A Perfect Week in Tuscany

Tour the treasures of Italy's Tuscany region, from Val d'Orcia through Chianti, on this week-long trip to Pienza, Montepulciano, Siena, San Gimignano, and Rome.

Country
Italy
Duration
8 days / 7 nights
From
$3,500 /person
Book this trip

Your trip at a glance

Top Activities

Tasting Montepulciano wines and pecorino cheese samplings on a guided vineyard visit

Truffle hunting in the Tuscan countryside with trained and friendly dogs

Walking in the shoes of gladiators and government officials in ancient Rome's Colosseum and Forum

Visiting the walled city of Siena, whose striped church ranks among Italy's architectural greats

Biking through Tuscan hills and local vineyards on an open-ended day in the region

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Preview:

Truffle Hunting and Cooking Class

Truffle 3

Overview

Dive into the fascinating world of truffles! You will meet an expert and local truffle hunter and, together with his faithful dog, start a walk in the woods hunting for the truffle. It will be an exciting experience, where you will be immersed in nature and you will learn a lot on this unique local product. At the end of the truffle hunt, you will start a fun hands-on cooking class, where you will learn the secrets of Italian cuisine and the focus will be on truffles. You will then enjoy a lunch with the delicious food you have just prepared. (Breakfast)

Highlights

Truffle hunt

Whoever seeks a truffle... finds a treasure! This wonderful gem is very appreciated all around the world, and truffle hunting is an art passed from one generation to the next one. Truffle hunting is an adventure in the bush, walking up and down hills always escorted by a faithful and friendly dog. The perfect end of this adventure is tasting the unimitable flavor of truffle.

Cooking Class and Lunch

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Accommodations

Hotel San Gregorio (or similar)

Hotel San Gregorio greets guests with a resounding welcome, set in the heart of Tuscany's Val d'Orcia. From the property's wonderful garden, you can set off to discover the surrounding landscapes, where rolling hills blur with the historic center of nearby Pienza. In your room, you'll find a home away from home, imbued with a sense of warmth, passion, and Tuscany's trademark charm.

Location:

Via Della Madonnina, 4 - Pienza

Phone:

+390578748059

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How it works

01

Fill out request form

Provide your ideal trip dates and details to be matched with one of our local planning experts.

02

Meet your expert

Schedule a call with your expert to confirm dates, pricing and any recommended edits to the itinerary.

03

Book your trip

Once your itinerary is set, it’s time to pay the deposit to secure your trip.

04

Take-off

Let the journey begin! Your expert will offer real-time support and concierge service while traveling.

Ready to Go?

Let our local experts plan your dream trip.

What's included

Included in the final price

  • Roadbook with local tips and expert recommendations
  • On-the-ground support
  • On-trip concierge service
  • Personalized trip crafting
  • Accommodations for seven nights, with daily breakfast included
  • All meals and culinary experiences mentioned in the itinerary
  • All activities, guided tours, and excursions mentioned in the itinerary
  • All transfers mentioned in the itinerary
  • Everything else listed as included in the itinerary
  • Rental car from Days 1-7 with automatic or manual transmission, depending on your preferences

Not included in the final price

  • International arrival and departure flights
  • Travel insurance
  • Personal expenses and gratuities
  • Anything not mentioned or listed as optional in the itinerary
  • Daily city taxes

Ready to see the full itinerary?

Submit a free request to talk with our local experts.

Let's Go
Day 1:
Benvenuti in Italia!
Day 2:
Val d'Orcia Wine, Pecorino Cheese, and Montepulciano's Majesty
Day 3:
Truffle Hunting and Cooking Class
Day 4:
Val d'Orcia to Chianti and Siena
Day 5:
Tuscan Countryside at Your Leisure
Day 6:
Chianti Wines and the San Gimignano Skyscape
Day 7:
Entering the Eternal City: Relics of the Roman Empire
Day 8:
Alla Prossima!