Siena - Day Trip/One Night/Two Nights?

Two nights in Siena gives you one full day, there is plenty to do, including a couple of stops on your way into/out of Siena. Plus you get the added bonus of seeing Siena at night. Twice.

I'm with Zoe. We spent the better part of a day in Siena this summer while on the Village Italy tour, and it wasn't nearly enough time. We didn't see half of what we wanted to see. Take two nights, and spend a full day in Siena. There's plenty there. Visit other hill towns another day.

Certainly more time in Siena is better than less, there is a lot to see and explore. Like many popular places, I found Siena to be more magical in the early morning and evening, as the city is awash with daytrippers from mid-morning through very late afternoon. I don’t think you can really consider Siena a ‘hilltown’, it is really a significant mid-sized city; most places considered hilltowns are much smaller.

I agree with the previous posters.

I would suggest that if you want to do day trips from Siena to the nearby hilltowns (and it is, I think, a better base for doing this than Florence), you stay 3 nights so you can have one full day in Siena and one full day to head out to towns like Pienza, Montalcino, and Montepulciano.

I would also recommend that you take the bus from Florence to Siena and only rent a car for the day you visit the hill towns. With five people, a car might be more economical, but you will have the massive headache of dealing with parking and traffic and ZTLs (no-car zones).

The first time I visited Siena, I was a day-tripper from Castellina in Chianti. We're talking the early 80's. My attempt to drive and park a manual vehicle there is an all-time classic story I tell over and over again. In spite of the parking woes, I fell in love with the place, but I regretted not scheduling more time there. My second visit to Tuscany the following year, I allowed three nights for Siena. Not one second of regret.

Siena is not easy to explore quickly like Pienza. Most people just pop in to visit the Campo so they can say they've been there. Others will include its famous Duomo, if they can find it, if they have time. The city-center can be quite hilly, so walking can get exhausting, quickly. There's a certain magic that happens at night, so limiting yourself to one night is a gamble on weather and how packed your itinerary is. You can't be in two places at one time. There are quite a few magical places in Siena to visit at sundown. Early morning can be a fun visual, too.

Those who fall in love with Siena can easily spend a week. Siena gets its share of repeat visitors. It's a fascinating place, and in some ways, it's more beautifully intriguing than Florence. The fact that you're considering at least one night is a good thing.

We went a couple of years ago and spent two nights in Sienna as an offshoot of our Florence trip for the exact same reasons you outlined. The amount of time was great and allowed us to explore towns like San Giminano and some wineries in the area we wanted to see.

Sienna itself was fine - not my favorite town by any means but still quaint. I will say it does hold my favorite church in all of Italy that we saw - absolutely breathtaking and worth a visit.

One note - make sure to note the local traffic laws in Sienna: there are many places (or all) within the old city walls that are local traffic only, i.e. you will get a ticket for parking in that area. There is plenty of parking outside the walls but note they are very strict on this and the ticket isn't cheap.

A lot depends on how many days you have in total. Florence needs at least two days (3 nights). Siena can be visited in a day. The trip is 75 min by bus, 90min by train. By car takes only one hour, but you need to consider the time necessary for the rental car pick up and return paperwork.

katiewil87, which church?

Thank you so much for your helpful replies. I may even be able to convince the family to stay for 3 nights! That way, we could visit more towns nearby.

Roberto, our itinerary at the moment (not yet fixed) is this. We are open to suggestions! :)

Arrive in Venice and stay for 4 nights
Florence – 5 nights
Siena – 2 nights
Rome – 5 nights - and leave from Rome

We have about 16 nights total.

Thanks again everyone.

You don't say when you are traveling.

For a first-time visit, five nights may be too much for Florence. Florence is a small town and can be very busy with long lines and large tour groups. Doing the tourist drill in Florence can get tiring quite quickly, unless everyone in the family is an art historian. :-)

Siena can be busy, too. Whereas, the smaller, beautiful towns of Tuscany will be a delight if you have a car. Depending on the time of year, I might add another night or two to country Tuscany. The country can be a great way to de-stress a trip like this.

Five nights in Rome works, but you could also cut that back by one night and still have a great visit. Rome is very layered. One can spend a lifetime there, so a lot depends on sensory overload limits.

I prefer to end a trip like this in Venice, but that definitely depends on the time of year.

If you keep five nights in Firenze, you can do a daytrip or two from there (Lucca-Pisa, Arezzo...). With three nights in Siena, you can daytrip to towns in southern Tuscany.

With five nights in Roma, you can visit Orvieto for a day, and/or one of the nearby hill towns, like Frascati, just to get away from the big city for a day - but there's plenty to do in Roma for five nights.

All of the places I named are easily reached by public transportation (bus or train).

Thank you again everyone.

NYCTravelSnob, we will most likely be going in May or early June.

"we will most likely be going in May or early June."

