5-Day Italy Self-Drive Road Trip With Itinerary from Bolzano traveling south to Sirmione and Florence

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Explore the best of Italy on a 5-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Bolzano, Verona, Sirmione, Florence, Siena, and San Gimignano. 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 Sirmione, and 1 night in Florence. 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. Verona Arena and Ponte Vecchio are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Piazza Della Signoria, learn more about the unique Piazza Del Campo, and immerse yourself in the vibrant atmosphere of Uffizi Gallery.

As you hit the open road and drive through Bolzano, Verona, Sirmione, Florence, Siena, and San Gimignano, 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
Verona ArenaPorta Borsaripiazza delle ErbePonte PietraArchaeological site of Grotte di CatulloCastello di Sirmione
Piazza della RepubblicaPonte VecchioUffizi GalleryBasilica of Santa Croce in FlorencePalazzo Vecchiopiazza della Signoria
Siena Cathedralpiazza del CampoPiazza del Duomo, San Gimignano
Funivia del Colle

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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.

Find your way to your hotel in Bolzano. We recommend choosing a hotel in a central location for easy exploring. Check-in typically starts between 2 and 4 PM at hotels in Italy. Settle in and make plans for the evening.

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.

If you’re not ready to end the night just yet, Café Gruber offers a perfect venue to relax and savor a drink. Similarly, Franzbar is well-suited for those looking to unwind in a social setting. Bar La Nuova Grotta Del Corso is another excellent spot to enjoy a nightcap after a delightful meal.

Raise a toast to the start of your 5-day road trip in Italy!

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Day 2

Day 2

  • Bolzano - Bozen
  • Sirmione
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Drive 207 km, 3 hours 36 min

  • Verona Arena
  • Porta Borsari
  • piazza delle Erbe
  • Ponte Pietra
  • Archaeological site of Grotte di Catullo
  • Castello di Sirmione
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On day 2 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Verona and Sirmione. When you’re not sightseeing, take time to relax at your selected hotel in Sirmione, where you’ll be staying for 1 night.

Set out on a day brimming with family-friendly attractions, romantic experiences, and breathtaking views. Start at the iconic Verona Arena, a symbolic stadium in Bolzano. Next, go to Porta Borsari.

After visiting Verona Arena and Porta Borsari, have a stroll along Bolzano's streets and take in the local charm. Continue your sightseeing by heading to Piazza Delle Erbe. This enchanting public square offers a unique experience. Ponte Pietra is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Archaeological Site Of Grotte Di Catullo, one of the most romantic places to visit in Bolzano. If you still have some time left for sightseeing, we also recommend stopping by Scaliger Castle.

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

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

Enjoy a delicious meal at Spiaggia Brema Beach Bar - Pizzeria e Grigliate, a top-rated dining destination in Sirmione. If you're in the mood to try something new, consider Ristorante Tancredi, another top spot with a mouthwatering menu. You might also want to secure a reservation at Hotel Dogana. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Sirmione this evening.

Unwind after your meal by stepping into Cafè Damm Atra. This venue is celebrated for its extensive drink selections and cozy vibes.

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 3

Day 3

  • Sirmione
  • Florence
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Drive 254 km, 3 hours 12 min

  • Piazza della Repubblica
  • Ponte Vecchio
  • Uffizi Gallery
  • Basilica of Santa Croce in Florence
  • Palazzo Vecchio
  • piazza della Signoria
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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 Florence. In the evening, you’ll end up in Florence, where you will stay for 1 night.

Today, you'll explore some of the most beautiful places in Sirmione, including a public square, a historical landmark, an art gallery, a church, a palace and much more! Start your day with a visit to Piazza Della Repubblica. This captivating public square is a must-visit in the city. When you’re ready for your next discovery, continue to Ponte Vecchio, which may be one of the most history-steeped places you will experience today.

One of the best things about exploring Sirmione 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 Uffizi Gallery, an impressive art gallery in the city. If you’re up for more discoveries, don’t forget to reserve some time for Basilica Of Santa Croce In Florence and Palazzo Vecchio. End your day with a visit to Piazza Della Signoria, a widely recognized public square that’s sure to leave a lasting impression.

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.

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

Dine in style at Ristorante Oliviero 1962, a top recommendation for dinner tonight. Or, for a change of pace, Di Poneta Novoli boasts a menu that's sure to impress. Also, be sure to check out Caffe San Firenze. Known as a local hotspot, it’s a great choice for tonight in Florence.

Keep the evening going at Manifattura, a great choice for enjoying the after-dinner hours with a drink. You could also go to Se·sto On Arno Rooftop Bar, which offers a similarly pleasant setting and great drinks. Another option is Il Vinile, which provides an inviting environment for unwinding after a busy day out.

Raise your glass to another unforgettable day in Italy!

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Day 4

Day 4

  • Florence
  • Bolzano - Bozen
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Drive 537 km, 6 hours 40 min

  • Siena Cathedral
  • piazza del Campo
  • Piazza del Duomo, San Gimignano
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Dive into day 4 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 Bolzano. You’ll stay here for 1 night.

Enjoy the perfect balance of relaxation and exploration in Florence today. One of the most locally renowned attractions included on the itinerary is Siena Cathedral. This visually striking church will help you start your sightseeing on top. Then, take a leisurely stroll to Piazza Del Campo and learn what makes this enchanting public square unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the worthwhile Piazza Del Duomo.

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.

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

Enjoy a lovely meal at Alumix Cafè Ristorante Pizzeria, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Castel Flavon is another top choice with a popular menu. You could also check for a table at Trattoria Filo d'Olio. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Bolzano tonight.

Round off your dining experience by visiting Tiffany Bolzano, a prime location for a drink. Alternatively, explore the distinctive characteristics of Corte - Bar & Bistro, a bar catering to every mood and preference. Hollywood likewise offers a unique atmosphere, perfect for a memorable night out.

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

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Day 5

Day 5

  • Bolzano - Bozen - Departure day
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  • Funivia del Colle
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Day 5 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 Kohlerer Bahn, a gorgeous tramway before you head out.

Maximize your last day in Italy and go on a shopping spree in Bolzano’s shopping center. Browse for souvenirs to remind you of your wonderful journey 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.

If you're in the mood to try something new, consider Black Sheep Drink Differently, another top spot with a mouthwatering 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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