• $3,355
  • $600
  • AHI
  • Moderate
  • Land Only

Immerse yourself in the rhythms of daily life in Tuscany on a seven-night journey. From our base in the romantic hilltop town of Cortona, we’ll journey through the Val d’Orcia, where golden fields touch the horizon and scarlet sunsets take your breath away. During daily excursions, we’ll fall in tune with life in Tuscany and Umbria, sip Brunello di Montalcino at a country wine estate and savor locally produced cheeses. In hilltop Orvieto, witness tranquil piazzas, bubbling with local conversation, and view the village’s impressive cathedral. Marvel at Siena’s remarkable Gothic architecture, Duomo and Piazza del Campo. Stroll ancient streets in the Etruscan city of Montepulciano and linger inside the Basilica of San Francesco in Assisi, hometown of Italy’s patron saint. Along the way, enjoy lunch and delicate olive oil on a family-owned olive farm, and gain insight into Renaissance art, Tuscan cuisine, contemporary Italian life and more from local experts. This small-group program includes first-class accommodations and an extensive meal plan, complemented by wine with dinner.


(with baggage handling.)

  • 7 nights in Cortona, Italy, at the deluxe Villa Marsili.
Extensive Meal Program
  • 7 breakfasts, 3 lunches and 3 dinners, including Welcome and Farewell Dinners; tea or coffee with all meals, plus wine with dinner.
  • Opportunities to sample authentic cuisine and local flavors.
Your One-of-a-Kind Journey
  • Discovery excursions highlight the local culture, heritage and history.
  • Expert-led Enrichment programs enhance your insight into the region.
  • AHI Sustainability Promise: We strive to make a positive, purposeful impact in the communities we visit.
  • AHI Connects: Local immersion.
  • Free time to pursue your own interests.
  • Welcome and Farewell Receptions.
  • A personal VOX headset to hear your English-speaking guide clearly.
  • Tipping of guides and drivers.
  • Complimentary travel mementos.

Day by Day Itinerary

Day 1 & 2

Florence, Italy | Cortona

Arrive at Florence Airport. Proceed through immigration to the baggage claim area and retrieve your luggage. After completing customs, AHI FlexAir passengers traveling on flights that qualify for the group arrival transfer and Land Program passengers who have purchased seats on the group transfer should exit the baggage claim area and proceed to the Arrivals Hall, where an AHI Travel representative will meet you.

Transfer to the Villa Marsili. Please note, if you arrive before check-in time, your room may not be immediately available.

This evening, meet your fellow travelers during a Welcome Reception and Dinner at the villa.

Accommodations – Villa Marsili
Meals – Dinner

A Note About Activity Levels

We want you to have a comfortable and enjoyable experience. That’s why we have rated all of our excursions with activity levels to help you assess this program’s physical expectations. Activity Level ratings indicate each excursion’s physical expectations. To make the best personal choice, please evaluate each excursion’s rating and your ability to meet the tour’s physical demands. Please note excursions on this program require you to: walk on cobblestones, unpaved paths or uneven surfaces; and get on/off motor coaches, boats and trains.
1–Mild:  walk under 1 mile on mainly flat terrain; navigate under 50 stairs; stand under 1 hour
2–Moderate:  walk 1-3 miles on flat/uneven terrain; navigate 50-100 stairs; stand 1-2 hours
3–Active:  walk 2+ miles on flat/uneven terrain, including up and down inclines; navigate 100+ stairs; stand 3+ hours
Depending on the excursion, more leisurely alternatives may be available.

Day 3


Start the day with a delicious breakfast served at your hotel each morning.

