Touring Tuscany: A Week of Food, Wine and Culture

Touring Tuscany: A Week of Food, Wine and Culture

Explore the magic of Tuscany with a sommelier and an expert local guide

Type Tour Wine Vacation
Tags brunello di montalcino / chianti / florence / italy / off the beaten path / siena / small group luxury tour / tour / tuscany


8 days, 7 nights.  Visiting Florence, Siena, Montalcino, Pienza, and San Quirico d'Orcia. Discover the delights of Tuscany over the course of a week. Visit leading wineries, restaurants, and cultural destinations. Experience ancient villages, wine cellars, and strolling amongst the rolling hills of the Chianti Classico region. Tuscany is known for its landscapes, history, artistic legacy, and its influence on high culture. The birthplace of the Italian Renaissance and home to many famous Italians influential in global history.


  • Discover Ancient architecture, sweeping piazzas, and soaring churches.
  • Florence is the capital of Tuscany, and home to many masterpieces of Renaissance art and architecture.
  • We will take a walking tour of Florence with a local City Guide, visiting the exteriors of Piazza Signoria, Santa Croce square, the Cathedral and Batipstery.


  • 5 winery visits and tastings, and 12 meals are included throughout the tour, including multi-course culinary experiences paired with local wines.
  • Luxuriate in historic villages, vineyard hillsides, and stunning sunsets


  • The Chianti region stretches between Florence and Siena and includes 14 towns.
  • The area is small but “Chianti Classico” has been produced there for over 2,000 years
  • We will visit an historic hamlet, the cellars of Castello di Volpaia, and the Poggio Amorelli winery.


  • Brunello di Montalcino is a famous red wine produced in the vineyards surrounding the town of Montalcino, in the province of Siena
  • Brunello di Montalcino is made 100% from the Sangiovese grape varietal
  • Our visit there will include stops at two (2) extraordinary local wineries.


  • Tuscany is one of the most abundant agricultural regions in Italy, featuring wheat, olives, olive oil —  and wines.
  • Many vegetables and fruits are cultivated, as are cattle, dairy, pigs, and poultry.


  • Siena is one of the most important cities from medieval Europe, and it is a UNESCO World Heritage Site.
  • We will meet up with a local City Guide and get an orientation of the rich history and unique traditions of Siena
  • Montepulciano is renowned for its delicious food, and it is known worldwide for its wine.
  • We will visit an award-winning local producer and taste 3 of their best selections.


  • Sam (at left with Tommaso Squarcia, Manager of Castello Tricerchi winery) is a WSET-certified sommelier and co-founder of Crush Wine Experiences, NY’s leading food & wine experience company.
  • He has traveled to Europe extensively on cultural and wine tours at some of the continent’s leading wineries.
  • Sam knows the wines, cuisine and local culture of Tuscany. And as a wine professional, he brings an added dimension to the tour.


Click here to view the day-by-day detailed itinerary.

DAY 1: Arrival Day

DAY 2: Florence

DAY: 3: Chianti Classico

DAY 4: San Gimignano

DAY 5: Brunello di Montalcino

DAY 6:  Pienza

DAY 7:  Siena

Day 8: Arriverderci


$3,850.00 per person, double occupancy (private room)

$4.350.00 per person, single occupancy (private room)

(Rates are inclusive of taxes and fees)

Click here to reserve your room

Note: This is a boutique, intimate tour experience, limited to 18 guests + 2 hosts

High quality of food, wine, destinations, and a small bus that can go where larger tours cannot.

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