14-Day Italy Self-Drive Road Trip With Itinerary from Ancona to Rimini, Venice, Florence, Siena, and Rome

On day 2 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Ancona. When you’re not sightseeing, take time to relax at your selected hotel in Rimini, where you’ll be staying for 1 night.

Ancona is brimming with adventures. Today’s wonderful stops include a palace, a museum, and a church. Begin your sightseeing adventure at the frequently visited Palazzo Degli Anziani. Just a short distance away is Museo Archeologico Nazionale Delle Marche, a photogenic museum that draws visitors from far and near.

Continue your journey to Cathedral Basilica Of St. Cyriacus, one of the city’s most up-and-coming spots that you shouldn’t miss.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Rimini. Rimini 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 Rimini. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Experience a symphony of flavors at Osteria de Börg in Rimini by securing a reservation in advance. Renowned for its Bib Gourmand distinction, Osteria de Börg delights its guests with its exceptional variety of meals showcasing delicious from romagna and traditional cuisine. For a palate-pleasing alternative, make sure to dine at Guido, acclaimed for its delectable seafood and modern specialties. This local 1-star Michelin establishment consistently satisfies guests, ensuring an unforgettable holiday experience. Want to go on another culinary journey? Delight your senses at Abocar Due Cucine, a top-rated restaurant known for its outstanding menu. Known as a top-rated 1-star Michelin establishment, it's a top choice for creative and international cuisine in the city.

Keep the evening going at Sunflower Beach Backpacker Hostels & Bar, a great choice for enjoying the after-dinner hours with a drink. You could also go to Caffè Il Borgo, which offers a similarly pleasant setting and great drinks. Another option is Primo Bacio Città Lounge Bar, which provides an inviting environment for unwinding after a busy day out.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in in Italy.

Embark on another extraordinary experience on day 3 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Rimini and Padua. At the end of the day, you will enjoy the comforts of a top-rated hotel in Venice, which will be your home away from home for 2 nights.

Immerse yourself in Rimini’s rich culture with today's sightseeing itinerary. Start your journey at Square Tre Martiri. This romantic public square is sure to ignite your curiosity. Next, dive into the photogenic features of Arch Of Augustus, a must-visit monument in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Prato Della Valle, a well-known public square. For a change of scene, check out The Basilica Of St. Anthony, known for its culturally significant features.

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

As dinnertime approaches, it's time to head out for a bite to eat in Venice. 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.

Start your culinary exploration in Venice by securing a reservation at Local. This renowned restaurant holds 1 Michelin star and offers an exceptional menu of contemporary cuisine. For another dining delight, visit Wistèria, celebrated for its delectable contemporary and venetian menu. This acclaimed 1-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Quadri, a top local spot known for its tantalizing modern menu. With a 1-star Michelin recognition, it guarantees an exceptional dining adventure.

After enjoying a fulfilling meal, continue your evening at Al Parlamento, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, The Caffe Rosso offers a welcoming atmosphere for easing into the nightlife. Similarly, Adagio provides an excellent environment for a relaxed and enjoyable evening.

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

On day 4 of your road trip, you will have an entire day to explore Venice. You’ll stay in Venice for 1 night and discover all the best things to see and do in the area.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Venice allows for both. Start by heading to Bridge Of Sighs. This locally renowned monument provides an insightful glimpse into the city's identity. Next, discover Doge's Palace, an UNESCO world heritage-designated palace, promising a delightful encounter.

Continue your sightseeing with a visit to St Mark's Basilica, a well-known church. When you’re done, don’t forget to make a stop at the wondrous Piazza San Marco. Round off your day at Rialto Bridge, another gem in Venice with romantic features to discover.

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 dinnertime approaches, it's time to head out for a bite to eat in Venice. 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 Generator Venice, a top recommendation for dinner tonight. Or, for a change of pace, Nevodi boasts a menu that's sure to impress. Also, be sure to check out Ristorante La Piazza. Known as a local hotspot, it’s a great choice for tonight in Venice.

Continue your lively evening at Il Mercante, a perfect place for winding down or revving up the night, depending on which mood you’re in. The Irish Pub Venezia is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Ai Stagneri ensures a night out tailored to your taste.

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

On day 5 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 Venice. In the evening, you’ll end up in Florence, where you will stay for 3 nights.

Discover a day packed with fun adventures, romantic experiences, and breathtaking views in Venice. Begin your sightseeing with Palazzo Contarini Del Bovolo. This captivating palace is one of the top attractions in the city. Proceed to Teatro La Fenice, another must-visit attraction that enhances the city’s allure.

As you wander through the inviting streets of Venice, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Santa Maria Gloriosa Dei Frari. This often recommended church is a traveler-favorite.

