One-Week Italy Self-Drive Road Trip With Itinerary from Ancona to Florence, Siena, and Rome

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Photo of the long staircase in the downtown of the beautiful ancient italian village.
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Explore the best of Italy on a 8-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Ancona, Florence, Pisa, Siena, San Gimignano, and Rome. This road trip itinerary in Italy seamlessly combines exploration with relaxation.

This perfectly planned road trip itinerary in Italy takes you through some of the best places to see in the country. You will spend 3 nights in Ancona, 2 nights in Florence, 1 night in Siena, and 1 night in Rome. 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 got you covered.

Upon arriving in Ancona, 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 Colosseum are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Pantheon, learn more about the unique Piazza Navona, and immerse yourself in the vibrant atmosphere of St. Peter's Basilica.

As you hit the open road and drive through Ancona, Florence, Pisa, Siena, San Gimignano, and Rome, 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, accommodation, 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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Driver’s age is 30 - 65
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Itinerary summary

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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
Parco Della Cittadella di Ancona
Parco Belvedere PosatoraLazzaretto of AnconaPiazza del PlebiscitoArch of TrajanGrotta Azzurra PathwayPassetto
Basilica of Santa Croce in FlorenceUffizi GalleryPonte VecchioPalazzo Vecchiopiazza della Signoria
Santa Maria della SpinaPalazzo BluKnights' SquareLeaning Tower of PisaPisa CathedralPiazza del Duomo, Pisa
Siena Cathedralpiazza del CampoTower of MangiaPorta San GiovanniSanGimignano1300Piazza del Duomo, San Gimignano
ColosseumRoman ForumTrevi FountainPantheonPiazza Navona
St Peter's BasilicaSistine ChapelObelisk of St Peter's SquareVatican Museums
Cattedrale di San Ciriaco

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Day 1

Day 1

  • Ancona - Arrival day
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  • Parco Della Cittadella di Ancona
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Welcome to Ancona, 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 immersing yourself in Ancona's charm before embarking on the next leg of your journey.

Ancona 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 Parco Della Cittadella Di Ancona, or just taking a stroll in the city center. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

Make your way to your chosen hotel. Check-in typically starts between 2 and 4 PM in Ancona. Make yourself at home and enjoy some downtime before heading out again.

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 Ancona, it's often a good idea to reserve a table in advance.

Make sure to reserve a table at Playa Solero, an iconic dining spot in Ancona. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Zucchero a Velò, a popular restaurant in Ancona. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Ristorante Il Giardino, a hidden gem nestled in Ancona. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Continue your lively evening at Posa Bar, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bar Four Roses is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Amarillo Beer Bar Ancona ensures a night out tailored to your taste.

Raise a toast to the start of your 8-day road trip in Italy!

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Day 2

Day 2

  • Ancona
  • More

Drive 17 km, 1 hour 18 min

  • Parco Belvedere Posatora
  • Lazzaretto of Ancona
  • Piazza del Plebiscito
  • Arch of Trajan
  • Grotta Azzurra Pathway
  • Passetto
  • More

Day 2 offers a multitude of experiences. You will stay in Ancona for 1 night more, offering you enough time to explore at a relaxed pace.

Get ready for an exciting day in Ancona. Today’s sightseeing agenda includes a park, a museum, a public square, a monument, a cave and much more! Begin your adventure at Parco Belvedere Posatora. This is an up-and-coming park you should not miss. Another must-see is Lazzaretto Of Ancona, an intriguing museum in Ancona.

When you’re ready for the next sight, head to Piazza Del Plebiscito. From there, take a leisurely stroll to Arch Of Trajan, another of the city’s locally appreciated attractions. We recommend continuing your self-guided tour at Grotta Azzurra Pathway, a mesmerizing place of interest in the city. If time allows, add Passetto to your itinerary. This up-and-coming monument offers the perfect finishing touch to your day in Ancona.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

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

Make sure to reserve a table at Amarcord, an iconic dining spot in Ancona. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Bontà delle Marche, a popular restaurant in Ancona. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Ristorante Pizzeria Da Romano, a hidden gem nestled in Ancona. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Following your dinner, dive into the local bar culture at Alla Tazza D'oro. Enjoy this evening's relaxed ambiance with delightful drinks.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

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Day 3

Day 3

  • Ancona
  • Florence
  • More

Drive 277 km, 3 hours 40 min

  • Basilica of Santa Croce in Florence
  • Uffizi Gallery
  • Ponte Vecchio
  • Palazzo Vecchio
  • piazza della Signoria
  • More

Dive into day 3 of your remarkable road trip in Italy. Today you will explore Florence, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Florence. You’ll stay here for 2 nights.

Today’s itinerary in Ancona covers several incredible sights, including a church, an art gallery, a historical landmark, a palace, a public square and much more! Start your adventure at Basilica Of Santa Croce In Florence. This interesting church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the picture-perfect wonders of Uffizi Gallery, a must-see art gallery in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Ponte Vecchio. This timeless historical landmark offers an enriching experience. For a change of pace, head to Palazzo Vecchio, where you can take in visually striking features. Conclude your self-guided sightseeing tour with a visit to Piazza Della Signoria. These sights offer a fulfilling end to a perfect day.

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.

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

Enjoy a lovely dining experience at Ristorante Oliviero 1962, 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 Di Poneta Novoli, 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 Caffe San Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Manifattura stands out as an excellent choice for a post-dinner cocktail. Alternatively, Se·sto On Arno Rooftop Bar offers an ideal atmosphere to enjoy the pleasures of the night. Il Vinile is also a great option that provides a perfect setting for a relaxing evening.

