Seven ways to travel Italy
Make the most of your time in Italy with a curated itinerary and a private driver.
Picture starting your morning in bustling Rome and ending the day sipping wine at golden hour on the cliffs of Orvieto. On the private car ride there, you pass dramatic volcanic landscapes and charming medieval villages. You stop to explore artistic Calcata Vecchia, and then Civita di Bagnoregio, a hilltop city being reclaimed by nature. This is just day one of our three-day excursion through Lazio and “Italy’s Green Heart,” Umbria.
Our itinerary suggestions help you make the most of your transit time with food, history, art, and culture. Whether you only have three days or six, a private driver makes it possible. These trips use classic destinations as overnight home bases and take the roads less driven between them. You’ll find the best of both Italy’s popular cities and its lesser-known highlights.
Italy’s diverse scenery shifts dramatically even on short journeys. On the train, you’re not immersed in these landscapes and often miss out on places off the main routes.
Italy looks different from a car window. The road between cities always has somewhere worth exploring.
About the authors
Evgenii Shchrebinin is a Europe-based content curator always in search of the continent's most captivating corners and hidden culinary gems. Morgan Carpenter is a US-based travel writer eager to plan her next culinary tour of Italy.
Highlights of Umbria: Roman ruins, cliff views, and traditional art
Maximize your sightseeing on a short three-day trip through Lazio and Umbria. You’ll start and end in Rome, spending one night in Orvieto and one in Assisi. On the way, your private driver will also take you to underrated destinations like Civita di Bagnoregio and Calcata Vecchia.
Maximize your sightseeing on a short three-day trip through Lazio and Umbria. You’ll start and end in Rome, spending one night in Orvieto and one in Assisi. On the way, your private driver will also take you to underrated destinations like Civita di Bagnoregio and Calcata...
Culinary adventures from Emilia-Romagna to the Valtellina Valley
Enjoy a 5-day journey that meanders from southern food capitals to alpine landscapes near the Swiss border. Start in Bologna and stay in Modena, Verona, Lago d’Iseo, and Sondrio, before ending your adventure in Tirano.
Enjoy a 5-day journey that meanders from southern food capitals to alpine landscapes near the Swiss border. Start in Bologna and stay in Modena, Verona, Lago d’Iseo, and Sondrio, before ending your adventure in Tirano.
Day 1: Bologna to Modena
Stop 1: Castelfranco Emilia
Sample homemade pasta in this quiet town thought to be the birthplace of tortellino.
Stop 2: Ferrari Museum Maranello
Stop in the Ferrari Museum, a massive immersive showcase of the classic Italian car.
Stop 3: Acetaia Giusti
Try balsamic vinegar from the world's oldest producer.
Arrival in Modena
Spend the night in elegant Modena, the birthplace of balsamic vinegar and home to a range of other incredible flavors.
Day 3: Verona to Lago d'Iseo
Stop 1: Brescia
Explore uncrowded Roman ruins at the Brixia Roman Forum, the largest archaeological complex in Northern Italy.
Stop 2: Ca' del Bosco (Franciacorta Wine Region)
Relax at this luxury estate in Italy’s capital of traditionally produced sparkling wine.
Stop 3: Dispensa Franciacorta in Adro
Enjoy upscale dining at this restaurant and enoteca (“wine library”) surrounded by lush vineyards.
Arrival in Iseo
Stay the night in Iseo, on the banks of the glassy Lago d’Iseo, an uncrowded natural wonder.
Day 5: Sondrio to Tirano
Stop 1: Teglio
Unwind on the sunny terraces of this mountain village, indulging in its signature dish, pizzoccheri.
Stop 2: Nino Negri Winery
Sip on the product of “heroic viticulture” (growing in extreme conditions) at this prestigious estate.
Arrival in Tirano
Stay in Tirano for a night, immersed in this storied town right near the Swiss border.
Southern Italy’s beaches, villages, and wines: from Puglia to Basilicata
Embark on a 6-day tour of Italy’s Southern cities. You’ll see everything from windswept coastal towns to historic villages and mysterious cave systems. Start and end in Bari, staying in Matera, Lecce, Ostuni, Alberobello, and Polignano a Mare, with sightseeing stops each day.
Embark on a 6-day tour of Italy’s Southern cities. You’ll see everything from windswept coastal towns to historic villages and mysterious cave systems. Start and end in Bari, staying in Matera, Lecce, Ostuni, Alberobello, and Polignano a Mare, with sightseeing stops each day.
Day 1: Bari to Matera
Stop 1: Altamura
Stop in the capital of southern bread-making and sample traditional sourdough.
Stop 2: Gravina in Puglia
Marvel at this canyon town and its dramatic stone bridge over a limestone ravine.
Arrival in Matera
Spend the night in this mysterious city built around ancient cave dwellings.
Day 2: Matera to Lecce
Stop 1: Grottaglie
Immerse yourself in Italian ceramic arts in this historic town.
