Siena or Florence in May

How do you plan to move around?

Train or bus primarily, but we're not opposed to renting a car for a day.

It depends on whether you have been to Florence before and whether you want to see it or not. Both cities are suitable for day trips with bus or train to Tuscan towns (although Siena has limited train service), it depends on which towns you want to visit. Some are more easily reached from Florence, others are more easily reached from Siena.

If you want to stay in another smaller location, then you should rent a car.

This a good guide to what you can see in Tuscany by train or train+bus.
https://www.wanderingitaly.com/maps/images/tuscany-rail-map.png

Siena is a big city by rural Tuscany standards but does give a good feel for what hill towns are like with old buildings, sites and tons of history. Siena deserves at least a day all by itself and is a good place to arrange for a tour of some nearby towns and/or wineries and get a glimpse of the rural Tuscan lifestyle.

Florence has an embarrassment of art, history and culture and deserves at least a couple of days to itself. Check the list of sites in Florence and see what might be on your must see list - David and Uffizi are big for many people - and see how much time you want to spend there.

I would suggest at least a couple of nights in Florence, then Siena with a potential day trip to one more rural towns with the amount of wine or food tasting that you're interested in.

Keep in mind that most people here count nights rather than days since it's clearer and helps you know where to book lodging but keep in mind that two nights somewhere is only one full day sandwiched between days of packing, checking out, traveling and then checking in. Stating how many nights you have makes it clearer for people when they suggest itineraries and how much time to spend in places.

Have a great trip,
=Tod

Thanks Tod, good suggestions. I clarified my post, we're planning 5 nights.

You can use the website below to determine what you want to visit.
https://www.borghiditoscana.net/en/

Florence needs at least 2 full days to see just the very basics. Siena is another day affair. Some people visit Siena from Florence on a day trip.

Besides Siena itself, Lucca, Pisa, Pistoia, Arezzo, Cortona, Northern Chianti, maybe Volterra (via Pontedera) are more easily reached from Florence.

Val d'Orcia (Montepulciano, Pienza, Montalcino, Buonconvento) is more easily reached from Siena.
Alta Val d'Elsa (Monteriggioni, San Gimignano, Colle Val d'Elsa) and Southern Chianti are between the two, but slightly closer to Siena.

If you've visited Florence before, I'd probably stay in Siena, unless you are interested in the towns that are more easily reached from Florence.
If you have never been to Florence before, then I'd probably opt to stay in Florence.
With only 5 nights I wouldn't split my stay, since the transfer from hotel to hotel takes time, and I'd rather use that time for an extra day trip.

I think I'd rather base in Florence for 5 nights. We stayed there for 6 nights as first timers in March 2023 and thought that we'd plan day trips but we found more than enough to do right there. It's a compact city so you can walk everywhere and really wander at your leisure so you can make it a more relaxed pace rather than hustle and bustle. There are a lot of options for day trips including doing a day tour of some of the hill towns and famous wine areas, these might be worth the splurge if you want to save the hassle or renting and driving yourself. Or you can use the many public transportation options to go in a few directions (Lucca, Pisa, Sienna etc).
I visited Sienna as a day trip, driving from our agriturismo in March 2025 and really enjoyed seeing the town but I'm not sure I'd want to base there because of limited train access.

We want to enjoy a leisurely time rather than hustle and bustle.

I don't think you will avoid hustle and bustle in either Florence or Siena. Both very crowded and touristy.
Sounds like you are looking for a hill town experience in the countryside and for that you would need a car.

Florence needs at least 2 days although that is woefully short if you are interested in art.

hey hey jbbynum
when you say 5 nights in tuscany, what town in tuscany? it's a big area with many small towns/villages outside of florence. staying in "tuscany" usually requires a car to get around since public transportation can be slim and takes time.
if you do rent a car, you will need an IDP (aaa.com/IDP) which is mandatory in italy, before leaving states. read up on all the rules and laws, ZTL zones, parking can be very slim and garages may be further away from hotel with walking with luggage, using both DL & IDP when driving.
stay in florence and do day trip from there. it will be busy & crowded, always is. so much to see and do. book attractions/activities early direct from website, many are date/time stamped, early mprning if possible then rest of day tor roam around or other things
may 1 is a public holiday "worker's day", limited transportation, many shops closed, culture activities/parades if you're there, check other holidays in the month of may
as roberto says, short train to other towns (lucca/pisa, pistoia, siena, montecatini therme baths, prato)
visitmontecatiniterme.com
bus ride from pistoia for a relaxing afternoon in the spa or thermal pools away from hustle & bustle then back to florence
thecrazytourist.com 15 best things to do in prato
educated-traveller.com wine windows of florence or winewindow.com
paintandwineflorence.it
have a great time, read up about the class and reserve. a fun time away from crowds, bring home your personal souvenir
visitflorence.com best gelato shops in florence
florenceboattour.com
gondola ride on river arno with wine
tuscan-wine-tours.com
take a look what they offer, if interested book
gustowinetours.com
marcosway.it
toursbyroberto.com
very popular with RS, busy and booked. you need to book online or email roberto for availabilty. you will get other companies for tours, so many of them
eatwith.com florence dates # of people
something different, residents offer their homes for home cooked meals, food tours. click to see what's offered does it suit your fancy.
mercatocentrale.com
roam around this huge place, click artisans, scroll over faces and see what they offer. have lunch/dinner/drinks. i love going to markets & cruise around taking my time, up and down stairs. i enjoyed going through seeing everything & having a glass of wine.
many people will be day tripping 10am ish to 4-5pm and leave. just some other options for you to think about with history/smaller museums in smaller towns, plus wine is everywhere in italy not only tuscany
i've been 3 times, had a great & fun time, sat outside bar cafe with wine/chacuterie board and people watched near the carousel. just enjoy yourself, see people/places/things other first timers may not
aloha

They are both great cities to visit, but Florence wins by far. There is so much to see you could do the entire 5 days in Florence.
Siena is a great place to use as a base to see smaller Tuscan towns. But first do Florence.

Thank you for all the comments - great suggestions. I think we will stay in Florence based on the comments. Definitely have a bit more search to do - thanks for the links.

To avoid some hustle and bustle, plus being near but not too near the train station, consider staying in the western part of the Oltrarno rather than near the main attractions. We've stayed on that side of the river twice now, once in Santo Spirito for 10 nights and once most recently in San Frediano for 35 nights. Look at a map and find the Porta di San Frediano and then check out the walking distances from there to the places you want to go to --- I think you'll be surprised, since I always am. 15 minutes to the train station, 21 minutes to the cathedral, 18 minutes to the Uffizi. There are also little buses like the C3 and C4. Anyway, we love the neighborhood and its restaurants. We've only gone on a few day trips from Florence, but Lucca, Prato, Arezzo, and Pistoia were all quick and easy by train.

Stay in the countryside if you want slow. Find an agriturismo between the two. Morning views are better than hotel noise, and you're still 20 minutes from everything