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

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Trieste lighthouse Phare de la Victoire and cityscape panoramic aerial view, Friuli Venezia Giulia region of Italy.
Trieste channel and Ponte Rosso square view, city in Friuli Venezia Giulia region of Italy
Photo of Landmarks and beautiful places (cities) of northern Italy - elegant Trieste town
The most important square in Trieste called "Piazza Unità d'Italia" (it means "Square of the Unity of Italy") - (Europe - italy -Trieste)
The Temple of Monte Grisa on Karst Plateau mountain above Trieste aerial view, Friuli Venezia Giulia region of Italy
Miramare castle with gardens on the gulf of Trieste on northeastern Italy.
The City Hall, Palazzo del Municipio, is the dominating building on Trieste's main square Piazza dell Unita d Italia. Trieste, Italy, Europe. Illuminated city square shot at dusk.
View at the Building of Palace of the Austrian Lieutenancy in Trieste - Italy
Gulf of Trieste. High cliffs Between boats, karst rocks and ancient castles. Duino. Italy.
Trieste, Italy. View of Roman Theatre Ruins.
photo of view of Canal Ponterosso, Trieste, Italy.
Miramare park in Trieste, Italy
photo of view of Piazza Unita Italia , Trieste, Italy.
photo of view of Grado Italy, Trieste, Italy.
Bridge Rialto on Grand canal famous landmark panoramic view Venice Italy.
Venetian gondolier punting gondola through green canal waters of Venice, Italy.
photo of view of Venice, Italy.
Couple of tourists on vacation in Venice, Italy.
Colorful carnival masks at a traditional festival in Venice, Italy.
Elegant woman with red sunhat enjoys the view to a canal with passing by gondola in Venice, Italy.
View of Basilica di San Marco and on piazza San Marco in Venice, Italy.
Colorful houses in Burano, Venice, Italy.
Street in Venice.
photo of  view of Colorful houses in Burano, Venice, Italy.
photo of view of View of Grand Canal with Rialto Bridge and gondoliers in Venice, Italy. Landscape with Rialto Bridge and gondola on the Grand Canal in Venice, Italy, Europe.
photo of view of A normal day in the beautiful city of Venice. View of the corridors, roads and bridges of the beautiful cities of Venice, Italy.
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photo of view of Venice, Italy.
Aerial view of the Cattedrale di Santa Maria del Fiore in Florence, Italy, overlooking the city
Photo of Florence Aerial View of Ponte Vecchio Bridge during Beautiful Sunny Day, Italy.
Photo of Woman enjoys beautiful view on famous Duomo cathedral in Florence, standing on empty cathedral square during morning time.
Photo of Summer street cafe on Piazza della Repubblica in Florence, Toscana province, Italy.
Photo of Giotto's Campanile - An aerial dusk view of Giotto's Campanile and the historical Old Town of Florence, as seen from the top of Brunelleschi's Dome of the Florence Cathedral. Florence, Tuscany, Italy.
Photo of Ponte Vecchio, old bridge over Arno River, Florence, Tuscany, Italy.
Photo of The Colossus of the Apennines, majestic stone sculpture by Giambologna located in the park of Villa Demidoff in Florence, Italy.
Photo of Fountain of Neptune in Florence in early morning.
Photo of Sunset view of Florence, Ponte Vecchio, Palazzo Vecchio and Florence Duomo, Italy. Architecture and landmark of Florence. Cityscape of Florence.
Vintage carousel and tourists in Piazza della Repubblica (Republic Square) and the arch in honor of the first king of united Italy on background in Florence, Italy.
Photo of Arches of the Vasari Corridor (Corridoio Vasariano) in Florence, Tuscany, Italy. View of the Lungarno degli Archibusieri.
cheerful senior woman cycling with her electric mountain bike above downtown of Florence with stunning view over the old city, Tuscany, Italy
Facade of Palazzo Pitti palace with Gallery of Modern Art large building on Piazza dei Pitti square in historical centre of Florence city, blue sky white clouds, Tuscany, Italy
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photo of view of Florence,Italy.
Photo of Siena in Italy by SimonRei
Photo of Siena cathedral against a bright blue sky in Italy.
Photo of Siena, Italy. Aerial view of Piazza del Campo with Palazzo Pubblico and Torre del Mangia.
photo of view of Siena, Italy. Charming medieval city in Tuscany known for its stunning cathedral, Torre del Mangia, beautiful piazzas, and the famous Palio horse race.
photo of view of Siena, medieval town in Tuscany, with view of the Dome Bell Tower of Siena Cathedral, Mangia Tower and Basilica of San Domenico, Italy
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photo of view of historic buildings and landmarks in magnificent medieval Siena,Tuscany, Italy.
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photo of view of Cathedral of the City of Siena in Tuscany region of Italy at sunset.
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photo of view of Medieval San Gimignano hill town with skyline of medieval towers, including the stone Torre Grossa. Province of Siena, Tuscany, Italy.
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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
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Welcome to Trieste, 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 Trieste's charm before embarking on the next leg of your journey.

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.

Treat yourself to a delicious dinner at Murphy's Meeting Point, an excellent option for tonight's dining. Looking for something different? Caffè Tommaseo offers a tantalizing alternative with its diverse menu. And don’t miss Al Barattolo. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Trieste.

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

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, scenic views, and photo-friendly 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 monumental church before continuing your journey. Piazza Unità D'italia is your next stop. This popular 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 eye-catching 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, an UNESCO world heritage-listed church that offers a memorable conclusion to your exploration.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in 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.

Have a fantastic dining experience at Bauer Hotel, a highly recommended choice for tonight's dinner. If you're looking to mix things up, L'Osteria Le Guglie offers an enticing alternative with its varied menu. Additionally, Corner Pub is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Venice.

