11-Day Italy Self-Drive Road Trip With Itinerary from Bolzano traveling south to Trento, Verona, Venice, Florence, and San Gimignano

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photo of view of Waltherplatz or Piazza Walther Von der Vogelweide is the main square in Bolzano city in South Tyrol, Italy.
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Experience the freedom of the open road in Italy as you embark on an unforgettable 11-day road trip! This experience caters to every traveler, featuring destinations like Bolzano, Trento, Verona, Venice, Florence, Pisa, Siena, San Gimignano, San Donato in Poggio, and Bologna.

This perfectly planned road trip itinerary in Italy takes you through some of the best places to see in the country. You will spend 2 nights in Bolzano, 1 night in Trento, 1 night in Verona, 2 nights in Venice, 2 nights in Florence, and 2 nights in San Gimignano. Anticipate well-spent days sightseeing, eating delicious food, and experiencing the highlights of each destination!

With this travel package, you can choose from an extensive selection of accommodations along your road trip route in Italy. We have handpicked the best hotels and places to stay across the country, including options for each budget. Whether you are in the mood for luxurious 5-star hotels or budget-friendly bed and breakfasts, we have got you covered.

Upon arriving in Bolzano, the rental vehicle of your choice will be ready for collection. From there, the road trip can begin! Experience the ultimate freedom and uncover Italy on your own terms.

An expertly curated travel plan makes sure you don’t miss out on any of the best things to see and do on your road trip in Italy. Piazza San Marco and Rialto Bridge are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Verona Arena, learn more about the unique Ponte Vecchio, and immerse yourself in the vibrant atmosphere of Leaning Tower Of Pisa.

As you hit the open road and drive through Bolzano, Trento, Verona, Venice, Florence, Pisa, Siena, San Gimignano, San Donato in Poggio, and Bologna, you will also enjoy plenty of opportunities to uncover hidden gems and experience the authentic charm of Italy. Whether you are exploring enchanting towns and villages, discovering scenic routes, or indulging in local cuisine, there is always something new and exciting to experience in Italy.

Throughout your road trip in Italy, take breaks from sightseeing to explore your favorite destinations' top shopping streets and markets. Discover unique souvenirs that will forever remind you of your self-drive adventure in Italy.

This package offers an all-in-one solution for your trip planning - choose flights, a rental car, accommodation, attractions, and tours that suit your needs and desires. You can customize each day of your road trip itinerary with flexible trip planning before and after booking.

The best services in Italy fill up quickly, so book your spot early. Select a date and start planning your road trip in Italy today!

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Driver’s age is 30 - 65
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Itinerary summary

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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
Waltherplatz
South Tyrol Archeological MuseumMUSEBuonconsiglio Castle MuseumPiazza del Duomo di TrentoTrento Cathedral
Giusti GardenPonte Pietrapiazza delle ErbeVerona ArenaCastelvecchio BridgeCastelvecchio Museum
Basilica S.Maria Gloriosa dei FrariBridge of SighsDoge's PalaceSt Mark's BasilicaPiazza San Marco
Rialto BridgePalazzo Contarini del BovoloTeatro La FenicePeggy Guggenheim CollectionSanta Maria della SaluteCannaregio
Basilica of Santa Croce in FlorencePalazzo VecchioUffizi GalleryPonte VecchioPiazza della Repubblicapiazza della Signoria

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Day 1

Day 1

  • Bolzano - Bozen - Arrival day
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  • Waltherplatz
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Say hello to Bolzano! Your exciting road trip through Italy is just about to start. Navigating the top places to see in the region is a breeze with a car. The rental vehicle of your choice will be ready for pickup upon your arrival in the city. You will stay in Bolzano for 1 night before you continue your adventure!

Bolzano is a beautiful city with plenty to discover. If you arrive before check-in time or prefer to get started on your sightseeing right away, we recommend checking out Waltherplatz, or just taking a stroll in the city center. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

As afternoon approaches, head to your chosen hotel in Bolzano. Check-in typically starts around 2 to 4 PM at hotels in Italy. We recommend staying at a hotel in a central location for easy access to the best attractions, restaurants, and bars in the city.

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 Bolzano, it's often a good idea to reserve a table in advance.

Dine in style at Anita, a top recommendation for dinner tonight. Or, for a change of pace, Stadt Hotel Città boasts a menu that's sure to impress. Also, be sure to check out Danny. Known as a local hotspot, it’s a great choice for tonight in Bolzano.

