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Looking for the absolute best Tuscany day trip from Florence? You’re in the right place!
This specific Tuscany tour made visiting on a quick day trip a breeze. From medieval towns to vineyard views and iconic landmarks, this tour crammed so much into a single day without feeling overwhelming.
Everything was included: tastings, entrance tickets, and transportation, which made the whole experience feel smooth and stress-free. And as people who’ve done our fair share of tours, we can confidently say this one delivered.
We’ll walk you through each stop, what we loved, a few things we didn’t, and everything you should know before booking it yourself. Let’s get to it!
Our Itinerary on the Tour
Meeting point – Santa Maria Novella train station
We met our guide at 7:45 am outside Santa Maria Novella train station, right by the taxi stand across from McDonald’s, where they held a clear WALKABOUT TOURS sign. After a quick check-in, our group was ready to go by 8:00 am. With coffees in hand and the city just waking up, we set off excited for the day ahead.
First stop – Sienna
The drive to Siena took about an hour and 15 minutes, and our guide used the time perfectly, explaining the itinerary, pointing out landmarks, and sharing fun facts about the region that made the ride fly by.
We spent three hours admiring Siena, one of Tuscany’s most iconic medieval hill towns. Our visit started with a one-hour walking tour alongside a local guide who brought the city’s history to life as we strolled past elegant spots like Piazza Salimbeni and the colorful Contrada della Torre. Standing in Piazza del Campo, home of the famous Palio horse race, we got a real feel for the heart of the city.
The highlight, though, was stepping inside the stunning Duomo, packed with intricate details and centuries-old artwork. After the tour, we had two hours to explore at our own pace, which we happily used to browse local shops and enjoy a cappuccino at an open-air café.
Second stop – Fattoria Poggio Alloro for lunch and wine tasting!
After exploring Siena, we settled in for a scenic 45-minute drive through the rolling hills of Tuscany to our next stop—Fattoria Poggio Alloro, a family-run organic winery that honestly felt like a dream. We spent about an hour and a half here, soaking in postcard-worthy views of the countryside while sipping wine and chatting with fellow travelers.
We kicked things off with a laid-back tasting where we got to sample a few of the estate’s wines—each one somehow better than the last. Then came lunch, and wow, they did not hold back: homemade pasta, a fresh garden salad, local cheeses, cured meats, and those crunchy little Tuscan biscotti to finish it off.
The food was farm-fresh and delicious, and the atmosphere couldn’t have been more relaxed. Before leaving, we had time to browse the little shop and pick up a bottle (or two) to take a piece of Tuscany home with us.
Third stop – San Gimignano
Just a short 15-minute drive from the winery brought us to San Gimignano, a charming walled hill town and a proud UNESCO World Heritage Site. Much smaller than Siena, it’s known for its skyline of medieval towers—once 72 of them! Only 14 remain today, but they still give the town its nickname: the “Little Manhattan of Tuscany.” If you feel like a climb, you can get incredible views from the Torre Grossa!
We had about an hour and a half here to explore at our own pace. Our guide gave us a map and pointed out some must-sees, like Piazza della Cisterna, Piazza del Duomo, and the Rocca of Montestaffoli. Wandering through the cobbled lanes, past artisan shops and hilltop views, felt like strolling through a living storybook.
We grabbed a quick gelato (from a place rumored to be the best in the world!) and took in the sweeping countryside views before heading off to our final stop.
Fourth stop – Pisa
Our last stop of the day was Pisa, and after a 1.5-hour drive (perfect for a little nap), we arrived at the famous Piazza dei Miracoli. I didn’t expect it to be so beautiful—the white marble buildings glowed against the green grass and felt surprisingly grand.
Our guide pointed out the highlights, then let us loose with about an hour to explore. We wandered past the Cathedral, Baptistry, and the Monumental Cemetery before making a beeline for the Leaning Tower. If you want to climb it (and you should!), definitely book the timed entry in advance. The views from the top are totally worth the slight dizziness from those spiraling stairs.
After one last photo, we headed back to Florence. One hour on the bus and just enough time to scroll through the hundreds of photos we somehow managed to take in a single day.
Book the exact same Tuscany tour we took here for FREE cancellation!
Related Read: Need some help planning the perfect Florence trip? Check out our detailed 3-day itinerary to get the insider scoop on all the must-see spots and best restaurants!
