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DISCOVER Tuscany and Umbria: Italy's Enchanting Hill Towns

9 days from $5,074 | includes airfare, taxes and all fees

Settle into historic properties in Tuscany and Umbria and venture out to experience the world-renowned cities of Florence and Siena as well as medieval hilltop towns where time stands still. Come face to face with art and architecture that changed history, from Michelangelo’s David to the ideal Renaissance town of Pienza. Step into another century in San Gimignano and Perugia, and sample local vintages along Chianti’s wine route.

Land Journeys

or Call 855-330-1542

Highlights

  • Siena and Florence: Explore these World Heritage-listed cities and their art and architectural gems with a guide and enjoy free time to experience them on your own.
  • Renaissance Art: Encounter incredible Renaissance art, from Michelangelo’s David to Giotto’ frescoes depicting the life of St. Francis, and tour the “ideal” Renaissance town of Pienza.
  • Unforgettable Lodgings: Stay in a restored monastery set among lush gardens outside Florence and a stunning historic residence near Perugia.
  • Hill Towns: Meander amid the iconic towers of San Gimignano, and discover the medieval underground of Perugia and the extraordinary Duomo of Orvieto.
  • Local Flavors: Taste wines at a Chianti winery and take part in a cooking demonstration at a family farm in Umbria.

Itinerary

To see itinerary, please click on an option below.

Days 1–2 — Depart U.S. for Florence, Italy

Arrive in Florence on an overnight flight and transfer to your historic hotel in a tranquil oasis just outside the city. After time to unpack and unwind, gather for a briefing about the journey ahead and a welcome dinner. (D)

Day 3 — Florence

Immerse yourself in the “cradle of the Renaissance” during a walking tour of historic Florence, a World Heritage site. Encounter beloved monuments including the octagonal Baptistery, the city’s oldest religious structure, known for its bronze doors crafted by Lorenzo Ghiberti; Giotto’s graceful bell tower; and the extraordinary Santa Maria del Fiore—also known as the Duomo—whose enormous 15th-centry dome still dominates the skyline and remains the largest of its type ever built. At the Galleria dell’Accademia, encounter Michelangelo’s masterpiece David and his pieces for the papal tombs. Then head off on your own to explore more of the city during an afternoon and evening at leisure. (B)

Day 4 — Siena and San Gimignano

Travel south to the fabled walled city of Siena, a rose-colored gem whose allure lies in its tightly held traditions and remarkable medieval and Renaissance architecture. On a guided walk through the World Heritage-listed historic center, stroll the fan-shaped Piazza del Campo, the stage for the famous Palio bareback horse race that has taken place nearly every summer since the Middle Ages. Inside the dazzling Duomo, striped with black and white marble, see stunning mosaics and works by Bernini, Donatello, and Michelangelo. You’ll have free time to discover the city on your own and savor some of its renowned Tuscan cuisine this afternoon. Later, ascend to the hill town of San Gimignano, known for its well-preserved architecture and the 14 remaining towers which have left its skyline virtually unchanged since medieval times. Return to your hotel via the Chiantigiana, a “wine road” that winds through the world-famous Chianti Classico wine region. Along the way, stop for a wine tasting to sample fine local vintages. Gather for dinner at the hotel tonight. (B,D)

Day 5 — Pienza/Perugia, Umbria

Journey today through the rolling hills of the Val d’Orcia, where statuesque cypress trees and picturesque villages dot a rolling patchwork of olive orchards, vineyards, and wheat fields. Stop in the hilltop town of Pienza, the hometown of Pope Pius II, who transformed it into the ideal Renaissance town in the 15th century. On a walking tour of the small historic center, another World Heritage site, experience its harmonious blend of human-scale architecture and thoughtful urban planning. At the edge of town, take in a panoramic view of the Val d’Orcia below. After lunch at a local restaurant, continue to Umbrian province of Perugia, and settle into your hotel. Dine together tonight. (B,L,D)

