Pienza vs. San Gimignano for 4 nights?
 

Hello -

We are a couple traveling to Italy the last week of October. Flying into Venice, out of Pisa. We are staying 2 nights in Venice then traveling by train to Florence and wil pick up a rental car. We have 4 nights in Tuscany and I am trying to decide on staying in San G or Pienza. We will do day trips but at night I would like to be able to walk to restaurants/bars in the evening. We know that we will need to keep the car outside the city centre in San G.

I know that Pienza is smaller then San G, but how small? Any thoughts would be appreciated.

I’ve stayed just outside of both. I didn’t do any night strolling in either though. I did what you’re talking about doing – spoked out and so, in the evenings we were strolling somewhere else or cooking dinner at our place. I will say that San G is one of my favorite hilltowns. In the end, you’ll be in Tuscany. I’m sure that whichever way you go, you won’t be disappointed.

Thank you - well said. Not a tough problem to have :)

I think it depends on where you want to explore. The options from SanG are not the same as the options from Pienza. The two towns are more than 90 minutes apart.

Since I like to limit the one-way distance for day trips to about an hour, I'd prioritize my sightseeing list and decide which town is closer to the most destinations.

I will point out that, if you're picking up the car in Florence, you could drive to one or two of your sightseeing towns on the way to your final destination. I.e., Volterra or down the Chiantigiana (route 222) through the heart of Chianti.

I didn't limit myself on travel distance. We left from San G and drove to Castiglioncello, Pisa and the like. I love driving in Italy.

Book that Venice to Florence train ASAP -www.trenitalia.com - Italian Railways site- to get nifty discounts over buying once there. www.seat61.com has great insights on that - for general info on trains - www.ricksteves.com and www.budgeteuropetravel.com.

I have never been to San G ( and I have the hardest time saying that name) but we did stay between Pienza and Montelpulciano for two weeks. We loved both towns and they both have numerous restaurants. There are also many smaller hill towns within a very short drive. It is an absolutely gorgeous area with lots of things to do and see. We had wonderful food, glorious wine and an overall great time. We are going back next year to further explore the Val D'Orcia area. I'm sure you can't go wrong with whichever area you choose. After all you will be in Italy!

Pienza for sure. Much more beautiful landscapes and many more towns and restaurants to enjoy.

I don't know about restaurants at night, but Pienza is in Val d'Orcia. The region is simply breathtaking.

I've stayed in both before. While San G seems to have a tad bigger historical area (not much as you can walk side to side in 10 minutes easily)I preferred the restaurants in Pienza.

Much of San G is ceramic shops. While there are nice ones, many have cheap looking stuff. Pienza has a lot of cheese shops.

I also prefer the towns near Pienza such as Montalcino and Montepulciano(and the countryside) over things around San G.

You should choose based on which areas/towns you intend to actually visit. Both are convenient to Siena.

I would probably visit San G for a few hours after picking up the car in Florence and then drive to Pienza to stay.

We havent been to San G, but have spent two weeks in Montepulciano over New Years and are going back with friends this year.

Here are our pics (during winter but still gorgeous)

https://www.flickr.com/photos/pug_gi...57639164500734

Only spend a day in Montepulciano and loved it - great small-town base in incredibly gorgeous surroundings.

Pienza hands down. It's picturesque and charming. We adored the Val d'orcia region in all of Tuscany. Montalcino, Montepulciano and Pienza and in close proximity. The Tuscany most photographed is that of this region. Dining at Latte di Luna is a must! Listen to the chanting at the Abbiza di Sant'Antimo and visit Fattoria di Barbi winery. I'd go back in a heartbeat. Cheers!