One-Week Italy Self-Drive Road Trip With Itinerary from Pisa to Florence, San Gimignano, Montefioralle, and Monterosso al Mare and surrounding area

Dive into day 2 of your remarkable road trip in Italy. Today you will explore Pisa and Florence, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Florence. You’ll stay here for 2 nights.

Today’s route brings fun adventures, breathtaking views, and picturesque spots. The first attraction of today is Leaning Tower Of Pisa. This iconic monument is a masterful place to see in Pisa. Continue your discovery at Piazza Del Duomo, Pisa, a breathtaking public square with stories to tell.

Fasten your seatbelt and make your way to your next stop. Florence, home to many well-known sights in the region, is a lovely destination on today’s itinerary. Keep in mind that your travel time from Pisa to Florence may take around 1 hour 20 min without traffic disruptions. Upon arrival in Florence, we highly recommend checking out some of the top attractions.

Savor the rest of your day by heading to Central Market, a popular food market that draws visitors from near and far. When you're done, continue on to Galleria Dell'accademia, where you can soak in the photogenic surroundings. Next, explore Cathedral Of Santa Maria Del Fiore, yet another extraordinary place to see in the area.

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.

As you explore more of Florence, 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 Ristorante Oliviero 1962, a highly-rated dining destination in Florence. If you're eager to try something different, consider Di Poneta Novoli, another top spot with a tantalizing menu. You might also want to secure a reservation at Caffe San Firenze. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.

Following your dinner, dive into the local bar culture at Manifattura. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Se·sto On Arno Rooftop Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Il Vinile provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

Day 3 of your road trip across Italy promises a magnificent time exploring Florence. You have 1 night left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

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

Set out on a day brimming with family-friendly attractions, romantic experiences, and breathtaking views. Start at the widely recognized Piazzale Michelangelo, an enchanting observation deck in Florence. Next, go to Uffizi Gallery.

After visiting Piazzale Michelangelo and Uffizi Gallery, take time to explore Florence's streets and absorb its charm. Continue your sightseeing by heading to Piazza Della Signoria. This enchanting public square offers a unique experience. Ponte Vecchio is another noteworthy stop.

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.

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 and reflect on the day's adventures.

Treat yourself to a delightful dinner at Ditta Artigianale, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Trattoria Da Burde? It's another excellent option with a diverse menu. Consider reserving a table at Casa Toscana as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

Continue your evening by exploring the vibrant nightlife scene at Bar 50 Rosso, a prime destination for a thrilling night out. Also, don’t forget to check out Bitter Bar, a bar that offers unique local touches. Likewise, Archea Brewery provides an excellent alternative for a fun evening.

Take some time to reflect on your day and savor another beautiful night in Italy.

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.

Enjoy the perfect balance of relaxation and exploration in Siena today.

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

Siena’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Florence behind. This drive usually takes around 1 hour 10 min. Siena welcomes you with a multitude of unique vacation experiences.

Begin your journey at Fortezza Medicea (siena) and explore the awe-inspiring features. Next, make your way to Palazzo Salimbeni, another highlight in the city. When you’re done exploring the palace, continue to Piazza Del Campo, an enchanting public square. Nearby, you will also find Siena Cathedral. This locally renowned church is a top place to see in the area.

Embrace the thrill of the open road as you wave goodbye to Siena and set your GPS to San Gimignano. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 42 min. Upon reaching San Gimignano, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Your self-guided tour starts at Porta San Giovanni, a curiosity-inducing monument that is sure to impress. Take in the surroundings and enjoy the freedom of exploring before you continue your journey.

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 day of adventure, treat yourself to an exquisite dinner at one of San Gimignano's best restaurants.

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 San Gimignano and Greve in Chianti. At the end of the day, you will enjoy the comforts of a top-rated hotel in Montefioralle, which will be your home away from home for 1 night.

Prepare for a day full of fun adventures, romantic experiences, and scenic views. When you’re ready, kick off your sightseeing adventure at Parco Della Rocca. This often recommended park is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Piazza Del Duomo, one of the village’s most promising highlights.

Next, check out Palazzo Comunale, Pinacoteca, Torre Grossa, one of the most underrated places to see in San Gimignano. This museum is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Chiesa Di Sant'agostino. Wander around and soak in the photogenic atmosphere this church offers.

After soaking in San Gimignano’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Greve in Chianti. Expect your car journey to take a minimum of 55 min. When you arrive in Greve in Chianti, it's time to take a break from the road.

Spend your afternoon discovering Castle Of Verrazzano, an increasingly popular castle known for its history-steeped features.

After soaking up all the sights of today's itinerary, you'll be ready to hit the road in the direction of your accommodation in Montefioralle. Montefioralle offers plenty of top-rated hotels and other places to stay on any travel budget. Take some time to relax before you head out to explore.

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

Don’t miss out on dining at La Castellana, a top-rated dining destination in Montefioralle.

Celebrate another amazing day of your road trip adventure in Italy!

On day 6 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 Lucca and Monterosso al Mare. In the evening, you’ll end up in Monterosso al Mare, where you will stay for 1 night.

When you’ve had your share of Montefioralle, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Lucca. Your travel time is around 1 hour 27 min.

Savor the rest of your day by heading to St Martin Cathedral, a frequently visited church that draws visitors from near and far. When you're done, continue on to Piazza Napoleone, where you can soak in the visually striking surroundings. Next, explore Guinigi Tower, yet another beloved place to see in the area. After the monument, make time to go to Piazza Dell'anfiteatro. This history-steeped public square is well worthwhile the visit.

When you’re ready to jump back into the car and say goodbye to Lucca, you’ll hit the road in the direction of Monterosso al Mare. This drive usually takes around 1 hour 36 min. When you arrive, enjoy some sightseeing.

Make your way to Parrocchia Di S. Giovanni Battista, a worthwhile church that draws attention for its instagrammable features.

At the end of the day, you will drive to Monterosso al Mare, 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 Monterosso al Mare. If you are looking to dine at a popular restaurant in the village, it's often a good idea to reserve a table in advance.

Treat yourself to a delightful dinner at Pizzeria La Smorfia, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try La Taverna di Monterosso? It's another excellent option with a diverse menu. Consider reserving a table at Hotel Albergo Degli Amici as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Monterosso al Mare.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Enoteca Da Eliseo, a well-loved spot among locals and tourists.

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

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

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Vernazza allows for both.

After soaking in Vernazza’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Pisa. Expect your car journey to take a minimum of 1 hour 50 min. When you arrive in Pisa, it's time to take a break from the road.

Make your way to Sentiero Monterosso - Vernazza, a worthwhile hiking area that draws attention for its romantic features. Spend some time soaking in the atmosphere before continuing to Church Of St. Margaret Of Antioch, a picture-perfect church that stands out in the village. Next, visit Ruins Of Doria Tower, an intriguing monument that offers a unique experience.

When you’re done exploring for the day, you’ll drive to your hotel in Pisa. Check in and spend some time relaxing 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 Pisa. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Enjoy a lovely meal at Ristorante Capodimonte Pisa, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, La Locanda Dei Pisani Doc Pisa is another top choice with a popular menu. You could also check for a table at Baribaldi Pisa. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Pisa tonight.

Explore the vibrant nightlife at Bar Mocambo after your meal, a hub for lively evenings and memorable moments. Or, head to Tree for a great selection of flavorful drinks and a charming setting. Furthermore, Chupiteria is perfect for those looking to extend their night with a touch of local flavor.

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