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Simpatico Italy’s Finest Wine & Food Tour to Italy 2023: Umbria, Marches, Medieval Festival & More

A Personal “Real Italy” Experience

Host: Bobbi Parlett, Simpatico, Italy’s Finest


May 4th – May 13th 2023


NOTE: We are hoping May 2023 will work out for us, but since everything is still uncertain, at this point I am taking names of those who are interested and once we understand the travel rules relative to vaccines, covid testing, etc., and them opening up fully then we will take deposits.

For Trip Information contact: Bobbi Parlett 610-209-5409;  


Join us on this “Real Italy” Wine & Food Tour, which is planned specifically for up to a maximum of 14 Foodies and Wine Lovers to join me and my co-hosts for an incredible experience! We will visit my favorite places based on 28+ years of trips to Italy, and finding the best experiences to share, and on this trip, our focus is on the under-discovered regions of Umbria, Le Marche, with a stop in Abruzzo on the way back to Rome, and more. Join me as we are immersed into the heart and soul of these delightful regions in the charming small hill towns, and enjoy amazing wines and foods, an incredible medieval festival, the beautiful countryside and culture of the people of Italy, shopping for Italian goods at direct pricing, and lots of laughter with new friends.  Andiamo!

Highlights of this Personal Tour:

We will explore small charming hill towns in Umbria, Le Marche and more including:

Umbria: Montefalco * Assisi & the Calendimaggio Festival * Gubbio Medieval City *Torgiano * Le Marche: Numana, Sirolo, Portonovo & More

 Truffle Hunt & Lunch * Wine Tasting 101 with Italian Sommelier Wine Ambassador * Five Vineyard/Wine Tours & Tastings         
Multi-Course Cooking Lesson  * Cheese Farm * Olive Oil Education & Tasting
- 9 nights in delightful hotels
- All meals every day are included in the cost, including hand-selected wines with lunch & dinner in local authentic restaurants
- Private Deluxe Transportation with Driver
- And More!

Pre-Tour: Depart USA on May 4th on a night flight. 

Day 1 May 4th, Thursday 

Group meets at the Hilton Rome Airport; Via Arturo Ferrarin 2 Fiumicino, Rome, 00054, Italy TEL: +39-06-65258 FAX: +39-06-6525 6525. This hotel connects to the Rome Airport. You may want to consider arriving a day early if you are prone to jet lag and stay at the Hilton. Then you will already be at the hotel for our meeting point. For those arriving the morning of the 7th, please plan air travel to arrive at the Rome Fiumicino airport around 9 AM.  Most overnight flights from the east coast arrive in this time frame. You will be able to rest on the motorcoach while we travel to Tuscany from Rome.

We will depart from the Hilton Rome Airport in our comfortable private deluxe motor coach about 10:15 AM Local Time, and drive toward Umbria, “The Green Heart of Italy” well known for its beautiful scenery, history, and of course wine and food.

  • -    Lunch in Casalina at Antico Forziere, the best restaurant in this area of Umbria. This is a wonderful place to start our journey, the menu is full of typical Umbrian dishes as well as new twists on typical cuisine. We will dine with the best of the local wines to accompany our lunch and the desserts are works of art. 


  • -    We will then drive a short distance to Montefalco, known for the big red of Umbria, Montefalco Sagrantino and as "the balcony of Umbria" because of its lofty position and views over the fertile plain below, the town keeps itself busy as the center of the Sagrantino wine zone.


  • -    After checking into the hotel Oro Rosso just inside the portal opening to the town, you will have Free Time to explore the town or rest. One of the significant sites here is the Church of San Francesco, which houses the magnificent fresco cycle of St. Francis’ life by Benozzo Gozzoli. It is now the town's museum, and, given its collection of art and artifacts, one of the most important museums in Umbria.  


  • -    We will meet for dinner at 7:30 PM in our hotel and enjoy a private dinner with a great introduction to the foods and wines of this area. 

