Tuscany & Umbria: Rustic Beauty in the Italian Heartland
Tuscan & Umbrian Countryside featuring Italy's Charming Hill Towns
DAY 1: Arrival at Pisa's international airport
DAY 2: Lucca
DAY 3: Pisa
DAY 4: Lari, Bolgheri
DAY 5: The Island of Elba
DAY 6: Full day on the island
DAY 7: Land of the Etruscans
DAY 8: Full day in the Tuscan countryside
DAY 9: Day in Cortona
DAY 10: Full day in Umbria
DAY 11: UNESCO Val d'Orcia
DAY 12: Truffle hunting
DAY 13: Departure day. If you wish to extend your holiday, this is a perfect location to add a few days visiting the Cinque Terre, Rome or Florence. For pricing on the extensions contact Audrey.
**FOR PRIVATE TOURS ONLY**
- Discover slow travel: a perfect balance of sightseeing and time at leisure
- Move beyond Italy’s signature cities and stay in countryside accommodations
- Savor tasty regional cuisine in specially chosen local authentic 'trattorias' and restaurants
- Spend a day in Pisa to see the leaning tower and explore the charming piazzas of Lucca
- Explore some of Italy’s most beautiful small towns, producing excellent wine and the highest quality of olive oil
- Experience the architectural beauty of Siena’s famous Piazza del Campo (home to the world-renowned Palio horse race)
- Learn about Etruscan history in the off the beaten path villages
- Visit the city of Assisi, where St Francis and the Franciscan order were born
- Walk through the iconic Tuscan countryside of yellow fields, golden grasslands and hillside villages in the famed Val d'Orcia
- Explore charming medieval and Renaissance villages, Etruscan museums, castles, cathedrals, beautiful piazzas and monasteries
- Enjoy the many culinary delights: private wine tastings in local wineries in unique locations like a medieval castle and its ancient underground cellar; visiting local farms to learn about olive oil; truffle hunting; tasting local culinary delights like Pecorino at a family farm
PRICING: Please inquire about 2022/2023 pricing
The price for a private tour is per-person sharing a double room, and it varies according to the number of guests on the tour, because of minimum fixed costs that need to be covered. With this tiered pricing structure we are able to offer competitive pricing for private groups of 6 to 8 guests.
Pisa, Lucca, Bolgheri, Isola Elba, Chianti, Pienza, Montalcino, Cortona, Assisi
Remember, this tour can be customized according to your own interests and preferences.
Tour starts in Pisa and ends in Florence
Your arrival and departure airports are:
Pisa International Airport, Galileo Galilei Airport (PSA)
Florence Airport, Peterola (FLR)
**FOR PRIVATE TOURS ONLY**
This tour showcases Italy’s fantastic food and wine, cultural and historical wealth in two of its most beautiful regions, Tuscany and Umbria. Taking you deep into the scenery and gastronomy of Italy’s Tuscan and Umbrian regions, famous for their wines, home to some of Italy’s greatest food, rugged hills, fertile valleys, ancient hilltop villages, Etruscan history and stunning coast line. This trip is a feast for all the senses.
The true essence of Italian family traditions lies within the ingredients that have been carefully grown and harvested in the same territories for centuries, and the regional recipes that shape the soul of every town you'll visit. This is where sipping on local wines is not merely relevant to pairing them to the flavors of a meal, but it is truly honoring the passion of the people who have dedicated their lives to creating such a unique masterpiece.
For many seasoned travelers, Italy continues to be their favorite country to visit. Most travelers want to return to Italy several times because it is not possible to experience and enjoy all that Italy has to offer in a single visit. Experience the delights and the real dolce vita on this unique tour. Join me in visiting our favorite foodie locations in these beautiful regions.
Day to Day Itinerary
DAY 1: ARRIVAL DAY
Welcome to Italia!
You'll arrive at the airport in Pisa or Florence around mid day, depending on your specific flight arrangements. I will be meeting you at the airport to escort you to your hotel in Lucca (a transfer of up to 1.5 hours by bus, depending on traffic). We stay for three nights in our hotel located in the historic center of Lucca. Depending on which hotel we stay at, amenities may include a restaurant, bar, and lounge area. Typical rooms include a minibar, safe, air conditioning, wireless internet, and private bath with hairdryer. After you checked-in to your hotel, your local host will take you on a brief walk around the hotel and surrounding area for a chance to get acclimated, find an ATM, or seek out a local market.
