A Magical 3 Day Tuscany Itinerary

I’ve been lucky enough to visit Florence and Tuscany multiple times over the years, and let me tell you, every single visit feels like a new adventure. Whether it’s my third or thirtieth time, Tuscany never loses its magic. So, if you’re planning your first (or maybe your fifth) trip to this stunning region, I’ve crafted the perfect 3-day itinerary to make sure you experience all of Tuscany’s best bits—without feeling rushed or overwhelmed. This itinerary includes Florence, San Gimignano, the Chianti region, and Siena (or Pisa) and will leave you with a camera full of memories and a heart full of joy.

You can totally base yourself in Florence and do this itinerary as day trips from Florence (trust me, it’s easy), or you can rent a car (check out affordable rental cars in Florence here!) and explore at your own pace. Either way, I promise, you’re in for an unforgettable ride. Let’s go!

Chinati wine is a must-try on a 3 day Tuscany trip
Chianti wine

THIS POST MAY CONTAIN COMPENSATED LINKS. PLEASE READ MY DISCLAIMER FOR MORE INFO.

3 Days in Tuscany

Day 1: Florence – The Heartbeat of Tuscany

Ah, Florence, the capital of Tuscany. The city that started it all—the birthplace of the Renaissance and the place that’s probably already on your bucket list. Florence has this way of pulling you in, like a magnet. I’ve lost count of how many times I’ve wandered the streets of this city, and each time, I still discover something new and breathtaking.

Why Florence?
Florence isn’t just a city; it’s an immersion into art, history, culture, and food ( ..well, let’s just say you’ll be dreaming of your next bowl of pasta for years to come). From the majestic Duomo to the world-renowned Uffizi Gallery, Florence is bursting with iconic sights and hidden gems. But it’s not just the museums and architecture that make Florence special—it’s the atmosphere. The city has this undeniable vibe that makes you want to slow down, sip a coffee at a charming café, and simply enjoy the beauty around you.

Palazzo Vecchio Florence
The Palazzo Vecchio and Piazza della Signoria in Florence, Tuscany

I’ve already mapped out a perfect one-day Florence itinerary, so if you’re looking for a day of pure Florence magic, check it out! But just to get you started, here are some things I highly recommend:

  • Take a moment at Piazza della Signoria and imagine life in the Renaissance.
  • Climb to the top of the Duomo for panoramic views of Florence (it’s totally worth the sweat).
  • Wander across the Ponte Vecchio, stopping to browse the jewelry shops and taking in the views of the Arno River.
  • And of course, eat. Florence is a food lover’s paradise. Go for a hearty Bistecca alla Fiorentina (Florentine steak) or indulge in some classic pasta at a local trattoria. Read more about the must-try food in Florence!

Where to Stay in Florence:

  • Luxury: Hotel Lungarno – If you want to wake up to views of the Arno River and feel like royalty, this place is for you. It’s steps away from major sights like the Uffizi Gallery and Ponte Vecchio, and you’ll be surrounded by art and luxury.
  • Mid-Range: Hotel Spadai – A short walk from the Duomo, this hotel blends modern style with old-world charm. Bonus: the breakfast is amazing and private parking is available.
  • Budget: Plus Florence – A super trendy and affordable option, especially if you’re traveling solo or with a group. They’ve got a rooftop pool, a bar, and an overall fun vibe.

Day 2: San Gimignano & Chianti – Tuscany at Its Most Picturesque

After soaking up all the art and culture of Florence, it’s time to head into the rolling hills of Tuscany. Day 2 of your 3 days in Tuscany is all about San Gimignano and the Chianti region—two places that truly feel like you’re stepping into a postcard.

San Gimignano – The Town of Towers
A quick drive (about 1 hour and 20 minutes from Florence), San Gimignano is this medieval fairy tale of a town with 13 tall towers that used to be symbols of wealth and power. These towers make San Gimignano instantly recognizable, and the whole town feels like it’s frozen in time.

Why San Gimignano?
I love how San Gimignano feels like you’ve stepped into a different century. You’ll wander through its narrow streets, browse local artisan shops, and treat yourself to some of the world’s best gelato (seriously, you’ve got to try Gelateria Dondoli). And while you’re there, don’t forget to taste Vernaccia, the local white wine. Trust me, it’s delicious.
Read about the top things to do in San Gimignano!

Where to Stay in San Gimignano (in case you are not visiting San Gimignano on a day trip from Florence):

  • Luxury: Relais Santa Chiara Hotel – If you want a peaceful retreat just outside the town, this place has stunning views of the Tuscan countryside. It’s like the perfect blend of relaxation and charm. the hotel has private parking.
  • Mid-Range: Hotel Leon Bianco – Right in the heart of the town, this hotel offers comfortable rooms and easy access to all the must-see sights. Public parking is available outside the historic walls, about 7 minutes away
  • Budget: La Cisterna – If you want to stay right in the middle of San Gimignano’s main square without breaking the bank, this is your spot. It’s simple, affordable, and charming. However, if by car, public parking is available outside the historic walls.
Strolling the historic centre is among the best things to do in San Gimignano
Piazza del Duomo in San Gimignano

Chianti – A Wine Lover’s Paradise
After exploring San Gimignano, it’s time to venture into the Chianti region (about 40 minutes from San Gimignano). This area is known for its vineyards, olive groves, and adorable hilltop villages. Whether you’re a wine connoisseur or just love a glass of red, Chianti is a place you can’t miss.