Day 2, May 5th, Friday 

  • -    After a leisurely breakfast, we will leave the hotel at 9:30 to start our day. Our first stop is the Calcabrina Biodynamic Farm, known for cheeses, wine, and olive oil. Our focus here will be tasting 8-10 cheeses accompanied by their wines. We will then travel a short distance to the Farchioni vineyards for a tour and incredible lunch in their private dining room supported by their Chef who has a Michelin star under his belt and the food certainly shows this. Farchioni also has a brewery for craft beers and produces Olive Oil. Our host from the winemaker will share their story and review each wine we enjoy with the most memorable meal. After this delightful experience we will travel to Assisi, known as the birthplace of St. Francis of Assisi, and where the Calendimaggio Medieval festival, which celebrates the arrival of spring, is taking place. We will view part of the 4-day festival which re-enacts a playful rivalry between the two parts of the city (upper and lower parts of the city). See this link for more information.  This event is unlike anything you have probably ever seen. 

  • -    We check into the Umbra hotel conveniently located just off the main Piazza Comune, and you will have Free Time until we regroup for dinner at one of our favorite restaurants accompanied by Umbrian wines.  We then take our seats in the temporary bleachers in the Piazza Comune to watch the incredible night activities of the Festival, a spectacle of drumming, fire, flags and more. 

Day 3, May 6th, Saturday 

Today after breakfast, we will go to the Basilica where St. Francis tomb is located and beautiful frescoes of his life are in the upper church. We will then travel about 15 minutes to Agriturismo Alla Madonna del Piatto, which has garnered a number of enthusiastic reviews online as well as a long list of mentions in the international press, including The New York Times, National Geographic, BBC TV and Geo and Saisons.  We will participate in a multi-course cooking class of typical Umbrian foods and enjoy our fruits of our labor with wine of the area as well. 

We then return to Piazza Comune in time for the major afternoon event of the Festival from about 4 PM to 6:30 PM. After a refresh at the hotel we will regroup for dinner in an old established restaurant of Assisi accompanied by wines of the area.

Day 4, May 7th, Sunday 

After breakfast in the hotel, we will enjoy Free Time in Assisi, where there are so many wonderful shops, galleries, churches, and more. 

We will then leave Assisi and travel to Torgiano, an important wine growing region of Umbria, where the Lungarotti family dominates the area. We will first visit a wonderful small artisanal vineyard Terre Margaritelli.  After a tour of their vineyard, we will have lunch and enjoy their wonderful wines, olive oil and their delicious culinary creations. They produce their own olive oil in Montefalco and it is what we have chosen as our private branded Simpatico Umbrian oil.  

After our visit, we will drive a short distance to the unique 5 star hotel Le Tre Vaselle Resort & Spa ( in the middle of Torgiano and check-in. After settling in, we will visit the Wine Museum, a short walk from the hotel, that Lungarotti sponsors, and then enjoy a tasting of their wine in their tasting room next to the Wine Museum. 

After a short break we will regroup for dinner at a local restaurant that is a short walk away, and enjoy a wonderful typical dinner accompanied by wines of the area.


Day 5, May 8th, Monday  

After breakfast in the hotel, we will tour the Olive Oil Museum, just down the block from the hotel. We will then tour the Lungarotti vineyard, and learn about the Balsamic production as well, and then enjoy their wonderful wines with lunch in their cellar. 

We leave Torgiano and drive to Gubbio, a fabulous Medieval walled city, also home to Simpatico’s Master Ceramicist Giampietro Rampini. Gubbio is considered by scholars and researchers the most beautiful medieval town in Umbria, for the preservation of its architectural monuments that bear witness to its glorious and ancient past. After check-in at the lovely Relais Ducale which is right on the main Piazza of the city, we will regroup and take a one-hour tour of the city on the Gubbio Express train. 

FREE TIME until Dinner. Gubbio will be abuzz with the pre-festival activities for their upcoming Festa dei Ceri, and there is great shopping in this wonderful city. 

8:00 PM Dinner will be at the Grotta del Angelo one of the oldest very authentic restaurants of the city, Our guest co-host for this dinner will be a representative from the Association of Italian Sommeliers who lives in Gubbio and he will talk to us about the wines of the region and wine tasting approaches, and answer any questions you may have.   

