It may be a toss up, but just thought it couldn't hurt to ask. We are narrowing down our day-trip options and making plans for when we will be in Tuscany, May 22-28th. We will be traveling with a 14 month old and will have a rental car. We are staying northeast of Florence at an agriturismo and I'm thinking of our five non-travel days there we will spend 3, maybe four of them sightseeing and the other one or two relaxing at our agriturismo. Florence will be one of those days and then I think Siena will be another. I'm wondering about our 3rd stop whether to make it Cortona, Montepulciano, Lucca, or fill-in-the-blank. If it was just the two of us, we'd fill up the time a lot more and try to do more than one of these towns in a day, but with the little one and me expecting (new news here!) less is more. So it may be a toss up, but do any of these have an advantage of being easier to get around with a little one (in stroller), more rental car accessible, or just have an edge for some other reason in your mind. (Note: wine is suddenly not-so-important, now that I'm expecting again).

Also, since we are traveling with the little one, I'm thinking it is a good idea to narrow it down to two things in each place that we really want to see and then if we get to see more...well that's just gravy. I'm torn on Florence between the Duomo and the Uffizi gallery or the Duomo and the Museo Nazionale del Bargello. Uffizi has more to offer, but also more crowds which with little one, might be more difficult. I'm drawn to the Bargello because the guidbook says it has "the cream of early Renaissance sculpture" (Michaelango's David excluded). Wondering if anyone might have anything to add to shed some light on decision making? Thank you in advance. I've really appreciated everyone's help so far. Just one week til we leave for Gorizia.

Can't help on all of it but we found Lucca very easy to get around, well worth the visit and only 15mins(from memory) drive from Pissa if you want to look at that as well

Lucca flat
Cortona very steep
Montepulciano (the clue is in the Monte) very steep

Small child in stroller.....

I'd go to Lucca, the walls are very big and very thick and are made into a park so you can picnic on them. You park just ourside Montepulciano, Lucca and Cortona.

Florence has almost too many wonders but I think I would go for the Uffizi. There are quiet places you can drop out to, worst case grab a coffee in the sit down part of the cafe (probably a bit more expensive) but normally a bit less busy than the downstairs bar. I'd also go for the early start there.

With Cortona and Montepulciano, are they just steep streets or are there also lots of stairs to navigate? I understand that they are both more scenic than Lucca, though Lucca also has its charms.

Cortona and Montepulciano are steep streets, not really stairs. For Cortona you'd likely park at the bottom of town and from there you'll find a series of escalators to get into the town proper. We did it when our daughter was 6 months. Didn't find it to be a problem. Also done Montepulciano with her at 15 months. Sure you'll huff up a hill or two but certainly not a reason to skip a town.

That said, if you're only picking one and Lucca is just as convenient it is really a great town and the walk around the wall is quite a nice way to spend some time. It is completely flat, so certainly easier with a stroller. It's also about 30 minutes closer (not sure exactly where you're staying) than either of the other two towns.

Consider Arezzo too. About the same distance as Lucca and a great town as well.

Driving in central Florence can be a problem. There are many ZTLs, locals-only driving zones. If you search Fodors, you will find many people complaining about getting tickets in the mail for driving in a Florentine ZTL, when they didn't even know they'd done it. (A camera photographs your license plate, the car rental company identifies you as the renter and charges you for the effort, and the Florentine authorities mail you a ticket.)

There's a nice lot up by the Piazzale Michelangelo, where you get a famous view of central Florence. It's a not too steep walk up and down.

uflecka--thanks for the info on Cortona and Montepulciano. That helps a lot. I'm not really afraid of steep walks, more having to lug a stroller up lots of stairs. I'm thinking I'd really like to see either Montepulciano or Cortona. Maybe we can also do Lucca, not sure.

Mimar, thanks for the advice about not-driving in Florence. I should have said that I thought we would train in there. I was thinking of driving to the other places because of the enjoyability of the scenery and hope that the baby will nap in his carseat along the way.

Now to decide between Cortona and Montepulciano... tough call. I think we'll play the last day by ear, and if we feel like more sightseeing, take Lucca in and if we feel like relaxing spend another day at the pool at the agriturismo.

TWB, you have been warned. Have you ever been to San Fransisco and walked up the steepest hill. there? These are worse

I say go where you want to go, within reason... of the three you mention, we loved Lucca the most, and that was without a child.

