Driver-Escorted Private Journeys
Journeys  /  Vineyards to Vistas
IIIHistoric towns and vineyards in a glorious week

Vineyards to Vistas

Exploring Tuscany and Umbria
8 days 7 nights Italy Chianti · Siena · Città della Pieve · Montalcino

An enchanting exploration of Tuscany and Umbria — stunning landscapes and deep cultural heritage, from the lush vineyards of Chianti to the ancient allure of Città della Pieve and the celebrated wine country of Montalcino.

The route
TUSCANYUMBRIATYRRHENIAN SEAFlorencePerugiaAssisiChiantiSienaCittà della PieveMontalcinoEnlarge ⤢
Routing & suggested hotels
  • 3 nightsChianti — Viesca
  • 2 nightsCittà della Pieve — Vannucci
  • 2 nightsMontalcino — Capanna Suites
Highlights

Chianti's wine country

Lush vineyards, tastings, and the quintessential Tuscan landscape.

Siena and San Gimignano

Medieval splendour, the historic Palio, and San Gimignano's famous towers.

The Val d'Orcia

UNESCO-listed rolling hills and villages — San Quirico, Pienza, Bagno Vignoni.

Cortona's charm

A hilltop treasure with sweeping views and a deep sense of history within its ancient walls.

Montalcino's wine excellence

Home of Brunello — vineyard visits, the winemaking story, and tastings of the world-renowned varietal.

Todi, Spoleto, and ancient Etruria

Medieval and Renaissance layers over the region's Etruscan roots.

Umbria, a soulful retreat

Assisi, Perugia, and the serene heart of Italy.

Pair this journey with your own driver-escorted minivan.

Every itinerary in this collection travels with a private minivan from our modern fleet — the same vehicle, start to finish.

Ask your VIT advisor
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