What we loved about this tour
You get to see a lot
For a day trip, we were seriously impressed with how much ground we covered. Siena, San Gimignano, a Tuscan winery, and Pisa? All in one smooth, well-paced itinerary. It’s the ideal way to see the highlights of Tuscany without needing to plan a thing—or rent a car. We left feeling like we got a real taste of the region, and it’s super convenient if you’re on a tight timeline.
All inclusive
No need to stress about extra costs, this tour covers it all. Transportation, entrance fees, the full Tuscan lunch, and the wine tasting are all included, which made it feel like a really great value. We loved just showing up and not having to pull out our wallets every five minutes. Everything was taken care of, so we could just enjoy the day.
Balance of guided tour and free time
We had an awesome guide who kept things informative without making it feel like a school trip. Each stop included just enough guidance to learn something new, but then we were given time to wander, eat, shop, or just chill. It was the perfect mix of structure and freedom, and we never felt rushed.
Included wine tasting
Tuscany and wine go hand in hand, so having a tasting built into the day was such a win. The visit to Fattoria Poggio Alloro was hands-down a highlight, with rolling hills, homemade pasta, and delicious local wine. It felt authentic, not overly touristy, and the setting couldn’t have been more beautiful.
Easy meeting point
This tour starts at Florence’s main train station, Santa Maria Novella, which is easy to find and super convenient. Hotel pickups can sometimes add nearly an hour of driving around the city, so we didn’t mind getting ourselves there at all. We walked straight to the meeting spot, checked in, and were on our way—quick, simple, and stress-free.
Highly rated and positive reviews
Before booking, we saw this tour had over 16,000 five-star reviews (see them all here!)—and now we totally get why. Everyone raves about the smooth organization, the guides, and how much you get to experience in just one day. Most people mentioned it was a true highlight of their time in Florence, and we couldn’t agree more. It’s one of those rare tours that actually lives up to the hype.
Free cancellation and flexible payment options
One of the biggest reasons we love booking tours on Viator is their flexible policies! You can book a tour months in advance and still have the flexibility to cancel or change your tour up to 24 hours before you go. This is helpful if you’re booking a super popular tour (like this one) and still ironing out the details of your trip. Book now, and worry about the logistics later!
You can also pay over time, which is helpful with the travel budget. Viator lets you reserve the tour whenever you book it, and not have to pay a cent until two days before your tour. Or you can spread out the payments – whatever works best for you!
Related Read: Looking for some other fun activities to do while in Florence? Check out our top ten favorite things to do here!
What I didn’t like about this tour
A lot of time on the bus
With so many amazing stops packed into one day, there’s naturally quite a bit of time spent on the road. While it’s not the tour’s fault—Tuscany isn’t exactly compact—it’s worth knowing ahead of time. I recommend bringing a book, downloading a podcast, or doing what we did: leaning back, relaxing, and taking in the rolling vineyard views between destinations!
Large group
This tour runs with a full coach of up to 40 people, which means a little more time getting on and off the bus and occasionally straining to hear the guide if you’re in the back. That said, the bigger group helps keep the cost super reasonable for everything that’s included. And once you arrive at each stop, you still have plenty of free time to explore at your own pace.
Long day – (but all the tours are)
It is a long day—we left early and didn’t return until after dark. But honestly, that’s the case with any tour that tries to cover this much of Tuscany in one go. By the time we got back, we were happily exhausted and amazed at how much we’d seen in just one day. Definitely worth the tired feet!
Would I recommend this tour?
Absolutely! It’s such an easy and enjoyable way to experience the best of Tuscany in just one day, especially if you’re short on time. Everything is taken care of, from transportation to lunch to entrance fees, so you can just relax and enjoy the ride.
The wine was delicious, the guide was friendly and knowledgeable, and the whole day ran smoothly from start to finish. And with thousands of glowing reviews, it’s clear we’re not the only ones who loved it!
Don’t miss out – book this top-rated Tuscany tour from Florence here!
Why We Book Tours with Viator
Viator is a trusted online booking system for tours around the world! We almost always book our tours using Viator for a couple of reasons:
- Free cancellation on most tours – Most of the tours on Viator allow you to cancel and get a full refund up to 24 hours in advance. This is handy in case plans change, or if booking an outdoor activity, the weather forecast is looking grim.
- Reserve now and pay later – You can secure your spot on some of the most popular tours well in advance and not pay until closer to the day of the tour.
- Lowest price guarantee – If you happen to find the same tour at a lower price elsewhere, Viator will refund you the price difference.
- Pay in your chosen currency – Avoid costly international transaction fees by choosing to pay in your home currency.