Evening: Your evening is on your own—you are free to rest in your room after your flight to prepare for tomorrow’s discoveries or your local host can make recommendations for you.
DAY 2: LUCCA
The day begins with breakfast at the hotel and a pleasant stroll along the streets of Lucca, to arrive in the historical center to meet up with your local expert guide who will introduce you to the history and art of this city, including sites like the Duomo di San Martino (San Martino Cathedral), Piazza dell’Anfiteatro (the Amphitheatre Square) and Torre Guinigi, a tower with trees atop it. Enjoy free time in the afternoon, sopping, visiting the National Art Gallery, the Puccini museum, renting a bike to pedal the walls, or whatever you like!
LUCCA: Remarkably well preserved, Lucca's narrow streets look much like they did when the ancient Romans established the town in about 180 BC. And the thick walls that encircled Lucca during the Renaissance era stand strong today. Completely intact, they once hosted car races and now serve as a pedestrian walkway. Lucca's quaint center is enclosed by these walls, and brick ramparts from the 15th and 16th centuries preside over the streets. The opera composer Giacomo Puccini was born here and the city holds Concert Festivals showcasing his works as well as operas every night in the San Giovanni Church.
DAY 3: PISA
After breakfast at the hotel, we will travel to Pisa to meet our local guide for a tour of Pisa’s famous sights - including the renowned Leaning Tower (La Torre Pendente) in Piazza dei Miracoli. After lunch at a local restaurant in the heart of Pisa, we will explore other sites in the historic downtown, a time also for shopping.
PISA: Pisa, once a maritime republic to rival Genoa and Venice, owes today its fame to the extraordinary leaning tower that has withstood the force of gravity for almost 600 years. It is one of Italy’s most photographed monuments, one of three Romanesque buildings on the lawns of Piazza dei Miracoli. Pisa is also home to other beautiful sites: the Duomo (Cathedral), the Baptistry, several palaces, museums, lovely public parks and other artistic and architectural marvels. This city is best enjoyed by foot and our exploration will include a stroll down the Corso Italia, a lively street where the best shops are found! Pisa’s gastronomy benefits from its proximity to the sea and the countryside; local recipes use meat as much as the freshwater fish and seafood. Typical dishes include Minestra di fagioli bianchi di San Michele (white bean soup of San Michele) and Trenette alla renaiola, a dish which consists of long pasta with anchovies and turnip greens. One traditional dessert of the Pisa province is the Torta co' bischeri, a cake filled with a paste made of rice and chocolate.
DAY 4: LARI, BOLGHERI, ELBA
With Pisa and Lucca behind us, we head to Piombino to take a ferry to Elba Island. On the way there, our first stop is in Lari, a lesser known Tuscan town located inside castle walls. The Famiglia Martelli has been making pasta there since 1926 and are always happy to show you how. Tour the pasta factory, Europe's smallest, and pick up a bag or two as a souvenir to bring home with you.
Second stop of the day is Bolgheri, a must, not only to drive along the famous Avenue of the Cypress but also to take a break for lunch and wine tasting of some Super Tuscans and enjoy this picturesque small village. When we get to Piombino, we will sail for the island of Elba. From Portoferraio, the main port city in Elba, we will take a short ride to our beautiful hotel overlooking the bay. Take time to settle in and unpack and get ready for our welcome aperitif followed by an outdoor dinner with a panoramic view.
BOLGHERI: Bolgheri is a lovely little village with small picturesque shops that take you back to another era. To get to Bolgheri, we will drive along the famous Viale dei Cipressi (Avenue of the Cypress) bordered by ancient and majestic cypress trees that lead to the Castle of Bolgheri. This boulevard has been immortalized in a poem by the 19th century Italian poet, Giosuè Carducci. From this area are the red wines Super-Tuscan Sassicaia, Bolgheri Superiore and Ornellaia and the white wine, Bolgheri Vermentino.
