Advice sought: In and around Tuscany and environs....where to stay, eat and what to see in early November?

Five days max in early November. All recommendations, especially for places to stay, but also to eat and tour, much appreciated!!


Also, for the record, I’ve never been to northern Spain.

Any must stays or eat here?:

If truffles appeal, worth trying to match dates with the events at the San Miniato Truffle fair (10th - 25th Nov, but it looks like the 12th is the big day). Personally it’s the truffle fair we enjoyed the least (preferring the biggie in Alba, but also a small one in Pianoro south of Bologna), but even the 3rd favourite truffle fair is one I’d visit again.

Loads of places to stay, and a very good selection of agriturismi. Factors I’d include in searching for accommodation would be:

  • Entry and exit flight points, as transfer time isn’t typically enjoyable
  • Accommodation that really suits in its own right, irrespective of location
  • Proximity to the places that really appeal to you in Tuscany e.g. wine regions, historic sites, superb countryside for walking or driving.

Ideally just a single base, and with each day trip option within easy reach, or that any longer day trips being ones where you expect appeal in the journey itself e.g. a scenic drive, or extended train trip without changes.

If flying in/out of Pisa or Firenze, then San Miniato is certainly close, sitting between the two. It might not be the worst idea to look around that area, such that a day trip into Firenze and/or Pisa, can blend with a trip to the truffle fair, and exploration of some of the smaller villages / nearby countryside. Lucca also in range and that’s another superb day trip option, with an excellent wine shop with aged stuff in the cellar out back. A more humdrum but authentic day trip option might be the port city of Livorno, with their local speciality a fish stew.

A quick note about Pisa. I describe it as an over-touristed blot on the landscape (as many do), but ALSO an under the radar gem. Avoid the direct walking routes from both train stations to the field of miracles and the area immediately surrounding it (they really are blighted by tourism), but the city to the west is much better, with good fairly priced food easy to get, a decent market and better farmers’ market, the pleasant aspect of a river running through it, and good interest just strolling around, with a decent evening passeggiata along the pedestrianised main shopping street. Also pleasant are the botanical gardens not too far from the field of miracles. It is still moderately touristy but not blighted by it.

@A_S_K_R_O_B_A_C_K - Have you firmed up where you’ll be flying into ? Will you hit Florence at all as part of the 5 days ?

Any preference on wine touring or if that’s important ?

Hi Drew;

In Florence now. Loving it, the weekend was downright tranquil, busier since Tuesday, but not crazy busy. (Pretty clean too).

But Tuscany is a big place; can you narrow down your interests? There is great food and drink everywhere in Tuscany, where to choose is more about city vs small town vs country living.

Re: Florence, I just got back from Entotecca Piti Goia (a board favorite), and THE place to get affordable aged Chianti. A very nice 1980 Sepvalpania Riserva for 12 euros a glass, many old bottles under 100 euros. Small food menu but very well done.

Cibreo is very good for upscale dining.

5 days isn’t a lot. If Florence isn’t your cup of tea, I might choose Sienna, great town (no cars in centri), and great day trips (montalcino for wine, San Gimignano for history and towers (especially in the evening after the tourist hoarded have left), Volterrs for Etruscan history).

Apologies for not being online to reap the benefits of your wisdom this week, but work has been crazy. Hence the need for a vacation! Thank you all. I’m sorting through all this now and will eventually throw out some follow-up itinerary thoughts for additional input if you don’t mind.

Any additional specific hotel recommendations in or around Tuscany or as a base for day trips?

I’m assuming a car rental is a must. Barry, I definitely want small towns to be included in the mix, but I’ve never been to the area so am up for anything.

Best airport to fly into/out of is Florence?




Thinking of flying into Florence (from Barcelona) but have not looked at flights as yet. Does that make sense? Better options?

This may be heresy on this board, but I have not seen my finance in a super long time due to the pandemic (long story) so spending time with her just enjoying the environs has my priority this trip. Sight seeing, dining and enjoying good vino is the goal. If that includes a must visit winery, so be it, but it’s not controlling for this venture.

Given the relative proximity of Pisa and Firenze, I’d suggest you have a good look at flight options next.

It might be that one is significantly more convenient than the other, either on your departure / return airport, or more likely one is simply more convenient on timings, or better on price. Also, you’re not tied to arrival and departure airports being the same, as it might be easier to fly into Pisa and out of Firenze (or vice versa).

Pisa is certainly a decent airport, not overly large, but with pretty good international connections, plus superb connections via train to the rail network (or by shuttle bus to the city, which bizarrely is often faster).

Hi Drew- if you’ve never been to Florence I’d encourage flying in and spending at least one night there. It’s a beautiful city to simply stroll around and take in the sights. November should be nice as I would think it may not be as crowded. Some fantastic wine and food spots too with Enoteca Pitti Gola a very worthy board favorite. You could spend one night there then pick up the rental car( it’s a must) at either the train station or airport. We’re using Sixt in October and they have locations at both.

Once you head out of Florence Pienza is a good spot to stay in. It’s a good location to visiti Montepulciano, Montalcino, Siena and even the southern part of Chianti. We’re staying here in Pienza Agriturismo Il Casalino -Pienza- in October.

