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"Nightlife" in Tuscany

Sorry if this has been brought up in the forum before, struggling to figure out the search terms to look for similar questions.

We're planning a two-week honeymoon for May and have whittled it down to (probably) 7 nights in Tuscany, 2 nights in Rome, and 5 nights on the Amalfi Coast. Tuscany feels impossible to get wrong but alas, we still have to choose a place to stay. I think the plan is to rent a car and set up base in either Chianti or Val D'Orcia and do day trips from there. I'm not so worried about making attractions work -- I think we're only going to commit one day to Florence itself and the rest of the week no matter what will be about lackadaisically exploring and finding good food, good wine, and good towns.

What I am struggling with is getting a sense for the character of the cities/towns/villages that are often recommended: Siena, Pienza, Montepulciano, Montalcino, Greve in Chianti, Arezzo, etc. Specifically I keep hearing that the countryside towns tends to shut down after 9 or 10. That's not a major problem because my wife and I are not the type to go clubbing (she would laugh if she even heard me say "clubbing") but she'd like to have a sense of connection with civilization and being able to walk around town at night, maybe find a place to grab a drink, etc would help. I think we might go a little nuts after 7 nights of lights-out at 10.

Basically the dilemma is that on one end we'd like to stay someplace that's on the grid enough to have some activity at night (doesn't need to be anything crazy) but rural enough that having a car won't be a hassle and that we won't be overrun by crowds in mid-May. Ideally I'd love to have some kind of access to transit so that we can leave the car at home for a daytrip to Florence, but I'd be fine passing on that. Do all the places I mentioned fit the bill? Any that we should take off the list or add on?

Posted by
3184 posts

Siena would probably be your best choice.
Arezzo second choice

Other towns you listed are very small and yes quiet in the evenings.

Posted by
98 posts

Lucca is worth a look but I think after 3 nights there you might be ready to move on. I would lean toward Sienna and spoke out from there. Or split up your 7 nights 3 and 4.

Posted by
696 posts

After prepping for a wedding for months... and an intercontinental flight... several early nights may not be amiss. Seven nights in Tuscany could also be split between a family run full-service Agritourismo that has meals and activities and makes a great base for driving to other places, and Siena or a larger town where walking in the evening and later meals will be more possible.

Posted by
1767 posts

Siena is a lovely place to spend the night if staying in the old town, however, ZTL zone laws prohibit driving in the city center in both Siena and Florence. You can obtain a special permit which I’ve never done and if you enter one of these zones without a permit, expect to pay a hefty fine. Here’s a website that gives additional information: https://www.discovertuscany.com/siena/tourist-info/parking-lots-in-siena.html.
I took a direct bus from Florence to Siena (1h 15m) that dropped me off outside the old town. Siena is a wonderful place to be at night after the tourists leave. You can get a lemoncello to go and sit on the pavement at Il Campo with the others and enjoy the moonlight, it’s priceless. The day you leave Siena is when you want to rent a car.

The next night I stayed in Montepulciano and loved it. At dinner I was seated with two other couples and spent the night laughing and drinking too much wine. You can take a direct train from Montepulciano to Siena (1h 15m) but you’ll need to take a bus or taxi between Montepulciano’s old town and train station.

Posted by
1117 posts

I think we might go a little nuts after 7 nights of lights-out at 10.

And here I am, having believed that's what a honeymoon is for. ;-)

(scnr)

Posted by
1549 posts

Highly recommend Relais ortaglia, a very short distance from Montepulciano. We did not have a car and they own was within walking distance. The setting and property of this B&B us absolutely incredible. Phil and Sandy, the owners, from the US, put their heart and sole into their business. We’ve stayed there twice during our 2 1/2 years living in Italy and is on the top of our list.

Sandy will give you suggestions for daily itineraries to keep you busy. Or just hang out at great infinity pool overlooking the vineyards and relax. Spend 3-4 nights here and enjoy your honeymoon! The pictures on their website are just a taste. In person us better.

Relais Ortaglia B&B

We also really enjoyed Montalcino!

Posted by
369 posts

We just returned from Italy, and our itinerary was close to what you are thinking of. We started with 2 nights in Rome, then 3 in Sorrento, 5 on the Amalfi coast (a home between Atrani and Minori), 7 in Tuscany (Val D'Orcia) and 2 more in Rome. We had no rental car until we left the Amalfi Coast. We rented the car in Salerno and drove it up to Tuscany, kept it until we arrived back in Rome. The one way fee to rent in Salerno and return in Rome was very modest.

In Tuscany, we stayed at Agriturismo Cretaiole, a five minute drive from Pienza, in the Val D'Orcia region. It is a centuries old property, beautifully renovated into seven lovely apartments with kitchens, and a common veranda room. The property is beautiful: a vineyard, an olive tree grove, cypress trees, a location high on a hill with a wonderful view of the Tuscan countryside. It was our second stay there. Our first was in June of 2017. Five of the apartments are for two people, while one holds 4 and one holds 6, so it can have up to 20 guests. Both times we were there, a honeymooning couple was among the other guests!