Day 6 — Perugia

A lively university town with an ancient heart known for decadent chocolate and an annual jazz festival, Perugia provides a snapshot of how many Italians conduct daily life against the backdrop of thousands of years of history. Below its cobblestoned alleyways and café-lined streets lies an underground city—the grand, vaulted remains of the Rocca Paolina, a fortress built by the papacy in the 16th century. Get acquainted with the town during a walking tour, and take the afternoon to explore further, perhaps discovering the nooks and crannies of Rocca Paolina or visiting the excellent National Gallery. Meet up for dinner tonight. (B,D)

Day 7 — Assisi

Set out for the hilltown of Assisi, where Saint Francis was born in 1182 and spent much of his adult life. The impressive Basilica of Saint Francis of Assisi, built soon after the saint’s death, still draws pilgrims from all over the world. Visit the basilica’s upper and lower churches, examining priceless frescoes by Giotto and Cavellini. Most stunning of all is a series of Giotto frescoes depicting the life of Saint Francis in the upper church. You’ll have free time for lunch and a walk through Assisi’s fountain-splashed piazzas and hidden lanes. Dine together at the hotel this evening. (B,D)

Day 8 — Orvieto/Fiumicino

Wind up steep slopes to Orvieto, dramatically perched on a plateau over vineyard-covered plains. Rising high above its tightly knit medieval streets is the glorious façade of the Duomo, covered in sculptures and glittering mosaics. Step inside to see a frescoed chapel by Fra Angelico and Luca Signorelli’s masterpiece The Last Judgment. Then head to a family farm for a cooking demonstration and lunch.  In the afternoon, travel south to the coastal town of Fiumicino on the outskirts of Rome, and bid “arrivederci to fellow travelers during a farewell dinner. (B,L,D)

Day 9 — Return home

After breakfast, transfer to the airport in Rome for your flight home. (B)

Included meals are denoted as follows: Breakfast (B), Lunch (L), Reception (R), Dinner (D)

Dates & Prices

Click on the departure date to see pricing. Click the for more information.

Dates

Availability

Price

Apr 10 - 18, 2027
Available
from $5,074

Special Value

Airfare Included! This tour is specially designed for a small group of 16 to 24 Smithsonian travelers and offers outstanding travel value. Along with airfare, prices also include airline taxes and departure fees, as well as transportation, accommodations, daily activities and excursions, and most meals.

Expert: Glenn Bugh

Tour cost including airfare: Boston, New York

Occupancy Double Single
Price $5,074 $5,869

Tour cost including airfare: Chicago, Washington DC

Occupancy Double Single
Price $5,374 $6,169

Tour cost including airfare: Atlanta, Baltimore, Charlotte, Cincinnati, Cleveland, Dallas, Denver, Detroit, Houston, Philadelphia

Occupancy Double Single
Price $5,474 $6,269

Tour cost including airfare: Los Angeles, Miami, Minneapolis, Orlando, Phoenix, Portland (OR), San Francisco, Seattle, Tampa

Occupancy Double Single
Price $5,574 $6,369

Land only (tour cost not including airfare)

Occupancy Double Single
Price $4,095 $4,890

Apr 24 - May 2, 2027
Available
from $5,074

Special Value

Airfare Included! This tour is specially designed for a small group of 16 to 24 Smithsonian travelers and offers outstanding travel value. Along with airfare, prices also include airline taxes and departure fees, as well as transportation, accommodations, daily activities and excursions, and most meals.

Tour cost including airfare: Boston, New York

Occupancy Double Single
Price $5,074 $5,869

Tour cost including airfare: Chicago, Washington DC

Occupancy Double Single
Price $5,374 $6,169

Tour cost including airfare: Atlanta, Baltimore, Charlotte, Cincinnati, Cleveland, Dallas, Denver, Detroit, Houston, Philadelphia

Occupancy Double Single
Price $5,474 $6,269

Tour cost including airfare: Los Angeles, Miami, Minneapolis, Orlando, Phoenix, Portland (OR), San Francisco, Seattle, Tampa

Occupancy Double Single
Price $5,574 $6,369

Land only (tour cost not including airfare)

Occupancy Double Single
Price $4,095 $4,890

May 15 - 23, 2027
Available
from $5,274

Special Value

Airfare Included! This tour is specially designed for a small group of 16 to 24 Smithsonian travelers and offers outstanding travel value. Along with airfare, prices also include airline taxes and departure fees, as well as transportation, accommodations, daily activities and excursions, and most meals.

