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Day by Day Itinerary

Small Groups: Never more than 10-16 travelers—guaranteed!

From the grape-laden vines of Chianti to the thick olive groves blanketing the hills of Trevi, Italy’s Tuscany and Umbria regions are ripe for discovery. Wander through fields of wildflowers to explore an abandoned abbey. Stand atop the walls of an ancient city, and gaze upon the marble churches and tree-lined piazzas below. Travel along the narrow lanes of small towns, marvel at medieval hilltop fortresses, and stroll between proud stands of elegant cypress trees. Immerse yourself in this rustic, romantic part of Italy, and enjoy a rich legacy of art, proud traditions in food and wine, and a local way of life as timeless as the rolling vineyards warming under the Tuscan sun.

Lucca Trevi Expand All
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    You depart the U.S. for Florence. The details of your arrival overseas will be included with your flight itinerary and airline tickets.

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    After an overnight flight, arrive at the airport in Florence, where an OAT representative will greet you. Then transfer to Lucca, where we'll check into our hotel. Enjoy some time to unwind before a brief orientation session and a Welcome Drink. You'll also meet those who traveled on our optional Bologna & Parma extension. This evening, dinner is on your own. Your Trip Leader will be happy to recommend restaurants in the area.

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    After breakfast at our hotel, we begin the morning by learning some key Italian phrases during a language lesson. Then, we explore Lucca on a walking tour. 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 charming center is enclosed by these walls, and brick ramparts from the 15th and 16th centuries preside over the streets. As we explore, we'll find quiet, tree-lined squares and ancient churches with ornate facades of green, gray, and white marble. Our stroll takes us by the Duomo di San Martino, or St. Martin's Cathedral, which was originally built in AD 1063.

    During the morning, we'll also experience the flavor of Tuscan life as we visit Lucca's typical shops where the locals still choose their daily fresh produce. Then, we'll see the city from a rolling perspective as we enjoy a fun, leisurely bicycle ride on the city walls. Wide and largely flat, they provide an easy ride as you complete a full loop around the city. After our tour, lunch is on your own, and your afternoon is at leisure.

    We'll enjoy a Welcome Dinner this evening in a local restaurant.

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    After breakfast, we'll depart for Carrara, a town situated along the Carrione River that was originally built by the ancient Romans to house workers in the nearby quarries. After a visit with a local producer of lardo, a Tuscan delicacy consisting of thin layers of pig’s fat aged in marble tubs, we'll board 4-wheel-drive vehicles and head up the slopes of the Apuan Alps for a visit to the famous Carrara marble quarries, where Michelangelo selected the block of white marble to sculpt his David. Our quarry tour includes a visit to some of the ancient marble tunnels and caves. Then, we'll have lunch at a local restaurant frequented by quarry workers (some 15,000 tons of marble are still extracted daily from the mountains). Upon our return to Lucca, the balance of the afternoon is at leisure.

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    This morning, we'll board a bus for our visit to Florence, birthplace of the Renaissance. We'll discover this legacy as we explore Florence's historic city center—a UNESCO World Heritage Site—on an included walking tour. We'll begin with some of the city's lesser known gems, including the Church of San Miniato al Monte, a breathtaking basilica that tops one of the highest points in the city. Admire the ornate Romanesque façade and the view of the city below before heading down toward the San Niccolo quarter, where we can experience a more intimate aspect of Florence. Then we'll cross the famous Ponte Vecchio (Old Bridge), from which we can glimpse segments of the Vasari Corridor, a private passageway built by Cosimo Medici so his family could pass from their home in Palazzo Pitti to the government palace. We end our walk in Piazza della Signoria, the heart of the civil power of the Medicis in centuries past.

    After lunch on your own, take some time to explore Florence at your leisure, perhaps beginning by the Mercato della Paglia and the Cathedral of Santa Maria del Fiore with its famous dome designed by Brunelleschi. Or visit the Church of San Lorenzo with the Medici Chapels.

    Later this afternoon, we depart Florence for the Chianti countryside, where we spend the next three nights.

