Rome • Orvieto • Montepulciano • Montalcino • Siena • Chianti • Bolgheri • Milan • Dolomites • NYC
| Date | Day | Flight / Travel | City | Lodging | Activities |
|---|---|---|---|---|---|
| Oct 6 | Tuesday | Depart IAD 10:20pm | |||
| Oct 7 | Wednesday | Arrive Munich 12:30pm, fly to Rome 1:30pm, arrive Rome 3:05pm (tight transfer) | Rome | Hotel Marisa | |
| Oct 8 | Thursday | Rome | Hotel Marisa | Roman Countryside & Lakes Tour (bestromedriver.it) | |
| Oct 9 | Friday | Rome | Hotel Marisa | Tivoli Tour (bestromedriver.it) | |
| Oct 10 | Saturday | Pick up Hertz car 8:00am at train station | Orvieto | Hotel Duomo | Cascate del Mulino hot springs en route to Orvieto |
| Oct 11 | Sunday | Montepulciano | Villa Nottola | Guided tour of Orvieto, then drive to Pienza and La Foce Gardens | |
| Oct 12 | Monday | Montepulciano | Villa Nottola | Montepulciano Best of Nobile — €400 pp | |
| Oct 13 | Tuesday | All wine tours arranged by Tours of Tuscany | Montalcino | Albergo Il Giglio | Brunello and Pecorino in the Heart of Val d'Orcia — €450 pp. Dinner at Drogheria |
| Oct 14 | Wednesday | Montalcino | Albergo Il Giglio | Brunello Wine Tour and Sant'Antimo Abbey — €270 pp (group) | |
| Oct 15 | Thursday | Siena | Villa del Sole Siena | Siena City Centre with Duomo — €250 pp | |
| Oct 16 | Friday | Siena | Villa del Sole Siena | Chianti Classico Wine Tour — San Gusme — €270 pp (group) | |
| Oct 17 | Saturday | 1 hour drive to Badia a Coltibuono, start of day tour 9:20am | Chianti | Badia a Coltibuono | Chianti Classico — €450 pp |
| Oct 18 | Sunday | Chianti | Badia a Coltibuono | Cooking Class 10:30am | |
| Oct 19 | Monday | 1 hour drive to Siena, start of day tour 9:20am, then 1h45m drive to hotel | Bolgheri | Locanda dell'Aioncino | Chianti & San Gimignano Wine Tour — €450 pp. Dinner at La Pineta |
| Oct 20 | Tuesday | Bolgheri | Locanda dell'Aioncino | Bolgheri & Super Tuscan — €650 pp | |
| Oct 21 | Wednesday | On our own — winery visit and lunch, ending in Florence area | Cinque Terre / La Spezia | Le 5 Terre La Spezia | Grattamacco at 11:00am. Lunch at Osteria del Tasso |
| Oct 22 | Thursday | Cinque Terre / La Spezia | Le 5 Terre La Spezia | Cinque Terre Tour — €550 pp | |
| Oct 23 | Friday | Drive to Dolomites | Tramin | Villa Naj | Explore region |
| Oct 24 | Saturday | Tramin | Villa Naj | Explore region | |
| Oct 25 | Sunday | Tramin | Villa Naj | The Best of the Dolomites in Just One Day | |
| Oct 26 | Monday | Tramin | Villa Naj | Explore region | |
| Oct 27 | Tuesday | Drive to Milan, drop off car 7:00pm | Milan | Crowne Plaza Malpensa | Explore Milan |
| Oct 28 | Wednesday | Milan | Crowne Plaza Malpensa | Two 3-hour guided tours AM/PM with Elena (lunch not included) | |
| Oct 29 | Thursday | Milan | Crowne Plaza Malpensa | Milan free day | |
| Oct 30 | Friday | Train from Milan to Verona 7:00am, return depart Verona 6:30pm | Milan | Crowne Plaza Malpensa | Tour Verona with guide Laura Z |
| Oct 31 | Saturday | Depart Milan Malpensa 12:10pm, arrive JFK 3:50pm | New York City | Dinner with Johnny | |
| Nov 1 | Sunday | New York City | Tour with Johnny | ||
| Nov 2 | Monday | Amtrak home | Home |