Revised Itinerary. Would this work better?. Home base for Tuscan region?

I think you can make it much more efficient. Here is one idea.
I'd put all Rome (3) time at the start, then Florence (2-3), then CT (2), then pick up car (La Spezia) and explore Tuscany, ending up near Rome airport for Ostia Antica and catacombs--as you can stay somewhere within easy reach of those sites and the airport (dropping car off before flight). The train time from Florence to CT is still unfortunate, but a solution is not jumping out at me, unless you are interesting forgoing the extremely crowded CT and considering a beautiful coastal park in southern Tuscany instead (It's called Maremma/Ucellina).
That gives you over a week to play with for Tuscany and I'd pick two bases--one more interior, rolling hills, the Tuscan dream thing, and the other in the south to put you in reach of the fascinating Etruscan ruins (Pitigliano is great).

For a Tuscan base, we love the Val d'Orcia area around Pienza. There are lots of small wonderful villages to explore in that area.

Im following this post.
Thank you so much

Another way to make it more efficient is Florence/Tuscany/CT/Rome. Take the train to Florence on arrival and have all your Rome nights at the end. There are one or two direct trains daily from the CT to Rome. You could visit some of the Tuscan towns by bus or train from Florence and not have to worry about parking, like Siena which is worth a full day. Then pick up the car for the rest of your time in Tuscany, drop it in La Spezia.

Even with a car, you probably can't visit more than two towns in a day. Assisi needs a full day. Decide on your priorities, use google maps or similar to plot out the towns you most want to see and choose one that's most/more central. Or you may want to find a centrally located agriturismo.

Valadelphia suggested you do Uccellini and Maremma. Pitigliano is really worth it and is not very far from Maremma/Uccellini. Volterra and Tarquinia (wonderful Etruscan Tombs).
(I would devote 4 days for this with a car)
Then arrange for 6 other days for Florence, Siena, Arezzo, Lucca San Gimignano with travel by bus or train out of Florence.
Eventually 1 day trip to Assisi but would rather leave it for another time when you visit Umbria.
The other 4 or 5 days - Rome

Hello Hokey Pokey (Love the name!),

For your stay in Tuscany, I would suggest Montepulciano. It's a fantastic lively town with wonderful restaurants and lots to do. For your Wednesday (#10) Itinerary, San Gimignano, Volterra, Pitigliano, Cortona, Assisi, and Arezzo are all easy day trips - but you won't be able to go to them all in 1 day.

For your Thursday (#11) Itinerary, there are just too many fantastic wineries that can be visited from Montepulciano, which is home to Vino Nobile di Montepulciano. Again, like above, you will have to choose wisely.

If you need winery suggestions or accommodations suggestions, just them me know. We travel to Montepulciano frequently and know it pretty well!

Posted by francoise
Valadelphia suggested you do Uccellini and Maremma. Pitigliano is really worth it and is not very far from Maremma/Uccellini. Volterra and Tarquinia (wonderful Etruscan Tombs).
(I would devote 4 days for this with a car)
Then arrange for 6 other days for Florence, Siena, Arezzo, Lucca San Gimignano with travel by bus or train out of Florence.

Francois & Valadelphia, I will look into Uccellini/Maremma, and thanks for the Pitigliano/Volterra input, as I wasn’t sure it would be worth it to go there; after a few of you have stated it is, my curiosity is piqued and I would really like to get there now.

Cinque Terre is the reason I booked a trip to go back to Italy. My husband and I went there last year, and we loved it so much we wanted to go back to see and hike through all the towns. We stayed in a wonderful location on the sea which was great. We also visited Rome, Florence, Orvieto, and a few other places in Tuscany, like Siena, but we didn’t plan enough time to enjoy it (Siena and Tuscany in general) because we rushed through them and I didn’t plan it well. We missed several places we wanted to visit like San Gimignano/Volterra. When we go back we want to take it slow and enjoy “being” there (and wherever we are).

I knew you all would be a great resource to help us plan our places and timing better and get great recommendations on places to go. Thank you for these suggestions.

• emphasPosted by crwawro 09/14/19 03:04 PM For a Tuscan base, we love the Val d'Orcia area around Pienza. There are lots of small wonderful villages to explore in that area.