Continue your lively evening at Café Gruber, a perfect place for winding down or revving up the night, depending on which mood you’re in. Franzbar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Bar La Nuova Grotta Del Corso ensures a night out tailored to your taste.

Raise a toast to the start of your 11-day road trip in Italy!

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Day 2

Day 2

  • Bolzano - Bozen
  • Trento
  • More

Drive 64 km, 1 hour 24 min

  • South Tyrol Archeological Museum
  • MUSE
  • Buonconsiglio Castle Museum
  • Piazza del Duomo di Trento
  • Trento Cathedral
  • More

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

Today’s agenda in Bolzano includes a museum, a castle, a public square, a church and much more! South Tyrol Museum Of Archaeology is must-visit museum and a great starting point for the day. Next, continue your journey to Muse, a popular museum, located just a leisurely stroll away. Next, head to Buonconsiglio Castle Museum, a stunning castle, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Bolzano. When you're ready, let your sightseeing route take you to the beloved Piazza Del Duomo Di Trento. If you’re looking for more, Trento Cathedral is also a curiosity-inducing attraction that is worthwhile a visit.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Trento. Trento 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 Trento. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Make sure to reserve a table at Ristorante Ca dei Gobj, an iconic dining spot in Trento. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of il Circolino bar/ristorante, a popular restaurant in Trento. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Urban Coffee Lab, a hidden gem nestled in Trento. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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

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

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Day 3

Day 3

  • Trento
  • Verona
  • More

Drive 104 km, 2 hours 4 min

  • Giusti Garden
  • Ponte Pietra
  • piazza delle Erbe
  • Verona Arena
  • Castelvecchio Bridge
  • Castelvecchio Museum
  • More

Experience an unparalleled adventure on day 3 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Verona. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Verona. You will spend 1 night here for some well-deserved relaxation.

Get ready for a day filled with fun adventures, romantic experiences, and natural wonders in the charming city of Trento. Your adventure starts at Giusti Garden, an underrated local hot spot. Another notable attraction to explore is Ponte Pietra. This captivating historical landmark is known for its noteworthy appeal.

After soaking in the highlights of these sights, take some time to wander Trento's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Piazza Delle Erbe. This history-steeped public square offers a fascinating experience that many visitors find memorable. Verona Arena is also worth visiting, along with Castelvecchio Bridge. These standout landmarks offer unique experiences that add to the day’s enjoyment. End your day at Castelvecchio Museum. This popular museum provides a fitting finale to your sightseeing.

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

Treat yourself to a delicious dinner at La Griglia, an excellent option for tonight's dining. Looking for something different? Vecio Macello offers a tantalizing alternative with its diverse menu. And don’t miss Via Fama Cafè | Verona. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Verona.

Continue your evening by exploring the vibrant nightlife scene at Archivio, a prime destination for a thrilling night out. Also, don’t forget to check out La Segreteria Café, a bar that offers unique local touches. Likewise, Grande Giove Cocktail Bar provides an excellent alternative for a fun evening.

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

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Day 4

Day 4

  • Verona
  • Venice
  • More

Drive 122 km, 1 hour 42 min

  • Basilica S.Maria Gloriosa dei Frari
  • Bridge of Sighs
  • Doge's Palace
  • St Mark's Basilica
  • Piazza San Marco
  • More

Embark on another extraordinary experience on day 4 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Venice. 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.

Today, you'll explore some of the most beautiful places in Verona, including a church, a monument, a palace, a public square and much more! Start your day with a visit to Santa Maria Gloriosa Dei Frari. This increasingly popular church is a must-visit in the city. When you’re ready for your next discovery, continue to Bridge Of Sighs, which may be one of the most UNESCO world heritage-designated places you will experience today.

One of the best things about exploring Verona 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 Doge's Palace, a locally renowned palace in the city. If you’re up for more discoveries, don’t forget to reserve some time for St Mark's Basilica and Piazza San Marco.

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 you explore more of Venice, 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 Bauer Hotel, an iconic dining spot in Venice. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of L'Osteria Le Guglie, a popular restaurant in Venice. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Corner Pub, a hidden gem nestled in Venice. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Continue the enjoyment post-dinner at Al Parlamento, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, The Caffe Rosso offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Adagio. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

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Day 5

Day 5

  • Venice
  • More

Drive 4 km, 36 min

  • Rialto Bridge
  • Palazzo Contarini del Bovolo
  • Teatro La Fenice
  • Peggy Guggenheim Collection
  • Santa Maria della Salute
  • Cannaregio
  • More

On day 5 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.