Another option closer to Florence would be to stay in Chianti region and explore it along with San Gimignano and Siena. I don’t know those villages as well so can’t be too much help but could suggest some good wineries to visit.

You’ll have so many great wine options at both restaurants and Enoteca’s in the main villages that you can easily pass on doing winery visits for other activities.

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Florence airport runway is short snd there have been times folks luggage haven’t been on their flight due to weight restrictions. I haven’t experienced that, but read it on the travel boards. An issue on departures, not arrivals.

So if it were convenient, I’d fly out of Pisa. If it’s your last stop, then no big deal if your bags don’t arrive in the same flight as you will be home, so leave from Florence.

Siena is a better base for day trips to small towns due to the hassle of getting in and out of Florence

But if you were into a day trip to Bologna or Siena from Florence, no car is needed.

Agree that winery visits are not that important for drinking great wine.

Lucca, near Pisa, is a cool town.

Personally. I’d stay 5 nights in one place. If you want to see Florence, spend the time there. With perhaps a day trip.

PS looks like nonstops on Vueling from Barcelona to Florence. I didn’t see any to Pisa.

PPS Do you want to get a car? For me, no car is blissful , car is stressful.


Not adding anymore to the great suggestions made here, but will say that if and whenever you can, book you restaurant plans in advance.
Most of the places mentioned are also locals favorites and you’ll be competing for available table with them.

@A_S_K_R_O_B_A_C_K - if you do stay in or near Pienza highly recommend doing dinner one night at La Bandita in town. The restaurant flys under the radar a bit as it’s part of the La Bandita townhouse but it’s really an excellent restaurant. Food right up there with any Michelin * we’ve had in Italy but in a casual fun vibe. Also a well priced smart wine list.

We’re doing at least one night there when we visit.



Yet another vote for La Bandita!

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If you find yourself in Cortona I recommend Molesini Market for a wine tasting.

Hopping on this thread as well, have 5 days in the Tuscany area also early Nov. Is Florence the best home base to stay? Or is it best to stay Florence a couple nights then rent a car and stay in Montepulciano or Siena for the other few nights as a base for exploring the region.

Some of us like to stay in one place and relax, others like to run around.

Siena over Florence for multiple day trips with a car. Or any small town outside Florence.

Florence for staying in Florence or doing day trips without a car (Sienna, Bologna)

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It depends what you think is important (and not a guide book, or randos on the internet).

Every transfer is holiday time wasted: Packing bags; lugging them down to reception; checking out; getting to the transport (in this case the car hire firm, filling out their forms etc); the journey from A to B; navigating to the next base (including issues with ZTLs if central); checking in; unpacking bags; getting your bearings in the new place.

That’s not to say I don’t do transfers, but on a 5 day holiday, they’re not a great option unless it’s planned as a ‘road trip’ from arrival to the airport, to departure from the airport. Day trips may end up with similar or longer distances covered, but without the luggage and hassle, the day trip journey itself can be a pleasure (e.g. we love the fast modern Freccia trains).

Given it’s November, the weather can still be decent, but you have less daylight hours, so we tend to lean towards a town or city stay, rather than being in the middle of the countryside. i.e. it’s not as good for exploring the region as (say) May or October. That said, a sunny early November walk through vineyards remains a joy.

Barry’s comment about Firenze is worth noting. Staying outside with a car leaves you the flexibility of easy (maybe using the bus or a pre-researched easy to access car park) day trip into the city. The beauty of the buses are they typically drop passengers right in the centre, whereas the train stations in Toscana tend to be outside the centre. It also gives you a peaceful retreat away from the city and other tourists, plus if planned well, has you avoiding having to head towards the city on day trips out and about.

I like Bologna as a day trip suggestion in November, as whilst it’s busy, it’s big city busy more than tourist busy, so will give a nice contrast. The trains ( are fast and reliable, with trading up to 1st often v. cheap when booking in advance. Bologna has extensive porticoed streets, so even if it’s raining, you’ll often be protected. The food shopping is exceptionally good, and that allows for a picnic to be procured for the return journey. Note however that the train station is a 30 minute walk from the centre (or cramped bus ride or taxi).

Lucca certainly in reach of Firenze and it makes for a lovely compact day trip, plus its train station is reasonably close (just outside the city walls, so 5 mins to get inside). Both Lucca (Enoteca Vanni) and Firenze (Enoteca Pitti Gola) allow a wine geek to indulge, without venturing near a winery, plus there will be other enoteche (for drinking or buying).

Pisa also an option, but avoid the obvious tourist routes to the field of miracles and do make good time for the city itself (see more on this above)


Hi again, all, and thanks. Finally booked flights!

After four nights in Barcelona, we will fly into Florence, spend two nights there just to see Florence. Then, train it to Siena to stay there four nights, both to see Siena and then (renting a car) to do day trips, before heading to Rome (train??) one one night before flying home.

Now … quick onto hotels and restaurants now that it’s a definite “go.”

Still looking at hotels, but does anyone have any thoughts on (or alternative recommendations to) the following?:



Rome?? One night to enjoy Rome but then early to airport. What would you do?

What day trips from Siena home base?


What is the best website to find internal Euro flights? This time, Barcelona to Florence?

Any airlines to avoid or favor?