The medieval hill towns of Tuscany and Umbria take center stage on this relaxed, 8-day road trip through the Italian countryside. Starting in the ancient city-state of Cortona, you'll set out on day trips to the stunning fortified towns of Montepulciano and Arezzo, discovering a treasure trove of Renaissance art and architecture. Hop over to quieter Umbria for spectacular scenery and more magical hilltop locales, visiting historic fortresses, cathedrals, and cities from your base in beautiful Assisi.


  • Marvel at the Tuscan countryside from your base in Cortona
  • Discover Renaissance art & architecture on day trips to Montepulciano & Arezzo
  • Explore lesser-known Umbria from the historic hill town of Assisi
  • Take in bird's-eye-views from the soaring Ponte delle Torri in Spoleto

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Florence, Drive to Cortona Cortona
Day 2 Day Trip to Montepulciano, Stop in Pienza Cortona
Day 3 Day Trip to Arezzo Cortona
Day 4 Drive to Assisi, Afternoon Walking Tour Assisi
Day 5 Day Trip to Perugia Assisi
Day 6 Day Trip to Spello & Gubbio Assisi
Day 7 Day Trip to Spoleto & Rocca of Albornoziana Assisi
Day 8 Assisi to Rome, Departure  

Detailed Itinerary

Day 1: Arrive in Florence, Drive to Cortona

Charming side streets in Cortona

Welcome to Italy! Upon arrival at the Florence Airport, you'll be met by your personal concierge, who will help you pick up your rental car and answer any questions you may have about your trip. Then it's time to set off into the Tuscan countryside, driving 1.5 hours south to the postcard-perfect hilltop town of Cortona. With Etruscan roots dating back to the 5th century BCE, the town was one of the region's most evolved medieval city-states, and it still boasts a dizzying selection of Renaissance art and architecture. It will serve as your base for the next three nights as you explore the surrounding hill towns and landscapes.

Get settled into your accommodations, then head out for a stroll around Cortona's main plaza and cobblestone streets. Highlights include the Piazza della Republica, Cortona's main square that dates back to the Roman age, Palazzo del Capitano del Popolo, the 16th-century residence of Cardinal Passerini, and the Palazzo Comunale. Visit the Medicea Fortress, erected in 1556 on the ruins of an Etruscan wall, and don't miss the Cathedral, constructed at the end of the 15th century.

Venture inside some of its museums to travel back in time. The MAEC Museum holds precious Etruscan artifacts and the Diocesan Museum is home to an array of Renaissance paintings. Head just outside of Cortona to the Monastery of  Saint Francis “Le Celle” for a peaceful experience and spectacular views of the surrounding valley. 

Day 2: Day Trip to Montepulciano, Stop in Pienza

The village of Pienza in the Val d'Orcia.
The village of Pienza in the Val d'Orcia.
Time to head further into the Tuscany countryside, visiting the famous village and surrounding wine region of Montepulciano. While driving, enjoy breathtaking views along the way with a stop at Pienza. Stretch your legs in the tiny village, which stands atop a high hill above the Orcia Valley. The charming town is known as the "ideal city of the Renaissance" and was designed by Enea Silvio Piccolomini, who later became Pope Pius II. Piccolomini used his money and influence to transform his birthplace village, then known as Corsignano, into his ideal Utopian Renaissance city.

The harmonious composition of the city includes the Cathedral, the Papal or Piccolomini Palace, the Town Hall, and the central square which sits between the buildings. Visit the Duomo or Cattedrale dell'Assunta to see unique paintings and the octagonal bell tower, and continue to the Palazzo Piccolomini to admire the hanging gardens, as well as the shooting locations for Franco Zeffirelli's film Romeo and Juliet.

Continue on your way to the historic village of Montepulciano, which sits along a ridge and is surrounded by walls and fortifications. Montepulciano is famous for its Renaissance buildings, churches, and historical Corso main street which leads through town, ending at the Piazza Grande—the town's main civic and religious center.

Tour the Piazza to see the Palazzo Comunale, the castle-like town hall with an iconic clock bell. Climb to the top for views of the Tuscan hillside, then visit the spartan 15th-century Duomo, whose unfinished facade stands out from the surrounding buildings. Continue to the Palazzo Cappelli and Gothic Palazzo Neri Orselli to see regional and national art.
As evening falls, return to Cortona in time for dinner and a spectacular Tuscan sunset.

Day 3: Day Trip to Arezzo

Piazza Grande - Arezzo
Piazza Grande - Arezzo

This morning you'll drive 40-minutes north to Arezzo, a handsome medieval hill town of Etruscan origins. Not usually included in the busiest tours of Tuscany, the town is a hidden gem that maintains its authentic traditions, architecture, and beauty and offers an escape from the crowds. Its exquisite medieval square is one of the city’s main attractions, famously used in the Oscar-winning film Life is Beautiful

For art lovers, Arezzo is a true delight. It is mainly thanks to the legacy left by its two most gifted sons: the stunning frescos by Piero Della Francesca in the Church of San Francesco, and the main square Piazza Grande with the elegant loggia designed by Vasari (the same Vasari who planned the Uffizi in Florence.)