ELBA: Elba is the third largest island in Italy, after Sicily and Sardinia. It was well known from ancient times for its iron resources and its valued mines. The island was invaded by the Etruscans and later (after 480 BC) by the Romans. In the Middle Ages, it was invaded by the Ostrogoths and the Lombards, then became a possession of the Republic of Pisa. In 1544, the Barbary pirates from North Africa devastated Elba and, two years later, part of the island was handed over to Cosimo I de' Medici, who fortified Portoferraio and renamed it "Cosmopoli". More recently, the island has become famed for its wine, beautiful landscapes and it is today a noted tourist resort.
DAY 5: PORTOFERRAIO
Delicious buffet breakfast at the hotel before leaving to Portoferraio. During the drive, enjoy the many scents of the island’s flowers and fruits. Our local expert guide will show us the villas where Napoleon took residence during his exile from France. Lunch with Tatiana - we will have time to enjoy seafood dishes before continuing our visit to other sites, including the Medicean Fortress with its breathtaking view. The visit to Portoferraio is almost at its end but not before some free time around town to shop or enjoy a gelato.
PORTOFERRAIO: Portoferraio is the most important town and major port of Elba Island. During the early 17th century Portoferraio saw an influx of Jews who were granted special privileges from Cosimo de Medici. This influenced the development of the industry and economy of Portoferraio. During this period, numerous fortifications were built, at the request of the Medici family, to protect the port from the Barbareschi pirates raids. In 1814, Elba Island was entrusted to Napoleon Bonaparte, who chose it as the seat of his first exile. During this period, the city grew in importance and modernity.
Portoferraio should be seen from every corner, with its characteristic houses, balconies full of colorful flowers, narrow alleys, lively piazzas and breathtaking views of the sea.
RESIDENZE NAPOLEONICHE: Napoleon Bonaparte was forced into exile (May 1814 - February 1815), after the abdication and the Treaty of Fontainebleau. Napoleon chose Portoferraio as the capital of his state where he settled in two villas; San Martino and Villa dei Mulini. In the town house, the Palazzina dei Mulini, Napoleon tried to recreate in a short time, at a reduced size, the atmosphere of the French court; this was supported by the presence of his mother and his sister, Pauline, who had joined him in exile.
DAY 6: ISLAND DISCOVERIES
Today starts with a visit to a local farm where he will show us his production of organic olive oil, wines and the mill where he grinds whole grain flour and makes delicious pasta. Dimitri will also be our host for lunch and prepare a menu that will include a pasta dish made with his products and a wine tasting. We will return to the hotel to relax and enjoy the landscape before getting ready for our next destination: Capoliveri, a beautiful and picturesque village perched on a hill overlooking the sea. A stroll, some souvenir shopping perhaps, and then we will drive to Porto Azzurro for dinner in one of the island’s best restaurants.
LA FATTORIA DI DIMITRI: Dimitri’s Farm is located in Portoferraio, a few hundred meters from the beach. The whole area is a natural habitat for wild and migratory birds, surrounded by olive trees and vineyards. We really like Dmitri’s olive oil and wines and especially enjoy the whole wheat pasta that he produces from durum wheat. Its color tends toward bronze and its strong taste evokes flavors from the past.
CAPOLIVERI: Capoliveri is a quaint, small village with a deep Etruscan and Roman heritage that played an important role in the economy and politics of Elba Island during the Middle Ages. Later on, after the Italian campaign of Napoleon I in 1799, the population of Capoliveri stubbornly resisted the French troops. This explains why in 1814, when he arrived in exile as King of Elba, Napoleon was greeted with skepticism in Capoliveri, while everyone else saluted him as a liberator. Capoliveri offers marvelous views of the sea and is also a wonderful place for shopping and relaxing.
PORTO AZZURRO: This very picturesque seaside town, on the western coast of Elba Island, has narrow streets with small houses painted in pastel colors, boutique shops, excellent restaurants, a town square in front of the marina and evening craft stands. It was called Porto Longone until 1947, when it changed its name to Porto Azzurro. Azzurro, Italian for light blue, describes the exquisite color of the sea; the town is also famous its beaches, with their dramatic rock formations and white sand.