In that case, you can't find a better time to drive through the hill towns of Tuscany. Flowers are in full bloom and greens are unlike anything you've ever seen. The beauty from a car is extraordinary. Knowing what I know about those two months, I would spend less time in busy Florence, Siena, and Rome, and add one or more nights to the country experience. You won't regret it.

May and early June are fabulous months to visit Venice, May in particular. Normally, I like to end my visits in Venice, because Venice is on the water. It has no cars and no Vespas = less stress. It's a nice way to end a busy trip. As long as you are away from Piazza San Marco and the Rialto Bridge, Venice can be quite glorious in spring. Since you have the chance to be in Venice in May at the start of your trip, I would keep that. May is probably the best month to visit Venice.

3 nights in Florence are probably sufficient for Florence alone.
If you stay longer you have time for a couple of day trips from Florence, or you could add to Siena area.
Florence is good to day trip to Lucca+Pisa, and Arezzo (maybe Cortona too). Pistoia is also an easy one from Florence. Fiesole is a nice evening getaway.
4 nights are sufficient for Rome IMAO. So you could, likewise, borrow one for Siena area.
Siena needs a day, if you stay longer, you can use Siena as a base for some day trips.
If you intend to take day trips to small towns by car, I recommend staying near Siena or Siena but if you stay in Siena you need to choose accommodations accessible by car and preferably with parking facilities. Large portions of the historical center are closed to non resident traffic.

Once again, thank you all so much. I'm going through all your helpful responses with the family.

NYCTravelSnob, I'm happy to hear that we'll be headed there at a good time. You mentioned spending less time in "busy Florence, Siena, and Rome, and add one or more nights to the country experience." I thought that staying in/near Siena, using that as our base, and driving to any towns nearby would already give the country experience. Are there other places that I'm missing? Somewhere else that you suggest that we should be staying? Sorry to sound a bit confused.

I thought that staying in/near Siena, using that as our base, and driving to any towns nearby would already give the country experience.

Some historical perspective on Florence and Siena might clear up any confusion. Florence and Siena are serious cities. Montepulciano and Montalcino, less serious.

Even though they are in Tuscany, I don't view Florence or Siena as "country" experiences. Yes, if situated properly, you may be able to sneak a view of the country from some isolated, elevated perch. Both are smallish cities, for sure, when compared to Rome and Milan, but they are dense, busy cities with some serious traffic issues.

Unlike most of Florence, Siena is a hilltop city. More like a mountaintop. Driving in and out of Siena can be intimidating. The roads at the base can be confusing. So can the drive up. The routes need to be learned. GPS can be unhelpful. Most first-time drivers to Siena come away with horror stories. I'm a crazy NYC driver (taxis are afraid of me), so I view driving challenges as an adventure. I think driving on the Amalfi Coast is super fun, especially in a convertible, so I'm not considered "normal" on most travel forums (and I enjoy that).

If you want to use Siena as a base to explore Tuscany with a car, it can be done, but the best in-and-out routes require study. You need to be extra careful how you plan your lodging. I find it easier to enter and exit the city from the south. If your lodging is not selected well, you can get stuck in serious traffic jams each time you attempt to depart and return to the city center. Parking is a serious obstacle within the walls of Siena, which requires visitors with a car an extra layer of lodging research.

Some people find it less stressful to use lodging in the countryside as a base. There are many lovely places within twenty minutes of Siena that offer a true Tuscan country experience. Parking and exploring with a car is much easier from lodging in the countryside. It's almost always free. My favorite parking lots in Siena's city center (parcheggi) are Il Campo and Stadio-Fortezza. Once you learn how to get to them and leave them, IMO, they offer the fastest way in and out of Siena. I have little-to-no patience for traffic jams. If you choose to rely on Siena's parking garages, you need to learn how to use them. The research never ends.

NYCTravelSnob, thank you so very much for your wonderful and helpful reply. I'm going to do more research. You are correct. The research never ends! I'll look for places to stay within twenty minutes of Siena. I have read Rick Steves' book. My problem is that my book is on a Kindle and I would have preferred it if it was a regular hard copy. I lose my patience with all the browsing and searching. Next time! I'll be getting hard copies of his books on specific locations.

@Jane

Apologies - I oversimplified chuch - I meant the Cathedral!

Thanks, Katiewil87; we loved the Cathedral. Did you go to the Crypt? There was one statue that mesmerized me - and some amazing frescoes.

Some friends and I stayed at a hotel in Siena, at one of the gates to the town, that had a garage attached. It was Hotel Minerva on via Garibaldi. Not quaint but comfortable, many rooms have views of the Siena skyline, and it was very easy to daytrip to surrounding cities. It was a 20-minute walk to the Campo.

Thanks again everyone!

Zoe, thank you for the hotel recommendation.

Even though I myself would love to spend 4 nights in Tuscany, I had to compromise a bit. Our teenagers love cities. Here's our updated itinerary. As always, I'm open to hearing any of your thoughts. Thank you!

Venice - 4 nights
Florence - 4 nights
Siena/somewhere nearby in Tuscany that's lovely - 3 nights
Rome - 5 nights