But, really, just go where you want and you will just have to adapt/adjust a little with the child. We were in Venice last month with a 11 month old and a 6 year old. Totally fine. Sure, a stroller was somewhat of a challenge, but we adjusted, and kids survived, and I don't think we offended too many around us.

Although the distances are manageable for a brief day visit, you have no idea how long it will take you to drive to your selected choice of towns and get settled for sight-seeing. These places may look like they are close on a map but, if you don't know exactly where you are going, if you've never driven to these places before, you could eat up a lot of your day-trip time by driving around and around, simply trying to get your car parked in a safe and convenient spot. You won't know how to define convenient until you start to walk into the city, and finally figure out where you parked your car in relation to everything else.

For Tuscany exploration, I prefer being based south of Florence. I find it more convenient. The northeast side of Florence is OK for a Lucca visit. The A11 is a straight shot. Siena and Cortona will require more time. And Montepuliciano even more. Driving time will depend on whether you wish to drive the scenic routes or the A1 autostrada. I prefer the scenic routes because they are FABULOUS, but if you want more time for city sight-seeing, you may opt for the not-so-scenic autostrada. With the distances you've chosen, there will be trade-offs. You don't want to drive Tuscany in the dark.

I've been to all your Tuscan towns with a car and some cities, like Siena, are very challenging for a first-time visitor. It took me a couple visits to figure out the ideal approach and to find my favorite parking spot. I spent many an hour driving around lost, trying to figure out my location on the map. And let me tell you, I'm a map queen. I love the art of smart navigation. For first-timers, there is a learning curve that comes with exploration, especially with a car. Most novice travelers overreach and ignore the time it takes to learn the area.

If you were without a small child in tow and not pregnant, I would say who cares. Get lost and see what you can. It's a slightly different consideration when you are caring for a toddler and you need to keep your energy up and eat when you are hungry. If you get lost for one hour and you get hungry, it could take another hour before you actually sit down to eat. If you and your hubby struggled to find a safe parking spot or navigation went askew, a testy fight could ensue, and a crying baby could make you all wish you never went on vacation in the first place. I say plan your day trips with care and check to see if your hotel pool is heated. Most are not.

Re SIENA....the parts you will WANT to visit, especially around the duomo are anything BUT flat. And getting to that part of the city on foot involves some hills but I urge you NOT to be put off by that because in many ways, the Siena duomo is just as impressive as the one in flatter Florence, especially the many large mosaics on the nave floor.

Well, I guess it's what you're used to, but I didn't find Siena very hilly. A little sloped yes, but hardly noticeable.

Yes Siena is relatively easy and has good town elevators for the bad bits. The Duomo is like a wedding cake in marble (and that is just the outside), inside it is like a fruit cake

San Francisco's highest elevation is 925 ft.

Siena: 1,056 ft.
Orvieto: 1,066 ft.
Perugia: 1,617 ft.

Most Tuscan towns were built on mountain tops to protect them from warring factions. Maybe some people need to be pushed over the edge to realize just how high they really are.

As with hiking, it's not the elevation, it's the elevation change. San Francisco's lowest elevation is sea level, so that's a delta of almost 1000 feet. Orvieto is basically flet once you get on top of the mesa (tufa plug), and there's an elevator/escalator that brings you to the top. Perugia is pretty steep but also has escalators.

My vote is for Lucca, different than most with the WALL! No one has mentioned San Giamogano, well worth a visit.

Restaurants

Florence

Trattoria Marione
Via della Spada 27R

Trattoria al Trebbio
Via delle Belle Donne47/49 R


Ristorante Pizzeria Dante Trattoria *****
Piazza Nazario Sauro 12 R

Acqua Al 2
Via Della Vigna Vecchia, 40
(Angolo via Dell’Acqua)

Coffee Shop
Maioli
Via Guicciardini, 43

Osteria Santo Spirito
Piazza S Spirito, 16

Ristorante Pizzeria Lorenzo De’ Medici
Via del Giglio, 49/51r
Via del Melarancio 10r

Trattoria Garga
Via del Moro, 48

Trattoria Sostanza – Troia
Via del Porcellana, 25r


San Giamigano

Bruschetteria Wine Bar *****
Antica Taverna
Vicolo Mainardi 10

If driving a car, invest in a GPS, it will save you hours each day and even if you get on the wrong road it will ghet you back on track quickly. First time we did Italy was with road maps and although I am a very good naviagator we go lost so many times. Second time with GPS was a toatl brezze.