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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Day 1
- Bolzano - Bozen - Arrival day
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- Waltherplatz
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Your road trip adventure in Italy begins as soon as you reach Bolzano and pick up your car. You’ll stay in Bolzano for 1 night and explore the best things to see and do, sample the local cuisine, and choose from a curated selection of the best hotels and places to stay in the city.
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.
Make sure to reserve a table at Anita, an iconic dining spot in Bolzano. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Stadt Hotel Città, a popular restaurant in Bolzano. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Danny, a hidden gem nestled in Bolzano. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.
Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Café Gruber stands out as an excellent choice for a post-dinner cocktail. Alternatively, Franzbar offers an ideal atmosphere to enjoy the pleasures of the night. Bar La Nuova Grotta Del Corso is also a great option that provides a perfect setting for a relaxing evening.
Raise a toast to the start of your 11-day road trip in Italy!
Day 2
- Bolzano - Bozen
- Trento
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Drive 64 km, 1 hour 24 min
- South Tyrol Archeological Museum
- MUSE
- Buonconsiglio Castle Museum
- Piazza del Duomo di Trento
- Trento Cathedral
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Embark on another extraordinary experience on day 2 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Bolzano and Trento. At the end of the day, you will enjoy the comforts of a top-rated hotel in Trento, which will be your home away from home for 1 night.
Bolzano is home to plenty of attractions that offer fun adventures, picturesque spots, and history-rich sites! Start at South Tyrol Museum Of Archaeology, an up-and-coming museum that is worthwhile a visit in the city. Nearby, you’ll find Muse, enchanting visitors with its instagrammable appeal. Continue your exploration at Buonconsiglio Castle Museum. This castle is one of the city’s most captivating spots.
Enjoy the freedom of exploring Bolzano at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Piazza Del Duomo Di Trento. After exploring the public square, head to the curiosity-inducing Trento Cathedral.
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 you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Trento. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.
Enjoy a lovely dining experience at Ristorante Ca dei Gobj, a popular restaurant in Trento. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Trento at il Circolino bar/ristorante, 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 Urban Coffee Lab. It’s yet another ideal choice to enhance your time in Trento tonight.
After enjoying a fulfilling meal, continue your evening at Tj Bar, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bar Pasi offers a welcoming atmosphere for easing into the nightlife. Similarly, Locanda Del Gatto Gordo provides an excellent environment for a relaxed and enjoyable evening.
Relax and reminisce about your day in Italy and look forward to more memorable moments to come!
Day 3
- Trento
- Verona
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Drive 104 km, 2 hours 4 min
- Giusti Garden
- Ponte Pietra
- piazza delle Erbe
- Verona Arena
- Castelvecchio Bridge
- Castelvecchio Museum
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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.
Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Trento allows for both. Start by heading to Giusti Garden. This frequently visited botanical garden provides an insightful glimpse into the city's identity. Next, discover Ponte Pietra, a romantic historical landmark, promising a delightful encounter.
Continue your sightseeing with a visit to Piazza Delle Erbe, a notable public square. When you’re done, don’t forget to make a stop at the timeless Verona Arena. Not far away from the stadium, you will find the stunning Castelvecchio Museum, perfect for a quick visit. Round off your day at Castelvecchio Bridge, another gem in Trento with visually striking features to discover.
When you’re done exploring for the day, you’ll drive to your hotel in Verona. 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 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.
Day 4
- Verona
- Venice
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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
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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.
Today's adventure in Verona promises more breathtaking discoveries and enriching experiences! Begin at Santa Maria Gloriosa Dei Frari. This picture-perfect church is a highlight of any visit in the city. Then, enjoy Bridge Of Sighs, another UNESCO world heritage-designated attraction that never fails to captivate visitors. Next, head over to Doge's Palace, one of the city’s most popular attractions, known for its enchanting features.
If you’re looking for more, spend time soaking in the atmosphere of St Mark's Basilica. This grand church is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Piazza San Marco, a wondrous public square, and take a stroll around the area.