Tour cost including airfare: Boston, New York

Occupancy Double Single
Price $5,274 $6,069

Tour cost including airfare: Chicago, Washington DC

Occupancy Double Single
Price $5,574 $6,369

Tour cost including airfare: Atlanta, Baltimore, Charlotte, Cincinnati, Cleveland, Dallas, Denver, Detroit, Houston, Philadelphia

Occupancy Double Single
Price $5,674 $6,469

Tour cost including airfare: Los Angeles, Miami, Minneapolis, Orlando, Phoenix, Portland (OR), San Francisco, Seattle, Tampa

Occupancy Double Single
Price $5,774 $6,569

Land only (tour cost not including airfare)

Occupancy Double Single
Price $4,295 $5,090

Sep 18 - 26, 2027
Available
from $5,274

Special Value

Airfare Included! This tour is specially designed for a small group of 16 to 24 Smithsonian travelers and offers outstanding travel value. Along with airfare, prices also include airline taxes and departure fees, as well as transportation, accommodations, daily activities and excursions, and most meals.

Tour cost including airfare: Boston, New York

Occupancy Double Single
Price $5,274 $6,069

Tour cost including airfare: Chicago, Washington DC

Occupancy Double Single
Price $5,574 $6,369

Tour cost including airfare: Atlanta, Baltimore, Charlotte, Cincinnati, Cleveland, Dallas, Denver, Detroit, Houston, Philadelphia

Occupancy Double Single
Price $5,674 $6,469

Tour cost including airfare: Los Angeles, Miami, Minneapolis, Orlando, Phoenix, Portland (OR), San Francisco, Seattle, Tampa

Occupancy Double Single
Price $5,774 $6,569

Land only (tour cost not including airfare)

Occupancy Double Single
Price $4,295 $5,090

Oct 2 - 10, 2027
Available
from $5,074

Special Value

Airfare Included! This tour is specially designed for a small group of 16 to 24 Smithsonian travelers and offers outstanding travel value. Along with airfare, prices also include airline taxes and departure fees, as well as transportation, accommodations, daily activities and excursions, and most meals.

Expert: Andrew Becker

Tour cost including airfare: Boston, New York

Occupancy Double Single
Price $5,074 $5,869

Tour cost including airfare: Chicago, Washington DC

Occupancy Double Single
Price $5,374 $6,169

Tour cost including airfare: Atlanta, Baltimore, Charlotte, Cincinnati, Cleveland, Dallas, Denver, Detroit, Houston, Philadelphia

Occupancy Double Single
Price $5,474 $6,269

Tour cost including airfare: Los Angeles, Miami, Minneapolis, Orlando, Phoenix, Portland (OR), San Francisco, Seattle, Tampa

Occupancy Double Single
Price $5,574 $6,369

Land only (tour cost not including airfare)

Occupancy Double Single
Price $4,095 $4,890

Oct 16 - 24, 2027
Available
from $5,074

Special Value

Airfare Included! This tour is specially designed for a small group of 16 to 24 Smithsonian travelers and offers outstanding travel value. Along with airfare, prices also include airline taxes and departure fees, as well as transportation, accommodations, daily activities and excursions, and most meals.

