Itinerary for italy in may

Montepulciano is not that close to Florence. A car is almost a must. Adding Siena to the mix would make it hard to see even with a car. For Siena only you don’t need a car.

San Gimignano can be done by bus. But if you want to add Volterra then it might be too much for a day by bus (it is doable by car).

If you don’t want to rent a car, then skip Montepulciano.

Understood. Thanks. Would you recommend doing BOTH San Gimi and montepulciano, or one will suffice?. How about day trip to either Venice or Verona? Which one is the way to go....

Florence t Venice by train is 2 hrs each way, Verona 1.5 hrs e/w.
In my view a) that's too long for a day trip and b0 both cities, but particularly Venice, need more than a day.
The best time to be in Venice is before or after the day trippers.

A direct train departing Florence (Firenze) SM Novella station to Venice (Venezia) S. Lucia station (the end of line) takes 2h 15m. I suggest getting an early start. A direct train from SM Novella to Verona Porta Nuova takes 1h 45m.
You will need to rent a car if visiting San Gimignano and Volterra on the same day. If you don’t rent a car, skip Volterra and take a bus to San Gimignano that involves a connection. The journey will take 2h each way. I did this once and it was a long day.
Are you flying home from Florence?
A bus from Florence to Siena is direct and takes 1h 15m. Montepulciano can be a day trip from Siena but not from Florence if you rent a car for the day.

Montepulciano is 2 hours driving from Florence, so it is a long day trip but not an impossible one if driving. Almost impossible by public transportation, as the Montepulciano station is so out in the country to be of little use, and getting there by bus is too long. But it looks to me that all these questions could be simply answered by looking at the places on a map. It is evident that Montepulciano is much more distant from Florence than San Gimignano.
All hill towns are basically similar, Volterra, San Gimignano, Montalcino and Montepulciano look the same on first instance. If you begin to delve into them, each one is somewhat different. San Gimignano has more towers and if you are into arts has a little more riches; if you are into architecture, Pienza is different (the Cathedral follows a German model). But, after all, what are you looking for in these day trips?

I think Florence as a 9 day base is a crowded and expensive option if you plan to do several day trips. You are setting yourself up for long tiring days and arriving with the throngs of day trippers.

Where are you flying in and out of? Unless you have an extensive list of things to do in Florence, I would look at staying in Venice for a night or two and also in the Val d'Orcia for a night or two. For the Val d'Orcia visit, I would rent a car. It would be lovely to spend the night and enjoy the peaceful mornings and the beautiful sunsets. Enjoy!

Thanks everyone for the helpful info. Yes flying in and out of florence so its ideal for a base for 7 days. Would like to do 3 day trips and rest of 4 days in florence. 3.5 days in cinque terre also, in addition to the 1 week. For Day trips, I am looking to see something different/unique that I won't find at home...so architecture, history, culture , bike tours etc. Do you recommend just doing Sienna and skipping San grimigano (SG) since can take train to sienna and will be faster? If SG has a special feel to it and more memorable then I would rather do that. Since verona is quite big, doesn't seem like a good idea to go there though I will reach there faster than I can reach Montepulciano , with the train. Don't want to do overnight in Val d'Orcia etc since check in/check out can basically consume half the day. So far for day trips: San grimigano (SG) hightly likely, may be lucca, and maybe Montepulciano vs verona. what u think?

The train from Florence SM Novella takes longer than the bus. Not only that, Siena’s train station is located a couple miles outside of Siena’s historic center meaning you then need to take a bus from Siena’s train station to the old town. The bus from Florence drops you off across the street from the old town so it’s a no brainer to take the bus to and from Siena.
If you have your heart set on visiting San Gimignano then maybe you should go there. I prefer Siena because San Gimignano is packed with tourists and it’s smaller with less to do and see. What I like most about Siena is spending the night because that’s when it’s most charming. If you’re not spending the night then maybe you should go to San Gimignano. However, Siena would be easier to get to compared to San Gimignano.
If you go to Montepulciano, get an early start and spend two nights in Siena. The next day rent a car and drive along Val d’Orcia: https://lovefromtuscany.com/scenic-drives-in-tuscany/ to Montepulciano. The drive along the Val d’Orcia is more scenic that driving to San Gimignano and Volterra. You will see many different landscapes with rolling hills, big brick well-maintained farm houses that only the wealthy can afford sitting on grounds with impeccable grounds. It’s well worth the drive.

