presents an insider’s view of

Southern Tuscany & Umbria

with Yvette Simpson

October 6- October 12, 2025

6 nights in Italy

Medieval, hilltop towns with breathtaking views. Sipping some of the best wines Italy has to offer while overlooking the Tuscan countryside. Tuscan food at its finest. We will visit the following wine regions – Orvieto, Vino Nobile di Montepulciano, Brunello di Montalcino & Chianti Classico.

We will be based in the exceptional town of Montepulciano for our 6 nights. Each day, we  will venture out for wine, food and a little bit of culture. At night, you are on your own to  wander the quiet streets of Montepulciano, watch the sunset over the Tuscan hills or just  continue your eating and drinking adventure. 

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Inclusions

This trip includes...

  • Accommodations in historic rooms and apartments in the heart of Montepulciano
  • Breakfast daily
  • Daily long lunch or dinner (includes pre-dinner drink, food, wine, gratuity)
  • Our experience is an exceptional lunch or dinner is more than sufficient.
  • Wine tastings – all, generally including tapas
  • Transportation – all
  • Admission and entrance fees – all

Does not Include: 
Airfare & Trip insurance, if applicable

$3,900 Cost per Person

Limited to 18  participants.
Single travelers welcome. If you prefer a single room, an additional charge is $750.

 We will be based in a few unique accommodations, all very proximate to one another in  the heart of Montepulciano. You will feel like you are living the Tuscan dream. All rooms have en suite bathrooms and are charmingly decorated with period furniture.

 

Are you ready to start your Wine Journey?

Join us and get ready to savor the finest wines, explore breathtaking vineyards, and immerse yourself in the rich traditions of winemaking. This tour promises an unforgettable experience that will tantalize your taste buds and leave you with lasting memories. Don’t miss out on this incredible adventure; book your Italy wine tour today and let the enchanting world of wine come to life before your eyes

Click the link below for $1,000 Partial Payment

BOOK NOW

Click the link below for Full Payment

BOOK NOW

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Current Itinerary

Pick Up In Rome and Drop Off in Florence

Pick up in Rome and drop in Florence. Please plan to arrive in Rome no later than October 5th, 2025.

On last day of tour, Sunday, we will drop you off in Florence at 10 am. If you need transportation to a different destination and/or at a different time, we can coordinate the transport for you. The cost varies depending on distance.

Arriving early or extending your stay

 We think Rome is best explored on your own or in very small groups. Our travel partners at Tinto Travels are happy to assist with hotel recommendations & things to see and do. 

Daily Activities

Eating, Drinking, & A Little Culture

Our tour has its own daily rhythm. Each day consists of a nice relaxed (not too early) breakfast before we head out for a bit of culture, a wine tasting and a long leisurely lunch or dinner.

Day 1

We will meet you at 10AM at Eataly, an easy meet up point near the Ostiense train station. The location is approximately 15-20 minutes from central Rome. We will have great wines and a fantastic lunch outdoors with Giovanni in Orvieto before heading to see the Duomo and wandering the charming streets of Orvieto for a bit. We will arrive in the late afternoon and check into our rooms in the heart of Montepulciano.

Evenings

In the evening, you can explore the beauty and stillness of Montepulciano. If you are full from today’s lunch, just grab a glass of wine and perhaps a bruschetta from a nearby wine bar. Still hungry? Among the 50 or so restaurants in town, there are at least a dozen restaurants in Montepulciano we enjoy.

Day 2

Cultural Stop Over

You will get to know your base of Montepulciano – history, cool shopping, views and ancient Etruscan wine cellars.

Lunch

Lunch is with our friend Massimo and his daughter Virginia at their elegant restaurant in Montepulciano called Le Logge del Vignola.

Wine Tasting

We will visit Olimpia and her picture-perfect winery called Le Bertille, a very small producer of Vino Nobile, just down the hill from Montepulciano.

Day 3

Cultural Stop Over

A visit to the gardens of nearby La Foce, a mini paradise. What will be in bloom in June?

Wine Tasting

A wonderful tasting of world-famous Brunello di Montalcino with Gianluca and his wife Kai at Santa Giulia.

Lunch

We get to eat lunch with the family with a delicious home cooked meal served up by Nona Mirella, Gianluca’s mom.

Day 4

Cultural Stop Over

A guided tour of medieval Siena (or wander the streets on your own if you prefer).

Eating

We will have a snack and wine in Siena at Pretto. Our main meal will be dinner tonight in Montepulciano.

Wine Tasting

We will meet up with Andrea of I Sodi winery at his family’s incredible vineyard in the historic Chianti Classico district. Most people say this is their favorite winery visit of the tour, and that is really saying something!

Day 5

Cultural Stop Over

This is a relaxing day to explore the village of Pienza. You may even consider purchasing your next residence in Pienza after spending an afternoon here. There are some unique boutique shops here, and probably the best gelato on your trip.

Lunch

We will have lunch together with our friend Massimo in Pienza. Now might be the time to try cinghiale.

Day 6

Cultural Stop Over

Panicale had its moment of fame when it was profiled in the New York Times.

Winery Tasting

We will have a special tasting of the wines of Goretti in the picturesque village of Panicale. It is a fun way to experience the unique grape varieties of Umbria.

Lunch

Young chef Nicola knows a thing of two about making Italian comfort food.

Day 7

We will drop you off in Florence at around noon for you to continue your Italian  adventure. 

Are you ready to start your Wine Journey?

Join us and get ready to savor the finest wines, explore breathtaking vineyards, and immerse yourself in the rich traditions of winemaking. This tour promises an unforgettable experience that will tantalize your taste buds and leave you with lasting memories. Don’t miss out on this incredible adventure; book your Southern Tuscany wine tour today and let the enchanting world of wine come to life before your eyes.

Click the link below for $1,000 Partial Payment

BOOK NOW

Click the link below for Full Payment

BOOK NOW
Default is for one person, but you can change number of persons in drop down menu

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