Have a magical day just outside of Florence! Enjoy a private day trip to the scenic vineyards of Chianti, to the beautiful Tuscan countryside or the medieval town of Siena. Discover more of the Italian culture with the local of your choice.
Have a magical day just outside of Florence! Enjoy a private day trip to the scenic vineyards of Chianti, to the beautiful Tuscan countryside or the medieval town of Siena. Discover more of the Italian culture with the local of your choice.
Always private. It’s just you and your local host. No strangers, no groups.
More you, less checklist
Let your local host tailor the experience completely to your wishes.
Travel that feels good
Our tours are designed with people, places, and the planet in mind.
Top 3 day trips in Florence
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City Escape: Tuscany Day Trip
111 reviews
7 hours | day trips | Florence
Imagine this: a scenic road trip from Florence to explore Tuscany with stops along the way to discover viewpoints, villages, incredible nature, and cultural gems. Sounds like a dream? No, it’s possible on a Withlocals day trip with a local host leading the way!
Imagine this: a scenic road trip from Florence to explore Cinque Terre with stops along the way to discover viewpoints, villages, incredible nature, and cultural gems. Sounds like a dream? No, it’s possible on a Withlocals day trip with a local host leading the way!
Explore San Gimignano, a UNESCO World Heritage Site, on a private tour with convenient Florence pickup. Enjoy its medieval charm, stunning towers, and a visit to a local farm for wine and olive oil. A perfect Tuscan escape!
"We were incredibly lucky to meet Fabio during our visit to Florence! He took us around the area in his very comfortable van, showing to us the beauty of the countryside of Florence, amazing towns of San Gimignano, Certaldo. Then we had a fantastic lunch, amazing food with great wine, the lunch worth traveling to Florence alone! During the tour Fabio was telling us the stories about life in this area covering the historical part, everything was fascinating and greatly enjoyable! At the end of the day we were filled with positive energy from this wonderful region!
Million thanks to you, Fabio!"
"Fabio was great. So informative and pleasant tour. Fabio was terrific! He was quite generous with us as Italian language learners. He switched effortlessly between English and Italian throughout the tour for us, allowing us to practice our Italian. An absolute wonderful and refreshing experience…."
"My husband and had a great day going to San Gimignano with Fabio. From pick up at our hotel in Florence to drop off, everything was wonderful. If you want to take a private day trip to this beautiful hilltop town known for its towers, don’t hesitate to use WithLocals and book with Fabio. He is knowledgeable, enjoyable to be with and kind enough to speak to me in Italian so I could practice mine! "
"Thank you Fabio for the fantastic day in Tuscany! You were very prompt in your communication leading up to the tour, had a nice, new and spotless van and were 100% professional. Your energy and knowledge made it easy to stay engaged. Thank you again and many recommendations to our friends and family in the future.
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"Fabio was fantastic! He was so knowledgeable and friendly, and everyone had an amazing time exploring Certaldo and a local winery. It was unforgettable, and we can’t wait to come back and see Fabio again! Highly recommend!!"
MelanieAbout local FabioFlorence, October 14, 2024
5.0
Fabulous with Fabio
"Four of us had a charming day with Fabio. We enjoyed his historical knowledge of Italy as well as his wit. San Gimignano was beautiful but the highlight of the day was our lunch. We toured a small family winery and experienced an intimate food and wine pairing, lovely! Highly recommended "
"Our tour of Pistoia was fantastic, Beatrice our guide was very knowledgeable and very personable. Since my grandparents came from this city it made for a very satisfying day. We learn about the history, great pastry shops and had a delicious lunch in one of the squares."