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.

Experience a harmony of flavors at Enoteca Pinchiorri in Florence by securing a reservation in advance. Known for its 3-star Michelin status, Enoteca Pinchiorri offers a delightful variety of dishes highlighting its delicious italian contemporary menu. If you're seeking an alternative culinary experience, be sure to explore Santa Elisabetta, a highly recommended restaurant known for its enticing creative and mediterranean cuisine. This popular 2-star Michelin-awarded venue consistently exceeds expectations, ensuring a memorable holiday experience. Ready for another culinary adventure? Indulge your senses at Gucci Osteria da Massimo Bottura, a highly acclaimed restaurant celebrated for its exceptional italian contemporary and international menu.

Explore the vibrant nightlife at Manifattura after your meal, a hub for lively evenings and memorable moments. Or, head to Se·sto On Arno Rooftop Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Il Vinile is perfect for those looking to extend their night with a touch of local flavor.

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

Day 6 offers a multitude of experiences. You will stay in Florence for 2 nights more, offering you enough time to explore at a relaxed pace.

Enjoy the perfect balance of relaxation and exploration in Florence today. One of the most interesting attractions included on the itinerary is David. Then, take a leisurely stroll to Galleria Dell'accademia and learn what makes this detailed art gallery unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the captivating Basilica Of Santa Croce In Florence. After exploring the church, head to Tower Of San Niccolò. This beloved monument is a highlight in Florence. Lastly, don’t forget to check out the extraordinary Piazzale Michelangelo. Enjoy exploring this incredible observation deck at your own pace.

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 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.

Treat yourself to a wonderful meal at Ditta Artigianale, a top-rated dining spot in Florence. If you're in the mood for something new, try Trattoria Da Burde, another premier location with a delectable menu. You might also want to book a table at Casa Toscana. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

If you’re not ready to end the night just yet, Bar 50 Rosso offers a perfect venue to relax and savor a drink. Similarly, Bitter Bar is well-suited for those looking to unwind in a social setting. Archea Brewery is another excellent spot to enjoy a nightcap after a delightful meal.

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

Day 7 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.

Get ready to discover some of the most iconic wonders in Florence, including a monument, a church, and a food market. Start your day at Giotto's Bell Tower. This enchanting monument is a frequently visited place to see in Florence. Then, wander over to Cathedral Of Santa Maria Del Fiore. If majestic sites excite you, this church will be right up your alley. Nearby, you’ll also find Brunelleschi's Dome. This romantic monument is a favorite among visitors.

Florence offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Central Market is a well-known spot in the city that will captivate you with its unique charm. When you’re done at the food market, don’t forget to check out the visually striking Basilica Di Santa Maria Novella, Firenze (fi). Take a moment to appreciate the fascinating details of this locally renowned church in Florence.

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 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.

Treat yourself to a delicious dinner at Ristorante Buca Mario, an excellent option for tonight's dining. Looking for something different? Agricola Toscana offers a tantalizing alternative with its diverse menu. And don’t miss Eataly Firenze. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Gosh*, a well-loved spot among locals and tourists. Or, head to Antico Caffè Del Moro - Art Bar Firenze. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Quelo Bar, another top-rated place in the area.

Raise your glass to another unforgettable day in Italy!

Experience an unparalleled adventure on day 8 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Florence. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Siena. You will spend 1 night here for some well-deserved relaxation.

Today’s route brings fun adventures, romantic experiences, and breathtaking views. The first attraction of today is Piazza Della Signoria. This extraordinary public square is a visually striking place to see in Florence. Continue your discovery at Uffizi Gallery, a historic art gallery 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 Ponte Vecchio. This wondrous historical landmark offers a history-steeped encounter with Florence. Pitti Palace is the last of our recommendations for today. 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.

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

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

Enjoy a lovely dining experience at Enoteca I Terzi, a popular restaurant in Siena. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Siena at Ristorante Tar-Tufo, 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 Antica Trattoria Papei. It’s yet another ideal choice to enhance your time in Siena tonight.

To truly maximize your evening out, consider visiting Meet Life Cafè after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Maudit Pub, another bar with an inviting ambiance. Similarly, Bar Impero Siena also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

Dive into day 9 of your remarkable road trip in Italy. Today you will explore Siena and Vatican City, 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 Rome. You’ll stay here for 4 nights.

Start your day with a visit to Piazza Del Campo. This extraordinary public square is a must-visit in the city. When you’re ready for your next discovery, continue to Siena Cathedral, which may be one of the most history-steeped places you will experience today.

One of the best things about exploring Siena 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 Saint Peter's Square, a locally renowned square in the city. If you’re up for more discoveries, don’t forget to reserve some time for St. Peter's Basilica.

