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Italian Hidden Gems: Tours

"A Magical Escape Back To A Simpler Time"
An Exclusive Italian Small Group Tour
Off The Beaten Path In Italy

Explore World-Famous Roman & Medieval Hill Town Gems

The heart of Italy is known for having some of the best undiscovered places in Italy. Imagine a place with stunning natural beauty, fabulous ancient towns, sparkling waterfalls, Roman aqueducts, olive groves, picturesque Italian vineyards, numerous rivers, and placid lakes. It is a lush scenic area that is well-known to Italians as having some of the most beautiful places of Italy.

You will explore iconic hidden hilltown gems -- originally built for defensive purposes -- that have some of the best-preserved fortifications, walls, and Roman gates in all of Europe.  


Each hilltop town is different.  Each has a distinct geography. Many Italian hilltop villages and towns were built during the age of the Etruscans over 2,500 years ago. They were reconstructed during Roman times, and then rebuilt again in medieval times.


During your 7 day Italy tour, you'll see some of the best of non-touristy Italy off the beaten path. You’ll visit unseen, little-known towns in some of the best secret spots in Italy.

Our Italian small group tours of Italy provide you a magical opportunity to travel back in time, off the beaten path. You'll visit palaces, historic sites, and various out-of-the-way off the beaten track places that few foreigners ever find on their own, all while enjoying amazing wine and Italian food.

There will be plenty of leisure time to do things on your own so you can fully enjoy your relaxing Italy vacation.

Typical Italian Itinerary


Hidden Gems Of Italy
Italian Small Group Tour
A Tour Of Italy Off The Beaten Path: Umbria
For 7 Days / 6 Nights

Sunday Day 1

Hidden Gems Of Italy

Italian Small Group Tour

Arrive In Italy And Travel To Enchanting Spello 

To Italy To Start Your Italian Small Group Tour

Arrive in Rome at Fiumicino airport. To start your 7 day Italy tour, you will be met by an Italian/English-speaking chauffeur who will whisk you away by private car for the start of your spectacular Italian small group tour in the heart of Italy.

Experience your first authentic 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 relaxing at your 4-star Italian hotel, lounging by the pool, and exploring the intriguing walled Roman town of Spello. We will start our evening early with an informal get-together and a brief local orientation while sampling Italian wine and appetizers in a 17th century Italian palazzo.

Included: Private driver from Rome Airport, lunch and beverages, and a light dinner with drinks and heavy appetizers.


Monday Day 2

Hidden Gems Of Italy

Italian Small Group Tour
Spello, Collepino & Assisi


After breakfast overlooking the beautiful rolling countryside, you will enjoy a short walking tour of Spello. You visit Spello’s magnificent Roman Gate, one of few left in all of Italy. We will then visit the nearby medieval village of Collepino and stop by a cozy coffee bar for a quick cappuccino coffee. 

Next comes a lovely drive over the mountain -- Mount Subasio – and a special 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 upon this town and the entire Region of Umbria.


After an informative guided walking tour of Assisi, you will have ample time to explore the town, shop, or people watch over an espresso or a glass of wine.


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

Included: All meals, coffee, tea, sparkling water, and local Italian wine, if desired.


Hidden Gems Of Italy

Italian Small Group Tour
Spoleto With Wine Tasting And Cellar Tour


After a quiet breakfast at your hotel, we will take a short drive to Spoleto. This unforgettable 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.

Today, you’ll be taken on an Italian small group tour conducted by one of our favorite tour guides of Spoleto and its magnificent 14th century castle. At the highest point of the town, you will 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 high 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 through the pastoral countryside dotted with vineyards and olive groves. 

We will visit one of the oldest wineries in Umbria and you’ll take a wine tasting tour of their great wines. We will sample their highly-regarded red and white wines along with their superb 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.

Included: All meals, coffee, tea, sparkling water, wine tasting and local Italian wine, if desired.


