9-Day Italy Self-Drive Road Trip With Itinerary from Rimini to Florence, San Gimignano, Monterosso al Mare, and Rome

On day 2 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Florence. In the evening, you’ll end up in Florence, where you will stay for 2 nights.

Set out on a day brimming with family-friendly attractions, romantic experiences, and breathtaking views. Start at the iconic Ponte Vecchio, a majestic historical landmark in Rimini. Next, go to Uffizi Gallery.

After visiting Ponte Vecchio and Uffizi Gallery, have a stroll along Rimini's streets and take in the local charm. Continue your sightseeing by heading to Basilica Of Santa Croce In Florence. This inviting church offers a unique experience. Palazzo Vecchio is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Piazza Della Signoria, one of the most symbolic places to visit in Rimini.

At the end of the day, you will drive to Florence, 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 Florence's best restaurants.

Enjoy a lovely dining experience at Ristorante Oliviero 1962, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Di Poneta Novoli, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Caffe San Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.

Let the evening flow smoothly from dinner to drinks at Manifattura, a top-rated bar in the area. For other recommendations, Se·sto On Arno Rooftop Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Il Vinile offers a memorable night with diverse drink options and excellent service.

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

Day 3 of your road trip will take you to the best attractions Florence has to offer. Cherish the 1 night you have left in Florence by discovering the best things there are to see and do in the city.

Start your day with a visit to Basilica Di Santa Maria Novella, Firenze (fi). This well-known church is a must-visit in the city. When you’re ready for your next discovery, continue to Central Market, which may be one of the most photogenic places you will experience today.

One of the best things about exploring Florence on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Cathedral Of Santa Maria Del Fiore, a spectacular church in the city. If you’re up for more discoveries, don’t forget to reserve some time for Galleria Dell'accademia and David. End your day with a visit to Piazzale Michelangelo, a famous observation deck that’s sure to leave a lasting impression.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

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

Dine in style at Ditta Artigianale, a top recommendation for dinner tonight. Or, for a change of pace, Trattoria Da Burde boasts a menu that's sure to impress. Also, be sure to check out Casa Toscana. Known as a local hotspot, it’s a great choice for tonight in Florence.

Following your dinner, dive into the local bar culture at Bar 50 Rosso. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bitter Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Archea Brewery provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

Experience an unparalleled adventure on day 4 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Siena and San Gimignano. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in San Gimignano. You will spend 1 night here for some well-deserved relaxation.

Start by visiting Siena Cathedral, a prime spot to begin your journey. This visually striking church is sure to impress. Next on your list is Piazza Del Campo, another must-visit landmark and impressive public square renowned for its UNESCO world heritage-listed features.

While exploring and sightseeing, take time to savor the culture of Florence by sampling some local delicacies. When you’re ready for more sightseeing, head to Porta San Giovanni. This historic monument is an essential place to visit for anyone looking for the full Florence experience. We also recommend visiting Piazza Del Duomo, an often recommended public square. Nearby, you'll also find Palazzo Comunale, Pinacoteca, Torre Grossa, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at Chiesa Di Sant'agostino and wrap up your day with its photogenic appeal.

When you’re done exploring for the day, you’ll drive to your hotel in San Gimignano. Check in and spend some time relaxing before you head out to tour the village.

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

Raise your glass to another unforgettable day in Italy!

Embark on another extraordinary experience on day 5 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Pisa and Lucca. At the end of the day, you will enjoy the comforts of a top-rated hotel in Monterosso al Mare, which will be your home away from home for 2 nights.

Get ready to discover some of the most iconic wonders in San Gimignano, including a church, a public square, a monument, a historical landmark and much more! Start your day at Battistero Di San Giovanni. This breathtaking church is a locally appreciated place to see in San Gimignano. Then, wander over to Piazza Del Duomo, Pisa. If historic sites excite you, this public square will be right up your alley. Nearby, you’ll also find Pisa Cathedral. This breathtaking church is a favorite among visitors.

San Gimignano offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Leaning Tower Of Pisa is a globally renowned spot in the city that will captivate you with its unique charm. When you’re done at the monument, don’t forget to check out the enchanting Mura Di Lucca. Take a moment to appreciate the fascinating details of this frequently visited historical landmark. Wrap up your self-guided tour of San Gimignano's top attractions with a visit to Porta San Pietro.

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

As you explore more of Monterosso al Mare, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Enjoy a delicious meal at Pizzeria La Smorfia, a highly-rated dining destination in Monterosso al Mare. If you're eager to try something different, consider La Taverna di Monterosso, another top spot with a tantalizing menu. You might also want to secure a reservation at Hotel Albergo Degli Amici. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Monterosso al Mare this evening.

Cap off your dinner by heading to Enoteca Da Eliseo, ideal for a leisurely evening with a drink in hand.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

On day 6 of your road trip, you’ll start and end your day in Monterosso al Mare, where you'll stay for 1 night more.

Prepare for a day full of family-friendly attractions, romantic experiences, and breathtaking views. When you’re ready, kick off your sightseeing adventure at Riomaggiore. This intriguing point of interest is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Castle Of Riomaggiore, one of the village’s best highlights.

Next, check out Presepe Di Manarola, one of the most curiosity-inducing places to see in Monterosso al Mare. This art installation is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Manarola Overlook Viewpoint. Wander around and soak in the eye-catching atmosphere this observation deck offers. Then, head to Cinque Terre National Park, a top-rated national park that adds another dimension to your day.

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

Indulge in a memorable dining experience at one of Monterosso al Mare's most popular restaurants, and connect with friendly locals for an authentic adventure.

Don’t miss out on dining at Ristorante Pizzeria Da Ely, a top-rated dining destination in Monterosso al Mare. If you're in the mood to try something new, consider La Cantina Di Miky, another top spot with a mouthwatering menu. You might also want to secure a reservation at Enoteca Internazionale. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Monterosso al Mare this evening.

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

On day 7 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Rome. When you’re not sightseeing, take time to relax at your selected hotel in Rome, where you’ll be staying for 1 night.

Brace yourself for today’s incredible lineup of attractions in Monterosso al Mare, featuring family-friendly attractions, romantic experiences, and scenic views. Start at Piazza Di Spagna, a wondrous public square in the city. Then, head to Trevi Fountain and soak in the ambiance of this detailed monument.

There are many interesting places to see in Monterosso al Mare, and when you are ready for more, go to Pantheon. This is one of the city’s most timeless culturally significant spots of interest. After exploring the monument, visit the world-famous Piazza Navona. Not far away, you'll also find Circus Maximus. This archeological site is a breathtaking highlight in Monterosso al Mare.

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

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

Dine in style at La Bottega Roma, a top recommendation for dinner tonight. Or, for a change of pace, Pasta In Corso boasts a menu that's sure to impress. Also, be sure to check out Trattoria Vecchia Roma. Known as a local hotspot, it’s a great choice for tonight in Rome.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at La Botticella Of Poggi Giovanni, a well-loved spot among locals and tourists. Or, head to Almalu Trastevere. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Bar Viminale Di Pepi Maurilio, another top-rated place in the area.

Head back to your accommodation in Rome and get some rest in preparation for another magical day of your road trip in Italy!