r/tuscany

Hello! I am visiting Tuscany in October and will be staying in Montepulciano. I will be there for 4.5 days and am trying to decide where to spend my last full day. I am thinking about taking a drive to Florence on Day 4. If not, my other plan was to visit Montalcino.

For context, I will have a car as I am flying into Rome and renting a car to drive to Montepulciano. I will be will my husband and parents who are healthy and capable of long walks. See my itinerary below:

Day 1 - Arriving late. Find a restaurant in Montepulciano

Day 2 - Explore downtown Montepulciano

Day 3 - Wine tour through private tour guide

Day 4 - Montalcino or Florence?

Day 5 - Depart Montepulciano

Thanks for your input in advance!

Hi everyone!

My friend and I are planning a 3-night stay at an agriturismo near Montepulciano, Tuscany, in september. We'll be coming from Florence and won't have a car.

I've done some research and know that:

We can take a bus or train+bus from Florence to Montepulciano town

OR take a train to Chiusi and call a taxi to the Agriturismo

Our stay is 3km outside the historic center of Montepulciano

My questions:

• Has anyone stayed at Montepulciano (or similar agriturismos in the area) without a car? How was the experience?
• Is it easy to get taxis from Montepulciano center to the agriturismo? Do we need to book in advance? How? Is there a specific cab or transfer company we can call?
• Did you manage to explore the area (Montepulciano, Pienza, Val d'Orcia) using public transport, e-bike or tours?
• Any tips for making this work smoothly?

We're okay with planning ahead and don't mind the occasional taxi, but want to make sure we're not setting ourselves up for stress! Thanks in advance for any advice!

Hi everyone,

I’m planning a road trip with my girlfriend from July 2 to July 12 and would love some feedback.

We live near Zurich, Switzerland and will travel by private car.

This would be my first time in Italy. I’m not really a sightseeing chaser — I don’t need to tick off every famous landmark. I’m more of a “vibes” person: good food, wine, beautiful towns, aperitivo, relaxed evenings, nice views and time to slow down. I love eating and cooking, so food is a big part of the trip for me.

This is the current itinerary:

Date	Place	Night	Idea	Goal	Morning	Afternoon
Day 1, Thu, July 2	Parma	1	Relaxed drive from Zurich	Start the holiday calmly without driving all the way to Tuscany	Leave early, drive via Gotthard / Milan towards Parma	Check-in, short walk, relaxed dinner
Day 2, Fri, July 3	Parma → Pisa → Tuscany base	1 of 4	Arrive in Tuscany with a short Pisa stop	Get the first Tuscany feeling without overloading the day	Drive to Pisa, quick stop if we feel like it	Continue to Certaldo / San Gimignano / Poggibonsi, check-in, pool, aperitivo
Day 3, Sat, July 4	San Gimignano / Certaldo	2 of 4	Free	Free	Free	Free
Day 4, Sun, July 5	Siena	3 of 4	Siena day trip	Culture, old town and good food	Drive to Siena, cathedral, Piazza del Campo, old town	Lunch in Siena, then return to the base
Day 5, Mon, July 6	Volterra	4 of 4	Quieter Tuscany day	Experience a more authentic town and slow down again	Drive to Volterra, old town, views, relaxed walk	Lunch in Volterra, then back to the hotel
Day 6, Tue, July 7	Tuscany base → Florence	1 of 2	Travel	Wake up in Florence on July 8	Slow breakfast, check-out, drive to Florence	Check-in, Oltrarno / Ponte Vecchio / aperitivo
Day 7, Wed, July 8	Florence	2 of 2	Anniversary day	Enjoy the day consciously and chill	Slow breakfast, no early pressure	Walk through Florence, rooftop aperitivo, nice dinner, evening by the Arno
Day 8, Thu, July 9	Florence → Bologna	1	Food / old town stop	More proper Italian city vibe	Slow check-out, drive to Bologna	Check-in, old town, porticoes, get ragù
Day 9, Fri, July 10	Bologna → Pontresina	1 of 2	Transition from Italy to the mountains	Push the return journey	Breakfast in Bologna, drive towards Engadin	Check-in, short walk, fresh mountain air, quiet dinner
Day 10, Sat, July 11	Pontresina	2 of 2	Quiet mountain ending	Wind down before going home	Muottas Muragl or Morteratsch	Coffee / cake, wellness or quiet afternoon, final dinner
Day 11, Sun, July 12	Pontresina → Zurich area	—	Drive home	Get home relaxed	Check-out	Drive back home