Expert: Pedar Foss

Tour cost including airfare: Boston, New York

Occupancy Double Single
Price $5,074 $5,869

Tour cost including airfare: Chicago, Washington DC

Occupancy Double Single
Price $5,374 $6,169

Tour cost including airfare: Atlanta, Baltimore, Charlotte, Cincinnati, Cleveland, Dallas, Denver, Detroit, Houston, Philadelphia

Occupancy Double Single
Price $5,474 $6,269

Tour cost including airfare: Los Angeles, Miami, Minneapolis, Orlando, Phoenix, Portland (OR), San Francisco, Seattle, Tampa

Occupancy Double Single
Price $5,574 $6,369

Land only (tour cost not including airfare)

Occupancy Double Single
Price $4,095 $4,890
Please call if your city is not listed in the price chart above or if you wish to customize your arrival and departure dates. Air-inclusive prices include airline taxes, fuel surcharges, and departure fees of $679, which are subject to change until final payment is made. Business class upgrade on round-trip transatlantic flight: $4,995 per person (subject to change). Premium economy upgrade on round-trip transatlantic flight: $1,995 per person (subject to change). Prices are per person based on double occupancy and all upgrades are subject to availability. Limited to 24 Smithsonian Journeys guests. 

Prices are based on rates of exchange, airfare & fuel (where applicable), tariffs, taxes, and other costs as of the tour publication date. We reserve the right to correct errors and to increase program prices to cover increased costs, tariffs, and taxes received after prices are published and to reflect currency fluctuations.

Experts

Departure: Apr 10 - 18, 2027

Glenn Bugh

Classicists

Glenn R. Bugh is associate professor of Classical and Byzantine Studies at Virginia Tech.  He holds a PhD from the University of Maryland and has …

Glenn R. Bugh is associate professor of Classical and Byzantine Studies at Virginia Tech.  He holds a PhD from the University of Maryland and has been a fellow at the American School of Classical Studies at Athens; the Institute for Advanced Study in Princeton; the Center for Hellenic Studies in Washington, D.C.; and a research scholar at the Hellenic Institute for Byzantine and Post-Byzantine Studies in Venice, Italy.  Glenn served as the Summer Session Director of the American School of Classical Studies at Athens in 2000 and 2011, and was the Whitehead Visiting Professor there in 2004–2005. Along with many articles, he has published two books, The Horsemen of Athens and The Cambridge Companion to the Hellenistic World.   

Glenn has served as an expert on Smithsonian trips to Greece, Italy, the Adriatic, Turkey, and the Black Sea since 1984, and offered numerous seminars for Smithsonian Associates, including “A Tale of Two Cities: Athens and Rome.”  He frequently teaches at Virginia Tech’s Center for European Studies and Architecture in Switzerland and has lectured at a variety of academic institutions. Glenn was featured in an A&E documentary on the Roman emperor Caligula. He lived in Verona and Livorno as a boy.

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Departure: May 15 - 23, 2027

Theresa Flanigan

Art & Archaeology Historian

Theresa Flanigan is a historian of late medieval and Renaissance art and architecture, primarily in Italy, where she lived and studied for several years, including …

Theresa Flanigan is a historian of late medieval and Renaissance art and architecture, primarily in Italy, where she lived and studied for several years, including as a fellow at the Scuola Normale Superiore in Pisa. While studying in Florence as an architecture student, she fell in love with Italian language, art, and culture and has immersed herself in researching, teaching, and sharing her knowledge about Italy ever since. She received a master’s in art history from Syracuse University’s Florence program, and a PhD from New York University’s Institute of Fine Arts.

Theresa is assistant professor and graduate coordinator of art history at Texas Tech University. She taught previously at the University at Albany (SUNY), New York University, Syracuse University, and elsewhere. She authored the book The Ponte Vecchio: Architecture, Politics, and Civic Identity in Late Medieval Florence, and co-edited Artistic Encounters in Trecento Italy. Theresa has also published on Florentine urban planning, emotional expression in Leonardo da Vinci’s Mona Lisa, Giotto’s paintings in Assisi and Padua, and on artworks by Domenico Ghirlandaio, Fra Angelico, Fra Filippo Lippi, and others. Her current research explores the influence of medical science on early Renaissance naturalism. As an educator, Theresa has led numerous study abroad trips to Italy and lectured in museums and at historical sites in Texas, New York, and throughout Italy.

