![Icon [object Object]](/_next/static/media/icon-copy-url.3ada483d.svg?w=16&q=90){kind=icon}
![Icon [object Object]](/_next/static/media/icon-check.bc62b17c.svg?w=15&q=90){kind=icon}
Curator’s statement
Tuscany is one of the most beautiful regions in Italy, checking every box for the perfect vacation. This slice of countryside heaven has so much to offer, from little towns full of medieval and Renaissance history, to luxurious villas for relaxation and of course so much good food and wine! While you could spend an entire month exploring every nook and cranny in Tuscany, I'm here to give you the best five-day itinerary to get an authentic and well-rounded taste of the region! The best way to visit Tuscany is by car, since most of the small towns are not reachable by public transit, and while there are nice boutique hotels one could stay at, I prefer to book a villa just outside the towns to indulge in some relaxation and luxury while embarking on this full itinerary. So, get your road trip playlist ready and set off on an unforgettable trip to picturesque Tuscany!
The Fora Difference
Book with Chiara to access exclusive perks and experiences on your trip.
![[object Object]](/_next/static/media/icon-travel-perks.a0f68fb9.svg?w=42&q=90){kind=icon}
Killer perks
Free upgrades, spa credits and more—we got you
![[object Object]](/_next/static/media/icon-recommendations.4eafc2de.svg?w=42&q=90){kind=icon}
Personalized recs
Customized travel planning for your style
![[object Object]](/_next/static/media/icon-inside-knowledge.e706581a.svg?w=42&q=90){kind=icon}
Insider knowledge
Expert advice from people who’ve actually been there
Where to stay
Villa San Paolo Resort & Spa Hotel San Gimignano
A Tuscan retreat where timeless elegance and tranquility embrace amidst the enchanting landscapes of San Gimignano.
La Collegiata
A charming retreat nestled in the heart of Tuscany, offering guests a serene escape with breathtaking views of the surrounding vineyards and countryside.
L'Olmo
A rustic yet elegant boutique hotel tucked away in the idyllic Tuscan countryside, offering an authentic Italian experience amidst olive groves and rolling hills.
Unlock perks by contacting Chiara to book your trip.
Day 1: Arrive in San Gimignano
Start in Florence, get your rental car, and make your way to San Gimignano, about an hour drive away. On the way, stop for lunch in Volterra and visit the beautiful medieval town! Inhabited since the 8th Century BC by the Etruscans and later the Romans, the town is full of ancient ruins and museums full of artifacts. The Palazzo dei Priori holds beautiful frescos and a bell tower that offers a 360° view of the countryside. Afterwards, check-in to your hotel in San Gimignano and head to the town for dinner at La Mandragola.
Day 2: Head to Siena
Head to Siena in the morning for a half-day visit and some lunch. A UNESCO World Heritage Site, Siena has a long and important history. Make sure to visit the Duomo and Piccolomini Library, Piazza del Campo (where the historic Palio di Siena is held yearly since 1633), tour the Palazzo Comunale which houses the Civic Museum and if you have the time (and energy!) climb the 400+ steps to the top of the Torre del Mangia to admire the city from above. TIP: wear comfortable walking shoes as Siena is mostly uphill and there are lots of stairs. Then make your way back to the hotel to enjoy the pool and some relaxation. Head to La Grotta di Fulignano for dinner and enjoy stunning views of the Tuscan rolling hills!
Day 3: Travel to Pienza
Get back in the car and drive to your next destination: Pienza. With just under 2,000 residents, Pienza, a UNESCO World Heritage Site, used to be the summer residence of Pope Pius II and is considered to be the ideal Renaissance town. There are four must-sees in Pienza: Palazzo Piccolomini, Pieve di Corsignano, Palazzo Comunale and Palazzo Massaini. Stop for a delicious meal with a great view at Osteria Sette di Vino or La Terrazza della Val D’Orcia.
Day 4: Visit Montepulciano
Make your way to the neighboring town of Montepulciano for a wine tasting at one of the many vineyards, my recommendations are the Talosa Winery and the Cantucci Winery, two of the oldest and most iconic in the region. TIP: book in advance as space is limited and this is a highly requested activity. Before returning to Pienza for the night, visit the town of Montepulciano where you can see the Duomo, the Civic Museum and the Pinacoteca Cruciali or relax at the world-famous thermal baths.
Day 5: Bask in the Tuscan Sun
Enjoy a slow morning while basking in the Tuscan sun at your hotel, then, it is sadly time to make your way back to Florence as our time in the countryside has come to an end.
Need to know
This trip is great for any kind of vacation, whether you are traveling with family, friends or a significant other. However, small kids and elderly persons will have a tough time visiting the towns as they have very old infrastructure including stairs and uneven sidewalks.
Travel Advisor
Chiara Caremoli
Get in touch with Chiara
Did you like this guide? Reach out to customize and book your own experience. Or, just to chat about travel in general.
You can normally expect a response from Chiara within a business day or so. You’ll also be subscribed to our travel newsletter (you can unsubscribe at any time).
For more travel tips, check out Fora Advisor Friedrica Curry’s itinerary, Places to Eat, Drink & Explore in Tuscany. This itinerary is part of our ongoing series on travel to Tuscany.