4-Day Italy Self-Drive Road Trip With Itinerary from Bologna traveling south to Siena

Your itinerary for day 2 of your road trip in Italy includes 2 stops and features some of the highlights of Florence and Siena. At the end of the day, enjoy the comforts of a top-rated hotel in Siena, where you'll spend 1 night.

Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Florence.

Fasten your seatbelt and make your way to your next stop — Florence, home to many well-known sights in the region. Keep in mind that your travel time from Bologna to Florence may take around 1 hour 36 min without traffic disruptions. Upon arrival in Florence, we highly recommend checking out some of the top attractions.

One of our top recommendations for your sightseeing is Basilica Of Santa Croce In Florence. Spend some time admiring the photogenic features of the church before you continue to your next stop. Then, head to Piazza Della Signoria. This extraordinary public square is a traveler-favorite in the city.

If you're keen to see more, continue to Ponte Vecchio. Feed your curiosity by learning something new about the historical landmark. Next, take your journey to Uffizi Gallery, an extraordinary art gallery. Conclude your sightseeing at Piazzale Michelangelo, known for its enchanting features.

Set your GPS to Siena and hit the road. Expect a journey of approximately 1 hour 7 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Siena beckons with new experiences!

Piazza Del Campo is a top-rated public square we recommend visiting today. Discover its history-steeped features before continuing your self-guided tour.

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.

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.

Enjoy a lovely meal at Enoteca I Terzi, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Ristorante Tar-Tufo is another top choice with a popular menu. You could also check for a table at Antica Trattoria Papei. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Siena tonight.

Extend your evening after a delightful meal by visiting Meet Life Cafè, which offers the perfect atmosphere for a night out. Moreover, Maudit Pub is another popular option for a drink or two. Likewise, Bar Impero Siena also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Raise your glass to another unforgettable day in Italy!

On day 3 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 3 destinations, including San Donato in Poggio, San Gimignano, and Lucca. When you’re not sightseeing, take time to relax at your chosen hotel in Bologna, where you’ll be staying for 1 night.

After soaking in Siena’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: San Donato in Poggio. Expect your car journey to take a minimum of 42 min. When you arrive in San Donato in Poggio, it's time to take a break from the road.

When you're ready for some sights, head to Osservatorio Polifunzionale Del Chianti, an up-and-coming astronomical observatory in San Donato in Poggio. Explore its breathtaking features at your own pace before you continue your journey.

Continue your road trip and head to your next destination, San Gimignano. This car ride takes around 32 min.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Porta San Giovanni, an underrated monument that everyone visiting San Gimignano should see.

Fasten your seatbelt and make your way to your next stop — Lucca, home to many well-known sights in the region. Keep in mind that your travel time from San Gimignano to Lucca may take around 1 hour 38 min without traffic disruptions. Upon arrival in Lucca, we highly recommend checking out some of the top attractions.

For a more meaningful self-guided tour of the village's best attractions, visit Mura Di Lucca, a beloved historical landmark that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey. Next, head to Piazza Dell'anfiteatro and admire its enchanting features.

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.

Treat yourself to a delicious dinner at Bononia Cafè, an excellent option for tonight's dining. Looking for something different? Via Con Me offers a tantalizing alternative with its diverse menu. And don’t miss Trattoria Pizzeria La Mela. Known for great service, it’s a fantastic choice for tonight in Bologna.

Unwind after your meal by stepping into Lime Bar. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Macondo - Cocktail Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Bar Onda Marina By Night, another top-rated bar in the area.

Savor another day of unforgettable experiences in Italy!