You’ve Got to Try This Incredible Italian Road Trip

Let’s be honest — who hasn’t dreamed of going on an Italian road trip? Whether you’re in it to feast on food or art, tour the rolling Tuscan countryside or the rugged Mediterranean coast, there’s a reason why Italy is everyone’s bucket trip of a lifetime. Each of the Bel Paese’s 20 regions offers its own alluring attractions, from Puglia’s enchanting fairytale villages to Florence’s fabulous Rennaissance architecture. Sip on sensational chianti in Tuscany or swerve your way along Amalfi’s ribbon-like roads — a road trip through Italy is what you make it, but never anything less than spectacular.

With over 400 million visitors to HotelsCombined, we’ve compiled our users’ favorite destinations and thrown a couple of lesser-traveled gems to create the ultimate 14-day Italian road trip plan. This incredible itinerary will take you from south to north, passing through some of the best scenery in Europe. Thanks to Italy’s fantastic public transport, you can complete this entire journey by bus and train — and we’ll show you how! However, if you’d prefer to hop in your own car and travel like a local, this route features some fantastic drives and villages along the way that will leave you spellbound.

Getting In: Bari

You’ll embark on your great Italian adventure from the southern city of Bari, on the sunkissed Puglia coast. As southeast Italy’s main regional hub, Bari can be reached directly from a number of European destinations, including London, Paris, and Barcelona, so consider making this Italian road trip part of a longer Eurotrip if you have the time to spare.

Bari downtown is only 20 minutes’ drive from the airport. Moreover, it’s well worth the visit with an enchanting maze-like oldtown sandwiched between two swimming beaches. Sadly, there’s not much time to hang around. Hop straight into your rental vehicle and head onto the SS16 highway, which which will take you past olive plantations along the Adriatic Coast, passing some lovely coastal towns if you fancy stopping to stretch your legs. If you’re going by public transport, make a beeline for the Bari Largo Sorrentino bus station. While it’ll take you over an inland route, the entire journey will only take an hour and costs less than 9€.

Days One and Two: Alberobello

Local legend says that Alberobello’s conical trulli houses were built in by peasant laborers who deliberately assembled the buildings without any mortar. Apparently, this was so the buildings would appear unstable, and therefore, the peasants would be able to dodge property taxes. Clearly, appearances were deceiving, because the fairytale dwellings have since survived a little over 500 years. You won’t find anything like Alberobello’s iconic architecture anywhere else on your Italian road trip, as trulli houses have only been built in the Puglia. Their uniqueness and remarkable preservation is just one reason why the whole old town of Alberobello was made a UNESCO World Heritage Site.

What to do in Alberobello:

• Visit Trullo Sovrano — Alberobello’s only two-floor trullo house, which contains a fascinating heritage museum. The house was built in the 18th century by the family of a wealthy priest.
• Admire the rooftops from Rione Aia Piccola — Many of the 400 trulli houses in this lesser-visited district still function as family homes. Many of the gift shops have rooftop lookouts where you can admire the town from above.
• Savor Colorful Apuglian Cuisine at Il Poeta Contadino — Housed in a former stable, this family-run osteria received a Michelin Star for its delightful regional fare.

Where to Stay in Alberobello: Le Alcove Luxury Resort Nei Trulli

No stay in Alberobello would be complete without an evening in one of its magical dwellings. Le Alcove Luxury Resort offers charming accommodation inside a beautifully restored trullo house. Each of its six rooms is elegantly decorated with double beds and period furniture. If you’re traveling with children, consider request to stay in The Knight, which has an extra two twin beds set on a mezzanine level. This gorgeous hotel’s magical setting is pretty difficult to say goodbye to. So if you feel compelled to extend your stay, know that they’re currently offering three nights for the price of four.

Star Rating: 5*
Price: USD 284 – USD 329
Guest Rating: 9.2
Address: 7, P.Zza Ferdinando Iv, Alberobello, Bari, Italy

Days Two and Three: Matera

This incredibly romantic city of crumbling buildings and winding streets has its origins in the 10th millennium BC. That makes Matera one of the oldest continually inhabited cities in the world, predating both the Romans and the ancient Greeks. One of the most striking things about the city is its vertical mess of Medieval churches and dwellings, which rise out of two canyons along the Gravina River. For the most breathtaking view of this, head out to the Belvedere viewpoint, just off the Statale 7 highway. Later, make your way into the ancient city to explore the Sassi di Matera, a UNESCO World Heritage Site of paleolithic cave dwellings which were lived in right up until the 1980s. Matera can be explored in a single day, but we recommend staying overnight to savor its unique flavor before you continue on your Italian road trip.

What to do in Matera:

• Explore the city’s rock-hewn Rupestrian Churches — These unique religious structures date back to the 15th century when innovative locals carved them out of the volcanic hillside.
• Enjoy Fine Dining in a Cave-Dwelling — Located an iconic cave-dwelling, the elegant Ristorante Francesca is a great place to try the local Basciliata cuisine. In other words, plenty of succulent lamb dishes. It’s also vegetarian-friendly if that’s more your thing.
• Eat the Bread — Matera isn’t big on pizza or pasta (save that for later in your Italian road trip). Boy though, do they love to bake! Matera’s rustic local loaves a traditionally served as sandwiches but also make great bruschettas. You can also take a cooking class and learn how to make one here.

