The Hidden Heart of Tuscany

53026 Pienza, Province of Siena, Italy

CW
Crush Wine Experiences
  • Email address verified
20 reviews
Apr 9 - 16, 2026
Group size: 6 - 16
The Hidden Heart of Tuscany
53026 Pienza, Province of Siena, Italy

Crush Wine Experiences
  • Email address verified
20 reviews

Apr 9 - 16, 2026
Group size: 6 - 16

About this trip

What’s included

  • Arrival transfer
    Transfer from Florence airport (FLR) to Pienza
  • Lodging
    4-star hotels, plus country farm house lodging
  • Ground Transportation
    Local transportation each day on private luxury vehicle
  • Full-time Guide
    Tour Manager for 8 days (fully-escorted tour and 24h assistance while on tour)
  • Meals
    14 meals and aperitivos
  • Cooking Class
    Hands-on class with a Tuscan cook, followed by lunch on site
  • Cheese farm visit
    Tour, tasting, wines, and lunch
  • Wine tastings
    2 DOCG winery visits, lunches, and tastings
  • Local tour
    Guided walking tour of Siena with a local guide, headsets included
  • Attractions
    Contrada Museum tickets in Siena
  • Local tour
    Guided walking tour of Lucca with a local guide
  • Local tour
    Guided walking tour of Florence with a local guide, headsets included
  • Hotel
    3 nights at Hotel Corsignano in Pienza
  • Hotel
    2 nights at Agriturismo il Piastrino in Vinci, in the Tuscan countryside
  • Hotel
    2 nights at Hotel Horto Convento in Florence

What’s not included

  • Airfare
    Flights to/from Italy
  • Travel Insurance
    Highly recommended
  • Gratuities
    For local guides and coach drivers

Available Packages

Double Occupancy
Deposit: $1,260
6 left
$4,200
Deposit: $1,260
Single Occupancy
Deposit: $1,470
Only 3 left
$4,900
Deposit: $1,470


Your Organizer


CW
Crush Wine Experiences
20 reviews
Experience small group, multi-day tours off the beaten path. Our food, wine, and cultural excursions span the world's most interesting regions, and include an American wine host/Sommelier along with charismatic local guides.

Reviews

We just returned from this incredible trip through Piemonte and Lake Como. The itinerary was well-paced, the food and wine were outstanding, and the group experience made it all even better. The truffle hunting and the time on Lake Como were definitely the highlights. A huge thank you to Sam, our overall host, for yet again putting together such a fantastic trip. And to Gabriele, our Tour Manager, who kept everything running smoothly and made sure we were always taken care of — from winery visits to water taxis. We came home with great memories, new friendships, and 4 cases of wine to help us relive it all. This was our 6th tour of Italy with Crush Wines and we have already booked 3 trips for next year. This is really the perfect vacation - great activities, beautiful locations, fantastic food and plenty of free time to explore. Crush Wines knows hot to do it right!
By Michael K for Piemonte & Lake Como on Oct 22, 2025
I previously reviewed our 2023 Tour of Tuscony with Crush Wines Experiences. We have now completed two new tours in 2025--Piemont and Lake Como, and then Lisbon and Southern Portugal. Both tours were amazingly good. Sam is the ultimate tour host, and finds perfect guides to join us. There is always a licensed professional tour guide who accompanies the tour everywhere we go, making sure that everyone is well taken care of, providing a depth of information, and providing great insight into the local culture. In addition, in specific cities, where appropriate, there will be a local licensed guide for that specific city. The food and wine we sampled were world class, and the cultural sites were fascinating. Sam finds the perfect balance between scheduled activities and time on our own. And, with the small groups involved in the tour, you make friends quickly with your fellow travelers. We are looking forward to trip No 4 with Sam and Crush Wine Experiences.
By Larry H for Piemonte & Lake Como on Oct 18, 2025
I previously reviewed our 2023 Tour of Tuscony with Crush Wines Experiences. We have now completed two new tours in 2025--Piemont and Lake Como, and then Lisbon and Southern Portugal. Both tours were amazingly good. Sam is the ultimate tour host, and finds perfect guides to join us. There is always a licensed professional tour guide who accompanies the tour everywhere we go, making sure that everyone is well taken care of, providing a depth of information, and providing great insight into the local culture. In addition, in specific cities, where appropriate, there will be a local licensed guide for that specific city. The food and wine we sampled were world class, and the cultural sites were fascinating. Sam finds the perfect balance between scheduled activities and time on our own. And, with the small groups involved in the tour, you make friends quickly with your fellow travelers. We are looking forward to trip No 4 with Sam and Crush Wine Experiences.
By Larry H for Southern Portugal - Lisbon & the Alentejo on Oct 18, 2025
Ines and Sam are professionals that took much pride in selecting only the very best hotels, restaurants, and wineries. Our days were filled by visiting unique places of interest. Also, they were supportive of everyone’s needs on a daily basis. I highly recommend Crush Wine XP for a truly fun- filled memorable travel experience.
By Jane L for Southern Portugal - Lisbon & the Alentejo on Oct 14, 2025
Wonderful trio, great mix of people, amazing itinerary , and a fabulous tour guide. Can’t wait for my next trip with Sam.
By Virginia B for Southern Portugal - Lisbon & the Alentejo on Oct 14, 2025
Thank you for your kind words, Ginny! They mean a lot. It was an absolute pleasure hosting you!
By Crush Wine Experiences on Oct 14, 2025
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