The Great Italian Road-Trip, Two-Week Bucket List Vacation in Italy

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  • Day 2 – Orbetello and Porto Ercole
  • Day 11 – Foggia and Parco Nazionale del Gargano

There are few more sought-after travel locations than Italy. With cities like Rome, Venice, and Florence with such an incredible wealth of history, there is much to explore. It is hard to pick just one destination on the Italian peninsula to travel to, so why not take a road trip.

This two-week road trip will take travelers from Rome northeast through Florence and Venice and then down south along the east coast before turning back north towards Rome. This is a can-miss two-week Bucket List Road-Trip in Italy.


Day 1 – Rome

After landing in Rome, Travelers need to first acquire their rental, but after that, they shouldn’t definitely explore a bit of Rome. The city is so full of both historical and modern culture that there is something for everyone to discover in this city.

Il Goccetto

It’s hard to get enough of the delicious food served at II Goccetto. Well known for both its wines and cuisine, this is a must-visit location for travelers to Rome.

Day 2 – Orbetello and Porto Ercole

Located in the Province of Grosseto, travelers can find both Orbetello and Porto Ercole. Orbetello is located just 35 kilometers south of Grosseto, on the eponymous lagoon. Porto Ercole is a prominent port city that travelers can also explore.

Day 3 and 4 – Florence

A Bastion for art and culture, Florence is a go-to destination for many traveling to Italy. With so much for travelers to discover, it is recommended that they spend two nights here. Whether travelers prefer to spend their time with food, art, or shopping, they will have plenty to do here.

Related: Cars Are Forbidden: How Else To Easily Get Around Capri, Italy

Trattoria Mario

This small restaurant in Florence offers some incredible and authentic Tuscan cuisine to its guests. Seating may be difficult to find here, so try to book in advance.

  • Address – Via Rosina 2r, 50123, Florence Italy
  • Contact – +39 055 218550
  • Cost – $$-$$$
  • Must-Try – Tuscan pot roast
  • Menu

Day 5 – Bologna

Although it sits right in the middle of Florence and Venice, Bologna doesn’t get nearly the same recognition. Travelers will find that despite not being on everyone’s go-to list, Bologna offers a lot for visitors to discover.

Mò Mortadella Lab

For some incredible and quickly prepared meals, Mò Mortadella Lab is an excellent choice. Its sandwiches are incredible and at a very fair cost.

  • Address – Via de’ Monari 1/C, 40121, Bologna Italy
  • Contact – +39 051 086 3992
  • Cost – $
  • Must-Try – Mortadella Sandwiches
  • Menu

Day 6 and 7 – Venice

Travelers are easily enchanted by the city of Venice, and it is easy to understand why. This city is magnificent in more than just its architecture and canals; it has tremendous history and fabulous restaurants to discover.

The Glam Restaurant

This Michelin star restaurant offers a selection that shows a deep appreciation for local cuisine. Travelers should not miss an opportunity to dine here.

  • Address – Santa Croce 1961 Palazzo Venart, 30135 Venice Italy
  • Contact – +39 041 523 5676
  • Cost – $$$$
  • Must-Try – Cuttlefish
  • Menu

Day 8 – Ravenna

This incredible city was once the Byzantine Empire’s capital in Italy. There is much left from that time including incredible mosaics and Dante’s tomb.

Day 9 – Arcona

Arcona is found along Italy’s Adriatic coast. It is known for its beaches and its Fontana de Calamo, a fountain with bronze masks of mythical figures. Travelers can take a moment and enjoy this stunning seaside town.

Day 10 – Pescara

Although full of concrete postwar architecture, Pescara is a functional port. Travelers enjoy flocking to its lively and prominent waterfront promenades and some of the longest urban beaches on the Adriatic.

Day 11 – Foggia and Parco Nazionale del Gargano

This southern Italian city is referred to as the “granary of Italy.” Parco Nazionale is the stunning coastal park found close by. With the stunning divide between mountains and coast, this is an incredibly beautiful location to visit.

Related: 10 Best Beaches In Italy That Are Worth The Trip

Day 12 – Taranto

Lying between Mar Grande and Mar Piccolo is the southern Italian city of Taranto. Bridges link the mainland with the old city, which is home to the 15th-century Aragonese Castle, the Spartan Museum of Taranto, and San Cataldo Basilica, with a baroque facade.

Day 13 – Naples

The largest city in southern Italy, Naples offers an intoxicating mix of Old World charm and modern toughness. As one of the oldest cities in Italy, Naples is full of pieces of the past that travelers can discover. The city is also quite famous for its wood-fired pizza.

Trattoria Pizzeria La Lazzara

Travelers looking for a taste of real Neapolitan pizza should visit Trattoria Pizzeria La Lazzara. Their prices are reasonable, and the quality is incredible.

  • Address – Piazza Francese 9/10, 80133, Naples Italy
  • Contact – +39 081 551 7854
  • Cost – $$-$$$
  • Must-Try – Margherita al Salame
  • Menu

Day 14 – Back to Rome

Travelers will now make their way back to Rome. However, it isn’t a terribly long drive, so travelers will still have plenty of time to enjoy Rome before it is time to mark the end of this road trip.

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