Tuscany’s Countryside Charm: Day Trips from Florence to Rolling Hills
Look, Florence is incredible. We all know it. But after two days of getting stuck behind tour groups and paying five euros for a bottle of water near the Duomo, you start to need a little… space. Thankfully, you can escape. The real Tuscan good stuff is just down the road. Think of it as a reset button, a day trip to places like Pisa or somewhere in the Chianti hills where the main agenda is a long lunch and a slow drive. It’s about finding those little towns that don’t feel like a movie set.
Tuscany’s Countryside Charm: a primer and quick facts
The countryside around Florence is full of all the stuff you see on postcards, hilltop towns, vineyards, and those skinny cypress trees. It’s the kind of place that’s best when you just slow down, trust me. The best part? You don’t have to go far. Most of the good stuff is less than a two-hour trip from Florence, so you won’t spend your whole day just getting there. Forget rigid plans. You’ll find the best markets, little family-run spots, and amazing views in the weirdest corners. Read this section to get quick practical pointers and a small table for key facts to copy into your planning notes:
| Quick Facts | Details |
|---|---|
| Best base | Florence |
| Top regions | Chianti, Val d’Orcia, Siena area |
| Typical day trip time | 6–12 hours |
| Transport options | Train, regional bus, car hire |
🔹 Tinker’s Tip: If you only have one day, aim for a single town and a scenic drive rather than trying to squeeze in three places.
Getting out of Florence: trains, buses and hire cars
First things first: how do you actually leave the city?
- Trains: A no-brainer for towns like Lucca and Pisa. They’re cheap, easy, and drop you right in the centre of town.
- Buses: Good for hitting the smaller villages where the trains don’t go.
- Rental Car: The best option if you want freedom to get lost on a backroad (in a good way). Just… get a small one. Seriously. The roads get tiny and parking can be a nightmare.
My method is to just start driving and stop when something looks interesting. You’ll be surprised what you find.
Train tickets can be found on Trainline.com! I use these because you can add the tickets to your apple or google wallets!
👉 Good to know: Booking trains in advance can save money, but for most regional routes you can buy tickets on the day at the station (expect more expensive tickets).
San Gimignano: Towers, Gelato, and Tourist Crowds
San Gimignano is an incredible pastry-box of towers and narrow streets that make for an easy, atmospheric day. The central square is compact and friendly, with great places to sit and watch the world. Try the local Vernaccia wine and pick a gelato shop that looks like it knows its flavours; I promise the queues are not random. Beyond the main streets there are small artisan shops with ceramics and leather, which are ideal for browsing without pressure. Allow time to walk the town walls and to cross the river for a quieter view.
💡 Fun fact: Those towers were basically medieval status symbols for rich families trying to one-up each other. A few of the originals are still standing.
🗺️ For Your Attention: Italy’s Coastal Towns: Gems of the Mediterranean
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Siena: The Big Rival with the Coolest Square
Siena was Florence’s big competitor, and it has a totally different vibe. The main square, the Piazza del Campo, is this giant, sloping, shell-shaped space that’s incredible for just sitting with a coffee. The cathedral is a marble masterpiece, and it’s fun to just get lost in the tiny back alleys. The whole city is pretty compact, so you can see the main hits without feeling like you’re running a marathon.
🔹 A tip from someone who learned the hard way: Check the opening times for the museums and cathedral. They have a habit of closing in the middle of the day for a long lunch break.
Chianti: Wine, Winding Roads, and Long Lunches
Alright, Chianti. This is the Tuscany you’re probably picturing. Rolling hills, cypress trees, and vineyards absolutely everywhere. The main road through the region, the “Chiantigiana” (SR 222), is the classic drive for a reason. It’s full of places to pull over and take a picture or stop at a winery. Most wineries are small, family-run operations, and they’ll give you an informal tasting with some local salami and cheese. If you want to drink without worrying, just book a small group tour, it’s what I did.
🔹 Pro tip: A lot of wineries offer simple tasting menus with cheese and bread. It’s often a better deal and more relaxing than a full-on restaurant lunch.