Discovery: The Tuscan Countryside.
Activity level: Moderate
Travel through the patchwork of burgeoning hill country of the Val d’Orcia. Let your senses succumb to the region’s provocative beauty, a land blanketed with shimmering olive groves, bucolic farmsteads, swaying cypress trees and red poppy playgrounds. Notice the carefully tended plots of land where vineyards are heavy with grapes. These verdant properties have supported Italy’s 3,000-year heritage of savory cuisine and extraordinary wine. Spy hilltop towns and distant villages, and contemplate the historic wealth of artistic and architectural treasures left by the Etruscans, Romans and Renaissance masters. These Tuscan hills, undulating in hues of gold and emerald, are sure to be among your most treasured memories of Italy. During your excursion, enjoy a tantalizing culinary experience at a family-owned winery in the Brunello di Montalcino region. Tour the winery and sample satisfying vintages and tasty local cheeses.

Back in Cortona, enjoy some time at leisure for lunch.

Enrichment: Cortona and its Environs.
Cortona is nestled in the hills of the Arezzo province. Examine the history of this typically Tuscan town and its relationship to greater Tuscany and Italy.

Discovery: Walking Tour of Cortona.
Activity level: Moderate
Often referred to as the Mother of Troy and the Grandmother of Rome, Cortona is believed to be one of Italy’s oldest towns. Admire Cortona’s artistic and historical treasures and, as you stroll past historic palazzo and through charming piazzas, notice the village’s exceptional Etruscan features. Dwell in the heart of Cortona in the Piazza della Repubblica, and admire the nearby 13th-century town hall. Contemplate the wide Brunelleschi-style columns inside the Romanesque cathedral, which was built on the foundations of a pagan temple. Appreciate the 11th-century façade of the prominent Museo Diocesano. Inside are splendid works from Luca Signorelli, the village’s native son, and Beato Angelico, painter of The Annunciation. After your walking tour, discover jaw-dropping vistas of fertile olive groves and Lake Trasimeno from the town’s ancient porta.

Accommodations – Villa Marsili
Meals – Breakfast

Day 4


Discovery: Siena.
Activity level: Moderate
Siena claims a lofty perch atop three hills and is a treasure chest of majestic Gothic architecture, cathedrals and museums. The streets are narrow, jumbled and steep, with shrines on corners, and are bordered with ancient red brick houses and low hanging, laden clotheslines. Siena is an ideal town to explore on foot as you can study the carvings above old doorways and count the brick bridges in ancient alleys.

All roads in Siena eventually lead to the Campo, the huge main square at the heart of the city. It is shaped like an amphitheater — the Sienese like to think that it is shaped like the protecting cloak of the Virgin, the city’s patron saint. This plaza is also the site of the bi-annual Palio horse race, one of Siena’s longest standing and most anticipated cultural traditions. See the architecture surrounding the Piazza including the 14th-century Torre del Mangia, the Piazza Chapel and the Civic Museum. Then step into a true masterpiece of Italian Romanesque-Gothic architecture when you visit the Duomo, home to fascinating works of art and sculpture.

Free Time: Enjoy lunch at leisure and spend time exploring Siena on your own. As you discover the peaceful ambience of Siena, feel your inner pace slow during a relaxing stroll. Savor a coffee at a sidewalk café, a perfect environment for participating in local life. Meander through the winding cobblestones or climb to the top of the Torre Mangia where you can admire a landscape of sprawling grapevines and hayfields. Before departing Siena, be sure to peak into one of Siena’s many specialty food shops to taste two Sienese staples: panforte and ricciarelli.

Enrichment: Renaissance Art.
Learn how the increased awareness of nature, the revival of classical learning and the more individualistic view of humanity shaped the art of the Renaissance.

Enjoy Tuscan fare for dinner at a local restaurant in Cortona while sharing your day’s highlights and adventures.

Accommodations – Villa Marsili
Meals – Breakfast and Dinner

Day 5


Discovery: A Taste of Orvieto.
Activity level: Moderate
Built by the Etruscans atop a rocky plateau, Orvieto stands sentry over the green Umbrian countryside. A walk through Orvieto is like brief glimpse into history! While strolling along the cobblestone streets, stop to visit the 12th-century Gothic-Romanesque Duomo that boasts a brilliant façade rendered in marble and colorful mosaics. The 14th-century Pozzo di San Patrizio (Saint Patrick’s Well) is based on a design of Antonio da Sangallo, and it has its double helix staircase.

