Where to stay in Tuscany?

I won't be travelling for about a year, but I am already excited and thinking about a solo trip back to Italy. Ideally, I would like to start my vacation relaxing in the Tuscan or Umbria countryside. I am thinking outside of either Lucca or Cortona or anywhere in between. (I'm not fussy, I love the Italian countryside and am just looking for peace, hills and beauty so I know that could be anywhere!) And I would like to do this mainly by train, and without driving myself (I don't want to rent a car). So my initial question then is.... if I fly into Italy, take a train to the nearest small town to where I would be staying, is it expensive to get a taxi to drive maybe 20km or so to a location outside of that small town. Also, any recommendations on what small town country side I should focused on? I know it's not much to go on, but any advice would be appreciated!

Hoping to spend 10-14 nights in Tuscany next April for the wife’s 50 birthday. We’re flying into Pisa and hiring a car. Been to northern Italy plenty of times but this will be our first trip to Tuscany. I’m really just looking for ideas where best to stay 2-4 nights in each place. Small villages, picturesque towns. No big cities. If people just shout out a few towns I’ll take a look and work out our itinerary.

Spending a couple weeks in Italy. Have a few days in Florence and I thought I would take the kids out into the countryside one day. Teenage boys and they love cars so thought even a vintage Fiat or some convertible. No destination in mind. Maybe leave about 10 or 11am drive an hour - 90 minutes out of town. Ideally a scenic drive. Not so much highways. Enjoy the scenery along the way. Stop for lunch around 1 or 2. Maybe hit a market or something ideally. Head back.

Any ideas? In addition to the scenery they like architecture. And history. Thought maybe San Gimignano. I know it’s often slagged in guidebooks as “touristy” but the distance is right. And obviously has some architectural appeal. But I don’t know if there is a scenic route there that is doable in half day?

Any other ideas? Thanks in advance

My husband and I visited Syracusa, Ortigia, and Catania a few years ago and promised we would return some day, and we are scheduled for 2 weeks in October! Can't wait!

We are interested in history, wine, biking, scenery, and local flavor. We do not want to be changing hotels every other day, so let me lay out what we are thinking and then get some feedback.

3-4 nights in Trapani: Fly into Palermo, rent a car at the airport, and drive to Trapani. If we aren't to tired we will detour to Segeste on the way. We would like to take the cable car to Erice, bike on Favignana, and then maybe visit salt flats.

Day 4: We were thinking that if we got up early we could make it to Agrigento, visit the ruins, and then continue on to Ragusa. If that's too much we would spend a night in Agrigento.

3-4 nights in Ragusa: We originally thought we would like to rent ebikes and visit wineries and other towns like we did in southern France and Tuscany, but as I'm researching I am wondering if that's a thing in that area. I couldn't find bike rental places in Ragusa and don't see any vineyards in that area either. (I did find a map that shows vineyards north of Vittoria and Comiso.)

3-4 nights in Palermo: We would do a day trip to Monreale cathedral, a day trip to Cefalu by train, and a day seeing the sights of Palermo.

Here are my questions:

1) Should we skip the Ragusa area and stay to the west, and if so, what should we do with those days? Should we stay in Vittorio or Comiso and try to rent bikes and visit those area wineries? Is that a pretty area? (I love the pics I've seen of Ragusa and Modica.)

2) Is there an area that has biking options (single day rides vs. multiple days). Ideally we would like to visit wineries on these rides, but scenery is a good incentive, too.

3) In my itinerary above I still have a few nights unaccounted for. Should I add another place, like Cefalu to the itinerary, or a place on the southern coast, or Marsalla, or should I just add the days to the places we are already staying?

4) We thought about visiting the Villa Romana del Casale, but it's about 2 hours north of Agrigento so not really on the way to any place unless we stayed in that area (Enna?) for a day or 2. Thoughts on that?

5) We also thought of staying overnight on Favignana to have 2 days of biking. Is that too much time allocated to see the island?

I will stop there. Vagabonda and others were so helpful on our last trip that I'm hoping for some common sense wisdom again this time. Thanks in advance!!

Kim

Would you recommend flying from Venice to Naples, taking a train or driving and stopping 1/2 way for a few nights in Tuscany (our original plan).

We fly into Venice for a few nights and then out of Naples. Originally was planning on spending 1/3 of our trip in Venice, 1/3 in Tuscany area and 1/3 around Amalfi Coast. Now I'm leaning towards longer time in Venice to day trip and longer time in AC area.

Hello,

My husband and I will be arriving in Florence on November 30 after 4 nights in Rome. On our trip booked for last September we were planning one night in Siena at an Agriturismo. Now that we are coming during late Fall would you recommend just staying 4 nights Rome/4 nights Florence and just taking a day trip to Siena/Tuscany? Is there anything still growing or in bloom in late November? I already have a voucher for 2 nights at San Firenze Suites but have not rebooked with them yet.

Thank you for sharing your travel wisdom. This will be our first trip to Italy.

First off- thanks in advance for any advice! (first time posting)

We are planning a ~2.5-3 week trip to Italy for May 2022 with our 2 kids (6 and 8).

My idea of a dream Italy vacay is cozy farms, beautiful scenery, amazing food, space for the kids to run and explore, bike rides, horse rides, and an authentic feel.

We also like to take our time in places vs trying to rush and see it all. I feel we have to see Rome and Venice but also know our kids will easily get overwhelmed and tired by the big cities.

Based on that, I have loosely come up with the following itinerary:

Fly into Rome (found a great points flight from our city); 3 nights here

5 nights in Umbria (agriturismo)

5 nights in Tuscany (agriturismo)

? 1-2 nights in Bergamo (my hubby has been and loves Citta Alta neighbourhood)

3 nights in Venice - fly home

Any thoughts on this? I love the idea of Cinque Terre but perhaps best to save it for another time (without the kids!).

Thank you!! Cait

We'll be in Florence at the end of June for 5 days. We would like to spend a few hours in the afternoon at a winery in the Tuscany countryside. We are not wine connoisseurs and are not looking for a tour, but are more interested in a very pretty winery with beautiful views so we may drink some wine and have a bite to eat. We are looking for a place that's within 45 minutes of Florence as we will take a cab. Thank you.

Hi all,

I am in the beginning stages of making plans for my late May, early June trip to Rome. I have decided on two side trips from Rome, Naples and Florence. While I am sure Florence is beautiful, and I will spend time roaming, I am also using Florence as a base for a few days, to take some bus day trips., to enjoy the countryside of Tuscany, and smaller towns. The one that I really want to go on will include Cortona, and Arezzo.

is this a good tour group to research ? if not, any suggestions, and also is it ok just to wait until I get to Florence to book these, or better plan more ahead.

Thanks for any help....

https://www.viator.com//tours/Florence/Tuscany-in-One-Day-Sightseeing-Tour/d519-5070TUSCANY?mcid=61846

My husband and I are planning to vacation in italy for our 25th wedding anniversary next year.

i am so overwhelmed with decision making and he is no help as he is very go with the flow and says yes to everything. which doesn't help me decide. lol.

we want to go to rome, pisa, florence, tuscany, amalfi coast

is it better to rent a car and travel this way or is it better to travel via train with all our luggage as we move from city to city?

or

could we be based out of one city for the entire vacation and travel to each place for the day trips?

if so, which city do you recommend to be based out of?

is renting a car a good idea?

i am planning a 14 day vacation to Italy, what is the best time of year to go?

thank you so much in advance for all of your help in planning this trip.