Cretaiole guests can sign up for the optional "Dolce Vita" package that provides a large welcome basket of food (enough to prepare breakfast every day and an appetizer platter every afternoon), along with the opportunity to socialize with other guests in a variety of activities throughout the week. (They also offer an ala carte opportunity to just pay for whichever of those activities you desire.) The huge guest book in each apartment, and the concierge at the property, provide tons of information on places to go, things to do, how to get there, when it's best to go, where to park, etc. And the concierge will make reservations for you. You will spend time with the family who own the property if you sign up for the Dolce Vita package . . . 81 year old Luciano, his son Carlo, possibly also his 22 year old grandson Niccolo--a recent graduate of a hospitality school in Switzerland--unless he has taken another job by May. Luciano's daughter in law, Isabella, wife of Carlo, was very present when we were there in 2017 but these days she spends all her time at the other property that she recently opened, La Moscadella in Castlemuzio. (La Moscadella is gorgeous, with a swimming pool and a beautiful dining room where you can have chef-prepared meals. We looked at staying there, but we wanted the more rustic property and our own kitchen.)

On the trip we just got back from, we did easy day trips to Pienza, Montalcino, Montepulciano, Cortona, San Quirico, all towns with a lot of shops and restaurants, and also wandered through some smaller towns in the area that were lovely to see but didn't offer much in the way of shops and restaurants at the off-season time we were there (first week of November). Those included Bagno Vignoni, Montechiello, Sant Angelo in Colle, Castlemuzio, Sant Antimo. One day we left Tuscany and spent the day in Orvieto in nearby Umbria. It was only a 1.25 hour drive. On our prior trip, we spent a day in Siena, and I remember that the honeymooning couple spent a day in Florence. The concierge does offer to set you up with a driver who will take you to Florence for the day, if you don't want to make the drive or take the train. A fun thing in June of 2017 was the afternoon we spent enjoying the hot springs at Bagno San Filippo.

Siena and Florence and Orvieto would give you plenty of night life but if you were staying at Cretaiole, you wouldn't want to be that far away that late at night. I don't know how lively any of the closer towns are after 9 or 10. We never stayed out that late on either of our trips. We were there with friends both times and did most of our socializing back at the property. In general, people in Europe dine late so I have to believe that the restaurants that serve dinner are open late, taking reservations past 9 p.m. Whether there's anything to do after you are done dining is unknown to me.

Posted by
12809 posts

I’m from Florence so I am probably biased, but you seem to be a young couple who like nightlife, as it should be at your age, therefore I would choose Florence for a longer Tuscan stay. Florence is a vibrant midsize city with lots of entertainment due to the presence of over 50,000 university students, including several thousands international students in foreign universities and other institutions with a branch campus in Florence.

I understand your concerns about day tripping by car from Florence, as Florence is notoriously car unfriendly (but so are Arezzo and especially Siena), therefore it would be beneficial to choose your accommodations judiciously to minimize the hassle of getting in and out of the city by car during your day tripping.

These are some quaint choices to consider, all have parking, easy access to highways, and a short distance from the city center (a longish 15-20 min walk or a 3 min taxi drive) that you can visit the city center while your car stays safely at the hotel:

http://www.classichotel.it/
http://www.villacora.it/en/index.php
https://www.hotelvillacarlotta.it/
https://villa-la-vedetta-florence.booked.net/
https://www.villalibertyflorence.com/
https://residencemichelangiolo.it/

Some are posh and expensive, others not so much, so take a look and choose according to your budget. There are more I can think of, but these are particularly well suited to your needs, as they are outside the ZTL (restricted traffic zone), have complimentary parking, are easy to access by car, are immersed in nature around the Viale dei Colli, just like a countryside location, yet close enough to the historical center that you can walk to it, or just take a taxi for a few min (literally under 5 min) ride.

Posted by
26 posts

Congratulation on your upcoming honeymoon! Like many others here, I recommend Montepulciano as a perfect homebase to explore Tuscany during your visit. It's large enough where there is a lot to do and small enough to have an authentic feel. Many of the restaurants are open late and as mentioned. In addition, there is 99 Gradi, which is a wonderful hotspot that is open late and E Lucevan le Stelle, which is a great wine bar that often has live music.

For accommodations, my favorite spot is Fonte Martino. I have been visiting for the past couple of years (2020 excluded for the obvious reasons) and it is an amazing B&B. The owners are American and created a modern retreat in the countryside minutes from Montepulciano - walking distance to town.

I wish you all the best on your honeymoon! -Norman

Posted by
5394 posts

Have the two of you been to Europe before? The reason I ask is, first, how much longer a dinner out is intended to take in (especially) Italy. People devote the entire evening and more (with after dinner drinks, for example) to an excellent (I don't mean "famous" or "destination") meal. That also means that restaurants don't expect to "turn" a table, so you can't reliably stroll somewhere else for dessert (if that's your thing.) I don't personally like making restaurant reservations, but in busy tourism cities, you can't expect to waltz into a restaurant without one. I will note that even in New York City, truly local or neighborhood restaurants tend to hold a few tables for regulars and neighbors. An empty table through the window doesn't mean you can sit down there.

We're not night-lifers, so I'm not really much help to you. But (going back some years now), when I was in Reggio Emilia for a week at a time, more than once, I found the stand-up breakfast in a bar near my family-owned hotel to be the most "living local" thing I did there.

More recently, maybe 2018, when we were having our big meal of the day at, in fact, "destination" restaurants affiliated with Tuscan wineries, we had to reserve and pay in advance. But for our objectives, it was worth the effort. I had our hotel make the reservations a few weeks before our arrival. (Not suggesting, just reporting.)

Also, there's night life and ... night life. If it survives Covid-19, Maggio Musicale is an incredibly famous classical music and dance festival in Florence.