We start with Parma as a relaxed first stop instead of driving all the way to Tuscany in one day. Then we stay four nights somewhere around Certaldo / San Gimignano / Poggibonsi as a base for Tuscany.

We then spend two nights in Florence before continuing to Bologna.

I originally considered another stop, but Bologna seems more food-focused and “Italian” in the way I’m looking for.

Finally, we drive to Pontresina in Switzerland for two nights before going home. This is meant as a calm ending in the mountains instead of having a very long drive home from Italy on the last day.

Main questions:

1. What do you think of this itinerary overall?
2. Is Certaldo / San Gimignano / Poggibonsi a good base for this kind of Tuscany trip? If yes, what kind of stays would you recommend there?
3. Since it’s our anniversary, what restaurant would you recommend for it?

Preferences:

• I care more about atmosphere, food, wine, beautiful views and relaxed evenings than ticking off landmarks.
• Hotels should be clean, comfortable, slightly modern and car-friendly.

Would love to hear your thoughts.

Ciao everyone!

My friend and I are planning a 3-night stay at an agriturismo near Montepulciano, Tuscany, in september. We'll be coming from Florence and won't have a car.

I've done some research and know that:

We can take a bus or train+bus from Florence to Montepulciano town

OR take a train to Chiusi and call a taxi to the Agriturismo

Our stay is 3km outside the historic center of Montepulciano

My questions:

- Has anyone stayed at Montepulciano (or similar agriturismos in the area) without a car? How was the experience?

- Is it easy to get taxis from Montepulciano center to the agriturismo? Do we need to book in advance? How? Is there a specific cab or transfer company we can call?

- Did you manage to explore the area (Montepulciano, Pienza, Val d'Orcia) using public transport, e-bike or tours?

- Any tips for making this work smoothly?

We're okay with planning ahead and don't mind the occasional taxi, but want to make sure we're not setting ourselves up for stress! Thanks in advance for any advice!

Hello there!

I'm planning on a short Tuscany trip, most of the days I'm gonna spend in Florence cause this is my first time and there are a lot of museums to visit, but I also want to visit other towns/cities in 3 days.

I'm gonna stay in Pontassieve, and want to travel everywhere by train if possible.

What my question is - where should I go?

Can I manage to visit two towns per day without being exhausted?

I already have Lucca on my list, so I need to know where else to go:)

I don't really need tourist attractions here, cause I think I'm gonna be full of them in Florence, mostly I just need beautiful, calm places with nice "Tuscany styled" houses, cafes, vineyards and etc. . And most importantly - fresh air !

I'm not a big fan of wine and cheese, but I think it would be not right to not visit any vineyard in Tuscany, so I need some specific recommendations here - would be even more great if it's a small business.

My friend and I are headed to Montepulciano June 15-19th. I need some help figuring out where to stay.

Any advice is appreciated! Here are some of our wants and needs:

• We have a car, so parking would be nice (or recs on where to park if we stay in the city walls)

• Walking distance to Montepulciano if it’s not within the city walls

• pool would be great but we may not need one?

• I am hoping to stay at $350 a night or less

Thanks in advance!!

Hey everyone,
I’m a 23yo gay guy visiting Italy for a bit and thought I’d try my luck here 😊
Would love to meet some locals or other travelers to hang out, explore, grab food/drinks, or just show me around the city a little.

I posted in here a little while ago as i have a morning to hit a few wineries, more so to pop in, see the grounds, and do a quick tasting/purchasing. The three wineries I’ve narrowed my list to that are within proximity, open at a decent time, and can do a tasting without a tour are:

1. Lamole
2. Volpaia
3. Castello di Albola

Question: Has anyone been to these/can speak to if they are worth it?