Beyond this, the impressive Church of Santa Maria Della Pieve and the Cathedral are also definitely worth a visit. A walk in the streets around Piazza Grande reveals picturesque corners, old botteghe (shops), and medieval buildings like the Palazzo Pretorio, its façade covered in coats of arms. It's also the perfect spot to relax and have a drink. The famous loggia, which once hosted artisan stalls, is now home to trattorias and coffee shops. On the first weekend of every month, the piazza becomes the grand setting for the most popular antique fair in Tuscany.

Take your time exploring Arezzo's many delights before heading back to Cortona for the night.

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Day 4: Drive to Assisi, Afternoon Walking Tour

Explore Umbria from the beautiful hill town of Assisi

This morning you'll bid Tuscany farewell and drive towards Umbria—a lesser-visited region that's equally stunning in its landscapes and hilltop towns. Your destination is the charming town of Assisi. Renowned as a pilgrimage destination and as the birthplace of Saint Francis, Assisi contains a wonder of medieval streetscapes to explore. 

After checking in to your hotel, take the afternoon to experience Assisi with a private walking tour to hear about the rich history that made the town into the marvel that it is today.  See for yourself the incredible Basilicas of Saint Chiara and Saint Francis and the artworks they hold, and tour the maze of cobblestone streets with your expert guide. Explore the city's unique architecture and take time to soak in the impressive views it offers of the Umbrian valley below.

In the evening, head to the stunning main square of Assisi, Piazza del Comune, to feel the town come to life as you pop into a nearby trattoria for dinner.

Day 5: Day Trip to Perugia

Views from Perugia
Rooftops of Perugia

Today's 30-minute drive takes you to the regional capital of Perugia, one of Italy's most underrated gems and a perfect day trip to compliment your Umbrian adventure. With its hilltop location and medieval architecture, the city is also home to one of Italy's oldest universities as well as an annual chocolate festival and summer jazz festival—giving it a new fresh vibe and a plethora of cafes and boutiques to explore. 

You'll feel one with the locals as you stroll amongst the ancient architecture and explore its many plazas, alleys, and archways. Venture to the central Piazza IV Novembre to get a feel for the city's enchanting atmosphere. Time seems to stand still as locals sit on the steps of the Gothic-style Cathedral soaking the sun or chatting, surrounded by centuries-old architecture. 

Day 6: Day Trip to Gubbio & Spello 

Panoramic views over Gubbio

Explore more of Umbria's charms today, as you drive 45-minutes north through picturesque countryside to reach Gubbio. Stacked at the base of a densely forested mountain, this magical, medieval hill town is famous for its beautiful Cathedral, home to an array of 16th-century treasures. Start your explorations at the scenic and panoramic Piazza Grande, which hosts the Gothic-style Consul's Palace. Inside you'll find the Municipal Museum, home to the seven "Eububine Tables," ancient bronze tablets dating to the third and fourth centuries BCE. 

In front of the Cathedral, you'll find the Ducal Palace, built in the 15th century for Duke Federico da Montefeltro. Admire the studio (a complete replica of which can be found in the Metropolitan Museum in New York) and stroll the wonderful inner courtyard, consisting of a series of arches supported by decorated columns.  

Don't miss a visit to St. Ubaldo's House, the ancient tower house where Gubbio's patron saint used to live. This structure dates back to a period between the 13th and 14th centuries, as evidenced by some traces of the original wall decorations on the inside.

In the afternoon, why not venture over to the nearby village of Spello? Just a 20-minute drive down the road, this little gem is home to a yearly flower festival that fills the place with incredible color. Take a couple of hours to explore its postcard-worthy streets and plaza, before heading back to your accommodations in Assisi for the evening.

Day 7: Day Trip to Spoleto & Rocca of Albornoziana

The Ponte delle Torri leading to Spoleto
The ancient capital of the Lombard dukes, Spoleto is a 35-minute drive south of Assisi, and the perfect destination for your penultimate day in Italy.  Of the hill town's scenic setting, author Herman Hesse famously wrote: "Spoleto is the most beautiful discovery I made in Italy... there is such a wealth of beauty almost unknown, mountains, valleys, forests of oaks, monasteries, waterfalls!"
Upon arrival, soak up the atmosphere of the Roman Empire with a visit to the remains of its 1st century AD Roman Theater, a stunning stone amphitheater that is still used for various shows and performances. 

Then stroll over to the Piazza del Duomo to visit the Cathedral, a rare example of Romanesque architecture with frescoes by Pinturicchio and Filippo Lippi, and the beautiful Roman House, attributed to the mother of Emperor Vespasian Polla.

Towering over the city is the formidable Rocca Albornoziana, a 14th-century fortress that hosted popes and governors during the heydays of the Renaissance. Surrounded by high perimeter walls and six square towers, it remains the iconic symbol of the city and is divided into two distinct areas: the main courtyard, with the National Museum of the Duchy, and the courtyard of arms, with an outdoor theater. If you're not afraid of heights, take a walk across the Ponte delle Torri (Bridge of the Towers) which connects the fortress and the neighboring town of Monteluco. Spanning 754 feet (230 m), the dizzying walkway was probably built between the 13th and 14th centuries. Today it offers spectacular bird's eye views across the Umbrian landscape.
As the day draws to a close, return to Assisi, where you can celebrate your final night in Italy with a memorable dinner.

Day 8: Drive to Rome, Departure

Sunset over Assisi
After breakfast, say your goodbyes to Umbria as you hit the road for a 2.5-hour drive to the Rome Fiumicino Airport to drop off your rental car and catch your departing flight. Arrividerci!

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