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    Our discoveries begin with an excursion to San Galgano, where a small round chapel sits atop a verdant hill. We’ll go inside the chapel of Montesiepi to see a famous sword preserved within. With only the hilt and a small portion of the blade exposed, the sword was clearly thrust into the rock from which it protrudes, thus bringing into question whether the “sword in the stone” myth has Celtic roots after all. Leaving the chapel, we’ll hike down the hillside and through Tuscan fields to find the Abbey of San Galgano. Now in ruins, the 13th-century Cistercian monastery lost its roof over the years, but the “ceiling” of sky arguably makes the structure more striking. Sunlight streams through arched windows, and many of the architectural elements remain intact; we’ll marvel at beautiful columns and intricately carved decorations as we wander.

    We’ll return to our hotel this afternoon for leisure time. This evening, savor the authentic flavors of Tuscany during a cooking lesson, where you’ll not only learn to prepare some of the local specialties, but enjoy your handiwork as part of the cuisine for an included dinner at our hotel.

     

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    After breakfast, we begin our day with a scenic drive through the Chianti countryside, traveling through Tuscany's rolling, vineyard-carpeted hills. We visit a local winery for a Chianti tasting. By this time, we’ve been in this world-renowned wine region long enough to have tried a few of the local varietals, but we’ll get a chance to learn much more about wine-making traditions as the winemaker shows us the vineyard during our visit. Next, we’ll continue to a nearby town to enjoy lunch at an agriturismo farmhouse. This visit allows us to enjoy a traditional meal while learning about everyday life in the Chianti region.

    After lunch, we return to our hotel to enjoy time at leisure for discoveries on your own this afternoon. Late this afternoon, we head to Monteriggioni, a medieval walled town mentioned in Dante’s Inferno. Along the way, we'll enjoy a mile-and-a-half hike in the countryside surrounding Abbadia Isola before arriving in Monteriggioni, whose main piazza is lined with Tuscan-style homes and a simple Romanesque church. After time to explore, we’ll be ready for a hearty Italian meal, which we'll enjoy together at a local restaurant.

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    Today’s transfer to Pienza begins with a short ride into Siena. A small city built along three distinct ridge-lines that meet to form a "Y," Siena is as elegant as it is ancient. Narrow, medieval passageways open suddenly to sweeping views of the city and surrounding countryside. A walking tour will be like stepping back in time to discover the palazzos, piazzas, and churches scattered throughout Siena's Old Town, a UNESCO World Heritage Site. Siena’s streets are paved with cobblestones, and the city is built over five hills, making for a challenging—yet rewarding—stroll. We’ll also enjoy an informative talk on Siena’s unique districting system. Siena’s seventeen districts, or contrade, were originally divided by the city’s buildings and their owners at the time, rather than by roads or other geographical markers. Each is named after an animal or symbol, and we’ll gather in one of these districts for our discussion. Then we’ll break for an included lunch in Siena before enjoying some time to explore independently.

    We meet again this afternoon in Piazza del Campo, the shell-shaped 13th-century plaza considered one of the most beautiful in Europe, and home to Siena’s most important civic events. We’ll stroll a half hour to the Porta Romana, an 18th century farmhouse amid vineyards and olive groves, where we board our motorcoach for a scenic drive which brings us through the Crete Senesi, known for its rolling hills and sometimes lunar-like appearance.

    Late this afternoon, we arrive in Pienza, our home for the next three nights. Formerly a small village named Corsignano, Pienza is the birthplace of Pope Pius II. Once elevated to his position, this native son declared that Corsignano should be rebuilt using the Renaissance urban planning model of a central piazza anchored with important buildings and the rest of the city radiating from this heart. This evening, we’ll enjoy dinner together in a local restaurant.

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    After breakfast, we’ll travel overland to Montepulciano, where we start our day with a visit to the domed Sanctuary of San Biagio, designed in the 15th century, on the same architectural plan that would later be used to build St. Peter’s Basilica. We then take a walk through the city center of this remarkably well preserved Tuscan village onto Via San Gallo, a historic street outlined with brick and stone buildings. After enjoying free time to explore the medieval streets of this charming city, we visit a family-run winery and sip some of their specialties over a light lunch.

