested it as a day trip. Is that to have 1 less hotel move or is Bologna not somewhere great to see at night?
2. If we do stay in Florence and day trip somewhere, I am thinking that either Arezzo or Pistoia might be a better choice. From what I can see, they are similar distances and have direct trains. Do you have experience with either town?

Thanks!

Not really "day" trip, spend the day in Bologna on your way to Verona.
Bologna is much larger than Verona, so a nite here would be fine. It's a very pretty city. And Verona does have a left luggage facility in its station.

Pistoia is a great trip from Florence.
City center is medieval and there's tons of art.