🗺️ Recommended Read: 10 Reasons Why Italy Should Be Your Next Stop
Recommended Tours from GetYourGuide
Val d'Orcia and Pienza: Postcard Views and a Lot of Cheese
This area is where they film all those car commercials and movie scenes (Gladiator). It’s almost ridiculously perfect-looking. The main town to visit here is Pienza, which is basically the capital of pecorino cheese. Go into any shop and they’ll let you try samples of different aged cheeses. Take a walk along the outside of the town walls for the best photos of the valley. The roads are fine, but you’ll probably have to park on the edge of town and walk in. Budget extra time for pulling over to take pictures. You will.
💡 The whole point of Pienza: It’s famous for its pecorino. Go find a small producer and they’ll let you sample cheeses until you can’t move.
🔥 Recommended Tour: Pienza Dairy Farm Tour with Pecorino Cheese Tasting
Lucca and Pisa: The Chill Town and the Famous One
You can totally knock out Lucca and Pisa in one day. They’re close to each other and easy to get to by train. Pisa has the famous leaning tower (it’s exactly what you think it is), but also a cool university-town vibe by the river. Lucca is the chill one. It’s relaxed and friendly, with these massive medieval walls you can walk or bike on top of. If you only have time for one, pick Lucca for a more laid-back day. I loved it!
👉 Seriously, do this: Rent a bike in Lucca. It costs a few euros, and you can ride the entire 4km loop on top of the city walls. It’s the best way to see the town.
Our Google Maps Legend
Save time pinning everything! Get lifetime access to our endless hours of research and time spent on the ground finding the best places to eat, drink, relax and explore in the area. You simply open the Google Map on your device and all our pins are at the touch of your fingertips.
Getting Lost: Finding Hidden Villages and Local Markets
Honestly, the best days are when you get off the main road and find some tiny village that isn’t in any guidebook. Market days are gold. It’s where you’ll find amazing produce, local cheese, and see real Italian life happening. Every town has one on a different day of the week, so just ask at your hotel or do a quick Google search. Find the one bar in the village, order an espresso, and just watch.
🔹 Tinker’s Tip: Just look for signs for a mercato (market) or a sagra (a local food festival). You can’t go wrong.
✋🏼 Fancy a Road Trip: All Our Road Trips + FREE Map
For People Who Can't Sit Still: Biking, Hiking, and Vespas
If sitting in a car all day sounds like a nightmare, you can actually get out and do stuff. The countryside is amazing for cycling, there are walking trails everywhere, and you can even rent a Vespa to zip around. Don’t worry about the hills, a lot of places rent e-bikes now, and they’re a complete game-changer. They make climbing those hills surprisingly easy. Just make sure you bring water and sunscreen.
🔹 Tinker’s Tip: A lot of local companies offer e-bikes now, which let you see so much more without destroying your legs. Makes a better trip in my opinion.
Family-friendly day trips and kid-tested ideas
Travelling with children changes the tempo of your day, but Tuscany is hugely forgiving for families. Choose towns with open spaces and short walks, like Lucca with its wall-top paths, or the broad piazza in Siena for running about. Farm visits are excellent if the kids want to see animals and learn about cheese or olive oil production, and many farms welcome short, supervised tours. Keep snacks on hand, schedule a slower lunch and plan for flexible nap times or downtime.
Many cafés offer children’s menus or simple pasta plates, and most gelaterie are happy to serve small portions. Look for playgrounds or shady parks for a mid-day rest, and consider a lightweight stroller for cobbled streets if you have a toddler. A relaxed plan with one big activity and small, flexible extras works best for family days.
Practical timing: best months and hours to travel
There’s no truly “bad” time to go, but each season has a totally different vibe. Picking the right one for you can make or break a day trip.
Spring (April-May): The Sweet Spot
This is probably the best all-around time. The countryside is ridiculously green, wildflowers (especially bright red poppies) are everywhere, and the temperatures are perfect for walking around without sweating through your shirt. The crowds are there, but it’s not the full-on chaos of summer yet. Just pack a light jacket, as a perfect sunny day can turn cool in a heartbeat.Summer (June-August): The Heat is On
Okay, summer. It’s going to be hot. Like, really hot, especially in the middle of the day. The trade-off is you get those long, golden evenings and the sunflowers are out in full force. If you’re traveling in July or August, you have to be strategic. Get out of Florence early—I’m not kidding, be on the road by 8:30 a.m. to beat the tour buses and the worst of the heat. Plan to do your main exploring in the morning and find a shady spot for a long, lazy lunch.Fall (September-October): The Delicious Season
This is my personal favorite. The crazy summer crowds start to thin out (still busy in Florence), the light gets soft and golden, and everything is focused on the harvest. You’ll see grapes being picked and smell the olive harvest in the air. The weather is usually beautiful and mild. It’s the perfect time for food-focused trips and wine tasting.Winter (November-February): The Quiet Season
If you truly hate crowds, this is your time. It can be chilly and a bit grey, but you can also get crisp, sunny days that are stunning. The landscape is more stark and dramatic without all the leaves. The best part? You might get a famous town like San Gimignano almost all to yourself. It’s the perfect season to disappear into a cozy little restaurant for a long lunch with a bottle of red wine.