    After lunch, we’ll set off for the Val D’Orcia, a UNESCO World Heritage Cultural Landscape. Known for its rising and falling contours, with broad plains punctuated by dramatic hills, and its beautiful array of farmhouses, shrines, and Renaissance villages, the Val d’Orcia has for years been the muse for countless artists and photographers. We get off the bus for a scenic hike in the countryside around Monticchiello, a picturesque medieval village in the heart of the Val d'Orcia. Then we'll enjoy an illuminating discussion about Tuscany’s role during World War II, including the Tuscan resistance and the stories of the men who tracked down Nazi-looted art from Italian museums and the famous cyclist Gino Bartali, who smuggled documents to the resistance. After some free time to wander Monticchiello's ancient streets on our own, we’ll enjoy dinner in a local restaurant before returning to Pienza.

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    After breakfast at our hotel, we embark on a full-day excursion that begins in Pitigliano. Jews began settling in Pitigliano in the 15th century, and the population increased when they sought refuge here after being expelled from the Papal State in Rome during the counter-reformation persecutions. During World War II, all the town’s Jews escaped the Nazis with the aid of their mostly Catholic neighbors, a rare feat in that era. A walking tour will reveal Pitigliano's rich Jewish heritage. After lunch at a local restaurant, we'll then set off for the ancient Etruscan necropolis of Sovana, where we'll hike through the woods of this ancient burial site.

    We return to Pienza late this afternoon in time for dinner on your own this evening.

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    We bid farewell to Tuscany and turn our eyes toward Umbria this morning. Considered “the green heart of Italy,” Umbria is rich with agriculture, olive oil making, and verdant forests. We arrive in the village of Tuoro around mid-morning to board our private boat on Lake Trasimeno, one of the biggest lakes in Italy at 50 square miles. Our small boat will bring us to Isola Maggiore, a tranquil island in the middle of the lake which was a bustling fishing village centuries ago, but is now home to just 17 permanent residents. We'll enjoy a nature hike around the island, followed by lunch at a local restaurant. Please note: In case of adverse weather conditions, our Lake Trasimeno cruise may be substituted with a visit to Bevagna

    This afternoon, we continue on to Assisi, the town best known for the legacy of Saint Francis and his followers, who practiced humility and compassion in the face of poverty. Here, we’ll visit the 13th-century Basilica, erected on the former “Hill of Hell” in his memory.

    We then travel overland to the countryside around Trevi and check into our hotel. Spilling down Monte Serrano, the medieval lanes of Trevi are rife with history, with architecture spanning Gothic to Renaissance to Baroque. Dinner is at a local restaurant this evening. Please note: Some departures will feature accommodations in the village of Bevagna, or in the countryside just outside of Trevi.

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    This morning, we’ll depart for a small mountain village nestled in a high plateau in the heart of the Appenines. Traditional Italian ways of life that have endured for generations in these mountain villages, and locals here still grow crops, tend sheep, and gather truffles and mushrooms from the surrounding natural birch forests. We’ll set off aboard 4-wheel-drive vehicles and meet up with some local truffle hunters and their dogs. We’ll all then set off into the woods on foot and discover if the truffle-hunting skills of the dogs can uncover any of the precious fungus. We return to the village for a lesson on cooking authentic Italian pasta, followed by lunch with some of the local villagers.

    Dinner this evening is on your own.

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    After breakfast, we transfer to Norcia, a small medieval town in the Nera Valley renowned for its salami and prosciutto. Surrounded by defensive walls, Norcia’s origins pre-date the Romans and its buildings have been rebuilt many times. We’ll visit with a local salami maker who will introduce us to Norcia’s famous local cured meats (or norcineria). We’ll also visit the centuries-old Basilica of San Benedetto, said to be the birthplace of Saint Benedict, and spend some time conversing with one of the local Benedictine monks.

    After lunch at a local restaurant, we’ll head to Scheggino, a medieval hilltown set along the Nera River. From here, we’ll set off on a rafting adventure along the Nera River (Please note: Rafting is available from mid-April until mid-October; other departures will feature an alternate activity). After returning to Trevi, dinner is on your own this evening.

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    We bid farewell to Umbria today and begin our overland transfer to the Roman countryside after breakfast. En route, we pause in Civita di Bagnoregio, the 2,500-year-old hamlet that was the birthplace of Saint Bonaventure. Perched on volcanic tufa above the Tiber River, it became a “dying city” as the population (now numbering about a dozen year-round, though others live here seasonally) dwindled in the aftermath of erosion and earthquakes. This hill town’s historic architecture has been preserved by its isolation; we’ll enter it via the footbridge that now provides the only access for visitors. Strolling along narrow lanes to Civita’s central piazza feels like stepping back in time.