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Departure: Sep 18 - 26, 2027

Rebecca Schindler

Classicist

Rebecca K. Schindler is Professor of Classical Studies at DePauw University in Greencastle, IN. She teaches courses in Classical art and archaeology, Latin, Greek and …

Rebecca K. Schindler is Professor of Classical Studies at DePauw University in Greencastle, IN. She teaches courses in Classical art and archaeology, Latin, Greek and Roman Mythology, and Classical literature. Rebecca has chaired the Department of Classical Studies at DePauw University and has served as the co-editor of the book reviews for The American Journal of Archaeology. Her research interests include the archaeology of Greek colonization in South Italy and Sicily, Greek religion, applications of Geographic Information Systems (GIS) in archaeology, and the ethics of cultural heritage. She received her B.A. from Wellesley College in Classical and Near Eastern Art and Archaeology and her PhD from the University of Michigan in Classical Art and Archaeology. She has also studied at the American School for Classical Studies in Athens and worked as a visiting scholar at the American Academy in Rome. Rebecca's archaeological field experience includes projects in Tunisia, Cyprus, Turkey, and Italy. Since 2015 she has been working with Umbra Institute in Perugia on a field project at Castiglione del Lago on Lake Trasimeno in Umbria, Italy. She is finishing a book on sanctuaries of Aphrodite in Italy and Sicily. She currently serves as the president of the Central Indiana Society of the Archaeological Institute of America and the co-PI of the Collaboratory for GIS and Mediterranean Archaeology. Outside of her professional life, Rebecca is passionate about Italian food and enjoys exploring traditional markets and learning new recipes.

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Departure: Oct 2 - 10, 2027

Andrew Becker

Cultural Historian

Dr. Andrew Becker was born in Burma (Myanmar), spent part of his childhood in Indonesia, and has continued to travel ever since—mostly Europe and Asia.  …

Dr. Andrew Becker was born in Burma (Myanmar), spent part of his childhood in Indonesia, and has continued to travel ever since—mostly Europe and Asia.  He has been lecturing in Italy since 1997, first as a professor teaching students abroad, then since 2015 with Smithsonian Journeys.  Andy is an associate professor in the Department of Modern and Classical Languages and Literatures at Virginia Tech (with stints teaching in Switzerland and London), and has won numerous local and national awards for teaching. He earned a BA from the University of Michigan, a master’s from Cambridge University, and a PhD from the University of North Carolina at Chapel Hill.

Andy’s scholarly specialties are ancient: specifically the cultures, literatures, and languages of Ancient Rome and Greece, as well as the constant, recurring re-engagement of many later civilizations with Ancient Rome and Greece.

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Departure: Oct 16 - 24, 2027

Pedar Foss

Classicist

Pedar W. Foss is Professor of Classical Studies at DePauw University in Greencastle, Indiana, where he has worked since 1999. As Dean of Academic Life …

Pedar W. Foss is Professor of Classical Studies at DePauw University in Greencastle, Indiana, where he has worked since 1999. As Dean of Academic Life from 2009-13, his duties included oversight of student advising, academic support, off-campus and service learning, and career services. As a teacher, he conducts courses in Latin, ancient history and literature, and art and archaeology. He received his B.A. in Chemistry and Classics from Gustavus Adolphus College, and his Ph.D. in Classical Art and Archaeology from the University of Michigan-Ann Arbor; he subsequently taught at the University of Cincinnati and at Stanford. Dr. Foss has edited for the Journal of Roman Archaeology, was co-editor of the book reviews for the American Journal of Archaeology, and co-edited the volume The World of Pompeii (Routledge 2007). He has now published Pliny and the Eruption of Vesuvius (Routledge 2022), a complete re-assessment of the AD 79 disaster.  His research centers on the relationships between ancient peoples and their landscapes. He has lived, led tours, and studied throughout the Mediterranean, working at such sites as Kavousi and Corinth (Greece), Carthage (Tunisia), Troy, Hacımusalar, and Çaltılar (Turkey), Pompeii, Rieti, and Castiglione del Lago (Italy). He maintains a professional blog at: http://quemdixerechaos.com.