DAY 7: LAND OF THE ETRUSCANS
We will have just enough time to enjoy our last breakfast in Elba and get ready to catch the ferry to the mainland. Before lunch, we will stop in Populonia to visit the Etruscan Museum and to appreciate the 360-degree view of the ocean and valley from the Fortress. After boarding the van, we will head to Cortona, our base camp for the rest of the tour, as it is close to many other beautiful places and activities. After unpacking and settling in our lovely hotel, situated in the center of the town, we will take a short walk to the restaurant where we will have dinner.
POPULONIA: In the 7th century BC, Populonia was already one of the largest and most important ancient Etruscan settlements. The only Etruscan city built along the coast and one of the major mining centers of the Etruscan metal industry. Populonia attracted thousands of inhabitants, with an acropolis, a necropolis, several ports and industrial districts. Populonia is notable now for its ancient ruins, the Etruscan walls, remains of Roman buildings and a medieval fortress, located in a panoramic position overlooking the Baratti Gulf.
CORTONA: Cortona’s rich history is evident in its streets, palazzos and piazzas. The city’s Etruscan roots date back to the 7th and 8th century BC and its alliance with Rome to the 1st century BC. In the 16th century, the Florentine Renaissance flourished here in Cortona. Cortona’s many points of interest include its distinctive 16th century clock tower located in the central square, the Palazzo Casali, the neoclassical Teatro Signorelli and the Etruscan Museum. The Museo Diocesano houses the beautiful Annunciation painted by Beato Angelico, and other religious masterpieces. Cortona also offers breathtaking views; you might have seen some in the film Under the Tuscan Sun, which was filmed in a beautifully restored 17th century estate just outside of Cortona.
DAY 8: TUSCAN COUNTRYSIDE
Today we visit the Tuscan town of San Gimignano, where time seems to have stood still. As you stroll through the winding streets, you’ll see what Tuscan hill towns looked like in the Middle Ages. A short drive will bring us into the heart of the Chianti classico for a wine tasting and included lunch in a castle in the famed Chianti classico. You’ll be treated like royalty at this small, family-run winery where you will visit the cellars, historic rooms and finish in their beautiful dining room.
For the afternoon, our local expert guide will take you on a private tour of the town of Siena, including a visit of its famous Duomo, one of the most beautifully churches in Italy.
SAN GIMIGNANO: San Gimignano’s hilltop setting, with its encircling walls and towers, is renowned for its unforgettable skyline. As with many other Tuscan cities, the history of San Gimignano dates back to the archaic Etruscan period, but it was during the Middle Ages that the city flourished and well off merchants and aristocrats built towers to show their wealth and power. A walk in the San Gimignano’s Old City, inside the 13th century walls, offers a glimpse of its past glory with 13 towers still standing out of the approximately 72 originally built. San Gimignano offers many local products, like saffron, extra virgin olive oil, salami and the renowned white wine, the Vernaccia di San Gimignano.
SIENA: Siena is one of the most unique and beautiful cities in Italy. It is truly an open-air museum, full of Gothic and medieval monuments and Renaissance art with a splendid landscape surrounding it. Probably the most well known site in Siena is the Piazza del Campo, the unique shell shaped square at the city center, where twice a year the Palio race is held. In the city’s boutique shops you can still find examples of fine craftsmanship like glazed terracotta, embroidered fabrics, gold jewelry and fine paper. Siena is also famous for its wonderful culinary tradition that evolved from ancient medieval dishes. Its wines and pastries include the famous Panforte and the Ricciarelli, almond paste cakes.
DAY 9: LEISURE DAY IN CORTONA & a cooking class
Today there is not any driving to reach far destinations but a quiet day in “Our Town” Cortona, exploring its art and surroundings, including the monastery l’Eremo delle Celle, where monks meet nature to create beauty as an expression of respectful synergy. We will enjoy lunch in town, followed by some free time before we participate in a cooking class and later enjoy a wonderful meal together.
L’EREMO DELLE CELLE: L’Eremo delle celle is a Franciscan monastery founded by St. Francis in 1211. Located in an enchanting valley where nature and man have lived harmoniously for the past centuries, this place has a special effect on visitors. After entering the monastery, many feel transported are surprised by the tranquil silence, interrupted only by the beautiful singing of birds and water flowing, that invites them to listen and look inside themselves. Some meditate, some pray, some feel closer to Nature, but everybody finds the Eremo to be a truly spiritual place.