    Then, we enjoy lunch in a local restaurant. Afterwards, we continue to a traditional agriturismo lodging located outside of Rome. Tonight, we toast our memories of Italy during a Farewell Dinner.

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    • Meals included:

    After breakfast at the hotel, we transfer to the airport for your return flight home. Or, begin your Rome, Italy extension.

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Weather & Regional

Before you travel, we encourage you to learn about the region of the world you'll discover on this trip. From weather and currency information to details on population, geography, and local history, you'll find a comprehensive introduction to your destinations below.

Visit our “What to Know” page to find information about the level of activity to expect, vaccination information resources, and visa requirements specific to this vacation.

What to Know

For more detailed information about this trip, download our Travel Handbook below. This document covers a wide range of information on specific areas of your trip, from passport, visa, and medical requirements; to the currencies of the countries you’ll visit and the types of electrical outlets you’ll encounter. This handbook is written expressly for this itinerary. For your convenience, we've highlighted our travelers' most common areas of interest on this page.

Download the Travel Handbook

What to Expect

Pacing

  • 5 locations in 14 days with one 1-night stay

Physical Requirements

  • Not appropriate for travelers using wheelchairs, walkers, or other mobility aids
  • You must be able to walk 3-5 miles unassisted and participate in 6-8 hours of physical activities each day
  • Agility and balance are required for embarking small boat

Climate

  • Daytime temperatures range from 35-95°F
  • Tuscany and Umbria share a typical Mediterranean climate, with hot, dry summers and warm, rainy winters, with occasional snowfall
  • Strong winds occur in March and October-December

Terrain

  • Travel and hike on some rugged paths, rolling hills, and many cobblestoned streets on foot, as well as over bumpy, narrow rural roads by bus

Transportation

  • Travel by 19-passenger coach and 50-passenger boat
  • Eight 4-hour drives

Accommodations & Facilities

  • Hotel rooms are smaller than in U.S.; a 1-night agriturismo stay features basic amenities
  • All accommodations feature private baths

Travel Documents

Passport

Your passport should meet these requirements for this itinerary:

  • It should be valid for at least 6 months after your scheduled return to the U.S.
  • It should have the recommended number of blank pages (refer to the handbook for details).
  • The blank pages must be labeled “Visas” at the top. Pages labeled “Amendments and Endorsements” are not acceptable.

Visas

U.S. citizens do not need a visa for this trip.

If you are not a U.S. citizen, do not travel with a U.S. passport, or will be traveling independently before/after this trip, then you may need a visa. Please check with the appropriate embassy or a visa servicing company. To contact our recommended visa servicing company, PVS International, call toll-free at 1-800-556-9990.

Vaccinations Information

For a detailed and up-to-date list of vaccinations that are recommended for this trip, please visit the CDC’s “Traveler’s Health” website. You can also refer to the handbook for details.

Before Your Trip

Before you leave on your adventure, there are at least four health-related things you should do. Please check the handbook for specifics, but for now, here’s the short list:

Step 1: Check with the CDC for their recommendations for the countries you’ll be visiting.
Step 2: Have a medical checkup with your doctor.
Step 3: Pick up any necessary medications, both prescription and over-the-counter.
Step 4: Have a dental and/or eye checkup. (Recommended, but less important than steps 1-3.)

What to Bring

In an effort to help you bring less, we have included checklists within the handbook, which have been compiled from suggestions by Trip Leaders and former travelers. The lists are only jumping-off points—they offer recommendations based on experience, but not requirements. You might also want to refer to the climate charts in the handbook or online weather forecasts before you pack. Refer to the handbook for details.

Insider Tips

Accommodations

Main Trip

  • Hotel San Luca Palace

    Lucca, Italy

    The Hotel San Luca Palace is located just a short walk from the Museo e Pinacoteca Nazionale and Casa di Puccini. Each of its 26 air-conditioned rooms includes satellite TV, minibar, safe, and private bath with hair dryer. Guests can also enjoy an Italian coffee at the on-site café, a snack at the deli, and a drink in the lounge.