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

Relax and recharge in preparation for another adventurous day 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 offers a multitude of experiences. You will stay in Venice for 1 night more, offering you enough time to explore at a relaxed pace.

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.

A blend of fun adventures, romantic experiences, and breathtaking views await you in Venice on today’s itinerary. First up is the world-famous historical landmark, Rialto Bridge. Afterward, continue to Piazza San Marco, a public square every traveler should visit.

As you explore Venice’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to St Mark's Basilica. This popular church is an essential stop. Following that, head to Doge's Palace, another must-visit site that will enhance your experience. Don’t forget to stop by Bridge Of Sighs, a notable monument in the city.

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.

Treat yourself to a wonderful meal at Generator Venice, a top-rated dining spot in Venice. If you're in the mood for something new, try Nevodi, another premier location with a delectable menu. You might also want to book a table at Ristorante La Piazza. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Venice.

Round off your dining experience by visiting Il Mercante, a prime location for a drink. Alternatively, explore the distinctive characteristics of The Irish Pub Venezia, a bar catering to every mood and preference. Ai Stagneri likewise offers a unique atmosphere, perfect for a memorable night out.

Savor another day of unforgettable experiences 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, you'll explore some of the most beautiful places in Venice, including a public square, a monument, and a church. Start your day with a visit to Piazza Santo Stefano. This locally appreciated public square is a must-visit in the city. When you’re ready for your next discovery, continue to Two Towers, which may be one of the most stunning 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 Bologna Cathedral, an up-and-coming church in the city. If you’re up for more discoveries, don’t forget to reserve some time for Fountain Of Neptune, Bologna and Piazza Maggiore. End your day with a visit to Basilica Of San Domenico, an increasingly popular church 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.

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

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.

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.

Raise your glass to another unforgettable day 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

Day 5 of your road trip will take you to the best attractions Florence has to offer. Cherish the 1 night you have left in Florence by discovering the best things there are to see and do in the city.

Florence is brimming with adventures. Today’s wonderful stops include a church, a public square, a historical landmark, an art gallery, an observation deck and much more! Begin your sightseeing adventure at the impressive Cathedral Of Santa Maria Del Fiore and allow yourself time to explore. Just a short distance away you'll find your next stop, Piazza Della Signoria, a romantic public square that draws visitors from far and near.

Continue your journey to Ponte Vecchio, one of the city’s most timeless spots that you shouldn’t miss. Another great site to visit is the impressive Uffizi Gallery. When you're finished at the art gallery, Basilica Of Santa Croce In Florence awaits your visit. This church is a culturally significant highlight on today's itinerary. Last up is an observation deck - the famous Piazzale Michelangelo.

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 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.

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.

To truly maximize your evening out, consider visiting Bar 50 Rosso after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bitter Bar, another bar with an inviting ambiance. Similarly, Archea Brewery also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Relax and recharge in preparation for another adventurous 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.

Brace yourself for today’s incredible lineup of attractions in Florence, featuring family-friendly attractions, breathtaking views, and photo-friendly spots. Start at Pisa Cathedral, a locally appreciated church in the city. Then, head to Piazza Del Duomo, Pisa and soak in the ambiance of this majestic public square.

There are many interesting places to see in Florence, and when you are ready for more, go to Leaning Tower Of Pisa. This is one of the city’s most wondrous culturally significant spots of interest. After exploring the monument, visit the beloved Guinigi Tower. Not far away, you'll also find San Michele In Foro. This church is a picture-perfect highlight in Florence. Before wrapping up your self-guided sightseeing tour, head to Piazza Dell'anfiteatro, a popular public square in the city.

At the end of the day, you will drive to Siena, 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 Siena's most popular restaurants, and connect with friendly locals for an authentic adventure.

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.

Following your dinner, dive into the local bar culture at Meet Life Cafè. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Maudit Pub, the perfect place for those looking to experience the best of the nightlife. Similarly, Bar Impero Siena provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

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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

On day 7 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Siena and Padua. When you’re not sightseeing, take time to relax at your selected hotel in Trieste, where you’ll be staying for 1 night.

Today's adventure in Siena promises more breathtaking discoveries and enriching experiences! Begin at Piazza Del Campo. This history-steeped public square is a highlight of any visit in the city. Then, enjoy Siena Cathedral, another romantic attraction that never fails to captivate visitors. Next, head over to The Basilica Of St. Anthony, one of the city’s most locally renowned attractions, known for its culturally significant features.

If you’re looking for more, spend time soaking in the atmosphere of Prato Della Valle. This visually striking public square is frequented by locals and tourists alike. To complete your memorable day, make sure to 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 Trieste. Trieste offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

As dinnertime approaches, it's time to head out for a bite to eat in Trieste. 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.

Treat yourself to a delicious dinner at Rustiko, an excellent option for tonight's dining. Looking for something different? Caffè San Marco offers a tantalizing alternative with its diverse menu. And don’t miss Osteria Marise. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Trieste.

After your meal, keep the night alive at a bar like Mast, known for its lively atmosphere. Urbanis is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Coktail Bar Trieste | La Preferita offers an excellent atmosphere for those looking to amp up the evening.

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

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Day 8

Day 8

  • Triest - Departure day
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  • Molo Audace
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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, we recommend visiting Molo Audace, a romantic pier before you head out.

Maximize your last day in Italy and go on a shopping spree in Trieste’s shopping center, the lively Il Giulia 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 Trieste.

Dine in style at Caffè degli Specchi, a top recommendation for dinner tonight. Or, for a change of pace, Osteria Istriano Of Giobi And Oxa boasts a menu that's sure to impress.

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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