Tuscany in Terracotta & Time: A 9-Day Journey Through Wine Roads, Hilltowns & Golden Light

Florence is a city of first impressions. From the second you step out of the taxi and see the Duomo rising above the rooftops, you’ll feel it—history, elegance, and beauty everywhere you look.

Check-in options:

Hotel Continentale: Sleek and romantic with modernist design, perfect for couples. The rooftop bar is a dream at sunset.

Grand Hotel Minerva: Classic luxury with an iconic rooftop pool and views of the Piazza Santa Maria Novella.

Afternoon Tip: Drop your bags, freshen up, and take a walk along the Arno River. Cross the Ponte Santa Trinita, wander into the Oltrarno district, and settle in at Volume for your first negroni sbagliato.

Dinner suggestion:

Trattoria Sostanza – Order the butter chicken and white beans. It’s loud, unapologetic, and still one of my favorite meals in Florence. (Cash only—and worth every euro.)

Florence is best in the morning, before the streets fill and the sun turns sharp. Start your day with a walk to Ditta Artigianale on Via dello Sprone—order a cappuccino and sit outside, where the corner hums with locals on their way to work.

If you love art, head to the Uffizi Gallery (reserve in advance). Focus on the Botticellis and the Caravaggios—don’t try to conquer it all. Let one painting hold you. Afterward, skip the gift shop and go upstairs to the rooftop terrace café. The espresso isn’t perfect, but the view is.

If art isn’t your thing, take a different path: a stroll through the quiet Brancacci Chapel in Santa Maria del Carmine. It’s never crowded, and Masaccio’s frescoes are haunting in their simplicity.

Lunch tip: Walk to Il Santo Bevitore in the Oltrarno. It’s elevated but warm, with exposed brick and the best fresh tagliolini with butter and anchovy crumble I’ve ever had.

Spend the afternoon walking along the Arno toward Ponte Santa Trinita (less crowded and more beautiful than Ponte Vecchio). Stop inside Farmacia Santa Maria Novella—part museum, part perfumery, and a total sensory dream. Pick up a bottle of rose water or bath salts made from 13th-century recipes.

End the day with sunset at Piazzale Michelangelo. You can walk (30 minutes uphill) or take a taxi, but go before 6:30 pm to find a spot on the wall. Bring a small bottle of wine or just sit and listen. Buskers will be playing. The city glows.

Dinner Tip: Trattoria Cammillo – classic, candlelit, family-run. Order the artichoke pie if it’s in season, and the roast guinea fowl if it’s not. It’s old-school Florence in the best way.

Sleep in if you can. This is the morning for a second espresso, silk robe, balcony light. If you’re staying at Grand Hotel Minerva, head up to the rooftop for a slow breakfast by the pool. It’s one of the only spots in Florence where the Duomo looks like it’s floating.

Start your day at Basilica di Santa Maria Novella, just steps away. Skip the guided tours—walk through the cloisters alone. The Tornabuoni Chapel glows with frescoes by Ghirlandaio, and if you’re there in the early light, you might have it all to yourself.

From there, wander up Via de’ Tornabuoni, Florence’s most elegant street. This isn’t about buying—it’s about observing. Stop into Angela Caputi for bold resin jewelry handmade in the Oltrarno. Or visit Madova Gloves near Ponte Vecchio, where the same family has been making soft leather gloves since 1919. The shop is barely bigger than a walk-in closet.

Lunch Tip: Cross the river and head to Lungarno 23 for a relaxed, riverside lunch. Order the tartare di Chianina with a glass of Vernaccia di San Gimignano—light and citrusy.

In the afternoon, visit the Bargello Museum—often skipped, always a treasure. It’s quiet, filled with Donatellos and ancient keys, and cool even on hot days. Or just walk with no plan. Florence rewards aimless afternoons.

Aperitivo Hour: Make your way back toward your hotel and pause for aperitivo at La Terrazza atop Hotel Continentale. Order a spritz or a glass of Franciacorta and toast the skyline.