Day 6, May 9th, Tuesday  

After breakfast, we travel through spectacular views of the surrounding mountains to the Pietralunga area of Umbria, and visit Giuliani Tartufi, a wonderful producer of truffle products. We will go on a Truffle Hunt expedition on their property (this year we saw real wild boar in the distance which took off as soon as they saw us!), and then enjoy an amazing multi-course lunch of truffle foods and local wines. After lunch we return to Gubbio and for those who want to take the Funicular up Mount Ingino, we will go together and visit the Church of Saint Ubaldo at the top of the mountain and enjoy the spectacular views.  Returning back down the mountain, we will have  FREE TIME until we regroup for dinner in a very local restaurant for a final dinner and wines in Gubbio.


Day 7, May 10th, Wednesday  

We leave Gubbio and travel east through magnificent mountains and hills toward white-pebble beaches of the Adriatic Sea in the Marches region, a hidden relatively unknown, outside of Italy, region of Italy. Le Marche is a thriving wine production region boasting 12 DOC and 2 DOCG wines. The best known of these wines is the white wine Verdicchio and the red Rosso Conero, along with many other wines of the region. We will visit a small family-owned winery and enjoy the wines with lunch. We will then travel to Loreto, very close on our way to the Adriatic Sea, where there is a pilgrimage site, Mary’s house, which was moved and rebuilt and surrounded by a cathedral. We visited here previously and felt it was a significant experience to share with the group. The view of the sea from this special place is breathtaking. We then drive onto Numana and check into our Hotel which overlooks the local port and is surrounded by beautiful beaches. After checking in we will have a break to walk up to the town and enjoy a pre-dinner glass of wine overlooking the sea, and then walk back to dinner overlooking the seaport at the hotel and enjoy the fresh local seafood and wines. Our host/owner at the hotel, Massimo, will guide us through a very memorable meal. 

Day 8, May 11th, Thursday   

After breakfast on the covered deck overlooking the port, we can walk down to see the catch of the day on the docks, and walk to the small beach close by for shelling or just for taking in the beauty that surrounds us. We will then take a short drive to the picturesque town of Sirolo, and enjoy an incredible view of the sea while we dine al fresco on the beach for the most amazing lunch with local wines. This is one of my most favorite memories in this area. We can then spend time in town exploring the shops, gelato and more. We will drive on to Portonovo which is also another beautiful area to see, and then return to Numana by late afternoon and have FREE TIME until dinner. Our wind-up dinner by the sea will again be in our hotel, overlooking the water and enjoying another fabulous meal chosen by Massimo of the local specialties and wines. 

Day 9, May 12th, Friday   

After breakfast, we then travel south along the Adriatic coast to an organic vineyard Ciu Ciu, in Offida, for a tour and tasting of their amazing line of white, red and sparkling wines and enjoy a lunch planned to pair with selected wines from their line. We then travel on toward Rome, through Abruzzo and may visit one last vineyard, time permitting. We then complete our day’s travel in Rome and check into Hotel Victoria Roma, Via Campania, 41 I - 00187 Roma Tel. +39 06 423701 Fax. +39 06 4871890, located just off the Via Veneto within walking distance of so many wonderful sites in Rome.  

We will celebrate our journey together at a special wind up dinner at Vladimir’s off the Via Veneto and then visit the Trevi Fountain after dinner to throw our coins in, to make sure we return to Rome someday again! 

Day 10, May 13th Saturday 

Leave for Home! Arrivederci Roma! 

Alternate extensions of the trip to stay in Rome or visit other places in Italy before or after our trip can be arranged through a local Easton, MD travel agent who helps our guests to plan an extended stay and also with travel insurance. If you need help, we will provide the contact information to you. Options include St. Peter’s/Vatican Tours, seeing Pope Francis on Sunday at his special weekly blessing, tour of Rome, excursions to Pompeii or Florence, Tivoli and more. 

Note: Schedule specifics subject to change. 

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