Tuscany Vineyards & Hilltowns

Italy6 days$$$SpringFall

About This Trip

Imagine the clink of glasses echoing softly as you toast under the warm hues of a Tuscan sunset, the air filled with the earthy scent of vineyards stretching out in sinuous rows. Here, in the heart of Italy's famed wine country, each day unfurls with the promise of the region's rich flavors and storied past. Your mornings begin with the sun lifting over the Val d'Orcia, its light spilling across golden fields and ancient cypress trees. A private tour of a venerable Chianti winery reveals secrets of the robust reds, a sommelier guiding your palate through layers of flavor developed over centuries. The cool cellars, lined with oak barrels, contrast vividly with the day’s growing warmth. As the day advances, you find yourself in a hands-on Tuscan cooking class, laughter blending with the sizzle of fresh ingredients hitting the pan. Here, in a rustic farmhouse kitchen, you learn to craft dishes that have comforted generations—pappardelle al cinghiale, ribollita—each recipe narrating its own slice of local tradition. The simplicity of the food belies its depth, much like the landscape surrounding you. Transitioning from afternoon into the dusky evening, you stroll the storied streets of medieval Siena. The city's illustrious history whispers through the piazza, where once, fierce horse races transformed the city into a dynamic spectacle. Now, it's the quieter moments that catch your breath—a detailed fresco in a tucked-away chapel, the smooth wear of marble steps underfoot, testament to centuries of thoughtful wanderers like yourself. Perhaps one of the most serene pleasures is a picnic among the vineyards. Surrounded by the gentle rustle of leaves and the occasional chirp of distant birds, you lay out a spread of local cheeses, crusty bread, and, of course, a bottle of the region’s finest wine. It’s moments like these that feel suspended in time, a connection to the land and its bounty as palpable as the earth beneath your blanket. As twilight blankets the landscape, you find a quiet spot overlooking the undulating hills. The vineyards carry a silent history, their roots intertwined deeply with the soil. In this tranquil moment, as the evening star begins its climb, the true essence of Tuscany reveals itself—not just in the grandeur of its history or the depth of its cuisine, but in the quiet majesty of the land itself, resonating deeply with those who wander and wonder here.

Trip at a glance

See the route before diving into daily details.

Arrival and Siena First Light
Day 1
Arrival and Siena First Light
Siena
Golden drive through rolling Tuscan countryside

Trip Highlights

Private tours of ancient wineries in ChiantiSunset views over the Val d'OrciaHands-on Tuscan cooking classesStrolls through medieval SienaPicnics amidst the vineyardsVisits to historic Tuscan villages

Trip Impressions

Your Journey — Preview

12 Activities
3 Signature Experiences
Day 1

Arrival and Siena First Light

Siena
Medieval Towns
Tuscan Cuisine
Wine Tasting

Land in Florence and slip straight into Tuscany’s rhythm as you drive south toward Siena’s warm brick skyline. After checking in, wander into the medieval center, letting the alleys funnel you toward the shell-shaped Piazza del Campo. Pause for an easy lunch and your first glass of Sangiovese, then drift past shopfronts and quiet side streets as the city settles into afternoon. As evening falls, sit down to a lingering, candlelit dinner in a vaulted stone osteria, easing jet lag with rich Tuscan flavors and deep, velvety reds.

Golden drive through rolling Tuscan countrysideFirst glimpse of Siena’s Piazza del CampoEvening wine and candlelight in a stone-walled osteria
Day 2

Chianti Castles and Cellars

Castello di Brolio, Chianti
Vineyards
Wine Tasting
Rustic Landscapes

Wake in Siena and head north into classic Chianti country, where vineyards drape over soft hills and stone hamlets crown the ridges. Your destination is Castello di Brolio, an imposing medieval castle surrounded by vines that have been in the same family for centuries. Spend the late morning exploring ramparts, gardens, and cellars before sitting down to a relaxed picnic among the rows. The drive back to Siena traces panoramic roads, leaving time for a leisurely aperitivo and a refined dinner featuring deeply flavored local dishes and elegant Chianti Classico.

Scenic drive from Siena into ChiantiCastle walk and barrel-lined wine cellarsPicnic spread between vineyard rows
Day 3

Siena Duomo and Medieval Secrets

Siena
Culture History
Medieval Towns
Tuscan Cuisine

Today belongs fully to Siena. Start at the dramatic black-and-white striped Duomo, where marble floors and intricate sculptures compress centuries of craftsmanship into one soaring space. After a long look inside, drift back toward the Campo for a relaxed lunch. The afternoon is for slow exploration: slipping down quiet contrade streets, tracing Palio flags, and pausing at small viewpoints over terracotta rooftops. As the light softens, toast the city with an aperitivo before a final dinner in the historic center, savoring dishes that feel both rustic and refined.

Gothic splendor of Siena CathedralFlag-draped medieval contrade streetsAperitivo overlooking Piazza del Campo

Days 46 await in the full itinerary

Day-by-day schedules, places, and insider tips — personalized to you.