Cannaregio is one of the highlights of today. Take your time exploring this iconic neighborhood in Venice, which offers a perfect blend of history and culture. Plus, it's close to many must-see landmarks in the city.

Get ready for an exciting day in Venice. Today’s sightseeing agenda includes a historical landmark, a palace, an opera house, an art gallery, a church and much more! Begin your adventure at Rialto Bridge. This is a wondrous historical landmark you should not miss. Another must-see is Palazzo Contarini Del Bovolo, an interesting palace in Venice.

When you’re ready for the next sight, head to Teatro La Fenice. From there, take a leisurely stroll to Peggy Guggenheim Collection, another of the city’s notable attractions. We recommend continuing your self-guided tour at Santa Maria Della Salute, a culturally significant place of interest 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.

As you explore more of Venice, 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 Generator Venice, a highly-rated dining destination in Venice. If you're eager to try something different, consider Nevodi, another top spot with a tantalizing menu. You might also want to secure a reservation at Ristorante La Piazza. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Venice this evening.

Cap off your dinner by heading to Il Mercante, ideal for a leisurely evening with a drink in hand. The Irish Pub Venezia is another bar that offers an enjoyable setting. Similarly, Ai Stagneri is also a popular place to go on a night out, perfect for relaxing and socializing.

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

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Day 6

Day 6

  • Venice
  • Florence
  • More

Drive 262 km, 3 hours 23 min

  • Basilica of Santa Croce in Florence
  • Palazzo Vecchio
  • Uffizi Gallery
  • Ponte Vecchio
  • Piazza della Repubblica
  • piazza della Signoria
  • More

Dive into day 6 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.

Today’s route brings fun adventures, picturesque spots, and historic treasures. The first attraction of today is Basilica Of Santa Croce In Florence. This captivating church is a standout place to see in Venice. Continue your discovery at Palazzo Vecchio, a history-steeped palace with stories to tell.

As you stroll around Venice, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Uffizi Gallery. This extraordinary art gallery offers a historic encounter with Venice. Next, make your way to Ponte Vecchio to add another highlight to your day. After that, visit Piazza Della Repubblica, a notable public square that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Piazza Della Signoria, an impressive public square 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 Venice.

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

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

Enjoy a lovely meal at Ristorante Oliviero 1962, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Di Poneta Novoli is another top choice with a popular menu. You could also check for a table at Caffe San Firenze. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.

Continue your lively evening at Manifattura, a perfect place for winding down or revving up the night, depending on which mood you’re in. Se·sto On Arno Rooftop Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Il Vinile ensures a night out tailored to your taste.

Savor another day of unforgettable experiences in Italy!

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Day 7

Day 7

  • Florence
  • More

Drive 198 km, 2 hours 59 min

  • Piazza del Duomo, Pisa
  • Campo santo
  • Pisa Cathedral
  • Leaning Tower of Pisa
  • Museo dell'Opera del Duomo
  • Knights' Square
  • More

On day 7 of your road trip, you’ll start and end your day in Florence, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Pisa. You still have 1 night left in Florence.

Today’s itinerary in Florence covers several incredible sights, including a public square, a cemetery, a church, a monument, a museum and much more! Start your adventure at Piazza Del Duomo, Pisa. This globally renowned public square is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the picture-perfect wonders of Campo Santo, a must-see cemetery in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Pisa Cathedral. This locally appreciated church offers an enriching experience. For a change of pace, head to Leaning Tower Of Pisa, where you can take in noteworthy features. Conclude your self-guided sightseeing tour with a visit to Museo Dell'opera Del Duomo and Knights' Square. These sights offer a fulfilling end to a perfect day.

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

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

Enjoy a delicious meal at Ditta Artigianale, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Trattoria Da Burde, another top spot with a mouthwatering menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

Extend your evening after a delightful meal by visiting Bar 50 Rosso, which offers the perfect atmosphere for a night out. Moreover, Bitter Bar is another popular option for a drink or two. Likewise, Archea Brewery also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

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Day 8

Day 8

  • Florence
  • San Gimignano
  • More

Drive 120 km, 2 hours 12 min

  • Siena Cathedral
  • piazza del Campo
  • Tower of Mangia
  • Porta San Giovanni
  • Town Hall, Picture Gallery and Great Tower
  • Piazza del Duomo, San Gimignano
  • More

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 Siena and San Gimignano. In the evening, you’ll end up in San Gimignano, where you will stay for 2 nights.

