Hilltop town of Orvieto rising above the Umbrian countryside with vineyards and cypress trees.

Home For Italy travel guideSeven ways to travel Italy

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.

Civita di Bagnoregio, a stone hilltop town on eroded cliffs with a footbridge and mountains behind.

Day 1: Rome to Orvieto

Visit Calcata Vecchia, the hilltop artists' village, and the crumbling clifftop Civita di Bagnoregio, then overnight in Orvieto.

Pale stone hill town of Assisi with bell towers and cypresses above the Umbrian valley in sunshine.

Day 2: Orvieto to Assisi

Enjoy a tour and tasting at Decugnano dei Barbi, then explore the peaceful town of Deruta before spending the night in Assisi.

Aerial view of Spello's rosy stone houses, twin-towered gate, and walls

Day 3: Assisi to Rome

Stop in medieval Spello for its art and architecture, then explore the mysterious Narni Underground on your return trip to Rome.

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.

Red starting-grid archway at the entrance to the Museo Ferrari in Maranello.

Day 1: Bologna to Modena

Eat fresh tortellini in Castelfranco Emilia, visit the Ferrari Museum in Maranello, and tour Acetaia Gusti before spending the night in Modena.

Mantua skyline of domes, towers, and palaces reflected in its lake on a clear day.

Day 2: Modena to Verona

Wander Mantua’s Renaissance streets and experience fairy tale wonder at Borghetto sil Mincio, then overnight in Verona.

Rows of vines across rolling hills with a farmhouse and cypresses at sunset.

Day 3: Verona to Lago d'Iseo

Visit the Roman ruins of Brescia, stop for a wine tasting at Ca’ del Bosco, dine at Dispensa Franciacorta, and overnight in Iseo.

Misty forested mountains reflected in a still lake with autumn foliage at the shore.

Day 4: Lago d'Iseo to Sondrio

See ancient cave carvings at Naquane National Park before continuing on to alpine Sondrio, where you’ll spend the night.

Aerial view of Tirano with the Basilica della Madonna and vineyards on the hillsides.

Day 5: Sondrio to Tirano

Try pizzocherri in the village of Teglio, then enjoy a wine tasting at Nino Negri before spending a night in Tirano.

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.

Stone aqueduct bridge over the ravine at Gravina in Puglia, with the old town above.

Day 1: Bari to Matera

Visit Altamura for local bread, then see Gravina in Puglia for its dramatic bridge, before heading to Matera for the night.

Stone arch framing a baroque church and war memorial in a tree-lined square.

Day 2: Matera to Lecce

Find ceramic perfection in Grottaglie, sip iconic red wines in Manduria, and tour the Gianfranco Fino Winery en route to Lecce for the night.

Whitewashed hilltown square with cafe tables and umbrellas at golden hour.

Day 3: Lecce to Ostuni

Stroll through the peaceful Abbazia di Santa Maria di Cerrate, visit walled Carovigno, and then stay overnight in Ostuni.

Cone-roofed trulli houses lining a sunlit cobbled street with flowers.

Day 4: Ostuni to Alberobello

See hilltop views in Cisternino, explore scenic Locorotondo, then overnight in fairytale-esque Alberobello.

Whitewashed clifftop town of Polignano a mare above turquoise sea with a boat passing below.

Day 5: Alberobello to Polignano a Mare

Stop to explore Castellana Caves and the fishing town of Monopoli, then stay overnight in Polignano a Mare.

Aerial view of an old town's rooftops and two basilicas beside a blue sea.

Day 6: Polignano a Mare to Bari

On the way back to Bari, stop in seaside Mola di Bari for its fortress, promenade, and incredible seafood.

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.

Hilltop medieval village above green fields with distant towers on the horizon.

Day 1: Florence to San Gimignano

Visit Tuscany’s terracotta capital, Impruneta, and the hilltop village of Certaldo before staying overnight in San Gimignano.

Terracotta rooftops climbing a wooded hillside to a stone bell tower.

Day 2: San Gimignano to Siena

Admire the crystal arts of Colle di Val d’Elsa, explore fantastical Monteriggioni, and spend the night in Siena.

Quiet brick-lined lane with potted plants, stone steps, and an archway.

Day 3: Siena to Montalcino

Explore the peaceful abbey of Monte Oliveto Maggiore, wander the walled Buonconvento, enjoy a tasting at Podere Le Ripi, and overnight in Montalcino.

Horti Leonini garden in San Quirico d'Orcia, below the town's rooftops.

Day 4: Montalcino to Pienza

See quaint San Quirico d’Orcia and thermal Bagno Vignoni, stop for lunch at Podere II Casale, and overnight in Pienza.

Cypress-lined gravel road winding uphill toward a Tuscan villa.

Day 5: Pienza to Florence

Stop in the wine-forward towns of Montepulciano and Castellina in Chianti on your way back to Florence.

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.

Cefalu's seafront houses and turquoise bay beneath the town's rocky crag.

Day 1: Palermo to Cefalù

Visit Bagheria’s unique villas and Caccamo’s hilltop castle before staying the night in Cefalù.

Stone archway framing a village street, bell tower, and green mountain.

Day 2: Cefalù to Corleone

Visit medieval Castelbuono and a royal hunting lodge, Real Casina di Caccia di Ficuzza, on the way to Corleone for the night.