Why Chianti?
Picture this: winding roads lined with cypress trees, rolling hills blanketed in vineyards, and charming towns like Greve in Chianti and Panzano where you can sip wine and enjoy the view. Take a break, relax, and enjoy a wine tasting at one of the local wineries. It’s the quintessential Tuscan experience. Panyano is 45 minutes and Greve in Chianti is 50 minutes from San Gimignano.
If you are not driving you can visit San Gimignano and Chianti with a visit to the 3 wineries and a typical Tuscan lunch on this popular tour from Florence.

Touring a Chianti vineyard is a must-have item on any 3 day Tuscany itinerary
Visiting Chianti vineyards is a must when 3 days in Tuscany
Chianti vineyards are a must-ahve item on any 3 day Tuscany itinerary
3 Day Tuscany Itinerary: Chianti vineyards are a must-see in Tuscany

Day 3: Siena or Pisa – Your Pick for the Final Chapter

Your last day in Tuscany is a toss-up between two incredibly iconic cities: Siena and Pisa. Both are within easy reach of Florence, and both will leave you with lasting memories.

Siena – A Medieval Masterpiece
Siena (about 1 hour and 15 minutes from Florence) is where you’ll find narrow, winding streets, a stunning Piazza del Campo, and the magnificent Siena Cathedral. This is a town that’s kept its medieval character beautifully intact, and as such is one of the most beautiful towns in Tuscany.

Why Siena?
There’s something magical about Siena—its medieval architecture, the main Il Campo square, and the overall vibe of stepping back in time. I love getting lost in its streets, popping into local cafes, and just soaking in the charm of this ancient city. If not driving, you can visit Siena on this tour from Florence. However, Siena offers so much to its visitors and deserves more time. Read about the best things to do in Siena Italy.

Visiting the Palazzo Publico is among the best things to do in Siena Italy
The Palazzo Publico (Civic Museum) and Piazza del Campo in Siena are a must-see in 3 days in Tuscany

Where to Stay in Siena (in case you are not visiting Siena on a day trip from Florence):

  • Luxury: Grand Hotel Continental – A true gem, located right in the center of Siena, this 5-star hotel is housed in a grand 17th-century palace. It’s all about elegance and style here. Plus, private parking is available.
  • Mid-Range: Hotel Athena – With a rooftop terrace that offers breathtaking views of Siena and the Tuscan countryside, this hotel is a great balance of comfort and value. Ther hotel has also a private parking.
  • Budget: Hotel Minerva – A great option if you’re looking for a no-frills stay near the historic center. The rooftop pool is a nice touch after a day of sightseeing and private parking is available.

Pisa – The Leaning Tower (and More)
If the Leaning Tower of Pisa has always been on your bucket list, then today’s your day! Pisa (about 1 hour 15 minutes from Florence) offers much more than just the famous tower. You’ll also find the beautiful Pisa Cathedral and the Baptistery.

Why Pisa?
Yes, you’ll definitely snap that obligatory pic with the Leaning Tower, but Pisa has a lot more to offer than just that. The city is full of energy, thanks to its university, and has a lovely, relaxed vibe. The Piazza dei Miracoli is a must-see, and wandering through Pisa’s historic center will give you a taste of Tuscan life beyond the big-ticket attractions.
If not driving a car in Tuscany, you can visit Pisa on this day tour from Florence!

Pisa Cathedral and Tower on my Tuscany road trip
Pisa Cathedral and Tower on my Tuscany road trip

Where to Stay in Pisa (in case you are not visiting Pisa on a day trip from Florence):

  • Luxury: Hotel Relais dell’Orologio – A boutique gem close to the Leaning Tower, this hotel has a charming, classic vibe and offers luxurious comfort.
  • Mid-Range: NH Pisa – Located near the train station, this modern hotel is super convenient for both sightseeing and travel.
  • Budget: Hotel Cecile – A budget-friendly option with simple rooms, located close to the center and perfect for an overnight stop.

How to Get Around Tuscany

You can definitely base yourself in Florence and take trains or buses for day trips to each of these locations—it’s super easy. But if you’re renting a car, you’ll have the flexibility to wander at your own pace, stop in small villages, and take in those postcard-perfect views of the Tuscan countryside. Plus, the drive through Chianti’s winding roads is absolutely magical.

Optional Day Tours From Florence on This 3 Day Tuscany Itinerary

3 Day Tuscany Itinerary with no car

Day 1 – Florence
Day 2 – San Gimignano & Chianti: San Gimiganano, Chianti and Wine day tour from Florence
Day 3 – Siena: Siena Tour from Florence
Day 3 optional – Pisa: Pisa Day Tour with Leaning Tower of Pisa from Florence

Final Thoughts on Spending 3 Days in Tuscany

I can’t think of a better way to spend three days than soaking in the art, history, and natural beauty of Tuscany. From the stunning streets of Florence to the medieval charm of San Gimignano, the rolling vineyards of Chianti, and the unforgettable vibes of Siena or Pisa, this 3 day Tuscany itinerary will leave you with memories to last a lifetime.

Trust me when I say, Tuscany will steal your heart. Take it slow, savor every moment, and let the magic of this region work its wonders on you. It’s a place that, no matter how many times you visit, will always make you feel like you’ve discovered something new.

YOU MIGHT ALSO ENJOY:
Tuscany Travel Guide
Best Traditional Tuscany Food to Try
The Ultimate Tuscany Road Trip Itinerary
The Perfect 2-Day Florence Italy Itinerary

Milijana
Follow me

Similar Posts

Leave a Reply

Your email address will not be published. Required fields are marked *