Rome • Orvieto • Montepulciano • Montalcino • Siena • Chianti • Bolgheri • Milan • Dolomites • NYC
| Date | Day | Flight / Travel | City | Activities |
|---|---|---|---|---|
| Oct 6 | Tuesday | Depart IAD | ||
| Oct 7 | Wednesday | Arrive Rome | Rome | |
| Oct 8 | Thursday | Rome | Roman Countryside & Lakes Tour (bestromedriver.it) | |
| Oct 9 | Friday | Rome | Tivoli Tour (bestromedriver.it) | |
| Oct 10 | Saturday | Pickup rental car | Orvieto | Cascate del Mulino hot springs en route to Orvieto |
| Oct 11 | Sunday | Montepulciano | Guided tour of Orvieto, then drive to Pienza and La Foce Gardens | |
| Oct 12 | Monday | Montepulciano | Montepulciano Best of Nobile | |
| Oct 13 | Tuesday | All wine tours arranged by Tours of Tuscany | Montalcino | Brunello and Pecorino in the Heart of Val d'Orcia. Dinner at Drogheria |
| Oct 14 | Wednesday | Montalcino | Brunello Wine Tour and Sant'Antimo Abbey (group) | |
| Oct 15 | Thursday | Siena | Siena City Centre with Duomo | |
| Oct 16 | Friday | Siena | Chianti Classico Wine Tour — San Gusme (group) | |
| Oct 17 | Saturday | Chianti | Chianti Classico | |
| Oct 18 | Sunday | Chianti | Cooking Class | |
| Oct 19 | Monday | Bolgheri | Chianti & San Gimignano Wine Tour. Dinner at La Pineta | |
| Oct 20 | Tuesday | Bolgheri | Bolgheri & Super Tuscan | |
| Oct 21 | Wednesday | On our own — winery visit and lunch, ending in Florence area | Cinque Terre / La Spezia | Grattamacco. Lunch at Osteria del Tasso |
| Oct 22 | Thursday | Cinque Terre / La Spezia | Cinque Terre Tour | |
| Oct 23 | Friday | Drive to Dolomites | Tramin | Explore region |
| Oct 24 | Saturday | Tramin | Explore region | |
| Oct 25 | Sunday | Tramin | The Best of the Dolomites in Just One Day | |
| Oct 26 | Monday | Tramin | Explore region | |
| Oct 27 | Tuesday | Drive to Milan | Milan | |
| Oct 28 | Wednesday | Milan | Two 3-hour guided tours AM/PM with Elena (lunch not included) | |
| Oct 29 | Thursday | Milan | Milan free day | |
| Oct 30 | Friday | Train from Milan to Verona | Milan | Tour Verona with guide Laura Z |
| Oct 31 | Saturday | Depart Milan Malpensa |