DAY 10: FULL DAY IN UMBRIA "The green heart of Italy"
After breakfast we will drive to the Umbria region and visit two of its most beautiful cities. We will enjoy a refreshing lunch, then head to Assisi, the hometown of Saint Francis. Deruta will be our last stop of the day, a town well known for its ceramics. We will stroll around the small town watching the artists at work in their shops and maybe buying a souvenir.
ASSISI: Assisi is famous as the birthplace of St. Francis and for the sacred sites related to the Franciscan Order but it is also a beautiful city on an idyllic hillside, full of medieval art. The city was also strongly influential in the development of the Italian Renaissance. One of the finest examples is the medieval masterpiece, the Basilica of San Francesco with its innovative architecture and paintings by Giotto, Cimabue, Simone Martini and Pietro Lorenzetti.
DAY 11: CHE BELLA CAMPAGNA
Today is another fun filled day of tastings and medieval villages!
Our first stop is one of Tuscany’s most charming villages, Pienza, the drive alone offers some of the most stunning views of the countryside. Pienza was built as the ideal Renaissance city by Pope Pius II who remodeled it according to his taste. Pienza’s historic center, which has been recognized by UNESCO as one of the best planned Renaissance towns in Italy, is perched high above the stunning rolling cypress lined hills of the Val D’Orcia.
Near Pienza, special treat! A visit of a Perorino family run cheese farm (Fattoria Biologica Il Casale). Discover how the local cheese is made and sample the traditional cheese that has been produced here for over 2000 years.
Our next stop is the beautiful hilltop town of Montalcino: a lovely hilltop town known primarily for its prized red wine, the Brunello di Montalcino. Here we visit a wine cellar with a sampling of a few different wines. Brunello wines are considered among the most prestigious of Italy. You will also visit the beautiful 9th century abbey Sant’Antimo, said to have been founded by Charlemagne and have a chance to walk among the golden wheat fields to a very special place in the hills of the Val d'Orcia with your local host.
MONTALCINO: Montalcino is a small walled town that is perched on top of a hill in Val d’Orcia and the home of the famous wine called Brunello. Brunello wines are considered one of Italy’s best and most expensive wines and is the only Tuscan wine that is made from 100% Sangiovese grapes. At our winery, we’ll be pleasantly immersed in the harmonies of Mozart music, played across the rows of vines through a hundred speakers, in ecstasy with nature. This is not something born to amaze the visitor, but rather the result of serious agronomic and scientific research concerning the beneficial effects of musical frequencies on the vines (Vitis Vinifera), supported by the Universities of Florence and Pisa, the center of agronomic research of Arezzo, and sponsored by the prestigious company BOSE, specialized in the production of audio systems.
DAY 12: TRUFFLE HUNTING
When traveling March through November, you may be able to enjoy a traditional truffle hunt. Ninety percent of all black truffles in Italy come from Umbria. Far away from the stress, in the green heart of Italy, Montone has its own truffle wood. On a unique truffle hunting expedition with dog and guide, you will discover the mysteries of the elusive black truffle.
DAY 13: DEPARTURE DAY
Transfer to the airport for your departure flight. Yes, it is time to leave this beautiful land with many wonderful memories, but we hope to see you back again soon.
