top of page
Italian Hidden Gems: Tours

10 Day Tour Of Italy
Italy Small Group Tour Of Italian Hidden Gems


"A Magical Escape Back To A Simpler Time"
Italy Off The Beaten Path: 10 Day Tour Of Italy

Explore World-Famous Roman & Medieval Hill Town Gems

The heart of Italy is known for having many 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 10 day tour of Italy, 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 escorted Italian small group tours provide you a magical opportunity to travel back in time, off the beaten path Italy. 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
Italy Small Group Tour Of
Italian Hidden Gems

A Tour Of Italy Off The Beaten Path: Umbria, Tuscany, Florence And Siena
For 10 Days / 9 Nights


Sunday Day 1
10 Day Italy Small Group Tour
Arrive In Italy And Travel To Enchanting Spello 

Travel To Italy To Start Your Italy Small Group Tour

Arrive in Rome at Fiumicino airport. 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
10 Day Italy 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.


Tuesday Day 3
10 Day Italy 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
10 Day Italy 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
10 Day Italy 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
10 Day Italy 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
10 Day Italy Small Group Tour
Trip To Tuscany For Tour Of Florence And Siena

We’re off today to see some of the most popular places in Italy. During the last few days of your Italian small group tour, you’ll see the incredible Tuscan towns of Florence and Siena.


Florence was once one of the wealthiest and most influential cities in the world. Today it is a major artistic, cultural, commercial, political and financial center. It is known for its extraordinary Renaissance architecture and is a UNESCO World Heritage site. Forbes ranked Florence as the most beautiful city in the world in 2010.


We’ll make the short trip to Florence by train to enjoy the beautiful Italian countryside as we depart Umbria and arrive in Tuscany for our Florence adventure.

When we arrive, we will check-in to your 4-star Italian hotel located in the heart of Florence. We’ll grab a light lunch at a restaurant that specializes in Tuscan cuisine including homemade pici pasta, Tuscan meats, various tomato or bean soups, great Tuscan red and white wines, and more.


After lunch, we’ll take a guided walking tour conducted by a knowledgeable local tour guide to get oriented to Florence.


Florence will be a marked change from Umbria since it is not a hilltop town. Instead the historic center is quite flat. It is also a great place to mingle, explore and walk since vehicle traffic is restricted for local residents, taxis and hotel guests.

After your walking tour you can continue to explore the labyrinth of ancient Florentine streets while admiring the exquisite renaissance architecture. You can stop to taste some creamy Italian artisan gelato; admire numerous quaint jewelry shops which line the oldest bridge in Florence, the famous Ponte Vecchio; walk along the Arno River; do some shopping at myriad small shops, or grab a cocktail or glass of wine from one of the many wine bars in Florence. There are lots of different things to do in Florence that we can recommend.

You’ll will have dinner tonight at one of our favorite restaurants. It is tucked away in a corner of an ancient piazza. The restaurant serves award winning authentic Tuscan foods. The fresh pasta and bread are prepared daily and made on-site. All dishes are based on the best seasonal ingredients and the menu changes with the season. For a special treat, you can also sample their deep green Tuscan olive oil which is produced on the restaurant owners’ estate outside of Florence. If you still have energy, you can go back to the sky terrace at your hotel to have a nightcap and enjoy a nighttime view of Florence.

Included: Transportation by train from Umbria to Florence, guided tour of Florence, all meals, coffee, tea, sparkling water, and local Italian wine (if desired) and lodging in Florence.


Sunday Day 8
10 Day Italy Small Group Tour
Tour Of Florence - Continued


Today, we’ll visit the Galleria dell’Accademia, one of Italy’s most popular museums. This well-known museum features Michelangelo’s colossal statue of David.


In addition to the David, there are six large unfinished marble statues that line the gallery. Many people grow quiet when they enter and stare in awe. The figures are so lifelike that they seem frozen in time.


After our experience seeing the David we will walk five minutes to the nearby Mercato Centrale. This 150-year old open-air marketplace features artisan food shops that cater to local residents and restaurants.

As part of your Italian small group tour you will be able to peruse the many interesting shops. They offer a vast selection local produce: cheeses, meats, salami’s, wine, liquors, soft drinks, and much more. We’ll get a whiff of the wonderful scents of all kinds of products and especially prosciutto hams with the local favorite called “Cinta Senese” that is prized throughout Italy. It is a lot of fun to sample and discover what you like best.


We will then have lunch at one of the authentic casual restaurants inside the market or from one of the many restaurants located outside, depending on your preference.