RobertAbout local BeatriceFlorence, September 23, 2024
5.0
A fabulous day exploring Tuscan jewels
"What an amazing day and what a wonderful guide. Fabio collected us from our hotel in Florence and whisked us towards first Siena and then Sam Gimignano - all the while giving us the historical context of both places in a fun and informative way. He brought the Palio to life for our group (of 8 with ages ranging from 11 to 60) with funny anecdotes about inter district rivalries! In between the 2 sites visited we stopped for a delicious lunch and wine tasting which was a real highlight and we left having exchanged numbers with our hosts and laden with fabulous wines to take on to our next Villa! We all thought Fabio was an excellent and thoroughly knowledgeable guide and would recommend the experience highly to everyone. Ciao Fabio - grazie mille 🙏"
"We thoroughly enjoyed our val d’orcia tour with Michele. He is very friendly, flexible and has vast knowledge about history and art. We liked listening to his stories about florence, italy and himself."
"Michele was a wonderful and thoughtful host as he drove me and my fiance and mother around Tuscany all day on a personalized experience based on our interests. We started the day visiting the American WW2 memorial in Chianti, then stopped in Monterigioni. Which was super fun. We had a long luxurious lunch at a vineyard that was a highlight of our trip then ended the day visiting San Gimnagno with wonderful gelato paid for by Michele. I would recommend him to anyone interested in the art and culture of Tuscany and just having a good time in general. "
Your tour is just for you. No strangers, no groups.
You’ll experience the city one-on-one (or with your own travel group) in a relaxed, personal way. No rushing, no scripted group tours.
Tailored to your wishes
From highlights to hidden gems, your host adjusts everything to fit you.
Want to skip a museum, add a food stop, or focus on street art? Just ask. Every experience is shaped around your pace, preferences and interests.
Chat before you book
Message your host directly to customize your experience.
Ask questions, get local tips, or make special requests. Our hosts are real people, ready to make your day unforgettable.
Travel that supports locals
Every booking supports independent locals and their communities.
We believe tourism should benefit the people who live there. Your host earns directly and often invests it right back into their neighborhood.
Feel good about where your money goes
You’re choosing meaningful travel, not mass tourism.
Withlocals is built on fair pay, human connections and travel that leaves a positive mark for both you and the places you visit.
Trusted by millions
Loved by over 1,000,000 travelers all around the world.
Withlocals hosts consistently earn 5-star reviews for their kindness, knowledge and the personal stories they share.
Secure & flexible booking
Book with peace of mind: safe payments and easy changes.
Your plans can shift and that’s okay. We offer flexible cancellation and real support when you need it.
Private & Personal
Your tour is just for you. No strangers, no groups.
You’ll experience the city one-on-one (or with your own travel group) in a relaxed, personal way. No rushing, no scripted group tours.
Tailored to your wishes
From highlights to hidden gems, your host adjusts everything to fit you.
Want to skip a museum, add a food stop, or focus on street art? Just ask. Every experience is shaped around your pace, preferences and interests.
Chat before you book
Message your host directly to customize your experience.
Ask questions, get local tips, or make special requests. Our hosts are real people, ready to make your day unforgettable.
Travel that supports locals
Every booking supports independent locals and their communities.
We believe tourism should benefit the people who live there. Your host earns directly and often invests it right back into their neighborhood.
Feel good about where your money goes
You’re choosing meaningful travel, not mass tourism.
Withlocals is built on fair pay, human connections and travel that leaves a positive mark for both you and the places you visit.
Trusted by millions
Loved by over 1,000,000 travelers all around the world.
Withlocals hosts consistently earn 5-star reviews for their kindness, knowledge and the personal stories they share.
Secure & flexible booking
Book with peace of mind: safe payments and easy changes.
Your plans can shift and that’s okay. We offer flexible cancellation and real support when you need it.
Private & personalized day trips in Florence with a local
Extend your adventure beyond Florence with a private day trips that takes you to nearby gems. Your local guide will design a day trip tailored to your interests, whether it’s exploring charming villages, natural wonders, or historic sites.
Enjoy the flexibility of a personalized itinerary that lets you travel at your own pace and focus on what excites you most. Skip the crowds and experience authentic local life, cuisine, and landscapes just a short trip from Florence.
Make the most of your time with a private day trip that reveals the best of the region around Florence.