Stop 2: Manduria
Visit one of Italy’s most famous wine regions and the birthplace of Primitivo di Manduria red wine.
Stop 3: Gianfranco Fino Winery
Dive further into world-renowned wine production at this modern estate.
Arrival in Lecce
Wrap up the day and admire Lecce’s theatrical architecture and Barocco Leccese style stonework.
Day 4: Ostuni to Alberobello
Stop 1: Cisternino
Visit a welcoming town known for its “ready ovens” culture and hilltop views.
Stop 2: Locorotondo
Explore this circular town with scenic valley views and an abundance of locally produced wine.
Arrival in Alberobello
Find yourself in a fairytale for the night in Alberobello, famous for its cone roofs and winding streets.
Day 5: Alberobello to Polignano a Mare
Stop 1: Castellana Caves
Sink underground into this 90-million-year old cave system featuring winding tunnels and crystal deposits.
Stop 2: Monopoli
Visit a traditional fishing port and admire the postcard-esque red-and-blue wooden boats.
Arrival in Polignano a Mare
Stay the night in this dramatic coastal town balanced on cliffs above clear blue water.
Slow Tuscany: vineyards, valleys, and hill towns
Embark on a scenic adventure centered on Tuscany’s history and culinary impact. Your 5-day journey begins and ends in Florence with your professional driver. On the way, you’ll spend the night in San Gimignano, Siena, Montalcino, and Pienza, with additional sightseeing each day.
Embark on a scenic adventure centered on Tuscany’s history and culinary impact. Your 5-day journey begins and ends in Florence with your professional driver. On the way, you’ll spend the night in San Gimignano, Siena, Montalcino, and Pienza, with additional sightseeing each da...
Day 1: Florence to San Gimignano
Stop 1: Impruneta
Explore Tuscany’s terracotta capital and watch local artists uphold centuries-old traditions.
Stop 2: Certaldo
Stop in this hilltop medieval village, the birthplace of the writer Boccaccio.
Arrival in San Gimignano
Spend the night in this iconic town, its skyline dominated by 14 medieval towers.
Day 2: San Gimignano to Siena
Stop 1: Colle di Val d’Elsa
Start your day in Italy’s “crystal capital,” known for its blown glass and multi-level layout.
Stop 2: Monteriggioni
Feel like you’re stepping into a fantasy novel as you enter Monteriggioni, a town surrounded by a defensive wall, famously appearing in Dante’s Inferno.
Arrival in Siena
Stay for a night in historic Siena, boasting Gothic architecture and a rich collection of art.
Day 3: Siena to Montalcino
Stop 1: Territorial Abbey of Monte Oliveto Maggiore
Kick off the day at this active Benedictine Monastery hidden in a cypress forest.
Stop 2: Buonconvento
Stroll through a walled medieval village, a quiet retreat packed with mud-brick buildings and flowering alleys.
Stop 3: Podere Le Ripi
Just before reaching Montalcino, stop at this biodynamic (“beyond organic”) wine estate.
Arrival in Montalcino
End your day in Montalcino, perched on a hilltop and known around the world for its Brunello wine.
Day 4: Montalcino to Pienza
Stop 1: San Quirico d'Orcia
Be mesmerized by this walled, Etruscan town tucked into the rolling Val D’Orcia landscape.
Stop 2: Bagno Vignoni
Unwind in this thermal village, built around a central square of steaming volcanic water.
Stop 3: Podere Il Casale
Indulge in a farm-to-table lunch at this organic farm just outside of Pienza.
Arrival in Pienza
Stay the night in an elegant town remodeled at the behest of Pope Pius II.
Day 5: Pienza to Florence
Stop 1: Montepulciano
Visit this iconic Renaissance town, home to cathedral-like wine cellars and elaborate palaces.
Stop 2: Castellina in Chianti
Enjoy one last stop on your way to Florence at this fortified medieval town and wine hotspot.
Arrival in Florence
Return to Florence, Tuscany’s crowning gem and the heart of the Renaissance.
The best of Sicily: coastlines, mountains, and cultural heritage
Trace your ancestral routes through Sicily’s sun-drenched coastal towns and dramatic interior mountains. Your 5-day journey starts in Palermo and includes nights in Cefalù, Corleone, Agrigento, Piazza Armerina, and Catania.
Trace your ancestral routes through Sicily’s sun-drenched coastal towns and dramatic interior mountains. Your 5-day journey starts in Palermo and includes nights in Cefalù, Corleone, Agrigento, Piazza Armerina, and Catania.
Day 1: Palermo to Cefalù
Stop 1: Bagheria
Wander this small town known as the “City of Villas,” once a retreat for Palermo’s royalty.
Stop 2: Caccamo
Stop in this medieval hilltop town crowned by a spectacular Norman castle, one of the largest in Italy.