Temple of Castor and Pollux in Agrigento's Valley of the Temples.

Day 3: Corleone to Agrigento

Enjoy a quiet break in mountainous Palazzo Adriano on your way to Agrigento for the night.

Building clad in multicolored tiles at the end of a narrow stone alley.

Day 4: Agrigento to Piazza Armerina

Experience a vibrant outdoor art hub, Farm Cultural Park, on the way to Piazza Armerina, where you’ll stay overnight.

Hand-painted ceramic vase on tiled steps decorated with blue and yellow patterns.

Day 5: Piazza Armerina to Catania

Visit Sicily’s ceramic center, Caltagirone, and the charming town of Grammichele before ending your trip in Catania.

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.

Sabaudia's dune beach curving between the blue sea and its lagoon.

Day 1: Rome to Sperlonga

Explore the walled city of Sermoneta and the enticing coastal town of Sabaudia before an overnight in Sperlonga.

Green cliffs and a winding coast road above bright turquoise sea.

Day 2: Sperlonga to Maratea

See Certosa di Padula, a massive monastery, then visit the coastal town of Sapri, and continue to Maratea for the night.

The abandoned hilltop village of Craco perched on its rocky crag.

Day 3: Maratea to Matera

See surreal natural beauty in Aliano and visit Craco Ghost Town before ending your trip in Matera.

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.

Day 1: Naples to Caserta

Visit Herculaneum, a quieter Pompeii, and explore around Mount Vesuvius before staying in Caserta.

The ruined Roman amphitheater of Santa Maria Capua Vetere.

Day 2: Caserta to Capua

Explore unique, royal Belvedere San Leucio, see the Basilica of Sant’Angelo in Formis, and overnight in Capua.

Stone castle with a round tower on a wooded ridge before hazy mountains.

Day 3: Capua to Benevento

See Spartacus’ training ground at Santa Maria Capua Vetere Amphitheater, then explore Montesarchio Castle, and overnight in Benevento.

Hand holding a glass of red wine in front of a wooden bottle rack.

Day 4: Benevento to Irpinia Wine Region

Marvel at peaceful Pietrelcina, enjoy a wine tasting at Feudi di San Gregorio, then head back to Benevento for another night.

Naples' colorful hillside villas above the bay, with Ischia on the horizon.

Day 5: Benevento to Naples

En route to Naples, stop at the awe-inspiring Complesso Basilicale Paleocristiano for its vast art collection.

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Great Experience

Roberto L. was my driver. He was excellent. I was so happy I made the choice to book a driver with Daytrip to take me from the Rome airport to Orvieto. It was a long travel day, and extending it by taking the Leonardo Express to Termini, and then on to Orvieto was not appealing. It was really worth it to book Daytrip. Thank you Roberto! And thank you for sharing your knowledge about some of the lovely towns in Umbria!

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May 31, 2026

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June 8, 2025

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Absolutely Incredible Experience with DayTrip Italy and Alessio! We recently used DayTrip Italy for our journey from Rome to Positano, and it was hands-down one of the best decisions we made during our trip to Italy. From start to finish, the experience was seamless, professional, and thoroughly enjoyable. A huge shoutout to Alessio, our driver, who went above and beyond to make our trip comfortable, informative, and fun. He was incredibly friendly, punctual, and knowledgeable about the regions we were passing through. His driving was smooth and safe, which made the long journey feel relaxed and effortless. Alessio also shared fascinating insights about Italian history, culture, and landmarks along the way — it felt like having a personal tour guide as well as a driver! He made great recommendations for stops along the route, including a charming little town for lunch that we never would have discovered on our own. Alessio was attentive to our needs and made sure we were comfortable the entire time. We genuinely felt cared for and appreciated his warm hospitality. If you’re considering a private transfer or day trip while in Italy, don’t hesitate to book with DayTrip Italy — and if you’re lucky enough to get Alessio, you’re in for a treat! Highly recommended!

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July 8, 2025

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Your Italy questions, answered

Most religious sites are free for visitors to enter outside of scheduled services. Major attractions like St. Peter's Basilica require tickets and are best booked in advance. Be respectful of quiet prayer times and follow posted dress codes (often requiring covered shoulders and knees).

Tipping is not required or expected in Italy, whether you're in small towns or the major cities. However, don't be surprised if you notice a "coperto" or "servizio" fee on your bill at a restaurant. This few-euro charge covers table service. Tour guides may appreciate a small gratuity.

People average 10-14 days in Italy, especially for a first trip. This allows you enough time to see the main hubs like Rome, Venice, and Florence, while stopping in smaller towns or visiting the lakes. Faster trips should focus on one or two major cities with private day trips to nearby sites.

Yes, carrying small bills is a good idea when exploring Italy, especially in small towns. Most hotels and restaurants accept major credit cards, but public restrooms, cafes, and quick meals can require cash. Leaving cash for the bill can also be faster when stopping for a quick coffee at a busy bar.

Travelers should book tickets to major attractions at least 30 days in advance for peak season visits. Booking 2-3 months in advance is best for guided tours or combination tickets for multiple attractions. Always book through an official website or reputable third-party service.

Learning a few basic Italian phrases can make it a lot easier to navigate smaller towns in Italy. In the major tourism hubs, English speakers are common, but not always in quieter rural areas. Learn polite phrases like "salve" and "grazie," and practice asking for directions and ordering food.

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