- Unwind for 12 nights at charming, locally owned boutique style accommodations that offer Italian hospitality, comfort and local character (Breakfast included):
- 3 nights in Lucca
- 3 nights on Elba Island
- 6 nights in Cortona
- Gain insider access to the Italian way of life
- Relax in the care of your dedicated local tour leader and driver-guide. Audrey, who speaks Italian and English fluently
- Private transfers (pick up and drop off) at Naples and Venice airports
- Private transportation and ferries
- Enjoy the freedom of leisure time to choose your own optional experiences
- Skip the lines with prepaid entrance fees and local expert guides in Lucca, Pisa, the island of Elba, Siena
- Orientation walks with your local host in Populonia, Pienza, Montalcino, San Gimignano, Assisi, Deruta, Cortona
- Immerse yourself in hand-picked exclusive experiences:
- A family farm to learn about their delicious pasta products, award winning olive oil and wines
- A family farm to learn about local cheese including lunch
- A truffle hunt in the hills of Umbria
- Wine tasting at a family run winery including lunch in their castle in the Chianti Classico
- Taxes & Fees: Local VAT taxes and government fees, City Tax, gas, highway tolls, city access licenses and permits, parking fees
- Sample and savor regional cuisine at carefully selected authentic trattorias and restaurants with local wines
NOTE: In the grand European traditions, I believe that dinner is a celebration of good food and wine, a celebration of culture and a celebration of family and friendship. Hosting this celebration is one of the joys of being a tour manager. I guide you to your favorite dish … or help you choose something you’ve never tried before. I choose the perfect wines and throw in some local delicacies to broaden your palate and surprise you a bit. When we are at a cooking lesson or a wine tasting, rest assured that you'll go home with new knowledge that will increase your appetite for more. On every tour, I have included dinners as a group as well as nights on your own. Of course, you are always invited to join me at my favorite places or as I explore new and interesting restaurant finds. I also have recommendations and would be happy to make reservations for you.
What's Not Included
- Passport fees, visa fees, immunization costs, entry clearing fees (when applicable)
- Optional enhancements like room upgrades
- Additional sightseeing, activities and experiences outside of your itinerary
- Early check-in or late check-out from hotels
- Personal charges such as laundry, phone calls, SIM cards or room service
- Lunches, dinners and drinks (alcoholic and non-alcoholic), unless specified in the itinerary
- Travel insurance (strongly recommended)
- Your international and domestic airfare
- Porterage: Please note that you'll need to carry your own luggage up and down stairs at hotels and across cobblestone
How it works
Here is how it works
- Schedule a consultation call with Audrey to discuss your dreams of traveling to this beautiful part of Italy!
- Some things we’ll discuss: Your interests and the interests of your traveling companions, your desires for the trip, and your ages and energy levels. Have you traveled to Italy before? If so, which countries did you visit? What would make your trip perfect, or what do you envision as your ideal day while on vacation?
- Audrey will start with this itinerary, but this is a custom trip, so we can also incorporate ideas that are specific to your group. You might say, “Yes, let’s go for it!” or you might want to discuss a few things, tweak some items, or compare different options. At the end of this phase, you will know the unique itinerary for your group.
- Each person in your small group pays a deposit, with final payment due 90 days before travel.
- Audrey and her team will book everything for you, help you prepare for your time in Italy, and take great care of you and your companions during your stay in Europe.
- You’ll be given a customized, day-by-day itinerary that's unique to your group with all the details you'll need. It's essentially a personalized guide book — with only the information that's relevant to you.
- All you have to do is sit back, and enjoy your fabulous travels! Let Audrey and her team personally take care of you while you are in Europe!
Prepare for Your Trip
European travel in general involves a lot of walking, much more than we are used to in the US. Most of our tours include city walking tours, visits to hilltop towns and villages, and meandering through cobbled streets. Keeping active and incorporating long walks into your busy schedule in the weeks before your departure will make your vacation much more rewarding.
- Don’t Overpack: A challenge even for some experienced travelers! Wash or dry clean some clothes during your travel. Some hotels and villas we choose offer laundry and dry-cleaning services and towns and cities have laundro-mats. Most also provide hair dryers. Toiletries and cosmetics can also be purchased at your destinations. Please contact us if you need some assistance.
- It is your responsibility to obtain the required documents to travel to Europe. Please verify with your own country's travel laws and government agencies. Your passport should be valid for at least 6 months after your return date.
The first day on tour is your arrival day into the city in which we meet. So, you would be flying the day before from the United States or Canada if you are not taking the option of spending a few days on location prior to start of your tour.
The purchase of TRAVEL INSURANCE is strongly recommended to help protect you and your travel investment against the unexpected. A Protection Plan can include coverage for trip cancellation, trip interruption, emergency medical and emergency evacuation/repatriation, trip delay, baggage delay and more.
Please read our Terms and Conditions here.