Custom Itineraries

The possibilities are endless and we can help you with almost everything in your itinerary planning!

-Hotels and we strive to find you the best prices and the highest quality.
-Car rental ideas for making your journey flawless and sensible.
-Customized tours whether it be from planning a simple appointment at a wine tasting or taking you on the wine tasting!
-Ideas for mapping out your trip in the best possible way
-Helping you plan your days so that you get the most out of your trip and savour it all!

Click here to see what clients are saying about our Custum Itineraries:
- “Asbsolutely Wonderfull”
- “She said "trust me" and I did!”
- "Highlight of our tour"

Here is a sample Itinerary


Day 1 - The Tuscan Countryside of Cortona   Wednesday October 17th

This morning we meet in the hillside town of Cortona  and our home for the next 4 nights, Poggio al Sole,  an old village high in the hills and just 3 km to Cortona.  Cortona is a hill-town made famous by Francis Mayes, author of "Under the Tuscan Sun". With swimming pool, outdoor dining, and an outdoor wood-fired oven, this is a paradise just for us.

This afternoon, we begin our adventure within the ancient stone walls of Cortona with our illustrious guide Giovanni who will share the treasures of the Etruscan sites, visit a monastery where St. Francis slept and explore Cortona during a leisurely and informative tour.   After our tour, we will visit an old olive mill where they still press in the traditional way. Here we will do an olive oil tasting with owner Massimo.  This evening a dinner of ‘Bistecca alla Fiorentina’ will be prepared in the Oven by our host Benedetta, well-known locally for her talents as a chef with a flair for Florentine, which are her roots.  (L,D)

Day 2 – Pienza and Perazetta,  Thursday October 18th

A typical daily breakfast at our Agriturismo includes everything from fresh fruit, yogurt and homemade pastries, to eggs from the hens outside, and Benadetta's own olive oil and hearth-fired breads.

Our first stop: the picture perfect hill town of Pienza. The views from the city walls show us the sheep that dot the valley floor, and Pecorino, the local cheese that is made from their milk, spills from the shops. You will enjoy a unique Balsamic Vinegar tasting like nothing your palate has experienced before! You will also taste the cheese of the area.

For lunch we will take you to the vineyard Perazzeta, where Alessandro Bocci makes award winning olive oil and wine. A passionate man, he names his wines after those he loves most: his daughter Sara, his wife Rita, and his father Irio. You will learn about this farmer’s pursuit of the most perfect wine, and how he will throw away twice as many grapes as he presses.

After a tasting and a tour, we are treated to a splendid lunch in the cellar, or if the sun is shining, on the terrace overlooking the valleys. Either way, the meal is impressive as Sara shows us her talents as an accomplished chef and winemaker, and the wine flows to match the delicious food.

The countryside here is glorious, and we enjoy more of it on our way back home, via Sant ‘Antimo. The Abbey of Sant'Antimo (Abbazia di Sant'Antimo) is a beautiful Romanesque church, in a picture-perfect setting just south of Montalcino in southern Tuscany. It sits in a large valley with views of the hill town Castelnuovo dell'Abate, rolling hills covered in olive groves and vineyards, and wild forests.

Dinner is on your own tonight and our guide has a few great suggestions!  (B,L)

Day 3 -  Making whoppie, I mean Gnocchi!!  Friday, October 19th

Our digs are so beautiful that it is really hard to leave.  So today, we are only venturing out briefly to Avignonesi.  It’s beautiful vineyard in the countryside not far from our Hotel.  The grow the world famous Vin Santo,.  It is so famous, that in May, when they open the 10 year old barrels, journalists from all over the world come to write about it.  We will be there at just the right time to see the gorgeous grapes drying in a special air-controlled room. Take a tour and tasting some of these wines is on the agenda.

After this delightful experience, we head back to our place for lunch, home-made wine and a fabulous cooking lesson.  We can plant ourselves right in Benedettas kitchen!  Benedetta grows her own wine , her own oil, and is a fabulous chef.  She is going to teach us how to make gnocchi, and a variety of other things, including her desserts, in a wonderfully relaxed and fun atmosphere.

At the end of the evening, we sit down to a feast that is fit for royalty….us!  (B,L,D)

Day 4 - Orvieto   Saturday, October 20th

This morning, we take the private motor coach to the hill town of Orvieto. Orvieto's magnificent Duomo (cathedral) is gorgeous thanks to architect Lorenzo Maitani, with a mass of mosaics, stained glass, frescoes and sculpture. We will visit the former palace holding a fine Etruscan collection, and Orvieto's underground. Orvieto is honeycombed with Etruscan and medieval caves, and our guide will weave for you a fascinating tale of archeological history.

Afterward, we are off to the estate of Emiliano Sirchia at the foot of the town..  We visit the estate and cantina Altarocca, a Small Vineyard Estate, for a wine tour and tasting and lunch in the restaurant of this beautiful place.  Tonight, dinner is on your own, and Canta Napoli is Monicas favorite.  (B,L)

Day 5 – Truffle Hunting in the countryside, Sunday, October 21st

While Tuscan truffles lack the brand-name recognition of those from Alba, San Giovanni d'Asso also lacks the circus atmosphere that can result in overpricing and over-hunting. And the quality, some say, is just as odoriferous. Truffles don't like pollution and, as you will see, there's nothing like pollution in San Giovanni d’Asso.  Nothing, that is, except for luscious wheat fields, crumpled clay hills and the ribboned vineyards of the Sangiovese grape, which is used to make two of Italy's finest wines: Brunello di Montalcino and Vino Nobile di Montepulciano.

