There are places that you visit, and then there is Tuscany — a destination that gently unravels around you, a place that refuses to be rushed. Tuscany is not a checklist; it’s a cadence. A slow drip of art, history, food, and light. It is early-morning sun spilling across terracotta tiles, the weight of handblown glass in your palm, and the scent of lavender wafting through the air just before dusk.
At Haute Retreats, we believe travel is most transformative when it’s savored. This carefully crafted 7-day Tuscany itinerary invites you to step into a world where time slows down, and every day blends curated elegance with timeless Italian charm.
Let the crowds rush by. You’ll be sipping Brunello in the garden, watching the hills blush at sunset.
Day 1–2: Florence | Renaissance Wonders & Rooftop Aperitivos
Start your journey in Florence — the city that gave us Michelangelo, Botticelli, and Brunelleschi, and still stuns with its effortless beauty. But Florence rewards the unhurried traveler. To truly experience it is to look up, linger, and allow yourself to be moved.
Morning: Stand beneath the soaring dome of the Duomo, still one of the most extraordinary feats of engineering in Europe. Step inside Santa Maria del Fiore, but more importantly — climb to the top. The view is incomparable, and the journey upward reminds you that perspective is earned.
Afternoon: Wander through the Uffizi Gallery, home to the masters. But don’t try to conquer it. Choose a few rooms. Stand in silence with Botticelli’s Primavera. Let Caravaggio’s shadows pull you in. Later, cross the Ponte Vecchio — busy, yes, but still glittering with old-world charm — and escape to the artisan district of Oltrarno, where cobbled streets hide ateliers, boutiques, and generations of craftsmanship.
Evening: Reserve a table at a rooftop lounge with sweeping views of the Arno River. Toast your arrival with a Negroni — Florence invented it, after all — and dine by candlelight in a restaurant that merges contemporary tasting menus with deep Tuscan roots.
Haute Retreats Tip: Arrange a private after-hours tour of the Accademia Gallery to stand alone in the presence of Michelangelo’s David. It’s an intimate encounter with genius that few travelers ever experience.
Day 3: Chianti | Vineyard Roads & Tastes of the Land
Today, the landscape shifts. As you leave Florence behind, the road begins to curve and climb through a countryside painted in deep greens and dusty golds. This is Chianti, the region where wine isn’t just produced — it’s lived.
Begin with a drive through cypress-lined lanes, past sun-bleached farmhouses and olive groves. Stop at a family-owned winery where the vines are generations old and the cellars echo with history. Learn about the distinct character of Chianti Classico, aged in oak and always paired with tales.
Pause in Greve in Chianti or Castellina, medieval towns where you can sip espresso in sunlit piazzas and browse for aged balsamic, truffle salt, or handwoven linens.
Lunch should be long. Think hand-rolled pici pasta with wild boar ragu, aged pecorino drizzled with chestnut honey, and the kind of red wine that makes you forget where you’re going next.
Haute Moment: We’ll arrange a private candlelit dinner among the vines, complete with curated wine pairings and live acoustic guitar. As night falls over the rolling hills, you’ll dine “Sotto le Stelle” — under the stars, with Tuscany wrapped around you.
Day 4: Siena & San Gimignano | Medieval Splendor & Towering Views
Where Florence celebrates the Renaissance, Siena holds fast to its medieval soul. Begin your day in this city of narrow alleys and terracotta rooftops, where time seems to have paused somewhere around the 14th century.
Stand in Piazza del Campo, one of the most iconic squares in Europe and home to the famous Palio horse race. Visit the Duomo di Siena, a masterpiece in black and white marble, and let your eye wander across its intricate mosaic floors.
By afternoon, make your way to San Gimignano, known as the “Medieval Manhattan” for its cluster of ancient stone towers that pierce the skyline. Climb Torre Grossa for panoramic views of the Tuscan countryside, then reward yourself with what may be the best gelato in Italy — you’ll find the queue in the main square.
