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, Florence. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 2 nights.

Set out on a day brimming with fun adventures, romantic experiences, and scenic views. Start at the spectacular Piazzale Michelangelo, a symbolic observation deck in Ancona. Next, go to Basilica Of Santa Croce In Florence.

After visiting Piazzale Michelangelo and Basilica Of Santa Croce In Florence, have a stroll along Ancona's streets and take in the local charm. Continue your sightseeing by heading to Uffizi Gallery. This history-steeped art gallery offers a unique experience. Ponte Vecchio is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Piazza Della Signoria, one of the most enchanting places to visit in Ancona.

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.

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.

Treat yourself to a delightful dinner at Ristorante Oliviero 1962, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Di Poneta Novoli? It's another excellent option with a diverse menu. Consider reserving a table at Caffe San Firenze as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

If you’re not ready to end the night just yet, Manifattura offers a perfect venue to relax and savor a drink. Similarly, Se·sto On Arno Rooftop Bar is well-suited for those looking to unwind in a social setting. Il Vinile is another excellent spot to enjoy a nightcap after a delightful meal.

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

On day 3 of your road trip, you’ll start and end your day in Florence, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Florence and Pisa. You still have 1 night left in Florence.

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.

Today, you'll explore some of the most beautiful places in Florence, including an art gallery, a church, a monument, a public square and much more! Start your day with a visit to Galleria Dell'accademia. This popular art gallery is a must-visit in the city. When you’re ready for your next discovery, continue to Cathedral Of Santa Maria Del Fiore, which may be one of the most symbolic places you will experience today.

One of the best things about exploring Florence 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 Leaning Tower Of Pisa, an iconic monument in the city. If you’re up for more discoveries, don’t forget to reserve some time for Piazza Del Duomo, Pisa.

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

As you explore more of Florence, 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.

Treat yourself to a delicious dinner at Ditta Artigianale, an excellent option for tonight's dining. Looking for something different? Trattoria Da Burde offers a tantalizing alternative with its diverse menu. And don’t miss Casa Toscana. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

After enjoying a fulfilling meal, continue your evening at Bar 50 Rosso, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bitter Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Archea Brewery provides an excellent environment for a relaxed and enjoyable evening.

Raise your glass to another unforgettable day in Italy!

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 Siena and San Gimignano. In the evening, you’ll end up in Ancona, where you will stay for 1 night.

Bring your curiosity for today’s adventure around Florence. Some of the city’s most loved attractions await! Siena Cathedral is the perfect place to start. This church is one of the most locally renowned places to visit in Florence. Next, head to Battistero Di San Giovanni Battista, an intriguing church, known for its heritage-rich features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Piazza Del Campo. This visually striking public square is a highly recommended experience. Nearby, you'll also find Tower Of Mangia and Porta San Giovanni. Visit these for an interesting touch to your journey.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Ancona. Ancona offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Ancona. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Enjoy a delicious meal at Amarcord, a highly-rated dining destination in Ancona. If you're eager to try something different, consider Bontà delle Marche, another top spot with a tantalizing menu. You might also want to secure a reservation at Ristorante Pizzeria Da Romano. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Ancona this evening.

After your meal, keep the night alive at a bar like Alla Tazza D'oro, known for its lively atmosphere.

Celebrate another amazing day of your road trip adventure in Italy!