Free Time: Enjoy some leisure time to make your own discoveries.

Discovery: Olive Mill Outing.
Activity level: Moderate
Visit a family-run olive mill for a guided tour and learn about the fascinating history and cultivation process of olives. Enjoy the smooth, sweet smells and buttery flavors of these regional specialties. Then relax over lunch at the olive mill before returning to Cortona.

Accommodations – Villa Marsili
Meals – Breakfast and Lunch

Day 6


Enrichment: A Contemporary View of Italy.
Attend an engaging discussion of Italy’s place in the European Union and an assessment of its modern-day political, economic and social status.

Discovery: Montepulciano.
Activity level: Active
Depart Cortona and travel through the Val di Chiana to the ancient Etruscan city of Montepulciano. En route to this walled-in city, stop below the hills of Montepulciano for a visit to the Church of the Madonna di San Biagio. Consecrated by Pope Clement VII in 1529, the church features large arches and bell towers. In Montepulciano, walk with your group up to Piazza Grande.

Free Time: Enjoy leisure time in Montepulciano. Revel in the scents and sounds of this special town — the aroma of cappuccino and warm baked goods wafting from little shops, the perfume of fresh flowers and the bustle of the main square. Lounge in a shaded corner of Piazza Grande and revel in its captivating atmosphere. Savor the sights of local Tuscan life around you; children engaged in a lively soccer game and silver-haired women slowly make their way to market. Near the Palazzo Comunale, soak up incredible panoramic vistas, perhaps spotting Siena and Mount Cimone in the distance! Then stroll the main street from the Piazza Grande to the bottom of the hill, taking time to chat with artisans in their workshops and peek into centuries-old wine cellars filled with famous Vino Nobile.

Dine on classic Tuscan cuisine for lunch in Montepulciano.

Free Time: The remainder of your evening is at leisure in Cortona to make your own discoveries.

Accommodations – Villa Marsili
Meals – Breakfast and Lunch

Day 7


Discovery: Assisi.
Activity level: Active
Encounter the magnificent walled city of Assisi. Stroll through Assisi and visit the Basilica of San Francesco, which is dedicated to the town’s most famous resident, St. Francis. Step inside the Basilica of Santa Maria degli Angeli, and enjoy free time in Assisi for lunch and leisure.

Explore the evening charm of Cortona while dining on your own.

Accommodations – Villa Marsili
Meals – Breakfast

Day 8


Discovery: Museum of the Etruscan Academy.
Activity level: Moderate
Discover the artistic legacy of the Etruscans, who first settled in what now is Cortona. Visit the 14th-century Praetorian Palace. Inside, the Museum of the Etruscan Academy will astound you with archaeological finds and important Etruscan, Greek, Roman and Egyptian works of art, mosaics and collections of engraved gems. Among its prized possessions is a bronze lamp from the fifth century B.C., decorated with alternating male and female figures.

Discovery: Tuscan Cooking.
Activity level: Moderate
Enjoy a delightful opportunity to learn about Tuscan cuisine as you watch a cooking demonstration. Afterward, savor a lunch of delicious Italian fare.

Tonight, gather with your fellow travelers for a Farewell Reception and Dinner.

Accommodations – Villa Marsili
Meals – Breakfast, Lunch, and Dinner

Day 9

Depart for gateway city

After breakfast, bid farewell to Tuscany. AHI FlexAir passengers traveling on flights that qualify for a group transfer and Land Program passengers who have purchased seats on the group transfer depart for Florence Airport for your return flights home. Your Travel Director will provide the details.

Meals – Breakfast and appropriate in-flight meal service