Dinner Tip: Book a final dinner at Buca Lapi—Florence’s oldest restaurant, hidden in the cellars beneath Palazzo Antinori. Ask for the bistecca alla Fiorentina if you’re feeling bold, or the tagliolini al tartufo if you’re leaning delicate. Either way, end with a grappa and take your time.

Night walk tip: After dinner, walk to Ponte Santa Trinita and look back at the Ponte Vecchio. It’s best lit at night, reflected perfectly in the river like a painting folded in half.

Today, you leave behind marble and rooftops for cypress trees and silence. Check out mid-morning, pick up your rental car (reserve ahead for an automatic), and take the scenic route out of Florence heading south on the SR2. This drive is more than a transfer—it’s a soft unraveling.

Stop just outside Montepulciano for lunch. Dopolavoro La Foce, near the historic La Foce estate, is the kind of restaurant where even the breadsticks taste elegant. Sit on the terrace if you can. The zucchini flan and homemade tagliatelle are honest, comforting, and seasonal. Ask what’s fresh—and trust them.

After lunch, continue through Castiglione d’Orcia and San Quirico d’Orcia — if the light is right, pull over near the Cappella della Madonna di Vitaleta. It’s a tiny chapel in a field of gold and green, framed by cypress trees. Iconic, yes—but still hauntingly quiet if you go in the late afternoon.

Where to stay (Choose one):

La Bandita Townhouse, Pienza: Intimate, design-forward, and nestled in one of the most peaceful hill towns in Tuscany. Stone walls, modern comfort, and an incredible in-house restaurant.

Villa Le Prata – Residenza del Vescovo, Montalcino: Surrounded by vines, with big-windowed rooms and warm hosts who might pour you a glass of Brunello as you check in.

Evening:

Unpack. Shower. Step outside at dusk and listen—in Val d’Orcia, even the silence has texture.

Dinner tip:

If in Pienza: La Bandita’s restaurant—sit in the candlelit library room and order the wild boar pappardelle.

If in Montalcino: Try Drogheria Franci, a stylish but grounded spot near the fortress. They do a perfect carbonara and an even better steak with Brunello sauce.

This is a day to walk softly.

Wake early and step into Pienza just as the shops begin to open. The entire town smells like pecorino—it’s not a metaphor. Stop inside Marusco e Maria and ask to sample the truffle-aged version. They’ll wrap it in wax paper and smile like they know you’ll come back tomorrow.

Wander to Via dell’Amore, the “Street of Love,” and lean over the stone railing where the hills fold into one another like painted silk. If it’s cool out, grab a cappuccino at Bar Il Casello and sit on their terrace, watching the light shift across the valley.

Late morning: Drive 20 minutes to Montalcino for a private wine tasting. My personal favorite: Le Ragnaie—an organic, high-altitude producer just outside town. Book ahead. Their Brunello di Montalcino V.V. is like velvet and violets, and they’ll pour a library bottle if you ask gently.

Lunch tip: Make a reservation at Osticcio, right in Montalcino. Ask for a window table overlooking the vineyards. Order the handmade pici with bread crumbs and anchovy (if available), and a glass of Rosso di Montalcino to keep things light. End with the ricotta mousse and sit a while.

Afternoon reset: Walk the Fortezza di Montalcino. Climb the ramparts. It’s simple, but the wind up there feels ancient. Or head back to your hotel for a nap and a shower—tonight deserves you at your best.

Dinner tip: If you stay in Pienza: Trattoria Latte di Luna is rustic, wildly loved, and fills fast. The roast pork with rosemary potatoes is the thing.

If you’re at Villa Le Prata: Ask them to arrange a private dinner on-site. Their chef can create a quiet, candlelit menu with paired Brunello that you’ll remember long after you leave.

