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Tuscany Road Trip: 7-Day Itinerary

7 Days

2 Stops

Self drive

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  1. Destinations
  2. Europe
  3. Italy
  4. Tuscany Road Trip: 7-Day Itinerary
From$1,500
per person
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Trip curated by Roman Karin
Expert

My team and I crafted this trip! Want to make it even more your style? Let’s chat — you can book a free planning call with me.

My team and I crafted this trip! Want to make it even more your style? Let’s chat — you can book a free planning call with me.

Recommended route

Customize at any time with an expert

Florence

Day 1 - 3

Florence, the beautiful capital of the Italian region Tuscany, lies in the center of the country. A small city with a big heart, and an even bigger offering of artistic and historical treasures. For centuries, travelers have journeyed to the birthplace of the Renaissance era to marvel at the many masterpieces of architecture and art: Michelangelo's iconic David, the impressive works of Botticelli, the Uffizi Gallery (packed with works by Caravaggio and Da Vinci), and of course, Brunelleschi's remarkable dome — the religious centerpiece of Florence that dominates the skyline. All are absolute must-sees on any itinerary. Once you've ticked off these renowned attractions, you can take a stroll through the vast Boboli Gardens or climb the hill to the church of San Miniato al Monte for a breathtaking view of this beautiful, enchanting city.

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Your accommodation

B&B Hotel Firenze Pitti Palace al Ponte Vecchio
B&B Hotel Firenze Pitti Palace al Ponte Vecchio
B&B Hotel Firenze Pitti Palace al Ponte Vecchio

B&B Hotel Firenze Pitti Palace al Ponte Vecchio

B&B Hotel Firenze Pitti Palace al Ponte Vecchio is located in Florence, Italy, close to attractions like the Palazzo Pitti. The hotel features comfortably furnished guest rooms that are equipped with modern amenities, including air conditioning, Wi-Fi access, a flat-screen TV, and a private bathroom. You can enjoy a breakfast buffet every morning during their stay. Additional facilities and services include meeting rooms.

Siena

Day 4 - 7

Spread across three hills in the heart of Tuscany, the compact city of Siena is a historic gem centered around the sloping Piazza del Campo. Overlooked by the magnificent Palazzo Pubblico, the city is known worldwide for the famous Palio, a horse race held around the piazza twice every summer. Siena has remarkably preserved its quaint old-world charm. Its stunning Gothic buildings include the city’s Duomo, which is arguably one of Italy’s most impressive Gothic cathedrals, along with numerous other architectural treasures. The city also boasts a wealth of exceptional early Renaissance art. Meanwhile, Siena buzzes with modern life, and each of its 17 neighborhoods is uniquely captivating.

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Your accommodation

NH Siena
NH Siena
NH Siena

NH Siena

The pet-friendly NH Siena hotel is located just a few minutes' walk from the heart of Siena with its wealth of historical sights, Gothic architecture and pavement cafés. The accommodation consists of 129 spacious guest rooms and suites, each equipped with air conditioning, television, minibar, hairdryer and safe. Start the day with a hearty breakfast buffet, dine in the on-site restaurant or relax with a refreshing drink at the bar. Room service is also available. Other amenities include free Wi-Fi, a 24-hour reception, a fitness room, a business center and three function rooms.

From$1,500
per person
Plan your trip

Accommodations
Transportation
24/7 support
Activities
Tourlane App
Travel plan
Flights

Why plan with an expert?


Roman Karin
Tourlane Expert
Tourlane Expert
Tourlane Expert

200+


Plan with professionals who are explorers themselves.

12+ hours of time saved

Our experts plan and book for you.

5+ Bookings managed

Everything is bundled in one place and perfectly planned.

5+ Transfers coordinated

For optimal transport and comfort.

Excellent

Why plan with an expert?


Roman Karin
Tourlane Expert
Tourlane Expert
Tourlane Expert

200+


Plan with professionals who are explorers themselves.

12+ hours of time saved

Our experts plan and book for you.

5+ Bookings managed

Everything is bundled in one place and perfectly planned.

5+ Transfers coordinated

For optimal transport and comfort.

Excellent

Itinerary inspiration

Experience the heart of Italy on a scenic road trip through Tuscany, where Renaissance cities, rolling vineyards, and medieval villages come together in perfect harmony. Begin in Florence, the birthplace of the Renaissance, where iconic landmarks like the Duomo, Ponte Vecchio, and world-class museums set the tone for an inspiring start. Spend your first days exploring historic streets, elegant piazzas, and local cuisine that reflects the region’s rich culinary traditions.

