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5-Day Italy Self-Drive Road Trip With Itinerary from Trieste traveling south to Florence

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Trieste lighthouse Phare de la Victoire and cityscape panoramic aerial view, Friuli Venezia Giulia region of Italy.

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Explore the best of Italy on a remarkable 5-day road trip! Combine exploration with relaxation on a self-drive tour featuring Trieste, Venice, Florence, and Siena.

This perfectly planned road trip itinerary takes you through some of the best places to see in Italy. You will spend 3 nights in Trieste 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 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 Piazza Della Signoria, and immerse yourself in the vibrant atmosphere of Piazza Del Campo.

As you hit the open road and drive through Trieste, Venice, Florence, and Siena, 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, accommodations, 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

Triest - Arrival day
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Unity of Italy Square
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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 2 nights discovering what to see in Trieste 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 Piazza Unità D'italia, 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 central location for easy access to key areas 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 delightful dinner at Murphy's Meeting Point, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Caffè Tommaseo? It's another excellent option with a diverse menu. Consider reserving a table at Al Barattolo as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Trieste.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bar G stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bar X offers an ideal atmosphere to enjoy the pleasures of the night. Antico Caffè Torinese is also a great option that provides a perfect setting for a relaxing evening.

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

Day 2

Triest
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Drive 320 km, 4 hours

Grand Canal
Doge's Palace
St Mark's Basilica
Piazza San Marco
Rialto Bridge
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On day 2 of your road trip, you'll get the chance to experience Venice. At the end of the day, you'll drive back to Trieste, where you still have 1 night left to stay.

Grand Canal is perfect for a self-paced visit during the day. This UNESCO world heritage-listed street is sure to impress. Next on your list is Doge's Palace, another must-visit landmark and notable palace renowned for its history-steeped features.

While exploring and sightseeing, take time to savor the culture of Trieste by sampling some local delicacies. When you’re ready for more sightseeing, head to St Mark's Basilica. This symbolic church is an essential place to visit for anyone looking for the full Trieste experience. We also recommend visiting Piazza San Marco, a timeless public square. Nearby, you'll also find Rialto Bridge, ready to add charm to your journey.

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

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.

Enjoy a delicious meal at Rustiko, a top-rated dining destination in Trieste. If you're in the mood to try something new, consider Caffè San Marco, another top spot with a mouthwatering menu. You might also want to secure a reservation at Osteria Marise. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Trieste this evening.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Mast, a well-loved spot among locals and tourists. Or, head to Urbanis. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Coktail Bar Trieste | La Preferita, another top-rated place in the area.

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

Day 3

Triest
Florence
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Drive 408 km, 4 hours 44 min

Basilica of Santa Croce in Florence
Uffizi Gallery
Ponte Vecchio
Piazza della Repubblica
piazza della Signoria
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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 place, which are Florence. At the end of the day, you will retreat to the hotel of your choice in Florence, where will spend 1 night.

Look forward to a unique sightseeing adventure at the captivating Basilica Of Santa Croce In Florence and allow yourself time to explore. Just a short distance away you'll find your next stop, Uffizi Gallery, a historic art gallery 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 popular Piazza Della Repubblica. When you're finished at the public square, Piazza Della Signoria awaits your visit. This public square is a history-steeped highlight on today's itinerary.

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.

Florence is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Florence.

Savor the flavors at Ristorante Oliviero 1962, a top pick for dinner tonight. Alternatively, Di Poneta Novoli beckons with its unique menu offerings. Also, consider Caffe San Firenze. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

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.

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

Day 4

Florence
Triest
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Drive 552 km, 6 hours 27 min

Fortezza Medicea
piazza del Campo
Siena Cathedral
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Your itinerary for day 4 of your road trip in Italy includes 1 stop and features some of the highlights of Siena. At the end of the day, enjoy the comforts of a top-rated hotel in Trieste, where you'll spend 1 night.

Catch Fortezza Medicea (siena) before the crowds roll in. This breathtaking monument is sure to ignite your curiosity. Next, dive into the romantic features of Piazza Del Campo, a must-visit public square in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Siena Cathedral, a captivating church.

When you’re done exploring for the day, you’ll drive to your hotel in Trieste. Check in and relax 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 Trieste. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Make sure to reserve a table at Caffè degli Specchi, 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 Osteria Istriano Of Giobi And Oxa, 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 Chimera di Bacco, 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 "life" New Bar Torinese Snc, ideal for a leisurely evening with a drink in hand. White Cafe is another bar that offers an enjoyable setting. Similarly, Café James Joyce is also a popular place to go on a night out, perfect for relaxing and socializing.

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

Day 5

Triest - Departure day
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Cattedrale di San Giusto Martire
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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 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 Cattedrale Di San Giusto Martire, a breathtaking church before you head out.

For a shopping spree in Trieste, we recommend the lively Il Giulia Shopping Center. Here, you'll find a range of shops you can browse for some souvenir shopping.

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

Treat yourself to a delightful dinner at Salsapariglia Italian Ristorantino Trieste, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Sbecolez Trieste? It's another excellent option with a diverse 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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Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.

Personalize your itinerary

Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.

Easily make changes

Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.

Enjoy seamless planning

With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.

Explore with confidence

From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.

Secure your spot

Confirm your package instantly and lock in the best rate with secure payment and guaranteed availability.

Get instant confirmation

Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.

Personalize your itinerary

Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.

Easily make changes

Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.

Enjoy seamless planning

With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.

Explore with confidence

From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.

We guarantee

Your trip is protected, personalized, and priced right. No surprises, no stress.

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