Curator’s statement
Cortona is such a special place nestled within Tuscany's rolling hills. This ancient town, with its Etruscan roots and medieval narrow alleys, offers a glimpse into centuries past. The views are unparalleled, offering sweeping vistas of the Val di Chiana, and connecting the town to its rich agricultural history. What makes Cortona even more special is its dedication to traditional cuisine and world-class wines. From rustic pici pasta dishes to exquisite Montepulciano wines, the town celebrates local flavors that have been honed over generations. Just beyond Cortona, there are endless ways to explore throughout Tuscany and gives me a reason to come back over and over.
The Fora Difference
Book with Megan to access exclusive perks and experiences on your trip.
Killer perks
Free upgrades, spa credits and more—we got you
Personalized recs
Customized travel planning for your style
Insider knowledge
Expert advice from people who’ve actually been there
Where to stay
Unlock perks by contacting Megan to book your trip.
Day 1: Arrive in Florence
If you choose to fly in, you’ll likely arrive at the Florence airport. From there, pick up a rental car.
Before starting your journey into the Tuscan hills, I highly recommend spending the day or at least a few hours in Florence. For lunch, stop at Gustapizza for incredible Margherita pizza. Then stop at Gelateria dei Neri for the best gelato in Florence.
Then make your way to Cortona, which is just a short 1.5 hour drive then check in to your accommodation.
Day 2: Explore Cortona
Next, head out to explore the rustic streets of Cortona.
Feel free to get lost in the winding alleys that go up and down the whole town. There are so many shops with locally made art, coffee and pastries, leather goods, and jewelry.
Antonio Massarutto has beautiful pieces of jewelry, and I picked up a gorgeous bronze necklace when I visited last.
Trattoria Dardano and Il Preludo are excellent restaurants for dinner and some of the best pasta and tiramisu you will ever have in your life.
Of course, there is no better way to end the night than a scoop of gelato from Gelateria Snoopy.
Day 3: Winery tour
Take a drive around the rolling hills of Tuscany and stop in for your wine tasting reservation at Baldetti, La Braccesca and Le Bèrne.
Learn about wine making, enjoy a delicious lunch, then grab a bottle of Syrah and extra-virgin olive oil to take home with you.
Day 4: Natural hot springs
Bagni San Filippo is a hidden gem in Tuscany, known for its natural thermal springs and otherworldly limestone formations. Nestled in the foothills of Monte Amiata, just over an hour drive from Cortona, these thermal baths are perfect for relaxation. They offer warm, mineral-rich waters that cascade into natural pools. The area feels tranquil and serene, ideal for soaking in the healing waters while surrounded by lush forests and dramatic rock formations.
Day 5: Tuscan coast
Start your day with a scenic 2-hour drive from Cortona to the vibrant coastal town of Viareggio, renowned for its Art Nouveau architecture and wide, golden beaches.
Once you arrive, head straight to Bagno Maurizio, one of Viareggio’s most beloved beach clubs. Stefano will get you set up with a sunbed and umbrella. Then unwind on the sandy beach with stunning views of the Apuan Alps in the distance and take a swim in the Ligurian Sea.
Before heading back to Cortona, as your last day in Tuscany, take time to explore Viareggio and stop at a beachside restaurant for dinner or catch a sunset along the coast.
Travel Advisor
Megan Woo
Get in touch with Megan
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 Megan within a business day or so. You’ll also be subscribed to our travel newsletter (you can unsubscribe at any time).
This itinerary is part of our ongoing series on travel to Tuscany. For more travel tips, check out Gillian Spatz’s itinerary, Discover the Best Things to Do in Cortona, Italy: A Traveler's Guide.