This relaxed 10-day itinerary gives you plenty of time to discover the hidden gems of central Italy. Start in eastern Marche, nestled between the Apennine Mountains and the Adriatic Sea. Tour the area's renowned wine country, settle into the medieval hill towns of Ascoli Piceno and Urbino, and spend a day exploring the tiny kingdom of San Marino. Head southwest across the mountains to end your stay in Perugia, where you'll discover its Renassaince history and immerse yourself in the regional cuisine.


  • Discover the central Italian regions of Marche & Umbria
  • Explore medieval hill towns
  • Tour & taste your way through renowned wine country
  • Visit the tiny mountaintop kingdom of San Marino
  • Experience the culture & cuisine of Perugia

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Ascoli Piceno Ascoli Piceno
Day 2 Wine Tasting in Marche & Abruzzo Ascoli Piceno
Day 3 Leisure Day in Ascoli Piceno Ascoli Piceno
Day 4 Ascoli Piceno to Urbino Urbino
Day 5 Tour San Marino Urbino
Day 6 Leisure Day in Urbino Urbino
Day 7 Urbino to Perugia Perugia
Day 8 Market Tour & Cooking Class in Perugia Perugia
Day 9 Leisure Day in Perugia Perugia
Day 10 Depart from Perugia Perugia

Detailed Itinerary

Day 1: Arrive in Ascoli Piceno

Ascoli Piceno's gleaming travertine piazzas.
Ascoli Piceno's gleaming travertine piazzas.

Welcome to Italy! Arrive at Perugia International Airport and transfer to your hotel in Ascoli Piceno. Located in the Marche region, this charming small city lies at the confluence of two rivers and is surrounded by mountains on three sides. Much of the historic center is carved of local travertine marble, giving its Renaissance plazas and squares an elegant formality. Once home to some two hundred towers in the Middle Ages, the town still boasts over fifty soaring turrets which can be seen from the surrounding countryside.

Once you’ve settled into your accommodation, head out on a walking tour of the town. Learn about the art and history of the city as you see architectural landmarks including Piazza del Popolo, Chiesa di San Francesco, and Ponte di Porta Solestà. Your local guide will share recommendations for great local restaurants and bars to end your evening.

Day 2: Wine Tasting in Marche & Abruzzo

Marche's stunning wine country.
Marche's stunning wine country.

Set out into the countryside to explore the rich winemaking traditions of Marche and neighboring Abruzzo. Arrange for a guided tour, so you're free to relax and taste the many varieties, learn about winemaking, meet wine producers, and stroll through scenic vineyards. Stop for a traditional Italian lunch to recharge before more touring and tasting in the afternoon.

Day 3: Leisure Day in Ascoli Piceno

One of the many idyllic walking routes around Ascoli Piceno.
One of the many idyllic walking routes around Ascoli Piceno.

Take today to explore Ascoli Piceno in your own time. Spend a quiet day wandering the town center, or plan an adventurous trek deep into the nearby Sibillini Mountains. Some local options include:

  • Take a stroll down Ascoli’s most romantic street. Located in the historic center, the charmingly cobbled Rua delle Stelle still holds many traces of the town's rich history
  • Discover fascinating ruins of the ancient city of Asculum, including a Roman theater located the foot of Colle dell’Annunziata.
  • Visit the Diocesan Museum and Civic Art Gallery of Ascoli, home to a small but extraordinary collection of works from the 15th century to the present.
  • Browse graphic and abstract contemporary Italian art at Galleria d'Arte Contemporanea Oswaldo Licini.
  • Try your hand at traditional Ascoli ceramic making at a local Pottery Lab experience.
  • Spend the day hiking in the spectacular Sibillini mountain range, or journey deep into the forests of the  Marche region to see the beautiful waterfalls of Prata and Volpara.

Day 4: Ascoli Piceno to Urbino

The rooftops of Urbino's medieval old town and Ducal Palace.
The rooftops of Urbino's medieval old town and Ducal Palace.

Today takes you north to the exquisitely-preserved hill town of Urbino. Nestled high above a sloping hillside, this walled fortress was a beacon of art and learning in the 16th century, and is still home to a remarkable collection of Renaissance art and architecture. Start with a walk through its atmospheric medieval center, then visit the famous Palazzo Ducale, home to the Galleria Nazionale delle Marche

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Day 5: Tour San Marino

The climb to San Marino's Rocca della Guiata castle.
The climb to San Marino's Rocca della Guiata castle.