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Tour Details

Accommodations

Villa Neroli
Florence, Italy

Set within a historic monastery surrounded by gardens on the edge of Florence, Villa Neroli offers a relaxing oasis along with easy access to the city's historic heart.  Guest rooms are tastefully furnished in simplicity and style, and offer a host of modern amenities. Elegant Tuscan cuisine is servd in the restaurant or alfresco, and the gardens feature an inviting pool and leafy patio. The hotel has a spa and relaxation area and a gym, and a fleet of e-bikes allows guests to tour the neighborhood or ride into the city centre.

Posta Donini 1579
Perugia, Italy

Posta Donini 1579 is an elegant residence just outside Perugia that was built in the 17th century as a summer retreat.  surrounded by private woods and landscaped gardens. Two connected villas—Villa Laura and Villa Costanza—feature rooms and suites appointed with antique furnishings and marble bathrooms as well as satellite TV and air‑conditioning. The Pantagruel restaurant presents fresh Umbrian and Italian cuisine in a charming setting that once housed the villa’s watchman. Guests looking to unwind can indulge in the hydromassage pool, Turkish bath, and Finnish sauna, as well as a range of spa treatments. Amenities extend to an outdoor pool and fitness room.

Hotel Tiber
Fiumicino, Italy

At the Hotel Tiber Rooftop & Wellness in Fiumicino, every detail of their rooms is designed to offer maximum comfort and luxury. There are 64 spacious rooms, many of which have a private balcony and are furnished with a modern design that combines elegance and functionality. Each room is completely soundproofed, guaranteeing a peaceful rest even near the airport. Equipped with air conditioning, flat-screen TV, minibar and free Wi-Fi, the rooms offer everything you need for a pleasant stay.

Activity Description

Expectations: This 7-night getaway features visits to medieval cities and hilltop towns and villages and stays at two hotels. Expectations include long touring days with full-day motor coach excursions, standing and walking for long periods of time during city tours, museum visits, and outdoor activities. Daily walks of up to five miles, sometimes including difficult terrain such as cobblestones, unpaved trails, and uneven pavement, stairs without handrails or access to elevators. Longer walks may be necessary to get to villages and sites where coaches are prohibited. Most full-day excursions last from four to six hours, and there is free time throughout the itinerary.

Appropriate for: Travelers who are physically fit and are comfortable with longer days of touring including driving excursions and walking tours.

Special Air Rates/Services

The Flexible Travel Option program allows air-inclusive guests to customize their travel experience in several ways. 

Please contact us if you want to customize your arrival and departure dates. 

Air-inclusive guests are free to take advantage of any or all these benefits: 

  • Arrive at your destination up to three days before the tour’s scheduled start date  
  • Extend your travel beyond the tour’s end date  
  • Reserve transfers from the arrival airport to the tour’s first hotel, or from the tour’s final hotel to the departure airport, to coincide with your alternate travel dates  
  • Reserve extra nights at the first and/or final hotel on your tour to coincide with your alternate travel dates 

Travel Insurance

For the convenience of our travelers, Smithsonian Journeys includes a basic medical expense and evacuation plan through Trip Mate, a Generali Global Assistance & Insurance Services brand, at no additional charge. This plan provides post-departure Medical and Dental coverage of $250,000 per person and Emergency Assistance and Transportation coverage of $1,000,000 per person (U.S. Residents Only). Note: For full details regarding these coverages please review the following Plan Documents here.

In addition, we recommend that travelers purchase a travel protection plan to help protect their travel investment from unforeseen events such as cancellation due to illness, flight delays due to adverse weather, baggage loss, and more. For your convenience, Smithsonian Journeys offers an optional Travel Protection Plan administered by Trip Mate, a Generali Global Assistance & Insurance Services brand. For those interested, optional "Cancel for Any Reason" coverage is available for an additional charge. Note: Certain eligibility requirements apply and Cancel for Any Reason coverage is not available to New York residents. For full details regarding this coverage please review the following Plan Documents here.

To learn more about the Travel Protection Plan, you may visit https://www.generalipartner.com/smithsonianjourneys or call the administrator, Trip Mate, a Generali Global Assistance & Insurance Services brand at (866) 501-3252.