Thanks!

Visiting Lucca and surrounding area in a few weeks. Would love to get recent recommendations on date night things, fun/easy hikes, wineries that are actually worth it, a dinner spot to splurge on (anniversary), and any good spas.

Goal is just to use local transportation! Want to stay away from areas where we’d just be bumping elbows with people.

Just got back from one week in Italy, fourth trip overall but first time doing Florence and Tuscany. Sharing the full breakdown since I spent an embarrassing amount of time planning this and maybe it saves someone else some time. Separate wine post covers all the winery visits in detail. We drove ourselves everywhere in a rental car. We were quoted 600 euros to be driven to two wineries and said absolutely not. I planned the whole thing so nothing was more than 20 minutes from our home base at Capanna Suites in Montalcino. We are a married couple, early 30's, travel abroad often.

One thing I did not plan well for: May weather in Florence. I've only been to Rome and southern Italy before and I assumed May would be warm and lovely everywhere. It was not. It was chilly, and it rained constantly. Learn from me.

Route: Rome arrival > Florence (2 nights) > Chianti / The Clubhouse Hotel (2 nights) > Montalcino / Capanna Suites (3 nights) > Rome (1 night) > home.

MONDAY: ROME TO FLORENCE

Landed in Rome around noon, train straight to Florence, didn't get in until around 3. First mistake: we walked our suitcases from the train station to the hotel. It's doable but it's not fun. Checked into Palazzo Ridolfi, apartment-style, huge amount of space, which was exactly what we needed after a long flight. No frills place, but huge which is hard to find in a city. Only weird moment: a maid (I think?) knocked at 2pm one day, didn't speak English, I think wanted to use the restroom in our apartment? That was a little sketchy, otherwise enjoyable. Staying in Santo Spirito was nice, away from the hustle and bustle a bit.

Drinks at Alle Logge rooftop for the views, which were great. Touristy and expensive, obviously, but nice. Dinner at Antico Ristoro di Cambi: jet lag was brutal, the food was decent, lots of tourists, but not a trap. Got pasta and osso buco. Gelato at Sbrino on the way home, yes.

TUESDAY: FLORENCE IN A TORRENTIAL DOWNPOUR

It rained the entire time we were in Florence. Not drizzle. Torrential, relentless, soaking-through-your-shoes rain that stopped and started every few minutes, never long enough to feel safe leaving the umbrella behind. We lost our umbrellas at some point anyway, because of course we did. It was also genuinely chilly, not what I packed for at all. We blow dried our jeans at one point. And our shoes. Florence is still stunning in the rain of course.

Climbed the Duomo at 8:15am with the first ticket of the day. Worth every bit of the advance booking hassle, do it. Bought perfume at Santa Maria Novella, which is a genuinely wonderful experience even if you don't buy anything, the store itself is something. Got a leather jacket at Misuri, slightly pushy but I got a great deal, I was just firm on not needing a $1k purse. Sandwiches at Panetteria e Stuzzicheria De Neri when they opened, excellent. Walked Ponte Vecchio, ate at Gustapizza (also excellent, no notes). Wine tasting at Enoteca Pitti Gola e Cantina was a genuine highlight, low-key, not touristy, great pours, highly recommend if you want a real wine experience in the city.

Had a reservation at Osteria Giglio d'Oro for dinner but by 8pm we were completely soaked and it was a long walk in the rain and we just couldn't. Last minute table at Braceria All'11 instead and honestly it was the right call. Had the bistecca, great steak, great service, barely anyone in there on a rainy weeknight. Would absolutely go back.

WEDNESDAY: FLORENCE TO CHIANTI

Walked our suitcases from the hotel to the rental car station in the puddles to pick up the car. Also not great. Also something to plan around if you can. Stopped at Antinori nel Chianti Classico on the way out, about 40 minutes from Florence. Full review in the wine post. Short version: I was warned, I didn't listen, I regret it. Also stopped at McDonald's on the way because sometimes you just need to.