Where to stay in Matera: Sextantio Le Grotte Della Civita

Once notorious for its squalid living conditions, the Sassi di Matera has undergone a complete transformation. You’ll find yourself spoilt for choice with this area’s many boutique hotels (honorable mentions go to the elegant Palazzo Gattini). Nonetheless, we challenge you to find accommodation as enchanting as Sextantio Le Grotte Della Civita. Set across 18 cave rooms and an ancient former church (now the communal area), this gorgeous hotel has retained all of its original medieval features. Modern features include freestanding tubs and a sensuous day spa. Many rooms also have spectacular city views.

Star Rating: 4*
Price: USD 400 – USD 845
Guest Rating: 4*
Address: Via Civita 28, 75100 Matera, Matera, Italy

Day Four, Five, and Six: Amalfi

The best way to travel from Matera to Amalfi by public transport is by coach. LISCIO operates a direct service as far as Salerno, where you’ll have to change to the 5120 (Corso Giuseppe Garibaldi Station). Of course, the Basciliata countryside and world-famous Amalfi coast will have you spellbound for most of the way, so if anything, the ride is a treat.

The town of Amalfi, as you’ve probably guessed, is located on the Amalfi coast, one of Italy’s top bucket list destinations. Its central location means that you’ll be able to explore much of what this enchanting stretch of sun and sand has to offer without losing too much time to transport. In particular, spots like the gorgeous Capri island and Positano are both Amalfi coast essentials. That being said, you should save at least a half-day to savor the town of Amalfi has to offer. Such as its cliff-hugging old town and the mystical Emerald Grotto.

What to do in Amalfi:

• Check out the Beach of Duoglio — A lesser-known pebble beach accessible only by sea or a vertical 400-step staircase. Still, it’s one of the most beautiful beaches of the Amalfi Coast.
• Be astounded by the Duomo di Amalfi; Cattedrale di Sant’Andrea — Since being first built in the 9th century, the church has been modified and expanded several times throughout history, displaying an array of architectural elements.
• Enjoy local fare and fantastic views at La Tagliata — This popular Positano bistro serves unfussy regional dishes on an airy ocean-view terrace.

Where to Stay in Amalfi Coast: Santa Caterina

The Santa Caterina guarantees you wonderful memories on this part of your Italian road trip. Its two in-house restaurants, Restaurant al Mare and Glicine Restaurant, both have stunning views of the sea — Glicine also has a Michelin Star. It’s excellent selection of local wines is exquisite (check out the list here), but not as exquisite as the rooms. We particularly love the princess beds and sea-facing balconies, perfect for starting the day with an early morning caffè. Santa Caterina’s cliffside location is one of its main draws. If you want to shop around and compare the views elsewhere on the coast, we suggest Il San Pietro di Positano, just up the coast. You can check out our review of it here.

Star Rating: 5*
Price: USD 1,100 — USD 4,592
Guest Rating: 9.5
Address: S.S. Amalfitana, 9, 84011 Amalfi, Salerno, Italy

Days Seven, Eight, and Nine: Rome

What Italian road trip could be complete without a visit to the Eternal City. The high-speed rail will whip you up from Salerno to Rome in as fast as two hours. That’s time that you want to save for Rome’s time-weathered monuments, awe-inspiring art, and terrific trattorias.

Obviously, you’re going to want to see all of the big dogs: The Colosseum, St. Peter’s Square, the Pantheon — because “when in Rome.” However, don’t forget to dip off the beaten path for a few hours. Rome has a lot (read: a lot) of surprises for traveler that veers from the main tourist routes, whether that’s a 2000-year-old pyramid or an opulent art-filled palazzo.

What to do in Rome (Just in case your list isn’t full already)

• Trastevere — A charming residential neighborhood full of cobbled streets, shuttered windows, and lip-smacking food that’s surprisingly less busy than the rest of the city center.
• Palatine Hill — Perhaps the earliest settled part of the city as some of its ruins date back to the 9th century BC. Palatine Hill was the site of many Roman palaces, so it’s a must-visit for anyone that didn’t make it to Pompeii.
• The Capuchin Crypt — A macabre yet significant chapel under the Santa Maria della Concezione dei Cappuccini which contains the remains of over 3,700 Caputian friars.

Where to Stay in Rome: J.K. Place Roma

With top sights like Piazza Navona, Castel Sant’Angelo, and the River Tiber just a short walk away, J.K Place is in one of the best areas to stay in Rome. It’s grand palazzo-style architecture, with high ceilings and four-poster beds offers an atmosphere of unmistakable luxury. But there’s also a bit of boutiquey flair to the place — particularly in the J.K. Cafe, with its forest green walls, modern art, and simplified interior. Make the most of your stay by requesting the JKMaster Balcony Room, whose intimate balcony is a great vantage point over the street below.

