Mother/Daughter Trip

We are getting a train pass and plan on using that to get from place to place

The collective wisdom is, for Italy, a train pass is not a money saver over just buying 'as you go'.

The way to save is to buy point to point tickets in advance for the high speed, longer distance, trains.
Regional and local trains have no 'early bird' discount

For specific advice on where to stay etc, knowing how long is the trip would be helpful

Thanks for the advise on the tickets. We plan on doing 3 nights in Florence, 3 nights in the "country", 3 nights in Rome.

Truthfully, having a car while in the countryside is a big plus. Trains just don't carry you off the beaten path, and Winter is not the best time to be outside walking. It gets cold in Italy--and it also snows.
We picked our rental car up at Hertz' city location in Florence and they gave me directions to the countryside. We stayed in an agriturismo outside of Certaldo and San Gimignano--just 5 miles northwest of Poggibonsi. Siena was to the south, but we found the city to be very congested and parking difficult to find. We loved Volterra. We dropped our rental car off in Orvieto across from the train station, spent the night and went into Rome Termini the next morning (70 minute ride.) Many travelers use Orvieto as a drop off point for Hertz cars.

Rather than speaking in generalities like "X nights here, Y nights there" (which can obfuscate inconvenient truths), please post specific travel dates (even if they're just proposed, not final - actually, it's preferable if flights are not finalized yet, as most first-time travelers often start out with wildly unrealistic itineraries which can result in a rushed, unsatisfying trip).

Before you start picking accommodations and how to get around, post your proposed itinerary.

What date do you arrive in Italy (and where are you coming from - presumably North America or someplace equally distant?), when do you depart, what are your arrival and departure locations (presumably you depart by boat from Naples)?

We like Montalcino in Tuscany a lot for that "country" feel. Small hilltown, great wine and restaurants, plus some bus access to neighboring hamlets and the fabulous abbey at Sant'Antimo. Alas, there is no train station.

Montepulciano would be an option as there is a train station, although it is a bit down the hill and a taxi or bus is required to get up to the town. That is manageable.

Siena is a true town, not so much "countryside" but you can take a great day tour with Tours by Roberto to drink wine and enjoy the Chianti area.

I love Assisi and it is transportation friendly with a train station well connected to the town by bus and taxi. Gusto Wine Tours can do a marvelous tour of Umbrian wineries.

With only three days and in January and with daughters I would day trip to Siena from Florence and maybe splurge for a driver to get to some wineries.Spending the night is equally doable especially if you travel light. Also don't miss Aperitivo time (happy hours) in towns from about 6:00-8:00 which is fun. Orvieto is on the way to Rome so it would make a nice two night stop by train. My daughter studied in Florence for both undergrad and her masters and has always loved Orvieto (as we do). There are also students there that make it more youthful plus Orvieto Classico Superiore Wine.

Fly into Florence. Stay there. Visit there. Eat there. Drink there. Only on foot or taxi
Then off to Rome via the high speed train to Rome. Stay there. Visit there. Eat there. Drink there. Only on foot or taxi.
Now you have to decide... Rent a car and experience some of the worst drivers in Europe (Italians have no concept of death!) or take a train to Naples and eat there, drink there, on foot and then get to Malta by whatever works best.

You can do trains but only between the major cities where you are limited to walking taxi or transit. The countryside requires a car rental (Sixt is my choice)
Enjoy your time with your daughters.
John

My guess is that the "countryside" will be uninspiring in January. The vineyards will be pruned back and look barren. Search online for a wine tour - again, my guess is that one will be much like another and one is enough. I'm not sure what "experience the wine" means to you. Do you want to tour 2-3 wineries and learn in-depth about wine production? Or do you want to do a lot of tasting? For that, you can drink lots of different local wines wherever you are. You can stay in Florence and day trip by bus or train to various Tuscan towns. Or you could stay in Bologna and day trip by train to nearby towns.

Do you know of a boat that will take you from Naples to Malta? The fastest and easiest way is to fly from Rome.

We plan on doing 3 nights in Florence, 3 nights in the "country", 3
nights in Rome.

Hi Marie and welcome to the RS gang -
Much as you want to go off to the countryside, it might not be all that much fun in January if it's cold and wet. 3 nights also only gives you 2.5 days for Rome and only 2 full days for Florence: not enough for either of them, IMHO. You would have greater flexibility for working around weather by trimming your trip down to just the two cities and taking a day tour or two from Florence by train, bus or driver. That way you'd have plenty of interesting indoor attractions to explore should Mother Nature not cooperate.

I'd think about 5 nights/4 FULL days in Florence (I'm subtracting the partial arrival day as those can be lost to jetlag) and 4 nights/3.5 days in Rome.

I could be missing something but at quick glance I'm not seeing ships direct to Malta from Naples, and would guess by sea would eat up serious time even if there were. Any reason for not just flying from Rome?

Thank you everyone for the advise. I can't remember where I saw the boat from Naples to Malta but it is quite possible I was seeing things. Will definitely look into a flight. I guess that is what doing lots of planning is all about as we never really thought about the wineries not really being open. Maybe staying put in Florence and Rome and doing day train trips is the way to go.

Is it worth staying a night in Montapulciano though or just doing a tour from Florence at that time of the year?

Marie

Another thing to consider about the 'countryside', and presumably the classic views at sunrise/sunset, is at that time of year the daylight hours are at their shortest. You will not have the 'sit on the patio with a glass of wine' at sunset experience, as portrayed in all the classic photos one sees.

There is no boat I know of that will take you from mainland Italy to Malta. The only one that exists is from the southern tip of Sicily in Pozzalo, which I found quite inconvenient to get to while I was in Sicily. Look into flying into Malta from whatever gateway makes sense (there are select cities you can do this from - e.g. Milan, Rome).

I was personally uninspired by Montapulciano plus it's up a huge hill. My sister went to Florence in November and found it cozy and fun with Italians instead of tourists and very good hotel prices. Lots to do inside if the weather isn't kind.

I love Tuscany but not in January! If you are looking at adding another destination to Florence and Rome, then in the winter, I would add Venice