9-Day Italy Self-Drive Road Trip With Itinerary from Rimini traveling west to Bologna, Florence, Siena, and Arezzo

Embark on another extraordinary experience on day 2 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Bologna. At the end of the day, you will enjoy the comforts of a top-rated hotel in Bologna, which will be your home away from home for 1 night.

Today, you'll explore some of the most beautiful places in Rimini, including a public square, a monument, a church, a palace and much more! Start your day with a visit to Piazza Santo Stefano. This increasingly popular public square is a must-visit in the city. When you’re ready for your next discovery, continue to Two Towers, which may be one of the most historic places you will experience today.

One of the best things about exploring Rimini 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 Bologna Cathedral, a worthwhile church in the city. If you’re up for more discoveries, don’t forget to reserve some time for Palazzo Re Enzo and Fountain Of Neptune, Bologna. End your day with a visit to Piazza Maggiore, a widely recognized public square that’s sure to leave a lasting impression.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Bologna. Bologna 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 Bologna, 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.

Make sure to reserve a table at Ristorante Ciacco, an iconic dining spot in Bologna. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Ristorante Ballarini, a popular restaurant in Bologna. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Sfoglia Rina, a hidden gem nestled in Bologna. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

To truly maximize your evening out, consider visiting Bar Al Bricco D'oro after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bar Freud E Squisito, another bar with an inviting ambiance. Similarly, Osteria Del Sole also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

Dive into day 3 of your remarkable road trip in Italy. Today you will explore 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.

A blend of fun adventures, photo-friendly spots, and budget-friendly activities await you in Bologna on today’s itinerary. First up is the notable food market, Central Market. Afterward, continue to Cathedral Of Santa Maria Del Fiore, a church every traveler should visit.

As you explore Bologna’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Florence Baptistery. This often recommended church is an essential stop. Following that, head to Ponte Vecchio, another must-visit site that will enhance your experience. Don’t forget to stop by Uffizi Gallery, an astonishing art gallery in the city. Finally, end your day with a visit to Piazza Della Signoria, an enchanting public square that offers the perfect conclusion to your sightseeing of the day.

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

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

Treat yourself to a delightful dinner at Ristorante Oliviero 1962, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Di Poneta Novoli? It's another excellent option with a diverse menu. Consider reserving a table at Caffe San Firenze as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

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.

Savor another day of unforgettable experiences in Italy!

At the end of the day, you'll drive back to Florence, where you'll stay for 1 night more.

At the top of the list of things to do today is to explore Oltrarno, a neighborhood that captures the true essence of Pisa. Take your time to uncover its best sides and enjoy its proximity to many of the area’s best attractions.

Get ready for a day filled with family-friendly attractions, breathtaking views, and picturesque spots in the charming city of Florence. Your adventure starts at Piazza Del Duomo, Pisa, an iconic local hot spot. Another notable attraction to explore is Leaning Tower Of Pisa. This timeless monument is known for its UNESCO world heritage-designated appeal.

After soaking in the highlights of these sights, take some time to wander Florence's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Basilica Of Santa Croce In Florence. This respected church offers a fascinating experience that many visitors find memorable. Piazzale Michelangelo is also worth visiting.

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

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

Enjoy a lovely meal at Ditta Artigianale, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Trattoria Da Burde is another top choice with a popular menu. You could also check for a table at Casa Toscana. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.

After your meal, keep the night alive at a bar like Bar 50 Rosso, known for its lively atmosphere. Bitter Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Archea Brewery offers an excellent atmosphere for those looking to amp up the evening.

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

Experience an unparalleled adventure on day 5 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Siena. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Siena. You will spend 2 nights here for some well-deserved relaxation.

Today’s route brings fun adventures, breathtaking views, and picturesque spots. The first attraction of today is Basilica Of San Domenico. This up-and-coming church is a picture-perfect place to see in Florence. Continue your discovery at Piazza Del Duomo, a visually striking public square with stories to tell.

As you stroll around Florence, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Siena Cathedral. This captivating church offers an inviting encounter with Florence. Next, make your way to Pubblico Palace to add another highlight to your day. After that, visit Piazza Del Campo, an impressive public square that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Tower Of Mangia, a curiosity-inducing monument in the city. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Florence.