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

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 Tower Of Mangia. This breathtaking monument is a sight to behold. To round off your sightseeing experience, visit Porta San Giovanni and Palazzo Comunale, Pinacoteca, Torre Grossa. If time allows, end your day with Piazza Del Duomo, a visually striking public square that offers a memorable conclusion to your exploration.

At the end of the day, you will drive to San Gimignano, 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 San Gimignano. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

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

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Day 9

Day 9

  • San Gimignano
  • More

Drive 129 km, 2 hours 52 min

  • Parco Sculture del Chianti
  • Castello di Brolio
  • Osservatorio Polifunzionale del Chianti
  • More

On day 9 of your road trip in Italy, you’ll start and end your day in San Gimignano, but spend the day exploring what’s beyond the village. Since you will return to San Gimignano for 1 night more, there’s no need to rush. Experience Pievasciata, San Regolo, and San Donato in Poggio to the fullest today with this curated day itinerary!

Set out on a day brimming with fun adventures, romantic experiences, and breathtaking views. Start at the underrated Parco Sculture Del Chianti, a noteworthy sculpture garden in San Gimignano. Next, go to Castello Di Brolio.

After visiting Parco Sculture Del Chianti and Castello Di Brolio, have a stroll along San Gimignano's streets and take in the local charm. Continue your sightseeing by heading to Osservatorio Polifunzionale Del Chianti. This picture-perfect astronomical observatory offers a unique experience.

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

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

Raise your glass to another unforgettable day in Italy!

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Day 10

Day 10

  • San Gimignano
  • Bolzano - Bozen
  • More

Drive 439 km, 5 hours 18 min

  • Fountain of Neptune, Bologna
  • Bologna Cathedral
  • Biblioteca Salaborsa
  • Piazza Maggiore
  • Two Towers
  • Piazza Santo Stefano
  • More

On day 10 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Bologna. When you’re not sightseeing, take time to relax at your selected hotel in Bolzano, where you’ll be staying for 1 night.

Brace yourself for today’s incredible lineup of attractions in San Gimignano, featuring fun adventures, photo-friendly spots, and history-rich sites. Start at Fountain Of Neptune, Bologna, a worthwhile monument in the city. Then, head to Bologna Cathedral and soak in the ambiance of this historic church.

There are many interesting places to see in San Gimignano, and when you are ready for more, go to Biblioteca Salaborsa. This is one of the city’s most curiosity-inducing respected spots of interest. After exploring the library, visit the spectacular Piazza Maggiore. Not far away, you'll also find Two Towers. This monument is a culturally significant highlight in San Gimignano. Before wrapping up your self-guided sightseeing tour, head to Piazza Santo Stefano, an up-and-coming public square in the city.

When you’re done exploring for the day, you’ll drive to your hotel in Bolzano. 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 Bolzano. 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.

Have a fantastic dining experience at Alumix Cafè Ristorante Pizzeria, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Castel Flavon offers an enticing alternative with its varied menu. Additionally, Trattoria Filo d'Olio is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Bolzano.

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

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

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Day 11

Day 11

  • Bolzano - Bozen - Departure day
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  • Franciscan Monastery
  • More

Day 11 of your road trip in Italy is your departure day. This is your chance to catch a last glimpse of Bolzano before saying goodbye to this wonderful destination. If you've still got time left, we recommend doing some last-minute shopping or sightseeing.

If you're up for some more sightseeing, begin at Franciscan Monastery. This up-and-coming monastery is a popular place to see in the city.

Explore local shops for souvenirs to remember your trip or find unique gifts for loved ones.

Before you conclude your road trip in Italy, drop by another restaurant for a last chance at a memorable dining experience in Bolzano.

If you're in the mood for something new, try Black Sheep Drink Differently, another premier location with a delectable menu.

You’ll then say farewell to Bolzano. Drive to the airport, return your car, and take the opportunity to get some last-minute souvenirs before you board your flight home. We wish you a pleasant journey and hope you leave with many wonderful memories of your road trip in Italy!

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