6-Day Italy Self-Drive Road Trip With Itinerary from Bologna traveling south to Siena, Rome, and Florence

1 / 65
Medieval and Renaissance buildings and structures feature in Bologna, Italy
Photo of panoramic view of Bologna,Italy.
6-Day Italy Self-Drive Road Trip With Itinerary from Bologna traveling south to Siena, Rome, and Florence
6-Day Italy Self-Drive Road Trip With Itinerary from Bologna traveling south to Siena, Rome, and Florence
6-Day Italy Self-Drive Road Trip With Itinerary from Bologna traveling south to Siena, Rome, and Florence
6-Day Italy Self-Drive Road Trip With Itinerary from Bologna traveling south to Siena, Rome, and Florence
6-Day Italy Self-Drive Road Trip With Itinerary from Bologna traveling south to Siena, Rome, and Florence
Perfect travel plans
Everything included
Fully customizable

Description

Included

Flights
Select dates
Hotel
Select dates
Car rental
Select dates
Tours & tickets
Select dates
Travel plan
From A to Z
Travel agent
24/7 fast service

Description

Explore the best of Italy on a remarkable 6-day road trip! Combine exploration with relaxation on a self-drive tour featuring Bologna, Siena, Rome, and Florence.

This perfectly planned road trip itinerary takes you through some of the best places to see in Italy. You will spend 2 nights in Bologna, 1 night in Siena, 1 night in Rome, 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 Bologna, 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. Trevi Fountain and Pantheon are just a couple of the bucket-list attractions that await your discovery.

As you hit the open road and drive through Bologna, Siena, Rome, and Florence, 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!

Read more

Travel details

Set your travel details to find the best price

Flights

Round trip
Round trip
Travel dates

Travelers

Rooms

Flights

Compare and choose from the best flights to Bologna

Car

Choose from the best car rental deals or see all options

Driver’s age is 30 - 65
I live in
Pick-up: 10:00
Drop-off: 10:00

Personalize your itinerary

Customize tours under each day and destination

Day1

Day 1

  • Bologna - Arrival day
  • More
  • La Piccola Venezia
  • More

Welcome to Bologna, 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 discovering what to see in Bologna before embarking on the next leg of your journey.

Bologna 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 La Piccola Venezia. Taking a stroll in the city center is a great alternative. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

As afternoon approaches, head to your chosen hotel in Bologna. 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 Bologna, it's often a good idea to reserve a table in advance.

Don’t miss out on dining at Ristorante Ciacco, a top-rated dining destination in Bologna. If you're in the mood to try something new, consider Ristorante Ballarini, another top spot with a mouthwatering menu. You might also want to secure a reservation at Sfoglia Rina. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Bologna this evening.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bar Al Bricco D'oro stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bar Freud E Squisito offers an ideal atmosphere to enjoy the pleasures of the night. Osteria Del Sole is also a great option that provides a perfect setting for a relaxing evening.

Raise a toast to the start of your 6-day road trip in Italy!

Read more
Day2

Day 2

  • Bologna
  • Siena
  • More

Drive 170 km, 2 hours 37 min

  • Piazza Maggiore
  • Two Towers
  • Piazza Santo Stefano
  • Basilica of San Domenico
  • Villa Ghigi
  • More

Experience an unparalleled adventure on day 2 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Bologna. At the end of the day, you will retreat to the hotel of your choice in Siena, where will spend 1 night.

Piazza Maggiore is an ideal stop early in the day. This astonishing 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 Bologna 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 Piazza Santo Stefano, an increasingly popular public square in the city. If you’re up for more discoveries, don’t forget to reserve some time for Basilica Of San Domenico and Villa Ghigi.

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

Siena 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 Siena.

Make sure to reserve a table at Enoteca I Terzi, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Ristorante Tar-Tufo, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Antica Trattoria Papei, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Keep the evening going at Meet Life Cafè, a great choice for enjoying the after-dinner hours with a drink. You could also go to Maudit Pub, which offers a similarly pleasant setting and great drinks. Another option is Bar Impero Siena, which provides an inviting environment for unwinding after a busy day out.

Savor another day of unforgettable experiences in Italy!

Read more
Day3

Day 3

  • Siena
  • Vatican City
  • Rome
  • More

Drive 241 km, 3 hours 23 min

  • Sistine Chapel
  • St Peter's Basilica
  • Saint Peter's Square
  • Vatican Museums
  • More

Dive into day 3 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Vatican City. At the end of the day, you’ll unwind at one of the finest accommodations in Rome, where you'll spend 1 night.

Continue your road trip and head to your next destination, Vatican City, Vatican City. This car ride takes around 2 hours 40 min.

Next, make your way to St. Peter's Basilica, another highlight in Vatican City.

Nearby, you will also find Vatican Museums. This world-famous art museum is a top place to see in the area.

At the end of the day, you will drive to Rome, 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. If you are looking to dine at a popular restaurant in Rome, it's often a good idea to reserve a table in advance.

