One-Week Italy Self-Drive Road Trip With Itinerary from Trieste to Venice, Florence, and Siena

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Explore the best of Italy on a 8-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Trieste, Miramare / Miramar, Prosecco / Prosek, Aquileia, Venice, Bologna, Florence, Pisa, Lucca, Siena, and Padua. 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 Trieste, 2 nights in Venice, 2 nights in Florence, and 1 night in Siena. 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 Trieste, 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 Ponte Vecchio, learn more about the unique Leaning Tower Of Pisa, and immerse yourself in the vibrant atmosphere of Piazza Del Duomo, Pisa.

As you hit the open road and drive through Trieste, Miramare / Miramar, Prosecco / Prosek, Aquileia, Venice, Bologna, Florence, Pisa, Lucca, Siena, and Padua, 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
Roman Theatre of Trieste
Cattedrale di San Giusto MartireUnity of Italy SquareMuseo RevoltellaMiramare CastleBarcola fountainBasilica of Our Lady of the Assumption, St. Hermagoras and St. Fortunatus
Rialto BridgePiazza San MarcoSt Mark's BasilicaDoge's PalaceBridge of SighsCannaregio
Piazza Santo StefanoTwo TowersBologna CathedralFountain of Neptune, BolognaPiazza MaggioreBasilica of San Domenico
Cathedral of Santa Maria del Fiorepiazza della SignoriaPonte VecchioUffizi GalleryBasilica of Santa Croce in Florencepiazzale Michelangelo
Pisa CathedralPiazza del Duomo, PisaLeaning Tower of PisaGuinigi TowerSan Michele in ForoPiazza dell'Anfiteatro
piazza del CampoSiena CathedralThe Basilica of St AnthonyPrato della Valle
Molo Audace

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Day 1

Day 1

  • Triest - Arrival day
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  • Roman Theatre of Trieste
  • More

Your road trip adventure in Italy begins as soon as you reach Trieste and pick up your car. You’ll stay in Trieste 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.

Trieste 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 Roman Theatre Of Trieste, 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 Trieste. 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 Trieste, it's often a good idea to reserve a table in advance.

Make sure to reserve a table at Murphy's Meeting Point, an iconic dining spot in Trieste. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Caffè Tommaseo, a popular restaurant in Trieste. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Al Barattolo, a hidden gem nestled in Trieste. 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 Bar G, ideal for a leisurely evening with a drink in hand. Bar X is another bar that offers an enjoyable setting. Similarly, Antico Caffè Torinese is also a popular place to go on a night out, perfect for relaxing and socializing.

Raise a toast to the start of your 8-day road trip in Italy!

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Day 2

Day 2

  • Triest
  • Venice
  • More

Drive 186 km, 3 hours 14 min

  • Cattedrale di San Giusto Martire
  • Unity of Italy Square
  • Museo Revoltella
  • Miramare Castle
  • Barcola fountain
  • Basilica of Our Lady of the Assumption, St. Hermagoras and St. Fortunatus
  • More

Embark on another extraordinary experience on day 2 of your road trip in Italy. Today, you will make 4 stops and experience some of the highlights of Trieste, Miramare / Miramar, Prosecco / Prosek, and Aquileia. At the end of the day, you will enjoy the comforts of a top-rated hotel in Venice, which will be your home away from home for 2 nights.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, breathtaking views, and picturesque spots. Whether you decide to explore Trieste on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Cattedrale Di San Giusto Martire is the first of them. Spend some time admiring this culturally significant church before continuing your journey. Piazza Unità D'italia is your next stop. This well-known public square is one of the best-rated sights in Trieste.

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 Revoltella Museum. This historic museum is a sight to behold. To round off your sightseeing experience, visit Miramare Castle and Barcola Fountain. If time allows, end your day with Basilica Of Our Lady Of The Assumption, St. Hermagoras And St. Fortunatus, a stunning church that offers a memorable conclusion to your exploration.

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.

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

Enjoy a lovely meal at Bauer Hotel, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, L'Osteria Le Guglie is another top choice with a popular menu. You could also check for a table at Corner Pub. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Venice tonight.