  • Villa Sabolini

    Chianti Region, Italy

    The 30-room Villa Sabolini is nestled in the wooded hills of Chianti. The historic home was named after its prominent 15th century occupants and later served as the hiding place for important Italian art during World War II. Each of its air-conditioned rooms includes satellite TV, minibar, safe, and private bath with hair dryer. Villa Sabolini provides guests with a range of amenities including indoor and outdoor swimming pools, a hot tub, and views of the Chianti region's surrounding landscape.

  • Piccolo Hotel La Valle

    Pienza, Italy

    Just steps away from downtown Pienza, the Piccolo Hotel La Valle is ideally located for exploring the Tuscan countryside. Each of the 15 rooms at this intimate property boasts a minibar, flat-screen TV, desk, as well as a private bath with hairdryer. Enjoy a stroll in the manicured garden, and savor an alfresco meal while looking out over the rolling Tuscan hills.

  • Hotel Antica Dimora

    Trevi, Italy

    The Antica Damora is located close to many of Trevi’s most popular sights, including Paolo Bea and Abbey of Sassovivo. Hotel amenities include a small outdoor pool, library, and cocktail lounge. There are 32 air-conditioned rooms, each with satellite TV, espresso maker, safe, and private bath with hair dryer.

  • Borgo di Tragliata

    outside Rome, Italy

    The Borgo di Tragliata is an agriturismo situated is the idyllic countryside outside of Rome. Amenities include an outdoor pool, massage treatment rooms, a bar and lounge, and a library. The 47 rooms each include TV and private bath with hair dryer.

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  • Hotel Porta San Mamolo

    Bologna, Europe

    The Hotel Porta San Mamolo is located in Bologna’s historical center, close to the Basilica of San Domenico and the Archaeological Museum. Hotel amenities include a coffee shop/café, and bar/lounge. There are 28 rooms, each with air-conditioning, minibar, safe, complimentary wireless Internet, satellite TV, and private bath with hair dryer.

  • Kolbe Hotel Rome

    Rome, Italy

    Originally built as a convent in the 15th century, the Kolbe Hotel Rome is situated in the heart of Rome, near the Trastevere quarter, just steps away from the Roman Forum, and a short distance from the Coliseum. There is a restaurant, bar, and lounge at the hotel, along with 72 air-conditioned rooms, each with minibar, satellite TV, and private bath with hair dryer.

Flight Information

Flight Options to Personalize Your Trip

You can choose to stay longer before or after your trip on your own, or combine two adventures to maximize your value. Here are more ways to create the OAT adventure that’s right for you:

  • Extend your adventure and lower your per day cost with our optional pre- and post-trip extensions
  • Choose our standard air routing, or work with us to select the airline and routing you prefer
  • Make your own international flight arrangements directly with the airline, applying frequent flyer miles if available
  • International airport transfers to and from your hotel, including meet and greet service, are available for purchase
  • Stay overnight in a connecting city before or after your trip
  • Request to arrive a few days early to get a fresh start on your adventure
  • Choose to “break away” before or after your trip, spending additional days or weeks on your own
  • Combine your choice of OAT adventures to maximize your value
  • Upgrade to business or premium economy class
  • Extend your Land Tour-only Travel Protection Plan coverage and protect the air arrangements you make on your own—including your frequent traveler miles

The air options listed above may involve additional airfare costs based on your specific choices.

Or, when you make your reservation, you can choose our standard air routing, for which approximate travel times are shown below.

Standard Air Routing

w/out standard air $2895
w/ standard air $3995
Gateway Travel Time*
Boston, New York (JFK) 11hrs
Chicago, Detroit, Newark, Philadelphia 12hrs
Atlanta, Dallas, Miami, Washington, DC (Dulles) 13hrs
Baltimore, Denver, Seattle 14hrs
Los Angeles, San Francisco 15hrs
Orlando 16hrs
Phoenix 17hrs

* Estimated total time, including connection and layover. Actual travel time may vary.

The information above reflects approximate flight times from the gateway cities listed to Florence, Italy. Routing is based on availability and subject to change. You will receive your final air itinerary approximately 14 days prior to departure.

