"A Magical Escape Back To A Simpler Time"

Hill Town Adventure

Explore World-Famous Scenic Roman & Medieval Hill Town Gems

The heart of Italy is known for its stunning natural beauty, remarkable ancient towns, its waterfalls, Roman aqueducts, rivers, olive groves, picturesque vineyards, and beautifully placid lakes. It is a lush, scenic, green area that is well-known to Italians but relatively unknown to foreigners.  

You will explore hidden hill towns -- originally built for defensive purposes -- which have some of the best-preserved fortifications, walls, and Roman gates in all of Italy.  


Each hill town is different.  Each has a distinct geography. Several hill towns were built during the age of the Etruscans over 2,500 years ago, then reconstructed during Roman times, and then rebuilt again during medieval times. You'll visit charming, little-known towns such as: Assisi, Bevagna, Montefalco, Gubbio, Orvieto, Perugia, Spoleto, Spello, Trevi, Gualdo Cattaneo, Deruta, Collepino and others.

You’ll travel back in time at a slow pace, off the beaten track, avoiding the major highways. You'll visit castles, palaces, historic sites and various out-of-the-way places that few foreigners find on their own, all the while enjoying amazing food and wine.

And best of all, at Italy!Adventures you can create your own private group.


We will reserve your tour solely and exclusively for you and your family, friends or trusted associates. This ensures that your tour is truly a private experience for up to eight people.

Our promise: No other travelers will be added to your tour, even if there are only two people in your group.

Typical Itinerary

Saturday – Depart For Italy
Sunday – Day 1 – Arrive In Italy & Travel To Enchanting Spello 

Arrive in Rome at Fiumicino airport. You will be met by an Italian/English-speaking chauffeur who will whisk you away by private car to the spectacular heart of Italy.

Experience your first Italian lunch at a restaurant that features an ancient 14th century interior and is known for fresh seasonal food specialties such as tartufo mushrooms, artichokes, wild boar, great local wines and more. 


Spend the remainder of your afternoon while relaxing at your local hotel, lounging by the pool, or exploring the intriguing walled Roman town of Spello. We will start our evening early with an informal get-together where you will receive a local orientation while sampling Italian wine and appetizers in a 17th century Italian palazzo.

Private driver from Rome Airport, lunch with Italian wine, and a light dinner with drinks and heavy appetizers included.

Monday – Day 2 – Spello, Collepino & Assisi

After breakfast with a wonderful view, you will enjoy a short walking tour of Spello including its magnificent Roman Gate, one of few left in all of Italy. We will then visit the nearby medieval village of Collepino where we will stop by a cozy bar for a quick cappuccino. 

We will then drive over the mountain – Mount Subasio – and stop just outside Assisi. There we will have a rustic lunch at a family-owned restaurant that specializes in delicious traditional Umbrian food cooked over wood-fired grills. 

After lunch, we’ll visit world-famous Assisi. Designated a UNESCO World Heritage Centre, Assisi was founded over 2,500 years ago and is the home of St. Francis of Assisi, the patron saint of Italy. St. Francis died almost 800 years ago but forever left his mark on this town.


After an informative guided tour, you will have ample time to wander the town, shop, or people watch over an espresso.


We will return to Spello and you’ll have dinner on your own -- at our expense -- at one of several enjoyable local restaurants.

All meals with Italian wine included.

Tuesday – Day 3 – Spoleto & Wine Tasting

After a quiet breakfast at your hotel, we will take a short drive to Spoleto. This famous town has occupied a strategic geographical position since the 5th century B.C. Surrounded by rugged mountains; Spoleto was unsuccessfully attacked by Hannibal of Carthage in 217 B.C.

You will take a guided tour of Spoleto and it's magnificent 14th century castle. You’ll see a 1st century Roman villa and visit the Archeological Museum and its 2,000-year-old Roman amphitheater. All of these places have wonderful views of the mountains and the 13th century aqueduct that towers over Spoleto. 

We will have lunch at a local restaurant that specializes in homemade pasta, pork specialties and steak. Later in the afternoon, we will take a drive in the countryside dotted with vineyards and olive groves. 

We will tour one of the oldest wineries in Umbria. We will sample their superb red and white wines along with their own locally-made prosciutto, cheeses and honey. 