After lunch, we will go up to a square on a promontory high above Florence – the famous Piazzale Michelangelo. From here you can see an incredible panoramic view of all of Florence. You’ll see the giant basilica of Santa Maria del Fiore which from this vantage appears to be small. You see the historic wall surrounding parts of Florence and arc of the Arno River. The square is a great place to take some fine photos.



We’ll then return to the center of old Florence. You’ll have some time to do things on your own before dinner. You can go back to relax at your hotel, continue shopping, or walk around Florence and explore the narrow streets.

Florence is an international city that offers you some wonderful international dinner options. We’ll recommend several restaurants where you can find Indian, Turkish, Thai, or Japanese cuisine.


Or, you can select from one of our many favorite Italian restaurants. Perhaps tonight is the night to try an authentic Florentine beefsteak -- Bistecca alla Fiorentina -- or select from numerous other tasty Tuscan specialties.


Included: Museum tickets, transportation within the city center, and all meals, coffee, tea, sparkling water, and local Italian wine, if desired. 

Monday Day 9
10 Day Italy Small Group Tour
Tour In Siena

After breakfast we’ll take you on a short public bus ride for your own Italian small group tour to one of the most beautiful cities in Italy – Siena.


Siena was first settled by the Etruscans around 2,500 years ago. It is a UNESCO World Heritage Site and was one of the most important cities in medieval Europe. Siena is famous for its food, art, museums and its medieval landscape. It also has one of the oldest universities in the world.


When you arrive in Siena, you will definitely feel like you have gone back in time.


You’ll see the gigantic Piazza del Campo which is regarded as one of Europe’s greatest medieval squares. It is renowned for its architecture and beauty and is lined with red brick buildings. Siena is also the site of a famous horse-race held twice each summer – the Palio of Siena.


After walking around a bit and having time to admire the piazza, we’ll have an early lunch at a Tuscan restaurant and pizzeria on the main square. You can do some people watching while enjoying a view of the piazza and all of its architectural glory.


After lunch we will stop at the Palazzo Pubblico across the piazza. The palace is a grand work of architecture in itself, with nearly every interior room frescoed. You can climb the stairs in the medieval tower next door to get a commanding view of Siena.


Siena is also a wonderful shopping town. We’ll walk around the medieval road that surrounds the piazza and is lined by all kinds of intriguing shops.

We’ll then visit the main duomo or cathedral located just a couple of blocks away. The duomo was completed in the 14th century and is a masterpiece of Italian Romanesque-Gothic architecture. It has an imposing zebra-like facade featuring alternating white and black marble.


You’ll have plenty of time to explore the town, do some shopping, or grab another gelato. Late in the afternoon we will take the bus back to Florence. There you can freshen up at your hotel.


We’ll then have a fond farewell celebration with cocktails, wine and a Tuscan dinner. There you can talk about the wonders of Italy and perhaps even start dreaming of a future return trip!


Included: Transportation to Siena and all meals with coffee, tea, sparkling water, and local Italian wine, if desired.


Tuesday Day 10
10 Day Italy Small Group Tour
Depart For Florence Airport Or Rome Airport


On the final morning of your 10 day tour of Italy, you will be picked up at your hotel to take you to the Florence airport for your flight back home. Instead, if you are flying out of Rome, we will escort you to the Florence train station and guide you to the high-speed train which will take you to Rome and Fiumicino Airport.

Transportation to Florence Airport or Rome Airport and breakfast are included.

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

What’s Included
Italy Small Group Tour Of Italian Hidden Gems

Newest ItalyAdventuresLogo copy.jpg
  • 10 Day Tour of Italy: For 10 Days / 9 Nights 

  • All-Inclusive In Italy Tour

  • Ground transportation from Rome airport upon arrival. Upon departure, transportation to Florence Airport Or Train Tickets from Florence to Rome airport if departing from Rome. Bus transportation to and from Siena to Florence

  • 9 nights lodging in two Italian 4-star hotels in Central Italy regions of Umbria and Tuscany

  • Transportation for each day of the tour as needed

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

  • Private dinner prepared by an Italian chef

  • Museum tickets

  • Cocktail party featuring heavy appetizers at a private storybook palazzo

  • Wine tastings will take place at cozy wine bars in Italian wine country. The tastings will also include tours of wine cellars and vineyards.

  • Professional Italian tour guide available during portions of the tour

  • Numerous opportunities to shop

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

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

What's Not Included
Italy Small Group Tour Of Italian Hidden Gems

  • 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 Italian 4-star hotels that are 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.

bottom of page