5-Day Italy Self-Drive Road Trip With Itinerary from Ancona to Florence

On day 2 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 Florence, where you’ll be staying for 2 nights.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Florence. This drive usually takes around 3 hours 18 min, without any stops or traffic disruptions.

For a more meaningful self-guided tour of the city's best attractions, visit Piazzale Michelangelo, an impressive observation deck 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 Basilica Of Santa Croce In Florence and admire its culturally significant features.

When you’re ready, continue to Uffizi Gallery, an impressive art gallery beloved by locals and tourists alike. Don't miss out on Ponte Vecchio, another highlight of the area that promises a memorable visit. Not far away, you’ll also find Piazza Della Signoria, a majestic place to see that you won’t regret spending some extra time discovering.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and relax before you head out to tour 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 Florence, it's often a good idea to reserve a table in advance.

Have a fantastic dining experience at Ristorante Oliviero 1962, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Di Poneta Novoli offers an enticing alternative with its varied menu. Additionally, Caffe San Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

Extend your evening after a delightful meal by visiting Manifattura, which offers the perfect atmosphere for a night out. Moreover, Se·sto On Arno Rooftop Bar is another popular option for a drink or two. Likewise, Il Vinile 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!

Greet day 3 of your road trip in Italy with a smile and start your day with a hearty breakfast. You have 1 night to stay in Florence, so get ready to make the most of your time in the region. On the agenda for this day, you’ll find only the best things to see and do in Florence and Pisa.

A top thing to do today is to explore Oltrarno, a must-see neighborhood in Florence. It's the perfect starting point for touring the top attractions in the area.

Your adventure in Florence is only getting started when you visit Galleria Dell'accademia, a locally renowned local hot spot. Another notable attraction to explore is Cathedral Of Santa Maria Del Fiore. This astonishing church is known for its detailed appeal.

When you’ve had your share of Florence, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Pisa. Your travel time is around 1 hour 12 min.

When you're ready for some sights, head to Leaning Tower Of Pisa, a wondrous monument in Pisa. Explore its culturally significant features at your own pace before you continue your journey to your next attraction, Piazza Del Duomo, Pisa. This world-famous public square is a top recommendation in the area.

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

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

Enjoy a lovely dining experience at Ditta Artigianale, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Trattoria Da Burde, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Casa Toscana. It’s yet another ideal choice to enhance your time in Florence tonight.

After your meal, keep the night alive at a bar like Bar 50 Rosso, known for its lively atmosphere. Bitter Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Archea Brewery offers an excellent atmosphere for those looking to amp up the evening.

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

Your itinerary for day 4 of your road trip in Italy includes 2 stops and features some of the highlights of Siena and San Gimignano. At the end of the day, enjoy the comforts of a top-rated hotel in Ancona, where you'll spend 1 night.

When you’ve had your share of Florence, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Siena. Your travel time is around 1 hour 12 min.

One of our top recommendations for your sightseeing is Siena Cathedral. Spend some time admiring the inviting features of the church before you continue to your next stop. Then, head to Battistero Di San Giovanni Battista. This frequently visited church is a traveler-favorite in the city.

If you're keen to see more, continue to Piazza Del Campo. Feed your curiosity by learning something new about the public square. Next, take your journey to Tower Of Mangia, a locally appreciated monument.

Continue your road trip and head to your next destination, San Gimignano. This car ride takes around 46 min.

Savor the day by heading to Porta San Giovanni, an underrated monument that draws visitors from near and far.

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

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

Savor the flavors at Amarcord, a top pick for dinner tonight. Alternatively, Bontà delle Marche beckons with its unique menu offerings. Also, consider Ristorante Pizzeria Da Romano. With its consistent customer satisfaction, it’s an excellent option for dining in Ancona tonight.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Alla Tazza D'oro, known for its inviting atmosphere.

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