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

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Day 4

Day 4

  • Florence
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Drive 196 km, 3 hours 7 min

  • Santa Maria della Spina
  • Palazzo Blu
  • Knights' Square
  • Leaning Tower of Pisa
  • Pisa Cathedral
  • Piazza del Duomo, Pisa
  • More

On day 4 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 Pisa. You still have 1 night left in Florence.

Discover a day packed with fun adventures, romantic experiences, and breathtaking views in Florence. Begin your sightseeing with Santa Maria Della Spina. This intriguing church is one of the top attractions in the city. Proceed to Palazzo Blu, another must-visit attraction.

As you wander through the inviting streets of Florence, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Knights' Square. This beloved public square is a traveler-favorite. Not far away, you’ll find Leaning Tower Of Pisa, another key site on your sightseeing itinerary. Pisa Cathedral is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Piazza Del Duomo, Pisa and uncover why it's recognized as one of the city's most timeless attractions.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Florence.

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

Make sure to reserve a table at Ditta Artigianale, an iconic dining spot in Florence. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Trattoria Da Burde, a popular restaurant in Florence. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Casa Toscana, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bar 50 Rosso, known for its inviting atmosphere. Bitter Bar is another great option if you’re looking for a place to get the night started. Similarly, Archea Brewery provides a great setting to enjoy the night away.

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

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Day 5

Day 5

  • Florence
  • Siena
  • More

Drive 158 km, 2 hours 58 min

  • Siena Cathedral
  • piazza del Campo
  • Tower of Mangia
  • Porta San Giovanni
  • SanGimignano1300
  • Piazza del Duomo, San Gimignano
  • More

On day 5 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Siena and San Gimignano. When you’re not sightseeing, take time to relax at your selected hotel in Siena, where you’ll be staying 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 well-known places to visit in Florence. Next, head to Piazza Del Campo, an impressive public square, known for its awe-inspiring 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 Tower Of Mangia. This breathtaking monument is a highly recommended experience. Nearby, you'll also find Porta San Giovanni and Sangimignano1300. Visit these for an interesting touch to your journey. Finish the day with a visit to Piazza Del Duomo, an enchanting public square in Florence.

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.

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

Treat yourself to a delightful dinner at Enoteca I Terzi, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Ristorante Tar-Tufo? It's another excellent option with a diverse menu. Consider reserving a table at Antica Trattoria Papei as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Siena.

After savoring a delicious meal, step into the vibrant nightlife at Meet Life Cafè, where the evening is just getting started. In the same way, Maudit Pub offers a unique charm perfect for experiencing the local bar scene in Siena. Bar Impero Siena is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Take some time to reflect on your day and savor another beautiful night in Italy.

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Day 6

Day 6

  • Siena
  • Rome
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Drive 242 km, 3 hours 37 min

  • Colosseum
  • Roman Forum
  • Trevi Fountain
  • Pantheon
  • Piazza Navona
  • More

Experience an unparalleled adventure on day 6 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Rome. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Rome. You will spend 1 night here for some well-deserved relaxation.

Discover a day packed with family-friendly attractions, scenic views, and photo-friendly spots in Siena. Begin your sightseeing with Colosseum. This wondrous archeological site is one of the top attractions in the city. Proceed to Roman Forum, another must-visit attraction.

As you wander through the inviting streets of Siena, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Trevi Fountain. This iconic monument is a traveler-favorite. Not far away, you’ll find Pantheon, another key site on your sightseeing itinerary. Piazza Navona is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Rome. Rome 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 Rome. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Dine in style at La Bottega Roma, a top recommendation for dinner tonight. Or, for a change of pace, Pasta In Corso boasts a menu that's sure to impress. Also, be sure to check out Trattoria Vecchia Roma. Known as a local hotspot, it’s a great choice for tonight in Rome.

Cap off your dinner by heading to La Botticella Of Poggi Giovanni, ideal for a leisurely evening with a drink in hand. Almalu Trastevere is another bar that offers an enjoyable setting. Similarly, Bar Viminale Di Pepi Maurilio is also a popular place to go on a night out, perfect for relaxing and socializing.

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

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Day 7

Day 7

  • Rome
  • Ancona
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Drive 313 km, 4 hours 17 min

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

Embark on another extraordinary experience on day 7 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Vatican City. At the end of the day, you will enjoy the comforts of a top-rated hotel in Ancona, which will be your home away from home for 1 night.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Rome allows for both. Start by heading to St. Peter's Basilica. This timeless major basilica provides an insightful glimpse into the city's identity.

Continue your sightseeing with a visit to Obelisk Of St Peter's Square, an intriguing point of interest. When you’re done, don’t forget to make a stop at the world-famous Vatican Museums.

When you’re done exploring for the day, you’ll drive to your hotel in Ancona. Check in and spend some time relaxing before you head out to tour the city.

As you explore more of Ancona, 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.

Enjoy a delicious meal at Pizzeria Pulcinella, a top-rated dining destination in Ancona. If you're in the mood to try something new, consider Donegal Irish Pub, another top spot with a mouthwatering menu. You might also want to secure a reservation at Vino E Cucina Miscia. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Ancona this evening.

As the sun sets on another day of adventure, rest up and recharge for the next leg of your road trip in Italy.

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Day 8

Day 8

  • Ancona - Departure day
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  • Cattedrale di San Ciriaco
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Day 8 of your road trip in Italy is your departure day. This is your chance to catch a last glimpse of Ancona 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 Cathedral Basilica Of St. Cyriacus, a historic church before you head out.

Make the most of your final day in Italy by visiting Ancona’s iconic markets and shopping establishments. Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing experience in Italy.

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

You’ll then say farewell to Ancona. 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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