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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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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Welcome to Bolzano, the perfect starting point for your road trip in Italy! Pick up your rental car and let the adventure begin. You will spend 1 night immersing yourself in Bolzano's charm before embarking on the next leg of your journey.

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.

Make your way to your chosen hotel. Check-in typically starts between 2 and 4 PM in Bolzano. Make yourself at home and enjoy some downtime before heading out again.

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.

Cap off your dinner by heading to Café Gruber, ideal for a leisurely evening with a drink in hand. Franzbar is another bar that offers an enjoyable setting. Similarly, Bar La Nuova Grotta Del Corso is also a popular place to go on a night out, perfect for relaxing and socializing.

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

Dive into day 2 of your remarkable road trip in Italy. Today you will explore Bolzano and Trento, 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 Trento. You’ll stay here for 1 night.

Savor the day by visiting some of the best places to see in Bolzano, 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 must-visit for travelers looking for a unique holiday experience. Make your way to Muse located in Bolzano for another exciting encounter.

Next, immerse yourself in the setting of Buonconsiglio Castle Museum. Its stunning features will captivate you. After the castle, continue your tour of the city with a visit to Piazza Del Duomo Di Trento. Visitors usually appreciate the symbolic features of this public square. Next up is Trento Cathedral, a highly recommended church.

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

Enjoy a lovely meal at Ristorante Ca dei Gobj, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, il Circolino bar/ristorante is another top choice with a popular menu. You could also check for a table at Urban Coffee Lab. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Trento tonight.

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.

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

On day 3 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 Verona. In the evening, you’ll end up in Verona, where you will stay for 1 night.

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, a frequently visited local hot spot. Another notable attraction to explore is Ponte Pietra. This captivating historical landmark is known for its serene 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 visually striking 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 interesting museum provides a fitting finale to your sightseeing.

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.

Don’t miss out on dining at La Griglia, a top-rated dining destination in Verona. If you're in the mood to try something new, consider Vecio Macello, another top spot with a mouthwatering menu. You might also want to secure a reservation at Via Fama Cafè | Verona. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Verona this evening.

Round off your dining experience by visiting Archivio, a prime location for a drink. Alternatively, explore the distinctive characteristics of La Segreteria Café, a bar catering to every mood and preference. Grande Giove Cocktail Bar likewise offers a unique atmosphere, perfect for a memorable night out.

Say good night to Verona and look forward to another great day of your road trip 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.

Enjoy the perfect balance of relaxation and exploration in Verona today. One of the most up-and-coming attractions included on the itinerary is Santa Maria Gloriosa Dei Frari. This culturally significant church will help you start your sightseeing on top. Then, take a leisurely stroll to Bridge Of Sighs and learn what makes this culturally significant monument unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the locally renowned Doge's Palace. After exploring the palace, head to St Mark's Basilica. This well-known church is a highlight in Verona. As your day continues, stop by Piazza San Marco, known for its romantic 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.

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

Treat yourself to a wonderful meal at Bauer Hotel, a top-rated dining spot in Venice. If you're in the mood for something new, try L'Osteria Le Guglie, another premier location with a delectable menu. You might also want to book a table at Corner Pub. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Venice.

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

Raise your glass to another unforgettable day 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.

A visit to Cannaregio in Venice is a must on the agenda today. This neighborhood is full of hidden gems and character, perfect for a leisurely stroll. Plus, you’ll be close to some of the city’s most famous sights.

Set out on a day brimming with fun adventures, romantic experiences, and breathtaking views. Start at the timeless Rialto Bridge, a visually striking historical landmark in Venice. Next, go to Palazzo Contarini Del Bovolo.

After visiting Rialto Bridge and Palazzo Contarini Del Bovolo, have a stroll along Venice's streets and take in the local charm. Continue your sightseeing by heading to Teatro La Fenice. This romantic opera house offers a unique experience. Peggy Guggenheim Collection is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Santa Maria Della Salute, one of the most history-steeped places to visit in Venice.

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

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.

Explore the vibrant nightlife at Il Mercante after your meal, a hub for lively evenings and memorable moments. Or, head to The Irish Pub Venezia for a great selection of flavorful drinks and a charming setting. Furthermore, Ai Stagneri is perfect for those looking to extend their night with a touch of local flavor.

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 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.

Get ready to discover some of the most iconic wonders in Venice, including a church, a palace, an art gallery, a historical landmark, a public square and much more! Start your day at Basilica Of Santa Croce In Florence. This culturally significant church is an interesting place to see in Venice. Then, wander over to Palazzo Vecchio. If visually striking sites excite you, this palace will be right up your alley. Nearby, you’ll also find Uffizi Gallery. This romantic art gallery is a favorite among visitors.

