Italy Travel Guide: The Ultimate 2-week Road Trip Italy Travel Guide: The Ultimate 2-week Road Trip

Italy Travel Guide: The Ultimate 2-week Road Trip

Italy, the country of pasta & pizza, architecture & history, jaw-dropping sceneries, world-famous cities & medieval little towns, and mouth-watering gelato. That’s right – Italy has it all, and that’s why it is one of the most-traveled destinations in Europe. Multiple visits are needed to see all the country’s highlights. Discover the best of Italy within 2 weeks in this Italy Travel Guide.

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Italy Travel Itinerary

All popular cities, like Venice and Rome, are well connected by train, car, or airplane. The best and fastest option is traveling by train, and the best way to see Italy is by car, so this Italy travel itinerary is a mix of those.

Day 1-3: Rome

Start your trip in the capital of Italy: Rome. Rome has some of the world’s most popular tourist attractions; the Colosseum and Vatican City. Flights to Rome are usually the most affordable, which makes it a great start location.

Day 4: Tuscany – Best of the Italy travel itinerary

Tuscany, with its rolling hills and vineyards, is one of the most picturesque regions in Italy. Escape the city, rent a car in Rome, Italy and drive 3-hours along Lago Di Bolsena to Saturnia, the thermal area. Spend the afternoon and have dinner in this tiny medieval village called Montemarano.

Day 5: Tuscany (Siena)

No better way to start your day than by dipping into the natural hot springs in Saturnia. Between 7-8 AM is the best time to visit, and if you stay at this hotel, it is just a 5-minute walk.


Hop back into the car and continue your Italy travel itinerary for 3 hours along the most scenic roads toward Siena. Do note that your navigation has to be set to ‘Avoid Highways’. Siena is a beautiful old city with a UNESCO status.

Close off the day by having a delicious Italian dinner at Osteria Permalico after that spend the night in charming Siena. (Our hotel)

Day 6: Tuscany (Siena to Florence)

On your last day in Tuscany, roam around Siena for a couple of hours, visit Piazza Del Campo and the cathedral Duomo di Siena.

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Italy Travel Guide: The Ultimate 2-week Road Trip

Siena’s old city center has a great ambiance. Cars are not allowed inside the old city center, therefore, the city is a favorite on every Italy travel route. Read more information about where to park your car in our Tuscany Guide.

Around noon, continue to your last stop: Florence. Optionally, visit San Gimignano or Volterra and drop off the car in Florence.

Day 7: Florence

Welcome to Florence. Spend the next 24 hours wandering around this ancient city and discover sites like the Duomo of Florence and the ancient bridge Ponte Vecchio.

While you’re in Florence, don’t miss out on a foodie adventure. Hop between cafes and restaurants, trying delicious fresh pasta and finding the best gelato!

Day 8-10: Cinque Terre

In the morning, take the train from Florence to Cinque Terre, a 2.5h journey. Cinque Terre is a national park with five incredibly picturesque villages with hiking routes where you want to spend as much time as possible. Spend two nights in Riomaggiore, Monterosso, or La Spezia, which is right outside the national park. (Find the best train tickets here)

Day 11: Cinque Terre to Venice

It’s time to head to Venice, your final stop on your Italy travel itinerary. Take the train from La Spezia to Venice, a 5-hour ride with one transfer in between. The train is super convenient in Italy as some of the best you will see in Europe.

Day 12-14: Venice

Welcome to the city where everything goes by boats and bridges. Venice is one of the world’s most unique cities and an absolute must-see when you travel to Italy. Spend your last days in Italy strolling along the canals, or crossing bridges sipping Italian coffee.

The mornings or late afternoon are the best times to stroll down the narrow streets of Venice as the city center gets busy during the midday as day trip arrives in the city.

Costs of traveling in Italy

The costs of traveling in Italy depend on where you eat, sleep, and how you get from A to B. These are the average expenses when you follow this Italy travel itinerary, eat at medium-priced restaurants, and travel by train + car.

  • Hotel: 65 – 300 USD / night
  • Food: 20-80 USD / day
  • Entrance fee: 18-45 USD
  • Transport: 20 USD / day
  • Water: 2 USD / 1.5L
  • Guesthouse: 40 USD / night

How to get around Italy?

Transportation plays an essential part in your Italian experience. Your Italy travel itinerary can be done by train, car, or plane. The fastest and most affordable way to travel in Italy is by train however, a car gets you to those scenic country roads.

Renting a car in Italy

For full flexibility and to go off the beaten path, driving a car is a perfect option. All major cities in Italy are well connected by train but to visit Tuscany or the Dolomites, you need to rent a car. Avoid popular cities by car, as parking costs are sometimes the price of a train ticket.

Italy by train

Traveling Italy by train is excellent. They are incredibly fast (up to 350 km/h!), affordable and much cleaner for the environment compared to an airplane. Book the train tickets a few days in advance to secure your spot on the train.

Italy by airplane

Same as the train, all major cities are connected by airplanes however, the train might be a faster option as the extra airport time adds up quickly.

Best Time to visit Italy

Tourism in Italy is huge because it is one of the most-visited countries worldwide, so it is recommended to avoid the high season. The best time to go to Italy is in spring, from April to June and fall, from September and October. Prices are lower, fewer tourists, and comfortable temperatures.

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