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

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Siena. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Savor the flavors at Enoteca I Terzi, a top pick for dinner tonight. Alternatively, Ristorante Tar-Tufo beckons with its unique menu offerings. Also, consider Antica Trattoria Papei. With its consistent customer satisfaction, it’s an excellent option for dining in Siena tonight.

After enjoying a fulfilling meal, continue your evening at Meet Life Cafè, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Maudit Pub offers a welcoming atmosphere for easing into the nightlife. Similarly, Bar Impero Siena provides an excellent environment for a relaxed and enjoyable evening.

Raise your glass to another unforgettable day in Italy!

Greet day 6 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Siena for your remaining 1 night in the city later today, but first, it’s time for some exploring! On the agenda for this day, you’ll find only the best things to see and do in San Gimignano and Siena.

Immerse yourself in Siena’s rich culture with today's sightseeing itinerary. Start your journey at Porta San Giovanni. This respected monument is sure to ignite your curiosity. Next, dive into the UNESCO world heritage-designated features of Piazza Del Duomo, a must-visit public square in the village.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Rocca Di Montestaffoli, a frequently visited castle. For a change of scene, check out Parco Della Rocca, known for its respected features. We also recommend visiting Chiesa Di Sant'agostino. This church is a must for anyone looking to experience the village to the fullest. Lastly, end your day with a visit to Fortezza Medicea (siena), yet another frequently visited attraction in Siena.

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

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

Don’t miss out on dining at Osteria Quattro Venti, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Fischi per Fiaschi, another top spot with a mouthwatering menu. You might also want to secure a reservation at Osteria da Divo. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

Cap off your dinner by heading to Charlie Mixology Bar Di Aldinucci Riccardo, ideal for a leisurely evening with a drink in hand. Bar Pinacoteca is another bar that offers an enjoyable setting. Similarly, San Paolo Pub is also a popular place to go on a night out, perfect for relaxing and socializing.

Raise your glass to another unforgettable day in Italy!

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

Brace yourself for today’s incredible lineup of attractions in Siena, featuring fun adventures, picturesque spots, and history-rich sites. Start at Casa Vasari, an up-and-coming museum in the city. Then, head to The Medici Fortress Park and soak in the ambiance of this romantic park.

There are many interesting places to see in Siena, and when you are ready for more, go to Piazza Grande. This is one of the city’s most well-known romantic spots of interest. After exploring the public square, visit the often recommended Santa Maria Della Pieve. Not far away, you'll also find San Francesco, Arezzo. This church is an instagrammable highlight in Siena.

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

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

Treat yourself to a wonderful meal at Il Covo dei Briganti, a top-rated dining spot in Arezzo. If you're in the mood for something new, try La Clandestina, another premier location with a delectable menu. You might also want to book a table at Ristorante Logge Vasari. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Arezzo.

Keep the excitement of the evening going by visiting a bar or two. Liquid Bar is an excellent place to start.

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

On day 8 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 Urbino. In the evening, you’ll end up in Rimini, where you will stay for 1 night.

Enjoy the perfect balance of relaxation and exploration in Arezzo today. One of the most well-known attractions included on the itinerary is Palazzo Ducale. This breathtaking palace will help you start your sightseeing on top. Then, take a leisurely stroll to Galleria Nazionale Delle Marche and learn what makes this breathtaking museum unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the intriguing Oratory Of St John The Baptist, Urbino. After exploring the church, head to Casa Santi. This beloved museum is a highlight in Arezzo. As your day continues, stop by Fortezza Albornoz, known for its awe-inspiring features.

When you’re done exploring for the day, you’ll drive to your hotel in Rimini. 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 Rimini. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Treat yourself to a delicious dinner at Osteria Brodo di Giuggiole, an excellent option for tonight's dining. Looking for something different? Hotel Touring offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante Lo Zodiaco Rimini. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rimini.

Unwind after your meal by stepping into Hobo's. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Sunflower City Backpacker offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Bar Capogiro, another top-rated bar in the area.

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