And a universal rule, no matter the season: Don’t be surprised when shops and even some restaurants just… shut down from around 1 p.m. to 4 p.m. for a long lunch break. It’s not you, it’s just how things work here. Plan your day around it.
👉 Good to know: Local festivals and harvest times can add magic but also affect opening hours and transport; plan around them if you prefer quieter days.
Costs at a glance
Costs depend on choices – public transport versus hire car, casual market snacks versus sit-down meals, and free walking versus paid museum visits. A sense of typical ranges helps with planning: regional trains are economical, tastings range in price by prestige and format, and a compact car hire is sensible for flexible itineraries. Consider splitting a tasting between two people if portions are small, and ask about combined museum tickets which sometimes save money. If budget is tight, focus on market lunches and free walking to keep costs manageable.
| Item | Typical cost (per person) | € EUR | $ USD |
|---|---|---|---|
| Regional train (round trip) | £10–£30 | €12–€35 | $13–$37 |
| Guided wine tasting | £15–£40 | €18–€47 | $19–$50 |
| Lunch at trattoria | £12–£30 | €14–€35 | $15–$37 |
| Car hire (daily, compact) | £35–£70 | €41–€82 | $45–$90 |
Suggested itineraries: one-day and two-day plans
If you have one day, pick a single destination and travel at a relaxed pace 😌. For two days, consider a base in Siena or a countryside agriturismo and split time between nearby towns and a dedicated food or wine experience.
One-day sample
- Morning: Train to San Gimignano, walk town
- Midday: Lunch in a local osteria 🍝
- Afternoon: Scenic drive back via wine estate 🍷
Two-day sample
- Day 1: Florence to Siena, explore, overnight in Siena 🏨
- Day 2: Morning market, afternoon Val d’Orcia trip 🌄, return to Florence
Our recommended Car Rental
What to know How to Plan or Save for a Trip? Here are our best:
Now, over to you…
Have you got a favourite day trip from Florence or a small farm you loved visiting? Share your stories and tips in the comments below 🌻 I read every one and I learn from fellow travellers. Tell us the place, how you got there and one unexpected delight you found, like a café or a viewpoint. If you tried one of these routes, say how it felt and what surprised you most. Your practical nuggets help other readers craft calmer, more joyful days out.👇🗣️
Adventure on,
The Travel Tinker Crew 🌍✨
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FAQs
Is a day trip from Florence worth it?
Yes. Many of Tuscany’s highlights are within an hour or two of Florence and a day gives you a satisfying taste of the countryside and local food.
How do I get to Chianti from Florence?
Regional buses and organised tours run frequently. Hiring a car offers flexibility for vineyards and small villages.
Can I visit wineries without a booking?
Some accept walk-ins, but many prefer bookings, especially for tastings and tours.
What should I pack for a countryside day trip?
Comfortable shoes 👟, sun protection, refillable water bottle, light layer for changes and a small day bag.
Are day trips child-friendly?
Yes. Choose places with outdoor space and simple activities like farm visits or wall-top cycling in Lucca.
Travel Planning Resources
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Book Your Flights: Kick off your travel planning by finding the best flight deals on Trip.com. Our years of experience with them confirm they offer the most competitive prices.
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Travel Insurance: Never travel without insurance. Here are our top recommendations:
- EKTA for Travel Insurance for all areas!
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Book Your Activities: Discover walking tours, skip-the-line tickets, private guides, and more on Get Your Guide. They have a vast selection of activities to enhance your trip. There is also Tiqets.com for instant mobile tickets.
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Nick Harvey
Hi, I am Nick! Thank you for reading! The Travel Tinker is a resource designed to help you navigate the beauty of travel! Tinkering your plans as you browse!
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