Florence Day Trip - Lucca OR Siena, San Gimignano, and Chianti?

Siena is really beautiful and I prefer staying there when visiting Florence because, to me, it’s Florence that seems crowded and filled with tourists. Siena is certainly worth visiting for at least one day, Lucca still has its medieval walls which encircle the town below, Lucca’s walls are so wide that you can rent bikes and ride them on top of the walls, Lucca’s also known for great restaurants and, as the hometown to composer Giacomo Puccini, quite often there are concerts featuring Puccini’s arias.

Hello jay_explores,

Siena is the classic day trip from Florence for good reason. It gives you a taste of what the Tuscan hilltop town experience is like in all of its ancient stonework walls, cathedral and great central piazza. Siena is easily manageable by yourself by either train or bus. The bus usually drops you in the center of town and saves you the walking from the less convenient train station but either works.

If you want to do wine tours or visit some of the further and smaller towns a tour is a good option for that since many of those towns are not well served by public transportation for a day trip.

I really like Lucca but it doesn't have a long list of big sights but it does have a fully intact old town inside the walls and offers the mix of new shops and restaurants but with an old world feeling. Lucca is easily reachable by train with the station lying just outside the huge ancient walls.

As much as I like Lucca if it is your first visit I would opt for the Tuscan hilltown experience just because it is one of the uniquely Italian/Tuscan experiences and the Tuscan countryside really is as beautiful as you've heard.

Have a great trip,
=Tod

Both are very accessible by train from Florence. We enjoyed Lucca best because of the atmosphere of the walled city. We thoroughly enjoyed renting a side by side bike and riding around the top of the walls. For us this was a unique activity. Enjoy your travels.

Another vote for Lucca.
I have stayed there twice and would happily go back .
It’s such a pretty town, not as many people, lots to see and the walls are wonderful to walk or bike on.
You can rent bikes very cheaply near the wall.
I’ve been to Siena and San Gimignano, also twice each, and was underwhelmed by both, but overwhelmed by the number of visitors cramming the streets.

I'd pick Siena. Take the bus and DIY. Go early, stay late. It is enchanting in the evening.
Siena is the classic hill town.

While Lucca has it's charms it doesn't really feel/look like a Tuscan hill town- at least it didn't to us. We stayed 2 nights, it was fine but not a lot to do/see.

An alternative thought:

When we were planning our itinerary for our last trip to Florence, we did exactly as you are: identified day trip options (and ended up with pretty much your same list.) Rather than book train/lodging, we maximized options/minimized obligations so that we could factor for on-the-ground variables like weather, how tired we were, etc. In the end, something we had not expected caused us to skip the day trip - we had fallen completely in love with the Oltrarno and couldn't get enough. We hit Siena, Lecco, and Chianti on other trips.