Get ready for an unforgettable culinary journey in Rome by reserving a table at La Pergola. Renowned as a 3-star Michelin restaurant, it offers an exceptional mediterranean and contemporary menu. For a different taste experience, head to Il Pagliaccio, recognized for its delicious creative and innovative dishes. This 2-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Enoteca La Torre, a local favorite known for its delightful mediterranean and creative cuisine in Rome. Nestled in the heart of the city, this restaurant with 2 Michelin star is an ideal choice for mediterranean and creative foodies seeking culinary excellence.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, La Botticella Of Poggi Giovanni stands out as an excellent choice for a post-dinner cocktail. Alternatively, Almalu Trastevere offers an ideal atmosphere to enjoy the pleasures of the night. Bar Viminale Di Pepi Maurilio is also a great option that provides a perfect setting for a relaxing evening.

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

Read more
Day4

Day 4

  • Rome
  • Florence
  • More

Drive 278 km, 3 hours 41 min

  • Piazza Navona
  • Pantheon
  • Trevi Fountain
  • More

Your itinerary for day 4 of your road trip in Italy includes 1 stop and features some of the highlights of Rome. At the end of the day, enjoy the comforts of a top-rated hotel in Florence, where you'll spend 1 night.

To truly experience Rome, make sure to drop by Piazza Navona. This wondrous public square is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Pantheon, one of the city’s best highlights.

Next, check out Trevi Fountain, one of the most world-famous places to see in Rome. This monument is a favorite among locals and travelers alike.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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.

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

Discover the culinary delights of Florence by securing a reservation at Enoteca Pinchiorri. Esteemed for its 3-star Guide Michelin recognition, this restaurant offers a remarkable selection of italian contemporary cuisine. For an alternative dining experience, try Santa Elisabetta, renowned for its delicious creative and mediterranean dishes. This esteemed 2-star Michelin-recipient consistently impresses guests, making it a must-visit spot during your holiday. Craving more culinary excitement? Head to Gucci Osteria da Massimo Bottura, a highly recommended local eatery celebrated for its mouthwatering italian contemporary and international menu. With its 1-star Michelin recognition, it offers an unforgettable dining adventure.

To truly maximize your evening out, consider visiting Manifattura after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Se·sto On Arno Rooftop Bar, another bar with an inviting ambiance. Similarly, Il Vinile also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

Read more
Day5

Day 5

  • Florence
  • Bologna
  • More

Drive 110 km, 2 hours 12 min

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

On day 5 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Florence. When you’re not sightseeing, take time to relax at your chosen hotel in Bologna, where you’ll be staying for 1 night.

Make a stop at Piazza Della Signoria. This spectacular public square is a must-visit for travelers looking for a unique holiday experience. Make your way to Cathedral Of Santa Maria Del Fiore located in Florence for another exciting encounter.

Next, immerse yourself in the setting of Ponte Vecchio. Its history-steeped features will captivate you. After the historical landmark, continue your tour of the city with a visit to Uffizi Gallery. Visitors usually appreciate the respected features of this art gallery. Next up is Piazzale Michelangelo, a highly recommended observation deck.

When you’re done exploring for the day, you’ll drive to your hotel in Bologna. Check in and relax 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 Bologna. Enjoy a relaxing evening as you savor delicious local cuisine.

Set out on a gastronomic journey in Bologna by reserving a table at Ahimè. Renowned for its Bib Gourmand award, this restaurant presents an outstanding menu of country cooking cuisine. For a different taste, head over to I Portici, renowned for its delectable creative and contemporary dishes. This distinguished 1-star Michelin-recipient is a favorite among guests, making it a worthy addition to your holiday plans. Craving more culinary excitement? Explore Trattoria di Via Serra, a highly rated local gem known for its exquisite emilian menu. With a Bib Gourmand acclaim, it promises a dining experience you won't want to miss.

After enjoying a fulfilling meal, continue your evening at Lime Bar, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Macondo - Cocktail Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Bar Onda Marina By Night provides an excellent environment for a relaxed and enjoyable evening.

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.

Read more
Day6

Day 6

  • Bologna - Departure day
  • More
  • Porta Castiglione
  • More

Day 6 of your road trip in Italy is your departure day. This is your chance to catch a last glimpse of Bologna 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 Porta Castiglione, a respected monument before you head out.

Take some time to indulge in shopping at Bologna’s popular marketplace, Quadrilatero. Look for keepsakes or souvenirs to remind you of your trip. Browse boutiques to find unique and stylish fashion pieces.

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

Enjoy a lovely meal at Va Mo Là, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Trattoria dal Biassanot is another top choice with a popular menu.

You’ll then say farewell to Bologna. 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!

Read more

How it works

Book your journey with Europe’s biggest travel platform—expert itineraries, instant confirmation, and full flexibility with 24/7 support.

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.
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.

Similar travel packages

Discover other popular vacations in Italy

Link to appstore phone
Install Europe’s biggest travel app

Download Europe’s biggest travel marketplace to your phone to manage your entire trip in one place

Scan this QR code with your phone camera and press the link that appears to add Europe’s biggest travel marketplace into your pocket. Enter your phone number or email address to receive an SMS or email with the download link.