14-Day Italy Self-Drive Road Trip With Itinerary from Florence to San Gimignano, Greve in Chianti, Perugia, Orvieto, Rome, and Naples

You’ll stay in Florence for 2 nights.

One of the most iconic spots you can visit today is Oltrarno. Allow yourself some time to explore this neighborhood and discover its unique quirks. You'll also find many of the best sightseeing spots nearby.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Florence, it's often a good idea to reserve a table in advance.

Say good night to Florence and look forward to another great day of your road trip in Italy!

On day 3 of your road trip, you’ll start and end your day in Florence, where you have 1 night left to stay.

When you’re done exploring for the day, you’ll return to Florence and your accommodation.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Florence, it's often a good idea to reserve a table in advance.

Raise your glass to another unforgettable day in Italy!

On day 4 of your road trip in Italy, your travel plans include 2 stops at the most scenic, wondrous, and interesting places in the region. Siena and San Gimignano are on today's agenda. In the evening, you’ll end up in San Gimignano, where you will stay for 1 night.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in San Gimignano. San Gimignano offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in San Gimignano. Enjoy a relaxing evening as you savor delicious local cuisine.

As the sun sets, rest up and recharge for the next leg of your road trip in Italy.

On day 5 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 3 destinations, including San Gimignano, Volterra, and Tignano. When you’re not sightseeing, take time to relax at your chosen hotel in Greve in Chianti, where you’ll be staying for 2 nights.

When you’re done exploring for the day, you’ll drive to your hotel in Greve in Chianti. Check in and relax before you head out to tour the town.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Greve in Chianti, it's often a good idea to reserve a table in advance.

Savor another day of unforgettable experiences in Italy!

Greet day 6 of your road trip in Italy with a smile and start your day with a hearty breakfast. You have 1 night to stay in Greve in Chianti, so get ready to make the most of your time in the region. On the agenda for this day, you’ll find only the best things to see and do in San Regolo and Castellina in Chianti.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Greve in Chianti.

After a day of adventure, treat yourself to an exquisite dinner at one of Greve in Chianti's best restaurants.

Relax and look forward to more memorable moments to come!

Experience an unparalleled adventure on day 7 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 places, which are Santa Maria degli Angeli and Perugia. At the end of the day, you will retreat to the hotel of your choice in Perugia, where will spend 1 night.

Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Greve in Chianti.

At the end of the day, you will drive to Perugia, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

Indulge in a memorable dining experience at one of Perugia's most popular restaurants, and connect with friendly locals for a true cultural experience.

Get a good night's sleep and look forward to another great day on the road in Italy!

Your itinerary for day 8 of your road trip in Italy includes 2 stops and features some of the highlights of Perugia and Orvieto. At the end of the day, enjoy the comforts of a top-rated hotel in Orvieto, where you'll spend 1 night.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Orvieto. Orvieto offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

Orvieto is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Orvieto.

Relax and recharge in preparation for another adventurous day in Italy!

Dive into day 9 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Rome and Vatican City. At the end of the day, you’ll unwind at one of the finest accommodations in Rome, where you'll spend 2 nights.

Throughout the day, make sure to take breaks to appreciate the surroundings.

When you’re done exploring for the day, you’ll drive to your hotel in Rome. Check in and relax before you head out to tour the city.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Rome. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Raise your glass to another unforgettable day in Italy!

Day 10 offers an itinerary packed with the best things to see in Florence. You’ll stay in Rome for 1 night more, offering you enough time to explore at a relaxed pace.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Rome. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Relax and look forward to more memorable moments to come!

On day 11 of your road trip in Italy, your travel plans include 2 stops at the most scenic, wondrous, and interesting places in the region. Ottaviano and Naples are on today's agenda. In the evening, you’ll end up in Naples, where you will stay for 2 nights.

At the end of the day, you will drive to Naples, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

After a day of adventure, treat yourself to an exquisite dinner at one of Naples's best restaurants.

Say good night to Naples and look forward to another great day of your road trip in Italy!

On day 12 of your road trip, you'll get the chance to experience Pompei and Naples. At the end of the day, you'll drive back to Naples, where you still have 1 night left to stay.

When you’re done exploring for the day, you’ll return to Naples and your accommodation.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Naples. Enjoy a satisfying meal that will recharge you for tonight's adventures.

As the sun sets, rest up and recharge for the next leg of your road trip in Italy.

On day 13 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, including Amalfi and Alberi. When you’re not sightseeing, take time to relax at your chosen hotel in Florence, where you’ll be staying for 1 night.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Florence. Florence offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Florence. Enjoy a relaxing evening as you savor delicious local cuisine.

Relax and look forward to more memorable moments to come!