From Florence, shuttle to Montalcino for a complementary welcome lunch at a winery-run restaurant. A loop hike covers the north side of Montalcino hill, passing by vineyards and stone farmhouses. At the hike's end, we'll stop for an introduction to Brunello, a structured, long-lived red is among Italy’s best wines. We’ll taste either the boutique winery Il Marroneto, which offers a vertical tasting of Brunello, or at Castello di Romitorio, owned by the artist Sandro Chia. For the first of our gourmet wine dinners, we go to a family-run restaurant with fabulous versions of traditional Tuscan fare, such as tagliatelle with porcini mushrooms, wild boar (cinghiale) ravioli, and rabbit stewed with black olives. L, D

Day 2  –  Montepulciano & Pienza

Pienza is famous for its Renaissance architecture and its pecorino cheese. After a short tour of town and a cheese tasting, we’ll embark on a beautiful walk over rolling hills lined with cypress trees to the town of Montepulciano. Here we’ll learn about Vino Nobile di Montepulciano. Beloved by nobles, this wine was a favorite of Thomas Jefferson and Voltaire. We'll visit Icario, a terrific up-and-coming winery, or Poliziano, one of the leaders in Vino Nobile’s renaissance in the 1980s. Dinner features elegant nouvelle renditions of classic Tuscan cuisine. B, D

Day 3 – Gregorian chants

Today we trek to the Abbey of Sant’ Antimo, where monks still live. The hike offers scenic views of Montalcino, then proceeds through lush forests and along hill crests until bringing to the Romanesque abbey in time to hear the monks chant. After lunch, we’ll taste Brunellos from the south side of the DOCG zone, either at Ciacci Piccolomini di Aragona, an historic estate with highly rated wines, or Fanti, an emerging star with powerhouse wines. Free time to explore the wine shops of Montalcino or visit the fortress of Montalcino, which houses an enoteca (wine bar). B

Day 4  –  The art of Siena

Today is devoted to Siena. We'll start with a cappuccino at Nanini, Siena's most famous coffee bar, then tour Siena's Palazzo Pubblico, which houses masterpieces of Italian Gothic art. We'll also visit Siena's striped cathedral, home to artworks by Michelangelo. Then there’s free time for lunch, shopping, or a visit the Enoteca Nazionale, Italy's national wine museum/wine bar. We then drive to San Gimignano, a hilltop city that bristles with medieval towers, and settle into our accommodations at a country inn with vineyard. Before dinner, an informal tasting offers an introduction to San Gimignano’s historic white wine, Vernaccia di San Gimignano. B, D

Day 5  –  Circling San Gimignano

Today's hike encircles San Gimignano, offering great views of the town and vineyards around every turn. Our afternoon wine tasting at Panizzi spotlights the various styles of Vernaccia di San Gimignano, a wine made since the 1100s. Visit San Gimignano to see its towers and exquisitely beautiful frescos in the main church. Dinner is in town, where we'll be treated to regional specialties like peasant vegetable soup with bread (ribollita) and giant lasagna (pappardelle), and learn the proper way to dip almond cookies (cantucci) in vin santo, a golden dessert wine first created by medieval monks. B, D

Day 6  –  Walk the Etruscan byways

The Etruscans planted Tuscany’s first vines. We’ll revisit this ancient civilization on our hike to Volterra, an Etruscan stronghold. There will be free time for lunch and a visit to the Etruscan museum, where this sophisticated culture comes alive. For our afternoon wine tasting, we head back to San Gimignano and visit Cesani, a small family estate that produces a superb Super Tuscan, as well as two excellent versions of Vernaccia. Our farewell dinner is in San Gimignano, allowing us to see the city in all its quiet magic at night. B, D

Day 7  –  Buon Viaggio!

A shuttle to Florence and assistance with your travel plans. B  

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