Keep the evening going at Al Parlamento, a great choice for enjoying the after-dinner hours with a drink. You could also go to The Caffe Rosso, which offers a similarly pleasant setting and great drinks. Another option is Adagio, which provides an inviting environment for unwinding after a busy day out.

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

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Day 3

Day 3

  • Venice
  • More

Drive 2 km, 29 min

  • Rialto Bridge
  • Piazza San Marco
  • St Mark's Basilica
  • Doge's Palace
  • Bridge of Sighs
  • Cannaregio
  • More

Day 3 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.

Don’t miss Cannaregio in Venice today, a must-see neighborhood that offers a glimpse into the city’s vibrant character. Take your time to explore its best features, and enjoy the convenience of nearby top-rated landmarks.

Get ready to discover some of the most iconic wonders in Venice, including a historical landmark, a public square, a church, a palace, a monument and much more! Start your day at Rialto Bridge. This culturally significant historical landmark is an iconic place to see in Venice. Then, wander over to Piazza San Marco. If history-steeped sites excite you, this public square will be right up your alley. Nearby, you’ll also find St Mark's Basilica. This visually striking church 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, Doge's Palace is a popular spot in the city that will captivate you with its unique charm. When you’re done at the palace, don’t forget to check out the visually striking Bridge Of Sighs. Take a moment to appreciate the fascinating details of this locally renowned monument 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.

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

Treat yourself to a delicious dinner at Generator Venice, an excellent option for tonight's dining. Looking for something different? Nevodi offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante La Piazza. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Venice.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Il Mercante, a well-loved spot among locals and tourists. Or, head to The Irish Pub Venezia. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Ai Stagneri, another top-rated place in the area.

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

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Day 4

Day 4

  • Venice
  • Florence
  • More

Drive 273 km, 3 hours 45 min

  • Piazza Santo Stefano
  • Two Towers
  • Bologna Cathedral
  • Fountain of Neptune, Bologna
  • Piazza Maggiore
  • Basilica of San Domenico
  • More

On day 4 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 Florence, where you will stay for 2 nights.

Today’s agenda in Venice includes a public square, a monument, and a church. Piazza Santo Stefano is must-visit public square and a great starting point for the day. Next, continue your journey to Two Towers, a well-known monument, located just a leisurely stroll away. Next, head to Bologna Cathedral, a breathtaking church, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Venice. If you’re looking for more, Fountain Of Neptune, Bologna is also a worthwhile attraction that is worthwhile a visit. Lastly, don’t miss Piazza Maggiore, an astonishing gem to see in the city.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Florence. Florence offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

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

Make sure to reserve a table at Ristorante Oliviero 1962, an iconic dining spot in Florence. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Di Poneta Novoli, a popular restaurant in Florence. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Caffe San Firenze, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Keep the excitement of the evening going by visiting a bar or two. Manifattura is an excellent place to start. You could also check out Se·sto On Arno Rooftop Bar, offering a different kind of charm. A last recommendation for the day is Il Vinile. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Celebrate another amazing day of your road trip adventure in Italy!

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Day 5

Day 5

  • Florence
  • More

Drive 8 km, 1 hour 2 min

  • Cathedral of Santa Maria del Fiore
  • piazza della Signoria
  • Ponte Vecchio
  • Uffizi Gallery
  • Basilica of Santa Croce in Florence
  • piazzale Michelangelo
  • More

On day 5 of your road trip, you will have an entire day to explore Florence. You’ll stay in Florence for 1 night and discover all the best things to see and do in the area.

Set out on a day brimming with fun adventures, romantic experiences, and breathtaking views. Start at the widely recognized Cathedral Of Santa Maria Del Fiore, an enchanting church in Florence. Next, go to Piazza Della Signoria.

After visiting Cathedral Of Santa Maria Del Fiore and Piazza Della Signoria, take time to explore Florence's streets and absorb its charm. Continue your sightseeing by heading to Ponte Vecchio. This visually striking historical landmark offers a unique experience. Uffizi Gallery is another noteworthy stop. End your self-guided sightseeing tour on top with a visit to Basilica Of Santa Croce In Florence, one of the most culturally significant places to visit in Florence.