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

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

Prepare for an extraordinary culinary adventure in Rome by booking a table at La Pergola, a 3-star Michelin restaurant that boasts an exceptional mediterranean and contemporary menu. For a different flavor experience, head to Il Pagliaccio, renowned for its delectable creative and innovative dishes. This 2-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Enoteca La Torre, a local gem known for its delightful mediterranean and creative cuisine in Rome. Nestled in the city's heart, this 2-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, La Botticella Of Poggi Giovanni stands out as an excellent choice for a post-dinner cocktail. Alternatively, Almalu Trastevere offers an ideal atmosphere to enjoy the pleasures of the night. Bar Viminale Di Pepi Maurilio is also a great option that provides a perfect setting for a relaxing evening.

Raise your glass to another unforgettable day in Italy!

Day 10 of your road trip will take you to the best attractions Rome has to offer. Cherish the 3 nights you have left in Rome by discovering the best things there are to see and do in the city.

One of the most iconic places you can visit today in Rome is Trastevere. 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.

Rome is home to plenty of attractions that offer fun adventures, romantic experiences, and picturesque spots! Start at Campo De' Fiori, an extraordinary public square that is worthwhile a visit in the city. Nearby, you’ll find Piazza Navona, enchanting visitors with its enchanting appeal. Continue your exploration at Basilica Di Santa Maria Maggiore. This church is one of the city’s most captivating spots.

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.

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

Enjoy a lovely meal at RomAntica, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Coso Ristorante is another top choice with a popular menu. You could also check for a table at DEROMA - Farine Romane. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Rome tonight.

To truly maximize your evening out, consider visiting Sant' Eustachio Caffè after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Yellowsquare Rome, another bar with an inviting ambiance. Similarly, Caffè Portofino also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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 11 of your road trip, you will have an entire day to explore Rome. You’ll stay in Rome for 2 nights and discover all the best things to see and do in the area.

Via del Corso is a fantastic place you can explore today in Rome. This street is a testament to the city’s character, and it's easy to spend hours just walking around and admiring the surroundings. Soak in the Rome-way-of-life and take advantage of the nearby must-see sights located nearby.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, romantic experiences, and scenic views. Whether you decide to explore Rome on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Piazza Del Popolo is the first of them. Spend some time admiring this enchanting public square before continuing your journey. Piazza Di Spagna is your next stop. This world-famous public square is one of the best-rated sights in Rome.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Spanish Steps. This visually striking public square is a sight to behold.

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 Rome. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Treat yourself to a delightful dinner at Hotel de Russie, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try La Taverna Italiana? It's another excellent option with a diverse menu. Consider reserving a table at The Parrot Bar as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Rome.

Continue your evening by exploring the vibrant nightlife scene at The Apartment Bar Roma, a prime destination for a thrilling night out. Also, don’t forget to check out Hotel Hassler Roma, a bar that offers unique local touches.

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

Day 12 offers a multitude of experiences. You will stay in Rome for 1 night more, offering you enough time to explore at a relaxed pace.

Today’s agenda in Rome includes a monument and an archeological site. Pantheon is must-visit monument and a great starting point for the day. Next, continue your journey to Trevi Fountain, a wondrous monument, located just a leisurely stroll away. Next, head to Roman Forum, a history-steeped archeological site, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Rome. If you’re looking for more, Colosseum is also a timeless attraction that is worthwhile a visit. Lastly, don’t miss Circus Maximus, a captivating gem to see in the city.

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 Rome's best restaurants.

Have a fantastic dining experience at Sofitel Roma Villa Borghese, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Centro offers an enticing alternative with its varied menu. Additionally, Ristorante Tema is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rome.

Say good night to Rome and look forward to another great day 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, Rome and Teramo. When you’re not sightseeing, take time to relax at your selected hotel in Ancona, where you’ll be staying for 1 night.

A blend of fun adventures, breathtaking views, and photo-friendly spots await you in Rome on today’s itinerary. First up is the popular monument, Altare Della Patria. Afterward, continue to Castel Sant'angelo.

As you explore Rome’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Villa Borghese. This impressive park is an essential stop that should not be missed. Following that, head to Santuario Madonna Delle Grazie, another must-visit site that will enhance your experience.

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

Get ready for an unforgettable culinary journey in Ancona by reserving a table at Sot'Ajarchi. Renowned as a Bib Gourmand restaurant, it offers an exceptional seafood and from the marches menu. If you're in the mood to try something new, consider Bontà delle Marche, another top spot with a mouthwatering menu.

Continue your lively evening at Alla Tazza D'oro, a perfect place for winding down or revving up the night, depending on which mood you’re in.

Raise your glass and celebrate another amazing day of your road trip in Italy!