Morning: Drive to Bagno Vignoni, a thermal village where the piazza itself is a hot spring. Skip the crowded spa pools—instead, book a half-day pass at Hotel Posta Marcucci. It’s quiet, surrounded by green, and the view from the lower thermal pool is almost biblical. Bring a book. Let the water do what it knows how to do.

Lunch tip: On your way back, stop in Monticchiello—a village so small it barely appears on maps, but it holds a special stillness. Park outside the walls and walk in.

Have lunch at Osteria La Porta, just inside the gate. Ask for a table on the tiny terrace if it’s warm. Order the rabbit ragu with handmade pici or whatever the chef recommends. The wine list leans local. The olive oil is their own, and the view—it doesn’t even look real.

Afternoon: Drive to the nearby Cappella della Madonna di Vitaleta, the stone chapel you’ve seen in a hundred paintings. Walk the cypress-lined dirt road, camera or no. If you time it for late afternoon, the sun will spill over the hill like honey.

Evening: Back at your hotel, take a long shower, open the windows, and let the cool settle in.

Dinner tip: Tonight, you stay in.

At La Bandita: order the saffron risotto with Parmigiano crema.

At Villa Le Prata: request the seasonal tasting menu—often featuring wild herbs and lamb raised nearby.

This is your last night in the countryside. Stretch it out. Take your time.

This morning, enjoy one last countryside breakfast—eggs with pecorino, fresh bread, homemade fig jam. Then check out and take the scenic drive to Siena (about one hour).

Check-in: Grand Hotel Continental Siena: The only 5-star hotel within the city walls, filled with frescoes, stone arches, and light that falls like velvet. Ask for a room with a city-facing balcony if available.

After check-in, walk slowly to Piazza del Campo, Siena’s shell-shaped square. Sit on the warm bricks near Fonte Gaia and just be. This is the soul of the city—and no one’s rushing.

Lunch tip: La Taverna di San Giuseppe—Carved into Etruscan stone, with a vaulted cellar and perfect house-made pici. Order the truffle carbonara if it’s in season.

Afternoon ritual: Walk to the Duomo di Siena—one of the most stunning cathedrals in Italy. The striped marble exterior is striking, but it’s the Piccolomini Library inside—with its Technicolor frescoes—that always catches people off guard. Buy a combo ticket that includes access to the Facciatone—the unfinished façade tower—for a quiet, panoramic view over the rooftops.

Dinner tip: Osteria Le Logge – Elegant but unpretentious. Reserve ahead and try the guinea fowl or the cacio e pepe with lime zest. The wine list is deep and local.

This morning, take a hidden tour: Cripta del Duomo or the Santa Maria della Scala Museum Complex, directly opposite the cathedral. Underground, it tells Siena’s story not through art, but through what was lived—as a hospital, shelter, and pilgrimage station for centuries.

Lunch Tip: Pian delle Ginestre—Just outside town, this spot offers a Tuscan tasting menu in a rustic house with sweeping countryside views. It’s small, so call ahead.

Afternoon: Wander Siena’s outer districts, known as contrade. Each has its own symbol, colors, and even an anthem. If you’re lucky, you’ll stumble into a quiet neighborhood celebration—it happens more often than you’d think.

Sunset Ritual: Head to Basilica di San Domenico, up on the ridge. It’s simpler than the Duomo, but holds the relics of Saint Catherine. The view from behind the basilica at dusk is one of Siena’s quietest, most sacred moments.

Dinner Tip: Ristorante Tar-Tufo – Sophisticated, romantic, and a bit hidden. Try the veal cheek with white truffle sauce or their signature risotto. Ask the sommelier to pair something Sienese.

No rush this morning. Take one last walk around Piazza del Campo while it’s still quiet. Maybe grab a pastry from Nannini (they’re famous for ricciarelli, almond cookies that melt in your mouth) and a cappuccino to go.

Check out. Drive gently. Let the land linger.

Whether you head toward Florence, Rome, or your next adventure, you’ll leave Tuscany not just with memories—but with a softness you’ll want to keep.