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 Florence's best restaurants.

Make sure to reserve a table at Ditta Artigianale, an iconic dining spot in Florence. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Trattoria Da Burde, a popular restaurant in Florence. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Casa Toscana, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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.

Raise your glass to another unforgettable day in Italy!

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Day 6

Day 6

  • Florence
  • Siena
  • More

Drive 251 km, 3 hours 53 min

  • Pisa Cathedral
  • Piazza del Duomo, Pisa
  • Leaning Tower of Pisa
  • Guinigi Tower
  • San Michele in Foro
  • Piazza dell'Anfiteatro
  • More

Dive into day 6 of your remarkable road trip in Italy. Today you will explore Pisa and Lucca, 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 Siena. You’ll stay here for 1 night.

Get ready for a day filled with fun adventures, breathtaking views, and picturesque spots in the charming city of Florence. Your adventure starts at Pisa Cathedral, a locally appreciated local hot spot. Another notable attraction to explore is Piazza Del Duomo, Pisa. This timeless public square is known for its breathtaking appeal.

After soaking in the highlights of these sights, take some time to wander Florence's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Leaning Tower Of Pisa. This culturally significant monument offers a fascinating experience that many visitors find memorable. Guinigi Tower is also worth visiting, along with San Michele In Foro. These standout landmarks offer unique experiences that add to the day’s enjoyment. End your day at Piazza Dell'anfiteatro. This locally renowned public square provides a fitting finale to your sightseeing.

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

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Siena. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Treat yourself to a delightful dinner at Enoteca I Terzi, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Ristorante Tar-Tufo? It's another excellent option with a diverse menu. Consider reserving a table at Antica Trattoria Papei as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Siena.

Explore the vibrant nightlife at Meet Life Cafè after your meal, a hub for lively evenings and memorable moments. Or, head to Maudit Pub for a great selection of flavorful drinks and a charming setting. Furthermore, Bar Impero Siena is perfect for those looking to extend their night with a touch of local flavor.

Savor another day of unforgettable experiences in Italy!

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Day 7

Day 7

  • Siena
  • Triest
  • More

Drive 468 km, 5 hours 41 min

  • piazza del Campo
  • Siena Cathedral
  • The Basilica of St Anthony
  • Prato della Valle
  • More

Experience an unparalleled adventure on day 7 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 Padua. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Trieste. You will spend 1 night here for some well-deserved relaxation.

Prepare for a day full of fun adventures, romantic experiences, and breathtaking views. When you’re ready, kick off your sightseeing adventure at Piazza Del Campo. This astonishing public square is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Siena Cathedral, one of the city’s best highlights.

Next, check out The Basilica Of St. Anthony, one of the most locally renowned places to see in Siena. This church is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Prato Della Valle. Wander around and soak in the enchanting atmosphere this public square offers.

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

As you explore more of Trieste, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Make sure to reserve a table at Rustiko, an iconic dining spot in Trieste. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Caffè San Marco, a popular restaurant in Trieste. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Osteria Marise, a hidden gem nestled in Trieste. 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, Mast stands out as an excellent choice for a post-dinner cocktail. Alternatively, Urbanis offers an ideal atmosphere to enjoy the pleasures of the night. Coktail Bar Trieste | La Preferita is also a great option that provides a perfect setting for a relaxing evening.

Raise your glass to another unforgettable day in Italy!

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Day 8

Day 8

  • Triest - Departure day
  • More
  • Molo Audace
  • More

Day 8 of your road trip in Italy is your departure day. This is your chance to catch a last glimpse of Trieste 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 Molo Audace. This underrated pier is a popular place to see in the city.

Make the most of your final day in Italy by visiting Trieste’s iconic markets and shopping establishments in the buzzing Il Giulia Shopping Center. 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 Trieste.

If you're in the mood for something new, try Osteria Istriano Of Giobi And Oxa, another premier location with a delectable menu.

You’ll then say farewell to Trieste. 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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