After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Venice. Venice offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.
As you explore more of 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.
Savor the flavors at Bauer Hotel, a top pick for dinner tonight. Alternatively, L'Osteria Le Guglie beckons with its unique menu offerings. Also, consider Corner Pub. With its consistent customer satisfaction, it’s an excellent option for dining in Venice tonight.
Unwind after your meal by stepping into Al Parlamento. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, The Caffe Rosso offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Adagio, another top-rated bar in the area.
Celebrate another amazing day of your road trip adventure in Italy!
Day 5
- Venice
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Drive 4 km, 36 min
- Rialto Bridge
- Palazzo Contarini del Bovolo
- Teatro La Fenice
- Peggy Guggenheim Collection
- Santa Maria della Salute
- Cannaregio
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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.
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, you'll explore some of the most beautiful places in Venice, including a historical landmark, a palace, an opera house, an art gallery, a church and much more! Start your day with a visit to Rialto Bridge. This world-famous historical landmark is a must-visit in the city. When you’re ready for your next discovery, continue to Palazzo Contarini Del Bovolo, which may be one of the most enchanting places you will experience today.
One of the best things about exploring Venice 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 Teatro La Fenice, a popular opera house in the city. If you’re up for more discoveries, don’t forget to reserve some time for Peggy Guggenheim Collection and Santa Maria Della Salute.
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 Venice. Enjoy a satisfying meal that will recharge you for tonight's adventures.
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.
After savoring a delicious meal, step into the vibrant nightlife at Il Mercante, where the evening is just getting started. In the same way, The Irish Pub Venezia offers a unique charm perfect for experiencing the local bar scene in Venice. Ai Stagneri is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.
Raise your glass and celebrate another amazing day of your road trip in Italy!
Day 6
- Venice
- Florence
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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
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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.
Enjoy the perfect balance of relaxation and exploration in Venice today. One of the most popular attractions included on the itinerary is Basilica Of Santa Croce In Florence. This heritage-rich church will help you start your sightseeing on top. Then, take a leisurely stroll to Palazzo Vecchio and learn what makes this enchanting palace unique.
Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the astonishing Uffizi Gallery. After exploring the art gallery, head to Ponte Vecchio. This iconic historical landmark is a highlight in Venice. As your day continues, stop by Piazza Della Repubblica, known for its romantic features. Lastly, don’t forget to check out the famous Piazza Della Signoria. Enjoy exploring this incredible public square at your own pace.
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 dinnertime approaches, it's time to head out for a bite to eat in Florence. 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 Ristorante Oliviero 1962, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Di Poneta Novoli offers an enticing alternative with its varied menu. Additionally, Caffe San Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.
After your delicious meal, get a taste of the vibrant nightlife with a visit to Manifattura, known for its inviting atmosphere. Se·sto On Arno Rooftop Bar is another great option if you’re looking for a place to get the night started. Similarly, Il Vinile provides a great setting to enjoy the night away.
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.
Day 7
- Florence
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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
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On day 7 of your road trip, you’ll start and end your day in Florence, where you'll stay for 1 night more.
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 timeless public square is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the breathtaking 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 up-and-coming church offers an enriching experience. For a change of pace, head to Leaning Tower Of Pisa, where you can take in culturally significant 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.
As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Florence. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.
Enjoy a delicious meal at Ditta Artigianale, a highly-rated dining destination in Florence. If you're eager to try something different, consider Trattoria Da Burde, another top spot with a tantalizing menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.
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.
Take some time to reflect on your day and savor another beautiful night in Italy.
Day 8
- Florence
- San Gimignano
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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
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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.
Prepare for a day full of fun adventures, romantic experiences, and breathtaking views. When you’re ready, kick off your sightseeing adventure at Siena Cathedral. This notable church is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Piazza Del Campo, one of the city’s best highlights.