- Peace of mind – When booking with tour operators you find in person on the street or in small booking offices, you are often promised one thing and given another. This online platform holds tour operators accountable with a written description of inclusions as well as the opportunity for customers to leave reviews.
Check out the Viator website here! Or, for more info, read our detailed review about Viator here.
Other Activities to do While in Florence
Visiting Tuscany is just one of the epic things to do in Florence! If you’re looking for more activities to fill your schedule, here are some of our favorite things to do. You can also take a peek at our ideal 3-day Florence itinerary for more suggestions!
- Learn how to make authentic pasta – If you travel like us, you travel for the food! So booking this pasta-making class was an easy addition to our Florence itinerary. We had so much fun learning the techniques to perfect our ravioli, but eating it was the best part!
- Visit the Uffizi and Accademia museums – As Florence’s most famous museums, the lines here can be very long! These skip-the-line tickets allowed us to breeze past the queue and spend more time seeing Michelangelo’s David and more!
- See the city from Brunelleschi’s Dome – Head to the top of the Duomo for the best view of Florence! This VIP tour had us climbing 463 steps up to Brunelleschi’s Dome, which was totally worth it! We also skipped the long line for the Duomo and had an amazing guide.
- Find the best food and drink spots – We thought this food tour was the best way to experience Florence! Not only did we find hidden gems with our local guide, but we also sampled over 14 dishes, sampled wine, and learned how to make Negronis – it was awesome!
- See Florence’s top sights in a golf cart – Florence is full of historic sights, so many that our feet hurt just thinking about walking to them all! That’s why we loved this golf cart sightseeing tour of the city. We covered so much ground in an efficient way, learned a ton, and had a lot of fun too!
Where to Stay in Florence
There are tons of accommodation options in Florence, whether you want a luxury, mid-range, or budget stay, and whether you want to be in a historic, trendy, or off-the-beaten-path area. I’ll leave a few recommendations below to narrow down your search.
Luxury – $$$
Located in the historic center of the city, the Donati Luxury Tower Suites is a stunning historic building. It’s been renovated into a 5-star hotel, and the design will have you never wanting to leave the hotel! Some rooms have views of the Duomo, and you can choose between deluxe rooms or suites – but everything will be of the highest quality!
Prices reflect this luxury, starting at €420. Check availability and reserve this stay on Booking.com.
Mid-range – $$
Hotel Porta Faenza is a moderately priced hotel in the old district, walkable to many local hot spots and main tourist sights. It’s also walkable to the train station, so you can get all around Florence! The rooms are quirky, cozy, and historic, making for a charming stay. You can book rooms for one to five people, ranging from €150 to €380.
Check availability and book this room on Booking.com.
Budget – $
You don’t have to sacrifice your budget to stay in the historic part of Florence. B&B Lorenzo&Lorenzo Vol.2 is a lovely, quaint hotel situated in the historic district. The rooms are simple, but comfortable and clean, and it’s a relaxed environment. Prices start at €65 and reach €180 during the busy time of year.
Check availability and reserve this stay here on Booking.com.
To see even more options, check out all the hotels in Florence here!
Related Read: For a full breakdown of the best areas and hotels in Florence, have a look at our detailed Where to Stay guide!
Don’t Forget Travel Insurance!
If you’re looking to save money on travel insurance, we currently use and recommend SafetyWing. We’ve been using their coverage since 2018 and they’ve had our backs when we needed emergency flights and got sick overseas.
SafetyWing is one of the cheapest providers out there and covers everything from medical costs to lost luggage, travel delays, and emergency flights. A huge difference we’ve found between them and other companies is that they let you take out a policy AFTER leaving your home country. We’ve also found it handy that it’s a monthly payment rather than a lump sum, and you can get a refund for unused time.
SafetyWing has helped us out in some scary situations before and their affordable coverage has given us peace of mind. You can read our honest review of SafetyWing for all the pros and cons.
Thanks for reading!
Visiting Tuscany from Florence was one of the highlights of our trip! It was such a treat to see Siena, San Gimignano, a Tuscan winery, and Pisa all in one easy day trip. All we had to do was sit back and enjoy the views (and wine!). I’d recommend this tour to anybody traveling to Florence!
If you’re looking for more exciting activities to add to your travels, check out our other Italy blogs. We’ve been all over this beautiful country and love sharing our favorite places and experiences. Here are a few more blogs that will help you plan your next getaway:
Where to Stay in Florence, Italy: 5 Best Areas & Hotels
How to Spend ONE or TWO days in Siena, Italy: 1 or 2 Day Itinerary