OT: Visiting Tuscany in October--Your favorite town?
 

My wife and I are traveling to Italy in late October; two weeks, our fourth time in Italy. First stop is Cinq de Terra for several days of hiking. But after that we have not set any plans. Beyond renting some city bikes, no plans for cycling. We like hiking and exploring small cities. We will have a car.

Curious if PL Forumites have a favorite town in or near the Tuscany region? :)

Monteriggioni is one of our favorites, a walled hilltop small town. San Gimignano is touristy but interesting with all of its towers.

Well, obviously Florence. Siena is very nice. Personally, I prefer Umbria. A bit quieter, cheaper, and has everything you want in Tuscany except Florence. Dozens of little hill towns and Assisi.

My wife and I recently spent 3 weeks in Florence. We used that as a base to do day trips to various Tuscan hill towns. The train/bus system in that region is terrific for that kind of traveling. You can catch a morning train to say Lucca, Bologna, Siena, spend whatever time there you’d like then return home. Go somewhere else the next day and so on. So many experiences that way, food, travel, sightseeing, interaction with a wide variety of people. Did I mention food?

The Renaissance walled city of Lucca and home of Puccini, fabulous place.

My wife and I have lived on and off in Florence and in Tuscany for the past 25 years, although we have not been for the past few Pandemic years. You do not need a car to visit the major cities, eg. Lucca, Firenze, Pisa where the train will work great, but if you want to go to Siena, San Gimingano or into the countryside of Chianti, the Mugello, the Maremma, Val D'Orcia etc. you really should drive, as train service is spotty and buses are slow and inconvenient (at least in my view) Some cool places to go include Pienza and Arezzo that are a bit less commonly visited. Bike riding is also great of course.

This was going to be my recommendation as well. Florence was wall-to-wall tourists (should be a bit better in October); Siena the same when we were there in June. Both are must-sees, but you need to book tickets ahead for the Duomo, the Ufizi and other places.

Lucca has an intact wall that you can cycle or walk around, nice restaurants and some tourists (mainly from other parts of Italy) and is just more chill.

Lucca +1

Did almost four weeks using Siena as a base in November of '19. Was very happy with the choice. Had been to Florence before, with a visit to Lucca and Montepulciano/Pienza. Did not want the over saturation of tourism in Florence (hypocrisy), but, also, Florence is awful as a driving base. Found an AirBnB just outside the walls of Siena with gated parking, and that worked out really well. Florence/Chianti north, Volterra/San Gimigano west, Montalcino/Montepulciano/Pienza/Val d'Orcia south, Umbria east, and we did a ton of it, although Siena is awesome, too. So, parking and mobility is key. Beware restricted driving zones in various towns. We have a traffic ticket from Spoleto we have no clue why. But, cool town.

My favorite is the coastal area. Castle Carducci was home to the Hampstead and Phinney bike camps. They were based at Hotel Zimartino which has a great restaurant. I enjoyed staying in Marina de Carducci which is the seaside cousin to Castle Carducci. Bulgheri is a very cool town nearby which is home to the super Tuscans.

The riding is fantastic and a little less steep than further east, although you can still access Voltera and the classic hilltop towns.

Lucca. A relaxing ride on the wall is a must. Rent a bike with a basket, pack a picnic and bring your camera.

Siena, Lucca, Montalcino, Pienza, San Gimignano. You can't go wrong wandering around any of them. If you have a car to get around it's worth spending a half day in each.

Siena is a bit larger than the others. Buy some Panforte to take home. It's the ultimate energy food on the bike. Worth at least 20 watts.

Skip Pisa. Other than the tower, it's a little grimy and not much to recommend it.

I'm headed over in September, staying outside Lucca.

Sienna was amazing, maybe my favorite place I've ever been - bustling, active, weird, cool, good food. Great after nightfall. So easy to find a b&b/agritourismo a few minutes outside the town and get to stay in gorgeous Tuscan countryside/hills/strade bianche.

Florence was a bit too jampacked for me, especially in the center city. When I go to Tuscany again, I'd want to explore Volterra, which seems really cool and a little bit off the map.

Cinque Terre

Last time we were there we couldn’t pull ourselves away from Cortona. The several days planned for Rome were sacrificed as a result, and no regrets. But this was not a bike-centric trip… other than catching the Giro while we were there.

Cinque Terre is glorious, no doubt. But (at least in late May) it was too busy and over-touristed. Might be OK in October.