Wineries and San Gimignano and private driver questions

Please help me with this idea. Based on a friends recommendation that did this on their own many many years ago I would like to do the following and would appreciate some other input from people that have been there recently. I would first need to hire a reasonably priced driver so that's my first need. We (husband and I) would like to go to Antinori nel Chianti Classico and also Tenuta Torciano and San Gimignano and return to Florence. What are your thoughts and suggestions. Thank you so much!



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Hi, where can you find the classic panoramic view with all towers of San Gimignano? Is there any viewpoint outside the town on top of a hill or something? Please let me know!

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Hi. I am hoping to visit Italy next year and I’m currently on the lookout for reasonable airfare for the end of March/beginning of April. Is this a pretty good time to come weather wise? Rome is a must do and there are several other places I’d like to see and I have to figure out a reasonable itinerary for 14 nights. Florence, Venice, Bergamo, CinqueTerre, Burano, Lucca, Orvieto, Amalfi Coast, San Gimignano are all on my wish list. This will be my and my husbands first trip overseas. I like culture and my husband likes the outdoors and hiking. I would like to also stay in a agroturismo during part of our stay. I think three full days in Rome would be good and the rest divided up perhaps between Florence, Cinque Terra and Orvieto might work? Perhaps flying in and out of Rome/Florence. Does this sound doable?

Last minute trip - can I wing it??

Long story short, I had two other trips in planning that my teen daughter eventually vetoed :)

She has requested a culture/sightseeing/city trip over the 'nature' and 'beach' options. She's had a really tough year and with all the anxiety about heading into high school, I would love to make this happen for her. I have about a month to plan this trip, so here's my first attempt at an itinerary. We will be flying in and out of Rome (only option for a direct flight), which we'll be skipping as we have previously visited:

Day 0: overnight flight into Rome, arrive 7:30 am

Day 1: Rome to Naples via high speed train, Napoli, Overnight in Napoli

Day 2: Pompeii tour, Overnight in Napoli

Day 3: Amalfi coast tour (bus tour or private driver), Overnight in Napoli

Day 4: Napoli in the morning, leave for Florence via high speed train, Overnight in Florence

Day 5: Florence, Overnight in Florence

Day 6: Tuscany day trip (bus tour or private driver), Overnight in Florence

Day 7: Train to Cinque Terre w/ stopover in Pisa, Overnight in CT

Day 8: Cinque Terre, Overnight in Cinque Terre

Day 9: Train to Milan, Overnight in Milan

Day 10: Milan in the morning, train to Venice, Overnight in Venice

Day 11: Venice, Overnight in Venice

Day 12: Venice in the morning, Venice to Rome via high speed train or flight, Overnight Rome near airport

Day 13: fly home

Would love to hear your thoughts:

- We like fast paced, but is it too fast paced? Any suggestions?

- I feel like Milan is a bit of a 'detour' and I wonder if it's worth just for one day?

- Should we get TrainItalia passes? Which one?

- I would love to have some flexibility and not prebook hotels in case we want to linger in one area more - is this too much of a risk? (I wouldn't have considered it but i feel like we could 'wing it' this year?)

- Is there anything else I need to pre-book? (ie. tours, transportation, admission tickets, etc).

Thanks all in advance!

Edited: 11:46 pm, July 10, 2021

Recommended Cities To Visit

We're tossing around the idea of returning to Italy (late July or August) and wondered if we could get some recommendations on cities. We've done some of the 'must sees' on previous trips (Rome, Venice, Verona, Florence, Milan, Genoa, Siena, San Gimignano, Naples) and are now looking to put together a schedule that includes other biggies we've missed and perhaps less touristy hidden gems. We'll have about 2.5 weeks.

Anything recs you could throw my way would be greatly appreciated!

Where to base, 4-5 nights in Tuscany

Hello! I'm feeling overwhelmed trying to find the right area and accommodation type for our first visit to Tuscany.

We do not want to stay in Florence and are absolutely willing to rent a car (not sure where we would pick one up). We will be coming from Rome by train and heading to Venice afterwards.

Would like to be in a country setting, but close enough to access some restaurants in the evening and convenient to visit/do the following:

Florence - 1 full day

San Gimignano

Siena?

Wine tasting

A cooking glass

Our budget: moderate. Willing to spend more for a something special (ie: winery property, a view, etc)

Thank you so much!!

Italy Itinerary - Questions & Would Love Input!

After cancelling our 2020 Italy trip, I've just booked a trip for spring 2022. We fly into Venice in late April and will be in the country for 21 nights before leaving from Rome. I've booked accommodations online but everything is cancellable so I'd love to know you suggest any changes to my itinerary. And I have a few questions. Any input would be much appreciated as I've never been to Italy!

Here's what I've booked:

3 nights Venice - Wander, see Doge's palace & St. Mark's Square

3 nights in Sirmione, Lake Garda - explore Roman ruins, drive around lake, maybe boat trip to Isola del Garde

3 Nights in Florence - Museums & sights. Rent car when leaving & drive to Montepulciano via Chianti.

3 Nights in Montepulciano - Wine tasting, explore hill towns in Tuscany (& maybe hot springs?)

4 Nights in Sorrento (day trips to Capri & Amalfi Coast & maybe Pompeii, but that would be all the days and I want to just relax & wander in Sorrento too)

4 Nights in Rome - Colosseum, Vatican, and maybe day trip to Tivoli or Ninfa Gardens (though my husband won't be that excited about the latter so may skip it)

Does this look like a good number of days / nights in each place?

Also, I have a few other questions... From Venice to Sirmione - Would I be better off to simply take the train from Venice to Desenzano and rent a car there, meaning I could drop it at the end of my Sirmione stay and not pay one-way charge? Or rent a car in Venice and drive to Desenzano? And when we leave Montepulciano to go to Sorrento, am I better off dropping the car in Chiusi and taking train from there to Sorrento, or driving back to Florence & dropping it there, taking the high-speed traing?

Or should I re-order the whole trip, driving from Venice to Sirmione and then to Montepulciano, then take the car back to Florence, spend 3 nights there and then train to Sorrento?

I've noticed that a lot of accommodations are booking up already for next spring so if my itinerary isn't logical, I want to switch it around now while there's lots of options. I know there's plenty of time for booking cars & trains, but does the order make sense? Thanks in advance for any input!!

Hilltop town help! 2 or 3 days which ones should we go to?

We have 2 or 3 days for some hilltop towns. Out of these which would be the top 4 or 5 must see?

Cortona

Spello

Civita di bagnoregio

Orvieto

Pienza

San gimignano

Volterra

We don’t want a big town like Siena. From my research they seem to be the top seven in the area unless I missed one and if I did could you please let me know.

The ones I was thinking about seeing are

Cortona

Civitia di bagnoregio

Orvieto

San gimignano

Volterra

We tend to move fast depending on the size of the town. Maybe this is too many for the 2 maybe 3 days?

We just don’t wanna make the mistake of seeing too many towns that are too similar we really want to see different looking towns if that makes sense.