When we return to Spello for the evening, you can relax by your hotel pool, go to an eye-catching wine bar, or, if you still are hungry after this day, you can have dinner on your own -- at our expense --  at  one of several recommended restaurants.

All meals with Italian wine and wine tasting included.

Wednesday – Day 4 – Etruscan Perugia

After breakfast we will drive to the ancient walled town of Perugia, which was one of the main Etruscan cities in Italy. Perugia was a wealthy medieval town and the stunning architecture reflects its medieval splendor. A tour guide will lead you on your informative morning tour of Perugia. 

You will have lunch at a restaurant with a marvelous view for miles around and a reputation for preparing traditional Umbrian cuisine. After lunch, you will have time to meander around Perugia, do some shopping, and if you like, visit an impressive art museum or Perugia’s highly regarded archeological museum. 

As we leave Perugia, we will make a short stop to visit an area outside of town that has a number of fascinating Etruscan chamber tombs. 

You can visit some of the remarkably large tombs that display various funerary urns and artifacts found in local excavations.


We’ll then return to Spello and for our evening meal at an authentic and enjoyable Italian, family owned, osteria.

All meals with Italian wine included.

Thursday - Day 5 – Civita di Bagnoregio & Orvieto

Our day starts early with a drive to the stunning town of Civita di Bagnoregio. This town is noted for its strategic position on top of a plateau of volcanic rock overlooking a massive valley.

It has curiously captivating architecture that spans a period of several hundred years. There are no modern roads leading into this hill town. 

One can only enter this town by a walking down a long pedestrian bridge where mules used to transport olives and other goods. You will have ample time to explore this fascinating town on your own for the rest of the morning.

We will then drive to Orvieto for lunch at a traditional, family-owned restaurant.

Orvieto is a stunning town that rises majestically above rock cliffs and is complemented by an extensive system of defensive walls. Here a knowledgeable local guide will show us around town. We will explore the striking monumental cathedral, the extensive medieval underground tunneling system, and other architectural wonders.

You will have plenty time to stroll through this beautiful town on your own and to shop for ceramics, clothing and other artisan goods at Orvieto’s well-stocked shops.

We will return to Spello where we’ll have dinner at a popular and colorful pizzeria known for its vast selection of tasty wood fired pizzas.

All meals with Italian wine included.

Friday – Day 6 – Medieval Gubbio & Private Dinner In A 17th Century Storybook Palazzo

Today we’ll go to the memorable medieval town of Gubbio, a unique place that is a favorite destination among Italians. We will have a short tour of the town conducted by a tour guide. You can then ramble around town on your own; capture some great selfies; visit museums; take a cable car up Mount Ingino high above Gubbio while enjoying a sweeping vista of the Apennine Mountains; and, have lunch on your own at our expense.


Return to Spello to enjoy your swimming pool, relish some afternoon private time and finish packing. We’ll have a farewell celebration and an early private dinner arranged just for you, specially prepared by a highly regarded local Italian chef.

All meals with Italian wine included.

Saturday – Day 7 – Depart For Rome Airport

You will be picked up at your hotel and travel back to Rome Fiumicino airport for your flight back home.

Private driver to Rome Airport and light breakfast included.

Please Note: This schedule may change subject to weather and availability.

What’s Included:
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  • Your tour for 7 days / 6 nights

  • Private transportation to and from Rome airport

  • 6 nights lodging 

  • Transportation for each day of the tour as needed

  • All breakfasts, lunches and dinners with Italian wine, including a private dinner prepared by an Italian chef

  • Cocktail party featuring heavy appetizers at a private, storybook palazzo

  • All wine tastings at vineyards, cozy wine bars, or palaces 

  • Professional Italian tour guide available during portions of the tour

  • Numerous opportunities to shop

  • Optional time for walks, hikes and bike rides

  • Additional private time to do things together or on your own

What's Not Included:
  • Flights to and from Italy.

  • Travel Insurance.

  • Passport Fees.

  • Most hotels in Central Italy are small, boutique hotels that are family-owned. Many are located in historic properties, some of which are centuries old. You will stay at a 4-star hotel that is charming and authentic, featuring modern amenities including: wi-fi, air conditioning and a private in-suite bathroom. Many travelers have remarked that our hotels are more quaint and memorable than chain hotels in North America.