Crwawro: We visited that area last year and loved it! Depending on how much time we have left from visiting the other towns on our list, we may try to get back there. We spent a lot of time in Montepulciano, and loved it!

*TJ
Hello Hokey Pokey (Love the name!),
For your stay in Tuscany, I would suggest Montepulciano. It's a fantastic lively town with wonderful restaurants and lots to do. For your Wednesday (#10) Itinerary, San Gimignano, Volterra, Pitigliano, Cortona, Assisi, and Arezzo are all easy day trips - but you won't be able to go to them all in 1 day.

Thank you for the name kudos and for the itinerary recommendations. This is really very helpful. I listed the places we desire to go all in one spot for convenience, and not that we would do them in a day. I learned the hard way last year on our visit to Italy, when we tried to do too much in one day, rushing through Siena and other lovely places as much.

For your Thursday (#11) Itinerary, there are just too many fantastic wineries that can be visited from Montepulciano, which is home to Vino Nobile di Montepulciano. Again, like above, you will have to choose wisely.
If you need winery suggestions or accommodations suggestions, just them me know. We travel to Montepulciano frequently and know it pretty well!

Do you have recommendations for wineries and B&Bs, or Agriturismo’s in this region? When we visited Montepulciano last year, which we absolutely loved, we tasted wine in the city at De Ricci and Contucci. We are hoping to get to a more intimate place to be in and of the culture there. A cooking class/vineyard tour wine taking where you can eat the food as well. Perhaps this question is for another forum?

Thank you and everyone for helpful information. There’s o much to think about and put together. You all make it easier to work it out.

You are quite welcome for the kudos!

Seems like we both learned the hard way - on one of our first trips, we tried to see way too much and were not able to truly enjoy the everyday culture in Italy. Since then, we base ourselves in 1 or 2 places max and explore from there.

Ok - for B&Bs, I would suggest Fonte Martino (fontemartino.com). We stayed there earlier this year and will be back in late October. The owners are wonderful and the place is amazing. It is just outside of Montepulciano (which it has a great view of), probably a 5 to 10 minute drive at most. If you want something in town, it's not necessarily a B&B, but more of an apartment, check our Charming Homes (charminghomemontepulciano.com). We have also stayed there and the owner is really nice, but Fonte Martino is our first choice hands down.

For wineries, you need to go to Avignonesi (avignonesi.it). There are 2 options there to choose from. The first is The Grand Experience, which is a tour followed by a 5-course lunch where each course is paired with one of their wines. They are VERY generous with the pours too! I think this cost us about 95 euros per person and well worth it. The 2nd option is to just take the tour and then you can sit outside of their tasting room and for about 50 euros, you can choose either a vegetarian platter or a vegetarian platter with charcuterie - it feeds 2 and you won't want to eat dinner because there is so much food. With either platter, you can choose to taste 3 wines for 15 euros or 7 wines (I forget the cost). Either choice is amazing - you can't go wrong. I know they also offer cooking classes, but we haven't experienced that...yet!

Two other great wineries to visit are Dei (cantinedei.it) and Canneto (cannetowinetasting.com). While they don't offer everything Avignonesi offers, they are quite wonderful to visit and sample their wines.

TJ
Thank you for the BnB and apartment suggestions. I’ll look into those for sure.

We hope to keep costs no higher than €130/night. If it’s an Agriturismo, perhaps a bit more. If we book 4-6 nights at any BnB, I’m hoping there’s a discount.

For wineries, you need to go to Avignonesi (avignonesi.it)..
I saw this winery/vineyard name in a book I’m reading. Sounds wonderful! I will definitely put it on my list of wineries to experience.

How do ,you choose what Tuscan towns to visit, seeing there are so many wonderful places to go? I realize that is a loaded question, and everyone has their list, but it is really hard to choose! I don’t want to do an “Amazing Race” through Tuscany.

I edited my itinerary. Does it look workable? What changes should I make based on what days I have and days of the week i.e. Sunday/Monday Rome and car pick up and drop off? Does anyone wing some days of where to go and where to stay? Is that leaving too much to chance to find a place?