Journey north today to spend a day in the fairytale mountain kingdom of San Marino. The fifth-smallest and arguably most intriguing of the world’s independent countries, this ancient republic sits high in Italy’s Apennine Mountains. Arrange for a personal guide to share stories of the small country's dramatic history as you stroll around the cobbled center, visiting Piazza della Libertà square, the Basilica of Saint Marino, and other highlights. Don't miss the steep climb to the precarious mountaintop First Tower; you'll be rewarded with breathtaking views of Apennine peaks and the Adriatic Sea.

Day 6: Leisure Day in Urbino

The atmospheric alleys of medieval Urbino.
The atmospheric alleys of medieval Urbino.

Get to know Urbino's myriad charms with a day spent exploring at your own pace. Visit the town's historic sites, or take a day trip farther afield to hike to ancient castles and monasteries. Some local highlights include:

  • Tour Casa Natale di Raffaello, where the 15th-century master artist Raphael was born and raised.  

  • Marvel at exquisite baroque frescoes in the small 14th-century chapel of Oratorio di San Giovanni Battista.

  • Climb to dizzying heights at the rock fortress of Forte di San Leo, where the castle’s museum hosts a large display of historical and military artifacts.

  • Hike to the beautiful forest sanctuary of La Verna—once home to the 13th-century Saint Francis. 

  • Venture underground to one of the most extensive underground cave systems in Europe at Grotte di Frasassi.

Day 7: Urbino to Perugia

Sunset over Perugia's beautiful historic center.
Sunset over Perugia's beautiful historic center.

After a leisurely breakfast, make your way southwest to the beautiful rolling landscapes of Umbria. Here you’ll settle into the region’s lively hilltop capital of Perugia. Brimming with historic sights dating back to the Etruscans, this university town attracts students from around the world and plays host to world-class galleries and an international jazz festival. 

Arrive at the upper town via a series of escalators, traveling up through the remains of the 16th-century fortress of Rocca Paolina. Spend your first afternoon in the city getting your bearings, with a self-guided ramble around the atmospheric plazas, or under the knowledgable direction of a local tour guide. Visit the Galleria Nazionale dell'Umbria (National Gallery of Umbria) to browse a prestigious collection of Renaissance and medieval art, or discover idyllic hidden gardens of the ancient church of Sant’Angelo.

Day 8: Market Tour & Cooking Class in Perugia

Make Umbria's strangozzi pasta by hand.
Make Umbria's strangozzi pasta by hand.

Today you’ll immerse yourself in Perugia’s culinary culture with a traditional cooking class. Head to a nearby market to source locally grown ingredients, then help prepare a four-course meal in the kitchen of your local host. Discover the secrets of Umbrian cuisine, learn how to pair dishes with regional wines, and finish the day with a celebratory dinner to savor your creations. 

A typical meal might start with oil and garlic bruschetta, followed by soup made with lentils grown in the heart of the nearby Sibillini Mountains. Pasta dishes are based around strangozzi, the region’s unique version of tagliatelle, and dessert is often a type of torcolo—a medieval sweetbread unique to Perugia.

Day 9: Leisure Day in Perugia

The exquisite hill town of Assisi, just 30 minutes east of Perugia.
The exquisite hill town of Assisi, just 30 minutes east of Perugia.

Today is free to explore Perugia and its surrounding areas at your leisure. Wander the historic center, take a day trip to the Umbrian countryside, or spend a lazy afternoon people-watching at an outdoor cafe. Some suggested activities include:

  • Browse the eclectic Palazzo Baldeschi al Corso museum, whose palatial 14th-century rooms showcase art and sculptures from the 16th through 20th centuries.

  • Stroll through souvenir and craft stalls in the bustling underground markets of the Rocca Paolina fortress.

  • Watch the sunset from Giardini Carducci, a tiny, picturesque park that looks out over the rooftops of the city and the Umbrian landscape beyond.

  • Take a day trip to nearby Lake Trasimeno or the famously beautiful Umbrian hill towns of Assisi and Orvieto.

Day 10: Depart from Perugia

Piazza IV Novembre, Perugia's scenic main square.
Piazza IV Novembre, Perugia's scenic main square.

It's time to say goodbye to this special corner of Italy. After one last cappuccino over breakfast, head to the airport for your connecting flight home. Safe travels!


Map of Undiscovered Central Italy: Marche, San Marino & Umbria - 10 Days
Map of Undiscovered Central Italy: Marche, San Marino & Umbria - 10 Days