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After immersing yourself in Florence, pick up your rental car and journey south into the Tuscan countryside. Winding roads lead through vineyards, olive groves, and postcard-perfect landscapes as you make your way to Siena. Here, time slows down as you explore Gothic architecture, lively squares, and nearby hilltop towns. With a balance of cultural highlights and relaxed countryside exploration, this itinerary offers a well-paced introduction to Tuscany’s timeless charm.

Day 1–3: Florence (3 Nights)

Begin your journey in Florence, where art, history, and architecture define the city.

Your Accommodation

B&B Hotel Firenze Pitti Palace al Ponte Vecchio

Highlights & Activities

  • Private transfer from the airport to your hotel

  • Explore Florence’s historic center and iconic landmarks

  • Visit sites such as the Duomo and Ponte Vecchio

  • Discover museums, galleries, and local markets

  • Enjoy Tuscan cuisine in traditional trattorias

Day 4–6: Siena (3 Nights)

Head into the Tuscan countryside and settle into Siena, a city rich in history and character.

Your Accommodation

Hotel NH Siena

Highlights & Activities

  • Pick up your rental car in Florence

  • Scenic drive through vineyards and rolling hills

  • Explore Siena’s historic center and Piazza del Campo

  • Visit nearby towns such as San Gimignano or Montepulciano

  • Enjoy wine tastings and local specialties in the region

Day 7: Departure

Your journey concludes with your return to Florence. Drop off your rental car at the airport and depart with lasting memories of Tuscany’s landscapes, culture, and cuisine.

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Tips for your 7-day Tuscany road trip

The best time for a road trip through Tuscany is during the spring (April–June) and fall (September–October). These seasons offer comfortable temperatures and plenty of sunshine, making it perfect for driving through the rolling landscapes of Val d'Orcia or exploring the medieval villages of San Gimignano and Monteriggioni.

➔ Best travel time Tuscany | Best time to travel Italy

On average, a one-week trip to Italy costs around $1,700 per person, excluding flights. The main difference in a road trip itinerary is the cost of transportation, which is around $70 per day for a small rental car. Budget stays can begin at about $50 per night, while dining at a casual restaurant costs around $20 per person.

➔ Travel cost Tuscany | Travel cost Italy

The highlights of a Tuscany road trip include the art and architecture of Florence and Siena, the Leaning Tower of Pisa, and the beautiful city walls of Lucca. You can also explore the historic fortress of Monteriggioni. Popular activities include a truffle hunt, a Vespa tour through the Chianti region, and wine tastings at local estates.

➔ Things to see Tuscany | Activities Italy

Booking tickets for popular attractions like the Uffizi Gallery in Florence and the Leaning Tower of Pisa in advance is highly recommended, especially during peak season. A road trip offers the freedom to discover the region’s thermal springs and picturesque villages at your own pace. Be sure to explore the traditional markets to taste local products.

➔ Insider tips Italy

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We would like to thank Alexandra Egertz...

We would like to thank Alexandra Egertz...

R

rosi eckstein

Friendly and competent advice that fulfilled all our wishes. We are looking forward to our upcoming trip to Italy and will get in touch again afterwards to let you know if everything went well.

08/27/2025
As always 😀👍🏻 very satisfied …

As always 😀👍🏻 very satisfied …

C

Carsten

Italy trip …

Italy trip …

M
Manuela Schumacher

Manuela Schumacher

Simply perfect

Simply perfect

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Eyvette Thompson

Italy trip

Italy trip

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Caroline Bohrmann

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  • We are once again very satisfied with Tourlane and the collaboration with Ms. Calabrese. She provided me with detailed information and prepared and organized the Italy trip excellently. Happy to book again 😊

    07/11/2025
  • It was a very nice trip and overall we are very satisfied. The Tourlane navigation could be a bit more precise. All the hotels were very good 👍 It was a wonderful time that we would happily repeat again and again.

    06/23/2025
  • We were interested in a round trip through Italy and shortly after our inquiry we already received an appointment for a consultation. The conversation with our Italy expert, Lara Schmidt, was simply great. She not only took all our wishes into account, but also rightly advised against one or two locations because of the weather/season. Shortly afterwards we received our offer (route, hotels, rental car), and what can we say — we got a perfectly arranged trip that really included and even exceeded all our wishes. That’s why we confirmed the trip with Lara directly in the next call and are super excited. @Lara: A BIG THANK YOU for the great exchange — you do this with so much heart and en...

    03/18/2025
  • Lara has organized my IT Trip for summer with my family. She had some many great ideas and provided so much information about the different regions. I´m really looking forward! Thank you Lara :-)

    02/11/2025