Checked into The Clubhouse Hotel at Le Fontanelle that afternoon. This was one of the best stays of the entire trip, up there with San Montano in Ischia for us. Only about 15 rooms, no kids, incredibly personable staff, the kind of place where people actually know your name. The room was spacious and private, the views over the vineyards were genuinely unreal, and breakfast every morning overlooking the property was something I looked forward to every day. Do not miss this view. Dinner at The Clubhouse restaurant, good with some standout dishes.

THURSDAY: CHIANTI DAY

Started with a spa day at The Clubhouse.The spa was excellent and surprisingly reasonable, around 130 euros for a 50 minute massage, booked the day before. It was a bit chilly at first but warmed up enough for an afternoon by the pool. We preferred The Clubhouse property over La Fontanelle, for reference. Vallepicciola wine tasting in the late afternoon. The hotel drove us over, it's 5 minutes away. Full review in the wine post but the short version is this was one of the best value tastings of the entire trip and came completely out of nowhere. We bought a case. Dinner at La Fontanelle restaurant. Neither hotel restaurant was mind blowing but both had standout dishes.

FRIDAY: DRIVE TO MONTALCINO + FIRST NIGHT

Drive from Chianti to Montalcino is easy and beautiful. Stopped at Capanna winery before checking in. Lunch in town at Alle Logge di Piazza. The eggplant parm is one of the best things I ate on the entire trip and I am still thinking about it. The pici was also excellent, as was the wine, of course.

Wandered the town, which is tiny and wonderful. Two afternoons during our stay we ended up at Enoteca Il Leccio, a tiny local bar with great Italian house music and essentially zero tourists. We stumbled in and kept coming back.

Dinner at Il Passaggio by Capanna: I booked this without realizing it was a full tasting menu, but we were staying at Capanna Suites so we committed. Around 200 euros per person with wine pairing. Pacing was surprisingly fast for an Italian tasting menu, service was outstanding, shoutout to Yosefina who sent us home with a bottle of Moscadello. The meal was great, and interesting, and probably incredible for the right person. We've been to the French Laundry, but I'm decidedly not an Italy tasting menu person, I just want loads of pasta. It felt like they're trying for a star though, and if you like tasting menus in Italy, this is for you. The pigeon was surprising, and the vegetable courses blew our minds.

SATURDAY: WINE DAY + BOCCON DIVINO

Castiglion del Bosco in the morning, Poggio Rubino for lunch, Cantina di Montalcino on the way back (one minute from Capanna Suites, wall to wall locals, 10 euro tastings, great spontaneous find). Full breakdown in the wine post.

Dinner at Boccon Divino. We were hesitant since we'd done a tasting menu the night before and we are again not tasting menu people, but a friend recommended it, and there's a cancellation charge within 72 hours. First seating at 7:30. We left at 11:30. I cannot stress enough how long this dinner is. The truffle gnocchi and onion soup were standouts, nothing else blew us away, portions are small, we left a little hungry. Prices were fair, I think 65 euros pp for one of the tasting options. A bottle of Fuligni recommended by the sommelier was a highlight. Worth going once but know what you're signing up for, time-wise.

SUNDAY: WINE + BEST DINNER OF THE TRIP

Podere Le Ripi in the morning (see wine post, this one is special), lunch at their affiliated restaurant, Patrizia Cencioni in the afternoon.

Dinner at Re di Macchia, a rec from our guide Irene at Podere Le Ripi. She worked with the owner in Napa. We showed up around 8 with no reservation, which I do not recommend, we were the only table without one and got lucky. The owner ran the entire restaurant himself the whole night. Bistecca fiorentina, truffle ravioli, and eggplant parm, all excellent, paired with a Rosso di Montalcino from Casanova di Neri. Tiramisu to finish. This was the best dinner of the trip, maybe one of the best meals I've had in Italy across four trips. Stop by in person the day before to make a reservation. Do not just show up and hope like we did.

