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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Explore the best of Italy on a 11-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Bolzano, Trento, Verona, Venice, Florence, Pisa, Siena, San Gimignano, San Donato in Poggio, and Bologna. This road trip itinerary in Italy seamlessly combines exploration with relaxation.

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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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
  • More

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.

Treat yourself to a delightful dinner at Anita, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Stadt Hotel Città? It's another excellent option with a diverse menu. Consider reserving a table at Danny as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Bolzano.

Round off your dining experience by visiting Café Gruber, a prime location for a drink. Alternatively, explore the distinctive characteristics of Franzbar, a bar catering to every mood and preference. Bar La Nuova Grotta Del Corso likewise offers a unique atmosphere, perfect for a memorable night out.

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 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 Bolzano and Trento. In the evening, you’ll end up in Trento, where you will stay for 1 night.

Today’s itinerary in Bolzano covers several incredible sights, including a museum, a castle, a public square, a church and much more! Start your adventure at South Tyrol Museum Of Archaeology. This worthwhile museum is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the visually striking wonders of Muse, a must-see museum 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 Buonconsiglio Castle Museum. This locally renowned castle offers an enriching experience. For a change of pace, head to Piazza Del Duomo Di Trento, where you can take in enchanting features. Conclude your self-guided sightseeing tour with a visit to Trento Cathedral. These sights offer a fulfilling end to a perfect day.

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

As you explore more of Trento, 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.

Savor the flavors at Ristorante Ca dei Gobj, a top pick for dinner tonight. Alternatively, il Circolino bar/ristorante beckons with its unique menu offerings. Also, consider Urban Coffee Lab. With its consistent customer satisfaction, it’s an excellent option for dining in Trento tonight.

Round off your dining experience by visiting Tj Bar, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bar Pasi, a bar catering to every mood and preference. Locanda Del Gatto Gordo likewise offers a unique atmosphere, perfect for a memorable night out.

Relax and recharge in preparation for another adventurous day 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.

Today’s well-planned self-sightseeing route offers several fun adventures, romantic experiences, and natural wonders. Whether you decide to explore Trento on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Giusti Garden is the first of them. Spend some time admiring this masterful botanical garden before continuing your journey. Ponte Pietra is your next stop. This well-known historical landmark is one of the best-rated sights in Trento.

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 Piazza Delle Erbe. This stunning public square is a sight to behold. To round off your sightseeing experience, visit Verona Arena and Castelvecchio Bridge. If time allows, end your day with Castelvecchio Museum, a picture-perfect museum that offers a memorable conclusion to your exploration.

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

Enjoy a lovely meal at La Griglia, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Vecio Macello is another top choice with a popular menu. You could also check for a table at Via Fama Cafè | Verona. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Verona tonight.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Archivio, a well-loved spot among locals and tourists. Or, head to La Segreteria Café. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Grande Giove Cocktail Bar, another top-rated place in the area.

Savor another day of unforgettable experiences 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

On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Venice. When you’re not sightseeing, take time to relax at your selected hotel in Venice, where you’ll be staying for 2 nights.

Verona is home to plenty of attractions that offer fun adventures, scenic views, and picturesque spots! Start at Santa Maria Gloriosa Dei Frari, a curiosity-inducing church that is worthwhile a visit in the city. Nearby, you’ll find Bridge Of Sighs, enchanting visitors with its romantic appeal. Continue your exploration at Doge's Palace. This palace is one of the city’s most interesting spots.

Enjoy the freedom of exploring Verona at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit St Mark's Basilica. After exploring the church, head to the globally renowned Piazza San Marco.

At the end of the day, you will drive to Venice, 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 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.

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.

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

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

Day 5 of your road trip will take you to the best attractions Venice has to offer. Cherish the 1 night you have left in Venice 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 Venice is Cannaregio. Allow yourself some time to explore this neighborhood and discover its unique quirks. You'll also find many of the best sightseeing spots nearby.

Today’s itinerary in Venice covers several incredible sights, including a historical landmark, a palace, an opera house, an art gallery, a church and much more! Start your adventure at Rialto Bridge. This globally renowned historical landmark is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the romantic wonders of Palazzo Contarini Del Bovolo, a must-see palace 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 Teatro La Fenice. This well-known opera house offers an enriching experience. For a change of pace, head to Peggy Guggenheim Collection, where you can take in romantic features. Conclude your self-guided sightseeing tour with a visit to Santa Maria Della Salute. These sights offer a fulfilling end to a perfect day.

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 Venice's best restaurants.

Make sure to reserve a table at Generator Venice, 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 Nevodi, 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 Ristorante La Piazza, a hidden gem nestled in Venice. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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.

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.

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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

Embark on another extraordinary experience on day 6 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Florence. At the end of the day, you will enjoy the comforts of a top-rated hotel in Florence, which will be your home away from home for 2 nights.