Thanks for the detailed reply. ya I am leaning towards San gimigano via bus. If I am going there is it really worth it to rent a car and go to Montepulciano but for day trip only? we want to stay in florence for all 7 days else check in/check out consumes lot of time.What other day trips you recommend (something different than other places we discussed): Lucca?......Bologna won't offer anything much different from florence so will skip that .Verona is 1.5 hr train ride from florence but town is so big that it may not be worth it for day trip.

Forget Montepulciano because it’s a day trip from Siena not Florence. Good day trips from Florence are Siena by direct bus (1h 15m) and Pisa and Lucca that can be done on the same day. There aren’t many direct trains from Florence’s SM Novella station to Lucca so take the 9:09a train (1h 30m). After a few hours in Lucca, you can go to Pisa and check out the sights there (45m). There are direct trains from Pisa to Florence SM Novella station taking 1h 15m: https://www.trenitalia.com/en.html.

Thanks a lot Marypat! Very useful info there. I notice that Sienna is close to San gimigano so is it really necessary to do both? And if I do day trip to San gimigano, then you think going to Lucca will be a worthwhile experience? I mean if it's just another small town, then perhaps I could just stick to one of them ie San gimigano OR Lucca OR Sienna. And I will try to convince my friend if he is ok with rental car to go to Montepulciano though it seems less likely given the responses here, unless we get a very early start. I am from Vancouver BC (canada) so we have lot of natural beauty here and the tuscany area looks similar to area called Okanagan in BC.

Secondly, we have 3.5 days in Cinque terre and will use La spezia as base. I feel 2 or 2.5 days there will suffice and add the extra day to florence to add more day trips from florence. Good idea? Or are there other places near La spezia we can explore as day trips?

It’s impossible to compare San Gimignano to Siena or Lucca because all three places are unique. Siena is best if you spend the night which you won’t be doing so remove Siena from your itinerary. I visited Lucca in 2006 before hordes of Rick Steves travelers showed up. The town was empty and I was bored. People on this website love Lucca. I’ve never read a complaint.
Follow your heart and decide what places you will visit when you get there. It’s obvious you’ve done your research. Trust your instincts and go with that.
Riomaggiore is a 15m direct train ride from La Spezia’s central station. There is also a 30m direct train from Monterosso back to La Spezia. Santa Margherita Ligure is a 1h direct train ride from La Spezia and Porto Venere is a direct 30m bus ride from La Spezia. There is also a 45m ferry that’s more expensive than taking the bus.

Consider splitting your time between Florence and Siena. Also, don't do a day trip to Venice. Go there when you can spend three nights.

”We want to stay in florence for all 7 days else check in/check out consumes lot of time. What other day trips you recommend..”

”Don't want to do overnight in Val d'Orcia etc since check in/check out can basically consume half the day.”

That is your decision to make, but think about the amount of total time you are taking to go back & forth for these day trips. Add up the amount of time at the end of your day trip you will need to walk back to a train station or walk back to car parking which is outside the ZTL center of the historical city, waiting time & then take the train or drive, and walk back to your lodging in Florence. I do a LOT of switching locations (much more than I would recommend for you). I really notice the advantage of arriving carefree at the next city, not needing to think about train schedules or transportation time the rest of the day vs. taking a day trip that’s longer than an hour away.