Star Rating: 5*
Price: USD 581 — USD 2,170
Guest Rating: 9.7
Address: Via Monte d Oro, 30, 00186 Rome, Italy

Days Ten and Eleven: Siena

A direct bus service takes you out of Rome Tiburtina and toward the famous rolling countryside of Tuscany. If you’re traveling by car, ignore what google maps tell you and leave the E35 highway at Chiusi, changing to the SR2. While it’s slower, it’s one of Tuscany’s most beautiful drives. What’s more, you’ll have the chance to stop off at swoon-worthy pitstops like Pienza and Montalcino.

Your destination, though, is Siena. Formerly the capital of a wealthy Rennaisance republic, little has tarnished about this spectacular Tuscan town. The 14th-century Torre del Mangia tops out its medieval magnificence, with sweeping views of the palazzos, churches, and fortifications that earned the old city a place on UNESCO’s world heritage list. Try rustic local dishes like pici, a simple pasta sautéd with seasonal vegetables, tomato, and white wine. Then humble yourself at the 13th-century Duomo di Siena, the jewel of this captivating city.

What to do in Siena:

• Sip sensational grapes at Azienda Agricola La Lastra — This family-run estate just outside Siena is known for its delicious dining and great chianti.
• Marvel at the Biblioteca Piccolomini — This 15th-century library is covered from floor to ceiling in vibrant frescos and is a true hidden gem in Siena.
• Eat Gelato outside the Imposing Palazzo Publico — A 13th-century structure that speaks volumes about the former significance of the Republic of Siena.

Where to Stay in Siena: Grand Hotel Continental Siena – Starhotels Collezione

This hotel’s remarkable setting in a 500-year-old palazzo is a dream for culture vultures and history nuts alike. The exquisite guest rooms are like a live-in history museum, with period furniture, princess beds, and unforgettable views of Siena’s medieval streets. A privileged location on the city’s main street means sights like Duomo di Siena and Piazza del Campo are just a short walk away. What’s more, you’ll have access to a superb 13th-century wine cellar, which features an extensive collocation of local grapes and offers a range of experiences.

Star Rating: 5*
Price: USD 263 – USD 1,016
Guest Rating: 9.0
Address: Banchi Di Sopra 85, 53100 Siena, Tuscany, Italy

Days Twelve, Thirteen, and Fourteen: Florence

This last leg of your Italian road trip is an easy one. Direct trains run north out of Siena Train Station, and by car, the Raccordo Autostradale Firenze-Siena will get you there in just an hour. Still, consider adding some time to your trip by taking the winding Chiantigiana Road, one of Italy’s most spectacular drives.

Regardless of its modern prestige as one of the most beautiful travel destinations in the world, the world owes a lot to Florence. It was here, after all, that the Italian Rennaisance began in the 14th century, that artists like Leonardo da Vinci and Michaelangelo gave us some of their greatest works, and that engineers and architects created some of the most stunning structures of the past 500 years. Pay your dues to this significant city at the prestigious Uffizi Gallery or in the Palazzo Vecchio’s Hall of the Five Hundred.

Of course, for all of Florence’s magnificence, it remains a place when life is to be slower and savored, from its slow afternoon walks to its sublime sunsets. Succumb to La Dolce Vita with an evening aperativo, or lose yourself in a stroll along the Arno River. Florence will reward you.

What to do in Florence:

• Wander across the Ponte Vecchio — Formerly this covered medieval bridge was the stomping ground of butchers and tanners. Now, it’s home to boutique jewelry shops and art dealers.
• Take in the view from San Miniato al Monte — This 11th-century basilica stands on one of the highest points in the city, meaning you’ll get a fantastic city panorama.
• Have an Anecdote-Worthy Meal at La Giostra — Dine under the same roof that Elton John once did at this upscale yet cozy join run by Austrian aristocracy.

Where to stay in Florence: Villa Cora

Nothing could end your Italian road trip on a high like staying in an authentic Tuscan palazzo. This exquisite manor house offers a full period-appropriate experience, with luxurious four-poster beds, Italian marble bathrooms, and fine art adorning its walls. The pool, set in bushy, rose-dotted gardens, is the perfect place to fritter away a final few hours while you reflect on your incredible journey. That’s equally true of the Bellevue Roof Terrace, with its sublime city views.

Star Rating: 5*
Price: USD 658 – USD 1,798
Guest Rating: 9.4
Address: Viale Machiavelli 18, 50125 Florence, Tuscany, Italy

Hotel Location

Where Will Your Italian Road Trip Lead You?

Perhaps we need to address our biases, but for us, few places can rival the Repubblica for historical, cultural, or culinary excellence. Perhaps that’s just our opinion. But start on your own adventure through this storied country and it might just win you over, too. For those with a little more time to explore, consider pressing further north to areas like the glittering Cinque Terre or the dramatic Dolomite mountains in South Tyrol. Italy has boundless surprises in store, which of them will your Italian road trip reveal?