MONDAY: DRIVE TO ROME

About 3 hours, easy and pretty until you hit the highway. Returning the rental car near Roma Termini was a genuine ordeal. We drove around for 20 minutes before finally finding the Hertz parking garage. Find the pin in advance, go straight to the garage, save yourself the stress.

Checked into Hotel Palazzo Dama, beautiful hotel, big room, wish we had more than one night. Third time in Rome for me so mostly just soaked it in. Lunch at Osteria Gnocco, pleasantly good. Drinks at Les Etoiles rooftop, one of the only genuinely sunny days of the whole trip, we sat up there for a while and earned it. Wandered to the Vatican for golden hour. Bought another watercolor from Salvatore Cosso (Art Atelier Coronari on Google Maps, @art.atelier.coronari on Instagram), we bought from him last year too, beautiful and affordable original art, highly recommend if you want to bring something home that isn't a magnet. Suppli at Supplizio, then dinner at Il Sorpasso in Prati. Three different prosciuttos from different regions plus two pastas. Shoutout to Anton for being an exceptional server. This was the best meal of the Rome leg. Gelato at Gelateria Cremilla after.

TUESDAY: LAST MORNING

Out at 7am for one last walk. Trevi Fountain and the Spanish Steps at that hour are a completely different experience, almost no one there. Espresso and a maritozzo, then the airport. Perfect way to end it.

A FEW NOTES

The rain was genuinely relentless through most of Florence and I was not prepared for it. I've done Rome and southern Italy and assumed May would be similar. It was not. Montalcino is worth building multiple days around rather than doing as a day trip if you love wine and if you love Brunello. We heard others at the wine tastings say things like 'we don't really love bold wines' while IN MONTALCINO. Read the room! Also- learn Italian! Speak Italian. It gets you a long way, even just saying please and thank you. Try to embrace the culture you are enjoying, and be respectful.

Happy to answer any questions! Grazie Italy, I'll see you again soon!

Hi,

Can you recommend me a good and trusted car rental in Tuscany? Preferably from Pisa airport.

I’ve read tons of reviews about damage scams from local companies. Any trusted that you can vouch for?

We'll be spending a few days in western Tuscany, near Pontedera.

Looking for recommendations for winery lunches in that area. Preference for great atmosphere, beautiful scenery, great wine, and good food, in that order 😄 - food could be cheese and cold cuts, wine should be nice but approachable on a lazy afternoon (although serious enough to be taken with us for dinner), but ambiance and scenery warm, friendly, and memorable.

Any suggestions would very welcome!

Is Assisi worth a day trip from Tuscany?

My partner and I are planning our first 10-day trip to Tuscany next September (Chianti hills + Val d’Orcia). We’ve been going in circles for weeks trying to sort villas, car rentals, and the best private winery experiences.

Can someone recommend a travel agent who actually specializes in Tuscany?

My wife and I spent five days in Florence over Christmas 2024 and have been to Rome several times in the past couple years. My wife really wants to see Tuscany in fall and I have hotel reservations for Tuscany in late September / early October this year. I made the reservations last fall and included some days in Rome at the end, but much as we love Rome, we ended up being there this spring (Buona Pascua!) and are not feeling like we need to go back quite so soon. Am looking for suggestions on what to put in the place of Rome in the following itinerary. I don't know whether I could extend any of the current cities (would require that rooms be available in any subsequent hotels so that I could change those reservations also).

Thoughts? Obvious is Venice. Maybe head to the mountains (Dolomites)? What other locations in Tuscany/nearby would you recommend--given where we're already planning to go? (We will be day-tripping to San Gimignano, Pienza, and several other towns near where we are staying.)

Where can you fly to nonstop from FLR for cheap and maybe do a couple days someplace else?

Thanks for any suggestions!

PS: what is post "flair" and why did I have to add it?? Confused!

https://preview.redd.it/makqiz4z461h1.png?width=2850&format=png&auto=webp&s=cbde1973df654ee7afcacf2f229744b28d1c808d