Haute Retreats Tip: Our concierge can arrange a local guide to lead you through hidden chapels, private cellars, and artisan studios in both cities — offering a layer of depth not found in guidebooks.
Related Tuscany Villas: Most Beautiful Interiors
Day 5: Val d’Orcia | Cinematic Landscapes & Tuscan Purity
Val d’Orcia is the Tuscany of your dreams — UNESCO World Heritage Site, and rightfully so. Its green hills, isolated cypress trees, and ancient stone houses provide a landscape that is consecrated.
Start your day in Pienza, city of elegant Renaissance architecture and of passion for pecorino cheese. Try the rounds aged in walnut leaves, or the new ones with fig jam.
Proceed to Montalcino or Montepulciano for wine tastings of the world-famous wines. A taste of Brunello di Montalcino, full-bodied and rich, is the story of soil and patience.
Do not chase after when the afternoon sun spills across the valley. Just watch. Now is the moment — the one you will take home with you.
Haute Tip: If you’re an early riser, experience the Cipressi di San Quirico d’Orcia at sunrise. When the mist is working its way through the hills and the sun comes through the trees, you’ll discover why so many artists — and visitors — lose their hearts here.
RELATED Chianti: Best Wineries to Visit
Day 6: A Final Adventure — Pisa, Lucca, or the Tuscan Coast
On your penultimate day, choose your own itinerary — each with a new face of Tuscany.
Pisa: The Leaning Tower‘s famous, sure — but so is the entire Piazza dei Miracoli, a spectacular assembly of Romanesque architecture. Spend sleepy hours exploring, then treat yourself to some Arno-side seafood lunch in the offbeat Marina di Pisa.
Lucca: For more languid times, Lucca is Tuscan chic incarnate. Its Renaissance walls, with enough width to ride your bike through, wraps the city in chic. Discover Romanesque churches, high-end boutiques, and emerald piazzas, then return to your villa just in time for sunset and aperitivo.
Maremma Coast: If the sea is calling you, head west along the Tuscan coast. The Maremma is wild beaches, hidden coves, and seaside towns that remain unblemished. Sample grilled branzino and Vermentino as the Mediterranean breeze blows through.
Wellness Add-On: For the ultimate treat, we’ll book you in for a truffle hunt followed by an al fresco yoga session with views over the hills. Fresh air, dirt, movement, and flavor — Tuscany in pure balance.
Day 7: Rest, Reflect, and Relish
The final morning is yours. Let it unfold slowly. Wander a market and pick up last-minute gifts — hand-painted ceramics, golden olive oil, linen towels that smell faintly of lavender.
Or simply stay in. Have brunch prepared by a private chef. Sink into the pool one last time. Let the silence and softness of Tuscany imprint itself into you. It’s the only souvenir that truly matters.
Depart when you’re ready — but know that Tuscany never quite lets you go.
When to Go: The Best Seasons for This Tuscany Itinerary
Spring (April–June): Wildflowers, green hills, and fewer crowds. A season of light and freshness.
Fall (September–October): Harvest season. Vineyards buzzing, golden landscapes, truffle festivals, and perfect sunsets.
Winter: Understated charm, fewer tourists, and warm evenings by the fire with Chianti in hand.
Each season casts its own spell — and each one tells a different story.
This Tuscany itinerary isn’t just a week away — it’s an invitation to rediscover the art of slowing down. Whether you’re exploring the gilded chapels of Florence, sipping wine beneath the stars in Chianti, or walking barefoot along the Maremma shore, Tuscany reminds you what it means to feel deeply.
At Haute Retreats, we don’t just curate villas — we create immersive journeys that unfold moment by moment, beautifully, deliberately.
Let us help you design the version of Tuscany that’s yours alone.
One Week is not enough to visit the entire region of Tuscany, but it is great to start with this itinerary and you will be back exploring other parts in future trips.
Ready to begin your journey?
Explore our handpicked collection of luxury villas in Tuscany — and let our concierge team craft a week that feels tailor-made, because it is.