If you don’t spread all of your stuff over a hotel room, check out & leaving is no more than 10-15 minutes extra. The transportation total time to get there is the same regardless of moving or just a day-trip. Check-in is hopefully at a hotel in the historical center of the city, so you’re not walking out of your way either way. And check-in is at the most another 15 minutes. So, realistically, you’re spending 30 minutes more to not need to take all of the time to return back to Florence.

Strongly consider staying a night or two in Siena, or lovely Montepulciano. And Venice is magical in the evening & morning before day trippers arrive - not as fun during the busiest time of day.

• San Gimignano - I would skip this one. It’s very touristy & not handy.
• Siena - a wonderful city with the unique Campo & overall wonderful Tuscan feel. Gorgeous church & read ahead of time about the Palio, so you understand the intense culture & flags.
• Venice - an amazing experience that’s not to be rushed. Put away all mapping devices, wander & purposely get lost to feel the atmosphere away from the crowds. If you stay overnight, be sure to go to the San Marco piazza late evening!
• Montepulciano - one of my favorite Tuscan cities. Again, an atmosphere that intensifies late afternoon through morning, although nice anytime of the day.
• Verona - an easy & pretty city for tourists. I wouldn’t give it a high priority for your limited days.

Some others:

• Arezzo is just an hour by train.
  
• Rome is 1.5 hours by Frecciarossa (faster) train.
• Ravenna is 2+ hours by train, but the mosaics are stunning. Take the early 7:46 am train to arrive shortly after they open.

Thanks a lot everyone! really appreciate it... i still prefer day trips as from my past experience I do better when one city is made as a base for long time, more relaxing that way. so far I am leaning towards day trips to:
Sienna, San grimignano and either bologna or Lucca for 3rd day trip. I know overnight in sienna is recommended but I would rather see it little bit or not see at all. Car rental will be a challenge so skipping Montepulciano for now. I need atleast 3 day trips for my 8 days in florence so trying to find the best option. We are making Monterosso as a base for cinque terre for 3 days. Any nice towns in that area we could check out? Santa Margherita Ligure looks beautiful and it's on our list! Also I hope the walk from train station in Monterosso to our hotel there is not too bad. Lastly, 3 days in cinque terre area enough or should we steal 1 day from the 8 days in florence and do cinque terre for 4 days and explore the nearby towns?

You need more than one day in Bologna. Go to Lucca instead.
In my opinion Monterosso is the perfect base in the Cinque Terre because of its access to the train station. It’s a charming town to stay in too.

Ok. So it will likely be Sienna, San grimignano and Lucca for day trips from florence. And from Monterosso , will explore Margherita Ligure region as a day trip. Thank you!

Hi. Florence is my favorite city and I am also a fan of day trips. I will be visiting Florence in a couple of weeks and signed up for a small group day trip/wine tour to the Val d’ Orcia area including Montepulciano from Florence. It will be a long day but I think it will be worth it for the views and spectacular wine.

Hello Cindy! Can you please share which tour you signed up for? Only thing stopping me from going to that area is the need for car rental but if it's a tour with nice company, I might consider.

I’m with you on the driving! I usually take buses and trains for day trips but sometimes splurge on day tours. There are numerous tours to Val D’ Orcia listed on the Viator site. I chose to go with Keys of Italy and booked directly. They stop in Montalcino, Montepulciano and Pienza. I’ve never travelled with them before but they have very good ratings and were responsive when I asked them questions. This is my fourth visit to Florence and I can say I’ve never been on a bad wine tour haha.

Edited to add that this is a very long day tour that leaves Florence at 8:00am and returns at 6:30pm. For me, it’s worth it because I am traveling solo with some limited mobility. I have never had any interest in driving in Italy and I would really like to visit these areas. Several years ago we stayed in Sienna and did a wine tour to Montalcino and the wine was fabulous. Over the years we have sometimes taken day trips with a focus on art workshops/experiences which have been wonderful as well. I usually find these on Airbnb experiences, Viator or Get Your Guide.