Venice offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Ponte Vecchio is a globally renowned spot in the city that will captivate you with its unique charm. When you’re done at the historical landmark, don’t forget to check out the history-steeped Piazza Della Repubblica. Take a moment to appreciate the fascinating details of this notable public square. Wrap up your self-guided tour of Venice's top attractions with a visit to Piazza Della Signoria.

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.

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

Enjoy a delicious meal at Ristorante Oliviero 1962, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Di Poneta Novoli, another top spot with a mouthwatering menu. You might also want to secure a reservation at Caffe San Firenze. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Manifattura stands out as an excellent choice for a post-dinner cocktail. Alternatively, Se·sto On Arno Rooftop Bar offers an ideal atmosphere to enjoy the pleasures of the night. Il Vinile is also a great option that provides a perfect setting for a relaxing evening.

Raise your glass and celebrate another amazing day of your road trip 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

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

Today, you'll explore some of the most beautiful places in Florence, including a public square, a cemetery, a church, a monument, a museum and much more! Start your day with a visit to Piazza Del Duomo, Pisa. This world-famous public square is a must-visit in the city. When you’re ready for your next discovery, continue to Campo Santo, which may be one of the most UNESCO world heritage-listed places you will experience today.

One of the best things about exploring Florence 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 Pisa Cathedral, an up-and-coming church in the city. If you’re up for more discoveries, don’t forget to reserve some time for Leaning Tower Of Pisa and Museo Dell'opera Del Duomo. End your day with a visit to Knights' Square, an often recommended public square that’s sure to leave a lasting impression.

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

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

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.

Cap off your dinner by heading to Bar 50 Rosso, ideal for a leisurely evening with a drink in hand. Bitter Bar is another bar that offers an enjoyable setting. Similarly, Archea Brewery is also a popular place to go on a night out, perfect for relaxing and socializing.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

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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

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 2 vibrant destinations - Siena and San Gimignano. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in San Gimignano. You will spend 2 nights here for some well-deserved relaxation.

Bring your curiosity for today’s adventure around Florence. Some of the city’s most loved attractions await! Siena Cathedral is the perfect place to start. This church is one of the most popular places to visit in Florence. Next, head to Piazza Del Campo, a widely recognized public square, known for its enchanting features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Tower Of Mangia. This historic monument is a highly recommended experience. Nearby, you'll also find Porta San Giovanni and Palazzo Comunale, Pinacoteca, Torre Grossa. Visit these for an interesting touch to your journey. Finish the day with a visit to Piazza Del Duomo, an enchanting public square 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.

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

Celebrate another amazing day of your road trip adventure 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

Greet day 9 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to San Gimignano for your remaining 1 night in the village 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 Pievasciata, San Regolo, and San Donato in Poggio.

Discover a day packed with family-friendly attractions, romantic experiences, and scenic views in San Gimignano. Begin your sightseeing with Parco Sculture Del Chianti. This beloved sculpture garden is one of the top attractions in the hamlet. Proceed to Castello Di Brolio, another must-visit attraction.

As you wander through the inviting streets of San Gimignano, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Osservatorio Polifunzionale Del Chianti. This up-and-coming astronomical observatory is a traveler-favorite.

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

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 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

Dive into day 10 of your remarkable road trip in Italy. Today you will explore Bologna, 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 Bolzano. You’ll stay here for 1 night.

Set out on a day brimming with fun adventures, photo-friendly spots, and historic treasures. Start at the frequently visited Fountain Of Neptune, Bologna, a heritage-rich monument in San Gimignano. Next, go to Bologna Cathedral.

After visiting Fountain Of Neptune, Bologna and Bologna Cathedral, have a stroll along San Gimignano's streets and take in the local charm. Continue your sightseeing by heading to Biblioteca Salaborsa. This eye-catching library offers a unique experience. Piazza Maggiore is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Two Towers, one of the most historic places to visit in San Gimignano. If you still have some time left for sightseeing, we also recommend stopping by Piazza Santo Stefano.

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 you explore more of Bolzano, 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 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.

If you’re not ready to end the night just yet, Tiffany Bolzano offers a perfect venue to relax and savor a drink. Similarly, Corte - Bar & Bistro is well-suited for those looking to unwind in a social setting. Hollywood is another excellent spot to enjoy a nightcap after a delightful meal.

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

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Day 11

Day 11

  • Bolzano - Bozen - Departure day
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  • Franciscan Monastery
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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 historic monastery before you head out.

Make the most of your final day in Italy by visiting Bolzano’s iconic markets and shopping establishments. Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing experience in Italy.

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

Dine in style at Ristorante Rastbichler, a top recommendation for dinner tonight. Or, for a change of pace, Black Sheep Drink Differently boasts a menu that's sure to impress.

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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