Living in Tuscany Helps Us Be In The Know For You!
Tuscany is a dream for anyone who loves to eat, sip, and soak in beauty. My daughter Alexandria lives in Tuscany full-time, and I split my life between Tuscany and Chicago, so we’ve seen the region from every angle — secret vineyards, rustic farm kitchens, and local trattorias tourists rarely find.
Here’s a curated guide to 10 of the most authentic wine & food tours in Tuscany, perfect for food lovers, wine lovers, and anyone who wants Tuscany to linger long after the trip ends.
Photo taken by Marie inn the hills of Cortona (under the Tuscan Sun) solo travel trip
Why Tuscany Is a Food & Wine Lover’s Paradise
- Tuscany isn’t just about famous wines — it’s about storytelling in every sip: Chianti, Montepulciano, Brunello, Vernaccia.
- Farm-to-table kitchens, olive oil mills, and family estates let you go beyond tasting — you feel the land.
- Fall through early summer is ideal: harvests in autumn, wine-making stories in winter, blossoms and fresh produce in spring.
- Getting out of Florence and Siena into the hills means quieter vineyards, authentic hosts, and more personal tours.
🍷 Top 10 Authentic Tuscany Wine & Food Tours
1. Chianti Wine Tour with Lunch at a Family Vineyard
Spend the day discovering the Chianti countryside. Visit two boutique wineries, enjoy a Tuscan lunch, and sample bold red wines among olive groves.
⭐ 4.9 stars – 1,200 reviews
💶 From $135 per person
Book this Chianti Wine Tour on Viator
2. Cooking Class in a Tuscan Farmhouse with Wine Pairing
Learn to make handmade pasta, tiramisu, and classic sauces — taught by a local chef in a countryside farmhouse. Includes wine pairing and printed recipes.
⭐ 5.0 stars – 800 reviews
💶 From $150 per person
Reserve your spot here
3. San Gimignano 3-Hour Cooking Class with Wine & Olive Oil
Hands-on cooking with a family in San Gimignano. Learn traditional recipes, taste estate wine and olive oil, and dine on your creations overlooking vineyards.
⭐ 5.0 stars – 500+ reviews
💶 From $234 per person
Book the San Gimignano Cooking Class
4. Florence Gourmet Food Tour: Traditional Tuscan Flavors
Walk through Florence tasting ribollita, panzanella, local wine, olive oil, and artisan gelato. A local foodie guide shares history and hidden gems.
⭐ 4.8 stars – 900 reviews
💶 From $102 per person
See details & book now for this once in a lifetime experience
5. Montepulciano Small-Group Wine Tour with Lunch
Sample six wines and a Tuscan lunch overlooking Montepulciano’s rolling hills. Ideal for those who want intimate vineyard stories and great photography.
⭐ 4.9 stars – 400 reviews
💶 From $82 per person
Get ready to be impressed with the Val d’Orcia Brunello Wine Tour Montalcino and Montepulciano
6. Cooking Class at a Medieval Castle in Tuscany
Prepare authentic Tuscan dishes inside a centuries-old castle. Includes a full wine tasting and dinner in a historic dining hall.
⭐ 4.9 stars – 700 reviews
💶 From $180 per person
Book your Small Group Pasta Making Class Wine Tasting in a Tuscan Castle
7. Walking Food Tour of Florence with Tastings & Wine
Discover Florence through its flavors — local markets, street food, wine bars, and traditional bakeries with your guide.
⭐ 4.8 stars – 1,000 reviews
💶 From $119 per person
Hand Picked Best Walking food tours in Florence!
8. Evening Food & Wine Tour in Florence
Wander evening markets and cozy wine bars, enjoy tastings, and savor Florence at dusk — perfect romantic foodie experience.
⭐ 4.7 stars
💶 From $70 per person
Evening WIne tour favorite or option to choose a wonderful day tour as well !
9. Private Villa Cooking Class in Tuscany
Spend the afternoon in a private villa with a local chef preparing a 4-course Tuscan feast. Personalized, intimate, and unforgettable.
⭐ 5.0 stars
💶 From $200+
Inquire or book private villa cooking class! 5 Stars!
10. Florence Food Tour with Antico Vinaio & Traditional Bites
Skip the lines at Florence’s legendary sandwich shop Antico Vinaio and enjoy a small-group tasting tour of classic bites and wines.
⭐ 4.8 stars
💶 From $70 per person
Book your Florence tasting tour and skip the lines with VIP access!
Bonus top pick and Voted top pick by travelers
Best Time to Visit & When to Book
Late Fall (Oct–Nov): Harvest festivals, fewer crowds.
Winter (Dec–Feb): Cozy cooking classes, festive markets, fewer tourists.
Spring (Mar–May): Flowering countryside, fresh produce, mild weather.
Summer (Jun–Aug): Long daylight, lively villages, full tour availability.
Insider Tips
- Book early: Viator allows free cancellation, so reserve ahead — popular tours sell out fast.
- Small groups or private tours: richer interactions and personalized tastings.
- Bring layers & comfortable shoes: Tuscany’s terrain and weather shifts throughout the day.
- Inform hosts about dietary needs: most are flexible and accommodating.
Final Thoughts
Tuscany is where you fall in love with Italy — one glass, one bite, one sunset at a time. These Viator tours make it easy to connect with authentic Italian life, guided by locals and seasoned insiders.