Tuscan and Umbrian cuisine

Simply sensational food in the Italian heartland

by Catherine Groux, Overseas Adventure Travel associate

Creating dishes infused with the flavors of olive oil, wine, and truffles, locals have mastered the art of turning simple ingredients into bold meals.

Italian cuisine is adored around the world. From the bustling markets of Seoul to the sloped streets of San Francisco, gluttonous gourmands are never far from the flavors of Italy, whether they crave a hot bowl of fettuccine Alfredo or a cold scoop of gelato. But although we tend to view Italian cuisine as a singular, mouthwatering masterpiece, it is better defined as a mosaic, with each region in Italy adding its own unique tile to the complete culinary creation.

Each region has its own specialties, its own go-to ingredients, and its own style of cooking—and Tuscany and Umbria are no exception. Relying on the robust flavors of fresh olive oil, truffles (knotty, pungent mushrooms), and wine, these regions are renowned for creating simple, yet savory dishes.

From the finest ingredients …

Tuscany and Umbria produce some of the highest-quality wines, olive oils, and truffles in Italy—and arguably the world—so it’s no wonder the regions’ cuisine relies on the rich simplicity of these ingredients. Creating dishes infused with the flavors of olive oil, wine, and truffles, locals have mastered the art of turning simple ingredients into bold meals.

It probably comes as no surprise that locals are serious about their olive oil. These oils come in varying levels of acidity, with the highest-quality oils being the least acidic. The more olives are bruised before they are pressed, the more acidic their oils will be, which is why the best olive oils are still picked by hand. Olive oils fall into one of four categories, with the best being extra vergine (extra virgin), as it has an acidity level of 1 percent or less. For this reason, extra virgin olive oil is a staple in most local kitchens—using anything less would be un-Italian.

Tuscan and Umbrian cuisine is also adorned with another prized ingredient: truffles. As both black truffles and rare white truffles can be found in Tuscan and Umbrian forests, they work their way into countless culinary classics, particularly in the fall when they’re in season.  In Umbria, truffles are grated over risottos or sliced atop crostini (fried bread), while Tuscany adds truffles to its game and pastas.

But of course, even the best meal would be incomplete without the right wine. In Tuscany, dry wines with decisive bodies pair perfectly with the light and flavorful local cuisine. The region’s most popular wine, Chianti, is said to be suitable for any Tuscan meal, from pastas to poultry. But while any good local meal is served with wine, many Tuscan and Umbrian dishes also include wine as a core ingredient. An example of this is gallina ubriaca (“drunken chicken”), a popular Umbrian dish of chicken cooked in wine.

… To the last crumb

Featuring the flavors of some of the world’s best wines, olive oils, and truffles, Tuscan and Umbrian cuisine comes with a certain level of sophistication. (In fact, many locals say Tuscany invented French cuisine—the epitome of culinary pretension—when Catherine de’ Medici brought her array of chefs to France upon wedding the Duke of Orléans.) However, in reality, Tuscan and Umbrian cuisine hasn’t strayed far from its humble, rural roots.

Many dishes still rely on the simple, inexpensive ingredients—such as game, beans, and seasonal vegetables—that have been consumed by peasants in the Italian countryside for centuries. To this day, most traditional restaurants serve dishes like minestra di fagioli (bean soup), zucchini ripiene (zucchini stuffed with minced meat), coniglio arrosto (roasted rabbit), and pasta e ceci (chickpea pasta).

And of course, holding true to its humble roots also means that in Tuscany and Umbria, no scrap of food is wasted. This is particularly evident in their use of bread. Fresh bread is typically served on the side of every meal, but when that bread goes stale, it is certainly not thrown out. Stale bread can be used in dishes like panzanella (cold bread salad) and pappa al pomodoro (tomato and bread soup), or even crushed to create delicious bread crumbs. As the old Italian saying goes, “A chi ha fame e buono ogni pane” (“All bread is good when you’re hungry”).

From their medieval hamlets to their grape-laden vineyards, Tuscany and Umbria are gastronomical gems. As they cling to the pastoral traditions of their ancestors and plunge onto the mainstream culinary scene with some of the world’s finest ingredients, these regions are proudly adding to the mosaic of magnificence that is Italian cuisine.