Perched on a craggy hilltop, San Giovanni d'Asso is also nothing like any other hill town. There are no postcard or craft stores, just a butcher shop that keeps irregular hours, a tobacco store and a hole-in-the-wall café that offers half-day truffle excursions.

Last November, in a bid to elevate its truffle stature, the village of 940 opened the country's first museum dedicated to the food.

Paying 100E a pound, we can put the dogs to shame and find our own truffles….do you think you can?  A visit to the Etruscan Museum, and a fresh truffle lunch will taste great after our walk in the countryside looking for the elusive truffle.  (B,L)

Day 6 – Assisi Monday October 22nd

We leave Tuscany for the day and visit Assisi in the region of Umbria for a guided  tour and a spectacular church visit. Assisi is best known as the birthplace of St. Francis of Assisi, patron saint of Italy, founder of the Franciscan order, and one of the most popular Catholic saints. We will experience Roman ruins, winding medieval streets, sacred shrines, and the main attraction: the 13th-century Basilica di San Francesco. The basilica contains the sacred relics of Francis and beautiful frescoes of his life. Marco, our guide, tells us the story of St. Francis in a way you will never forget.   After we can shop and everyone can grab a lite lunch on their own, before heading to our cooking class.

We will spend this evening with Jennifer Bidi. Jennifer is an American married to Italian winemaker and Olive oil producer Federico Bidi.  Federico is one of Small Vineyards newest additions. We have the pleasure of spending the evening with them, eating in their kitchen and making pasta with them. We will then dine on our creation of an authentic Etruscan "poor man’s" dinner with the wines from the estate. (B,D)

Day 7 –   Just Say Cheese!   Tuesday, October 23rd

After another wonderful breakfast in our Agriturismo, we will make a short drive over to San Martino. Here we will meet Silvia and Riccard, at their beautiful Relais Chateau, Il Falconiere.

They will quickly become some of your favorite characters in Italy, and Riccard will teach us the art of cheese making. From local sheep and cow’s milk we will make ricotta, mozzarella, and the pecorino that is so famous from these verdant valleys. Along with our cheese making we make Pici pasta and a fabulous sauce of fresh tomatoes for our hand-made pasta. It will be a most delicious feast!  Riccardo Baracchi and his wife Silvia make award winning wines and champagne and we will enjoy it all. Afterward, there will be some time to spend as you choose, where you can wander the cobblestone streets of Cortona, visit the Duomo, enjoy the musuem and shopping, catch up at the internet café, or take in the magnificent valley views.

Back at Poggio al Sole this early evening we will get our hands in some dough and learn to make Italy's famous Pizza with many different toppings which will accompany some organic salads and antipasta fresh and seasonal, as well as a Small Vineyard Wine Sampling with Monica as our educator of Small Production wines.   (B,L,D)

Day 8 - We say our farewells  Wednesday October 24th

This morning after a hike in the countryside and an authentic Italian breakfast, we say our farewells.  With last minute photos and promises to stay in touch, it is always difficult to leave the Italian countryside!

Transfer to train station is available.

In the unlikely event that some outings may change, replacement outings will be of equal quality.


  • Everything listed in the itinerary while we are with Doumina
  • Lodging in 4 star accommodations w/private bath.
  • Ground transportation
  • Guided tours
  • Every breakfast and at least one main meal, every day, and the foods involved in the various tastings.
  • Wine tastings
  • Vinegar tasting
  • Olive oil tasting
  • Admission fees
  • Cooking classes
  • Doumina’s priceless expertise and carefully nurtured relationships
  • Precious company and entertainment provided by the people of Italy, who will stay in your hearts and minds forever.

Does not include:

  • Airfare
  • Single Supplement Fee (If requested, 675.00)
  • Occasional supplemental meals
  • Travel for personal errands/meals/shopping while on the tour.

Doumina can help arrange:

  • All other transportation and Ideas for other destinations

Contact us for prices at


Our Most Popular Tours

Etruscan Hike in Cortona

One Day Wine Tours in Tuscany

Bountiful Brunello
Brunello and Backroads

One Day Hikes in Italy

Etruscan Hike in Cortona

Ancient Rome

Christian and Renaissance Rome
Ancient Rome Tour
Rome as a Pilgrim
Archeological and Renaissance Rome
Women of Rome
Small Vineyards Tour

Eight Day Food And Wine Tours

6 times a year, a small group of food and wine lovers gather together to embark on a journey that we hope is life-changing.
The tours are offered in different parts of Italy, but always involve activities such as wine tasting, making pasta, sightseeing and getting to taste the real Italy.
Please inquire to find out the dates and prices of these fabulous adventures.
click here to see what clients are saying about this journey!

We Offer Transportation!

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