Wednesday Day 4

Hidden Gems Of Italy

Italian Small Group Tour

Perugia: An Ancient Etruscan Town


After breakfast we will drive to the ancient walled town of Perugia, which was one of the main ancient Etruscan cities in Italy. Perugia became a wealthy medieval town and the stunning architecture reflects a medieval splendor. During the morning, a tour guide will escort you on an exclusive Italian Small Group Tour of this wonderful hilltop town.

You will have lunch at a restaurant that is renowned for preparing traditional Umbrian cuisine and its marvelous landscape views. After lunch, you will have time to explore around Perugia, do some shopping, and if you like, visit an impressive art museum or explore Perugia’s highly regarded archeological museum. 

As we leave Perugia, we will make a short stop at an area off the beaten path outside of town that has a number of fascinating Etruscan chamber tombs. If interested, you can tour some of the remarkably large tombs that display funerary urns and artifacts discovered over many centuries during local excavations.


We’ll then return to Spello and enjoy our evening meal at an authentic quaint Italian osteria owned by good friends.


​Included: All meals, coffee, tea, sparkling water, wine tasting and local Italian wine, if desired.


Thursday Day 5

Hidden Gems Of Italy

Italian Small Group Tour

Civita di Bagnoregio & Orvieto


Our day starts early with a drive to one of the best Italian hidden gems: Civita di Bagnoregio. This hill town is distinguished by its strategic position on top of a plateau of volcanic rock overlooking a massive valley. The vantage from the summit gives you the illusion that you have travelled back in time to another world.

The curiously captivating architecture spans a period of over 2,500 years. There are no modern roads. The town is accessible only by a walking down a long pedestrian bridge where mules used to transport olives and other goods. You will have ample time to tour and 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 rises majestically above rock cliffs and is protected by an extensive system of defensive walls. Here a knowledgeable local guide will give us an escorted Italian small group tour 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 place 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.

Included: All meals, coffee, tea, sparkling water, and local Italian wine, if desired.


Friday Day 6

Hidden Gems Of Italy

Italian Small Group Tour

Gubbio & Private Dinner At A 17th Century Storybook Palazzo


Today we’ll take a drive through the beautiful Italian countryside and through the mountains to reach the memorable Roman and medieval town of Gubbio.


This town is one of the most remarkably unique places in Italy to visit  and is one of the best hilltop villages in Italy off the beaten path. Gubbio is a favorite destination among Italians. It is picturesque and especially pretty when the red and white geraniums are in bloom along the road that leads to town. Perched halfway up Mount Ingino, Gubbio commands some memorable views.


We will take a guided tour in Gubbio using one of our favorite tour guides. After our short Italian small group tour, you can ramble around town on your own. You can capture some great selfies, pop into several museums, purchase some artwork or ceramics, take a cable car up Mount Ingino high above Gubbio for some sweeping vistas of the Apennine Mountains, and grab an informal lunch on your own at our expense.


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

Included: All meals, coffee, tea, sparkling water, and local Italian wine, if desired.

Saturday Day 7

Hidden Gems Of Italy

Italian Small Group Tour

Depart For Rome Airport

On the last day of your 7 day Italy tour, 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

Hidden Gems Of Italy

Italian Small Group Tour

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  • 7 day Italy tour 7 days / 6 nights

  • Private transportation to and from Rome airport

  • 6 nights lodging in an Italian 4-star hotel

  • Ground transportation for each day of the tour as needed

  • All breakfasts, lunches and dinners with local Italian wine, if desired.

  • Private dinner prepared by our favorite Italian chef

  • Cocktail party featuring heavy appetizers at a privately owned storybook palazzo

  • All cellar and vineyard tours with wine tastings taking place at a winery in Italian wine country, at cozy wine bars, or in palaces 

  • Professional tour guide available during portions of your Italian small group tour

  • Numerous opportunities to shop

  • Optional time for walking, hiking, trekking, cycling, biking, e bike, or e-biking

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

What's Not Included

Hidden Gems Of Italy

Italian Small Group Tour

  • Flights to and from Italy

  • Travel Insurance

  • Passport Fees


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

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