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5-Day Tuscany Itinerary Tour: Chianti, Val d’Orcia & Florence Experience

5 DAYS / 4 NIGHTS

Florence, Chianti, Val d’Orcia
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A Tuscany itinerary 5 days, a journey for the senses through the region’s most iconic flavors and landscapes.

From Chianti’s ruby reds to Brunello’s bold elegance, discover historic cellars, farm-fresh cuisine, and medieval towns wrapped in vineyard views. Slow down, sip deeply, and savor the Tuscan art of living.

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Description

Highlights

  • Taste world-class wines: Chianti Classico, Vernaccia di San Gimignano, Brunello di Montalcino
  • Farm-to-table Tuscan meals in authentic countryside settings
  • Discover three UNESCO treasures: Florence, San Gimignano, Pienza
  • Experience the art of slow travel through rolling vineyards and medieval hill towns

 

Itinerary

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• Day 1 | Welcome to Florence – start of your Tuscany itinerary 5 days

Arrive in Florence, the heart of the Renaissance. Spend the afternoon wandering its cobbled streets, artisan workshops, and lively piazzas. For dinner, why not start your journey with a Tuscan feast of handmade pasta, local cheeses, and Chianti wine?
Overnight: Florence

• Day 2 | The Essence of Chianti

Venture into the rolling hills of Chianti Classico. Visit a family-run winery, where rows of vines meet centuries of tradition. Enjoy a cellar tour, a guided tasting, and a long lunch of seasonal Tuscan dishes paired with ruby-red Chianti wines. In the afternoon, explore the medieval villages of Greve or Castellina.
Overnight: Florence or Chianti countryside

• Day 3 | San Gimignano & the White Wines of Tuscany

Step into San Gimignano, famous for its medieval towers and timeless skyline. Stroll through winding streets, taste the crisp Vernaccia white wine in a historic cellar, and perhaps try the town’s award-winning gelato. Don’t miss local saffron, one of San Gimignano’s oldest treasures.
Overnight: Siena area

• Day 4 | Val d’Orcia & Brunello di Montalcino

Travel through the dreamlike landscapes of Val d’Orcia, a UNESCO World Heritage site and highlight of any Tuscany itinerary 5 days, with cypress-lined hills and golden fields. Visit a renowned Brunello winery for a tour and tasting of one of Italy’s most prestigious reds. In Pienza, enjoy a rustic lunch featuring the town’s celebrated pecorino cheese.
Overnight: Siena area

• Day 5 | Arrivederci Toscana – end of your 5 day itinerary

Your journey ends after breakfast, with the option to extend your stay in Siena or return to Florence for one more Renaissance stroll.

What’s included?

  • 4 nights accommodation in boutique hotels or countryside agriturismi
  • Daily breakfast
  • 2 winery visits with tastings (Chianti & Brunello)
  • 1 guided tasting of Vernaccia di San Gimignano
  • 2 traditional lunches with local specialties (Chianti countryside & Pienza)
  • Self-guided walking suggestions in Florence, San Gimignano, Siena, and Pienza
  • Travel kit with maps, tips & recommendations

Exclusions

  • Arrival/departure transfers (available on request)
  • City taxes (to be paid locally)
  • Meals not mentioned under inclusions
  • Personal expenses (drinks, shopping, tips)
  • Travel insurance

Important

  • The package is possible all year round except August. However, some hotels/farm stays could be closed during low season (November-April). Please ask for your quote at least 20 days before the requested date.
  • Prices vary based on departure season
  • Single supplement to be applied
  • Special discount during low season period (Nov-Mar)

REQUEST A DETAILED ITINERARY AND YOUR QUOTE.
Let us help you customize your perfect trip.

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Ask for your quote

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Additional information

Duration

5 days / 4 nights

Difficulty

Easy

Live tour guide

English

Chianti

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Florence

Tuscany

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