Arrival in Cefalù
Step into a postcard for the night in charming Cefalù, where rugged cliffs collide with the sparkling Tyrrhenian Sea.
Day 2: Cefalù to Corleone
Stop 1: Castelbuono
Take your first sightseeing break in medieval Castelbuono, surrounded by the Madonie Mountains.
Stop 2: Real Casina di Caccia di Ficuzza
Explore a neoclassical hunting lodge once used by King Ferdinand IV.
Arrival in Corleone
Spend the night in Corleone, a town steeped in history and surrounded by dense forests and dramatic cliffs.
Day 5: Piazza Armerina to Catania
Stop 1: Caltagirone
See Sicily’s ceramic capital, a UNESCO World Heritage site honed by its artistic culture.
Stop 2: Grammichele
Explore this unique hexagonal city, rebuilt after an earthquake in 1693.
Arrival in Catania
End your trip in volcanic Catania, Sicily’s bustling second city.
Italy as seen on screen, from “The Godfather” to “007”
Take a 3-day journey through some of Italy’s most iconic filming locations. Let a private driver guide you through mountain passes and coastal roads as you leave Rome for nights in Sperlonga, Maratea, and Matera.
Take a 3-day journey through some of Italy’s most iconic filming locations. Let a private driver guide you through mountain passes and coastal roads as you leave Rome for nights in Sperlonga, Maratea, and Matera.
Day 1: Rome to Sperlonga
Stop 1: Sermoneta
Start your adventure in this walled medieval village that appeared in Italian comedy We Just Have to Cry and the period drama The Red Violin.
Stop 2: Sabaudia
Stop in this sleek coastal town favored by filmmakers for its uniquely geometric Rationalist architecture.
Arrival in Sperlonga
Stay the night in whitewashed, breezy Sperlonga, the backdrop for Contempt starring Brigitte Bardot.
Day 2: Sperlonga to Maratea
Stop 1: Certosa di Padula
Explore the largest monastery in Italy, containing centuries of history.
Stop 2: Sapri
See the train station where 007 parts with Madeleine Swann in No Time to Die and explore the rest of this coastal gem.
Arrival in Maratea
Close out the day at the “Pearl of the Tyrrhenian,” where mountains meet the sea in a dramatic and unforgettable landscape.
Day 3: Maratea to Matera
Stop 1: Aliano
Immerse yourself in the surreal natural beauty that made the silver screen in Francesco Rosi’s Christ Stopped at Eboli.
Stop 2: Craco Ghost Town
Wander this abandoned medieval village used in Mel Gibson’s The Passion of the Christ, and Marc Forster’s 007 film Quantum of Solace.
Arrival in Matera Arrive for a night in one of the world's oldest and most fascinating cities, used as a backdrop in The Passion of the Christ and No Time to Die.
Inland Campania highlights: volcanoes, winemaking, and Roman ruins
This 5-day trip takes you inland to Campania’s volcanic landscapes and ancient royal powerhouses. Start in Naples, spending nights in Caserta, Capua, and Benevento, while stopping for sightseeing each day.
This 5-day trip takes you inland to Campania’s volcanic landscapes and ancient royal powerhouses. Start in Naples, spending nights in Caserta, Capua, and Benevento, while stopping for sightseeing each day.
Day 1: Naples to Caserta
Stop 1: Herculaneum
Explore a unique alternative to Pompeii in this Roman town preserved by hot volcanic mud after Mount Vesuvius’ eruption.
Stop 2: Mount Vesuvius
Witness the foreboding giant whose infamous eruption redefined the region.
Arrival in Caserta
Spend the night in the royal city of Caserta, known for its massive royal palace and cascading waterfalls.
Day 2: Caserta to Capua
Stop 1: Belvedere San Leucio
Take the day’s first stop in Belvedere San Leucio, a unique site that’s part royal palace and part socialist village.
Stop 2: Basilica of Sant’Angelo in Formis
Take an hour to marvel at this medieval wonder built on top of ancient Roman ruins.
Arrival in Capua
Spend the night in Capua, a charming medieval escape tucked into a bend of the Volturna River.
Day 3: Capua to Benevento
Stop 1: Amphitheater of Santa Maria Capua Vetere
Head just outside of Capua to Italy’s second largest amphitheater, where the legendary Spartacus trained and led a gladiator revolt.
Stop 2: Montesarchio Castle
Deep dive into the region’s archaeological marvels at this imposing fortress.
Arrival in Benevento
Stay the night in this “City of Witches” brimming with ancient architecture and folklore.
Day 4: Benevento to Irpinia Wine Region
Stop 1: Pietrelcina
Spend a morning wandering this quiet village, the birthplace of Padre Pio.
Stop 2: Feudi di San Gregorio
Unwind at this avant-garde wine estate and experience how Campania’s volcanic soil influences its winemaking traditions.
Return to Benevento
Spend another night in Benevento, relaxing at golden hour in the charming town.
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