citychicnyc

Hi! I am leaving for my 14 day trip to Italy in approx two weeks and have pretty much finalized my day-by-day itinerary except for one day in San Gimignano + Siena. My boyfriend and I will have 3 full days in Val D'Orcia and will be staying in Montichiello [Terre di Nano] for 3 nights. On the fourth day, the plan is to wake up early and drive up to San Gimignano and Siena. INSTEAD of going INTO San Gimignano, I was thinking of having a picnic lunch OUTSIDE of it... some where we will have a view of San G's magnificent skyline and the surrounding landscape. Then, we will continue on, drop off the car in Siena, explore the city [including an early dinner @ L'Osteria] until we have to catch the 7:15 PM bus @ Piazza Antonio Gramsci to Santa Maria Novella Station in Florence.

Does this sound like a good plan for San G/Siena? Can anyone recommend where we can stop to pick up food/drinks on the way and a lovely spot for our picnic?

I would also appreciate any feedback on the rest of my itinerary in Tuscany. I basically google mapped Stu Dudley's driving itinerary and each planned day. I split up his drive into two days. I also incorporated some bike rides to the sites + towns that are close to Terre di Nano. We will get to the remaining sites by car.

DAY 1
+ 1:00 PM Arrival from Positano
+ Get settled in, relax a bit
+ 2 hour bike ride to La Foce [if we're up for it]
+ Cooking Class + Dinner @ Terre di Nano

DAY 2
+ Morning: Bike to Pienza and explore town
+ Drop off bikes, pick up car and then have lunch @ La Porta
+ Afternoon: Montepulciano
------ explore town, stop in at Cantina del Redi
------ 3PM wine tour + tasting @ Avignonesi
------ 9PM dinner @ Osteria dell'Acquacheta

DAY 3
+ Early Morning: Bagni San Filippo [hot springs + travertines]
+ Stu Dudley's drive through Bagno Vignoni, San Quirico d'Orcia, Castiglione d'Orcia, St. Antimo's Abbey
+ Lunch @ Boccon di Vino
+ Afternoon: Montalcino
------ explore town
------ 3PM wine tour + tasting @ Ciacci Piccolomini
------ dinner @ Osteria Osticcio

DAY 4
+ Abbey Oliveto Maggiore on the way to San G + Siena
+ Picnic lunch outside of San G
+ Siena
------ explore town
------ dinner @ L'Osteria
------ 7:15PM bus to Florence

I hope I didn't overplan it. My bf and I are in our late 20s, very active, and have successfully executed my ambitious past itineraries. Thanks in advance!

CStoneTX

We just returned from Tuscany, and I am already ready to go back. you are going to have such a great trip. I think your itinerary looks full, but doable. I just have a couple of suggestions - there are others out there who are much more the experts than I am, so I am sure they will have ideas and feedback as well.

First, I noted that most of your dinners are not in Monticchiello. Driving at night in Tuscany is scary - it's very dark, and the roads are curvy and hilly. You may want to rething dinner in Montalcino on Day 3, and have dinner at La Porta in Monticchiello that night. We had dinner there, on the terrace, and it was outstanding! Probably our best dinner of the trip. There are plenty of places to eat lunch in either Pienza or Montepulciano on Day 2, so you won't lack for options!

Good luck on the bike ride to Pienza - it is beautiful (but hilly) countryside. I am sure that the views you get from the bike will be amazing.

On day 4, I think San G is a bit out of the way from where you'll be coming from. I would skip that, and just go from the Abbey to Siena. you could eat a picnic lunch at the Abbey, or in Siena. Keep in mind that the driving times in this part of Italy are always deceiving - the twists and turns of the roads, plus many of them are just one lane going each way, means that it takes much longer to travel from one place to another than you might anticipate. And you'll find yourself wanting to stop and take pictures, etc. along the way, too!

Have a great time!

Lexma90

For your picnic lunch, why don't you pick up picnic supplies (including, of course, wine) in Montalcino when you're there the day before? I'm sure there are places to pick up bread, cheese and salumi there.

In terms of where you'd eat it, I can't really help you. San Gimignano is visible for miles around, but other than stopping by the side of the road, I can't think of anywhere in particular. As long as you're obviously not on some farmer's land, the side of the road should work. I do recall seeing people who'd stopped their cars to take pictures of San G. in the distance, so there must be places where you can pull your car to the side.

I second the comment about the difficulty of driving on those roads after dark. And remember Italian (European) drinking and driving laws are very strict, so the designated driver will need to be drink lightly. We try to arrange our lodging so we stay IN the towns where we're eating, but that doesn't always work. Just know that you'll have some careful driving after dinner.

Driving from Montichiello to San G. is a bit of drive, but it is a gorgeous little city. You could see how you feel about driving further after your visit to the Abbey, as you pass Siena on your way to San G. Another option, less scenic but still beautiful, is to stop in Monteriggioni, a tiny walled town just north of Siena. There are several restaurants there with large outdoor dining in their gardens.

Early dinner at l'Osteria, in Siena? Do you know what time they open for dinner? Most restaurants in Italy open at 8, or 7 at the earliest. As an alternative, have drinks and appetizers at Liberaments Osteria, a lovely wine bar with food that's located right on the Campo. Then have dinner after you arrive in Florence.

Enjoy!

bobthenavigator

Nice plan, but you are underestimating drive times. You cannot do all of this. And, eat close to home---not further than Pienza or Montepulciano.