Savor the day by visiting some of the best places to see in Venice, including a church, a palace, an art gallery, a historical landmark, a public square and much more! Start your adventure at Basilica Of Santa Croce In Florence. This captivating church is a must-visit for travelers looking for a unique holiday experience. Make your way to Palazzo Vecchio located in Venice for another exciting encounter.

Next, immerse yourself in the setting of Uffizi Gallery. Its picture-perfect features will captivate you. After the art gallery, continue your tour of the city with a visit to Ponte Vecchio. Visitors usually appreciate the majestic features of this historical landmark. Next up is Piazza Della Repubblica, a highly recommended public square. For a change of pace, head to Piazza Della Signoria. As one of the most impressive attractions in Venice, this public square is the perfect place to end your self-guided sightseeing tour.

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.

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

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.

After savoring a delicious meal, step into the vibrant nightlife at Manifattura, where the evening is just getting started. In the same way, Se·sto On Arno Rooftop Bar offers a unique charm perfect for experiencing the local bar scene in Florence. Il Vinile is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Get a good night's sleep and look forward to another great day on the road 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, where you'll stay for 1 night more.

Enjoy the perfect balance of relaxation and exploration in Florence today. One of the most world-famous attractions included on the itinerary is Piazza Del Duomo, Pisa. This UNESCO world heritage-listed public square will help you start your sightseeing on top. Then, take a leisurely stroll to Campo Santo and learn what makes this UNESCO world heritage-designated cemetery unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the up-and-coming Pisa Cathedral. After exploring the church, head to Leaning Tower Of Pisa. This world-famous monument is a highlight in Florence. As your day continues, stop by Museo Dell'opera Del Duomo, known for its UNESCO world heritage-listed features. Lastly, don’t forget to check out the increasingly popular Knights' Square. Enjoy exploring this incredible public square at your own pace.

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

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.

Keep the excitement of the evening going by visiting a bar or two. Bar 50 Rosso is an excellent place to start. You could also check out Bitter Bar, offering a different kind of charm. A last recommendation for the day is Archea Brewery. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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 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

Dive into day 8 of your remarkable road trip in Italy. Today you will explore Siena and San Gimignano, 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 San Gimignano. You’ll stay here for 2 nights.

Immerse yourself in Florence’s rich culture with today's sightseeing itinerary. Start your journey at Siena Cathedral. This romantic church is sure to ignite your curiosity. Next, dive into the romantic features of Piazza Del Campo, a must-visit public square 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 Tower Of Mangia, an often recommended monument. For a change of scene, check out Porta San Giovanni, known for its historic features. We also recommend visiting Palazzo Comunale, Pinacoteca, Torre Grossa. This museum is a must for anyone looking to experience the city to the fullest. Lastly, end your day with a visit to Piazza Del Duomo, yet another increasingly popular attraction 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 San Gimignano. San Gimignano 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 San Gimignano. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Raise your glass to another unforgettable day 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

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

A blend of family-friendly attractions, romantic experiences, and breathtaking views await you in San Gimignano on today’s itinerary. First up is the beloved sculpture garden, Parco Sculture Del Chianti. Afterward, continue to Castello Di Brolio, a castle every traveler should visit.

As you explore San Gimignano’s charming streets, take in the lively atmosphere and get to know the character of the hamlet. Next, make your way to Osservatorio Polifunzionale Del Chianti. This frequently visited astronomical observatory is an essential stop.

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

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 and celebrate another amazing day of your road trip 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 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 Bologna. In the evening, you’ll end up in Bolzano, where you will stay for 1 night.

Brace yourself for today’s incredible lineup of attractions in San Gimignano, featuring fun adventures, photo-friendly spots, and historic treasures. Start at Fountain Of Neptune, Bologna, an often recommended monument in the city. Then, head to Bologna Cathedral and soak in the ambiance of this breathtaking 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 beloved heritage-rich spots of interest. After exploring the library, visit the impressive Piazza Maggiore. Not far away, you'll also find Two Towers. This monument is an instagrammable 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.

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

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

Treat yourself to a delicious dinner at Alumix Cafè Ristorante Pizzeria, an excellent option for tonight's dining. Looking for something different? Castel Flavon offers a tantalizing alternative with its diverse menu. And don’t miss Trattoria Filo d'Olio. With its reputation for pleasing customers, it’s a fantastic choice 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 reminisce about your day in Italy and look forward to more memorable moments to come!

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Day 11

Day 11

  • Bolzano - Bozen - Departure day
  • More
  • 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, we recommend visiting Franciscan Monastery, a stunning monastery before you head out.

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.

Have a fantastic dining experience at Ristorante Rastbichler, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Black Sheep Drink Differently offers an enticing alternative with its varied 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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