Top 2 Siena Food & Wine Trips for 2026-2027

Discover the flavors of Tuscany on one of Adventure Life's 2 food and wine tours for 2026 and 2027. Immerse yourself in the region's culinary traditions with a hands-on cooking class in fresh pasta-making, or sample some of Montepulciano's and Montalcino's finest red wines. Enjoy sampling Italy's iconic cheeses, savor aged balsamic vinegar, or uncover the history of Il Palio, Siena's renowned horse race. All our food and wine trips to Siena range from $3,000 to $9,877 for 8 to 10 days itineraries - contact us here for help planning your next seamless trip!

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- Siena

Walking the Tuscan countryside at sunset

from $3,000

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Tuscany Walks & Chianti Wines

Italy Small Group Tour - 8 Day Itinerary

Taste wines at Certaldo
Explore Radda in Chianti
Visit Siena’s stunning duomo
Discover Florence’s Renaissance art
Learn about Tuscan wines

Starts / Ends: Certaldo / Florence
Activities: Village Visits, Wine Tasting, Hiking
Activity Level: Easy Active

Discover Tuscany on this 8-day tour. Explore the Via Francigena, savor wine tastings, visit Siena and Florence, and enjoy scenic walks through Chianti vineyards and San Gimignano.

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Discover distinctive Venetian architecture

from $9,878

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Classic Italy

Venice to Rome - 10 Day Itinerary

Ride the gondola in Venetian canals
Discover the Sistine Chapel
Explore the Vatican Museums
Marvel at the architecture in Siena
Savor authentic Tuscan cuisine
Enjoy the Tuscan countryside

Starts / Ends: Venice / Rose Garden Palace
Activities: Archaeological Site Visits
Activity Level: Easy Active

Explore Italy's rich culture, history, UNESCO World Heritage sites, and gourmet countryside on this 10-day classic Italian vacation. From Venice to Rome, tour the countryside and world-class sites in Florence, Siena, Colle di Val d'Elsa, and Rome.

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Looking over Florence at the Basilica di Santa Maria del Fiore. — Italy

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