Yes, there have been countless films and books about the region—but Tuscany is definitely one of those destinations that lives up to the hype. I fell in love with Tuscany on my very first trip there—a trip filled with good company, and even better food & wine. I have been back multiple times throughout the years.
I love curating full itineraries to Tuscany for clients who share my love of food and culture. This blog post is but a taste of what Tuscany has to offer. Here is my breakdown of how to spend one perfect day in the region—in particular, the Tuscan areas of San Gimignano and Chianti:
Morning:
Tuscany is made for slow mornings. Once the light starts filtering through the bedroom window of your villa, make yourself a cup of espresso and enjoy it while admiring your view out over the quintessential Tuscan landscape of undulating hills and grape vines.
When you are ready to start your day, make a pit stop at a local cafe to pick up a simple breakfast pastry or stroll through a local market —there is one on Thursday mornings in San Gimignano, or take a drive to the largest market in Siena on Wednesdays. After your market stroll, head into the Tuscan hills for an invigorating hike. Tuscany’s picturesque hilltop towns are sometimes only a short drive away from one another and offer a vast array of beautiful settings to take in on your hike.
Mid-day:
After a noontime nap, windows open to catch the breeze, you’ll head to Querceto Di Castellina, a family-run wine estate with an organic approach. On my first visit to Tuscany, I spent a blissful afternoon here, and it’s where I really began to fall in love with Tuscan food and wine traditions.
You’ll start your visit with a tour through the winery, where the estate produces the area’s famed Chianti Classico. Then, your tour will take you through the estate’s olive groves, so you can see how they produce their own olive oil, from branch to bottle.
Finally, it’s time to roll up your sleeves and get cooking, with a hands-on cooking class—featuring wine, olive oil, and balsamic vinegar all produced on-property. You’ll dine on a late afternoon al fresco lunch featuring all the delicacies you just created in the kitchen! During my cooking class we drizzled the freshest mozzarella imaginable with the tangy zest and sweetness of their balsamic vinegar, cooked up fall-apart-tender pork, and finished with a light sorbet topped with fresh berries.
Evening:
The Italians eat late—between 8 and 9 pm—so you have time to work up an appetite again after your winery feast. Satiate it at the cutest little trattoria in San Gimignano, a hilltop town of Tuscan splendor.
I recommend booking a table at Osteria Baccano, a traditional trattoria with stone walls and wood-beamed ceilings. Everything there is prepared with love and planned according to what is in season—when I dined there in September, we dug into a local delicacy called “Pappardelle Cinghiale” with boar and other dishes with lots of truffles.
After dinner, stroll through the cobblestone streets of San Gimignano to work off your day of indulgence—and admire the multitude of bell towers lit up at night. The tourists will have largely cleared out by now, so you will have the quiet streets practically all to yourself. The town is so well preserved you will feel like you are stepping back into history, specifically San Gimignano’s 13th-century heyday!
Ready for your own Tuscan journey? Let Travel Becomes You plan it all, all according to your interests and preferences. Learn more at travelbecomesyou.com or book your complimentary Discovery Call to start planning now.