Next, check out Tower Of Mangia, one of the most up-and-coming places to see in Florence. This monument is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Porta San Giovanni. Wander around and soak in the picture-perfect atmosphere this monument offers. Then, head to Palazzo Comunale, Pinacoteca, Torre Grossa, a top-rated museum that adds another dimension to your day. Finally, visit the intriguing Piazza Del Duomo, the last of our attraction recommendations for today.
When you’re done exploring for the day, you’ll drive to your hotel in San Gimignano. Check in and spend some time relaxing before you head out to tour the village.
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.
Savor another day of unforgettable experiences in Italy!
Day 9
- San Gimignano
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Drive 129 km, 2 hours 52 min
- Parco Sculture del Chianti
- Castello di Brolio
- Osservatorio Polifunzionale del Chianti
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On day 9 of your road trip, you’ll start and end your day in San Gimignano, but spend part of the day exploring places of interest outside the immediate village. On today's itinerary, you'll find attractions in Pievasciata, San Regolo, and San Donato in Poggio. You still have 1 night left in San Gimignano.
Prepare for a day full of family-friendly attractions, romantic experiences, and scenic views. When you’re ready, kick off your sightseeing adventure at Parco Sculture Del Chianti. This often recommended sculpture garden is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Castello Di Brolio, one of the hamlet’s best highlights.
Next, check out Osservatorio Polifunzionale Del Chianti, one of the most up-and-coming places to see in San Gimignano. This astronomical observatory is a favorite among locals and travelers alike.
When you’re done exploring for the day, you’ll return to San Gimignano and your accommodation.
Indulge in a memorable dining experience at one of San Gimignano's most popular restaurants, and connect with friendly locals for an authentic adventure.
Get a good night's sleep and look forward to another great day on the road in Italy!
Day 10
- San Gimignano
- Bolzano - Bozen
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Drive 439 km, 5 hours 18 min
- Fountain of Neptune, Bologna
- Bologna Cathedral
- Biblioteca Salaborsa
- Piazza Maggiore
- Two Towers
- Piazza Santo Stefano
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Embark on another extraordinary experience on day 10 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Bologna. At the end of the day, you will enjoy the comforts of a top-rated hotel in Bolzano, which will be your home away from home for 1 night.
Get ready for an exciting day in San Gimignano. Today’s sightseeing agenda includes a monument, a church, a library, a public square and much more! Begin your adventure at Fountain Of Neptune, Bologna. This is a curiosity-inducing monument you should not miss. Another must-see is Bologna Cathedral, an underrated church in San Gimignano.
When you’re ready for the next sight, head to Biblioteca Salaborsa. From there, take a leisurely stroll to Piazza Maggiore, another of the city’s famous attractions. We recommend continuing your self-guided tour at Two Towers, a historic place of interest in the city. If time allows, add Piazza Santo Stefano to your itinerary. This curiosity-inducing public square offers the perfect finishing touch to your day in San Gimignano.
After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Bolzano. Bolzano 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 Bolzano's most popular restaurants, and connect with friendly locals for an authentic adventure.
Make sure to reserve a table at Alumix Cafè Ristorante Pizzeria, an iconic dining spot in Bolzano. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Castel Flavon, a popular restaurant in Bolzano. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Trattoria Filo d'Olio, a hidden gem nestled in Bolzano. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.
Explore the vibrant nightlife at Tiffany Bolzano after your meal, a hub for lively evenings and memorable moments. Or, head to Corte - Bar & Bistro for a great selection of flavorful drinks and a charming setting. Furthermore, Hollywood is perfect for those looking to extend their night with a touch of local flavor.
Head back to your accommodation in Bolzano and get some rest in preparation for another magical day of your road trip in Italy!
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, begin at Franciscan Monastery. This often recommended monastery is a popular place to see in the city.
As your final day in Italy unfolds, enjoy a last-minute shopping spree in Bolzano's best shopping area. Enjoy finding the perfect gift or keepsake to remind you of your wonderful trip to Italy.
Before you conclude your road trip in Italy, drop by another restaurant for a last chance at a memorable dining experience in Bolzano.
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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