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Tuscany Road Trip: 7-Day Itinerary
7 Days
2 Stops
Self drive
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Trip curated by Roman Karin
ExpertDriving south from Florence on the Chiantigiana through Greve and Radda before arriving in Siena is where this road trip earns its internal logic, and it's the day I'd never sacrifice. The terraced vineyards, the cypresses on the ridgelines, and the medieval towers above the valley floors place the Renaissance art you've been absorbing in the exact landscape that funded it. San Gimignano before 10am is a genuinely different town from the midday version; the towers and the Piazza della Cisterna in that first quiet hour are the site at its most atmospheric. Siena's Piazza del Campo quiets significantly after 3pm when the main day-trip groups return northward; that late afternoon shadow of the Torre del Mangia crossing the terracotta brick is the version that makes the medieval geometry of the campo fully visible, and it's worth timing the stay to experience it.
Driving south from Florence on the Chiantigiana through Greve and Radda before arriving in Siena is where this road trip earns its internal logic, and it's the day I'd never sacrifice. The terraced vineyards, the cypresses on the ridgelines, and the medieval towers above the valley floors place the Renaissance art you've been absorbing in the exact landscape that funded it. San Gimignano before 10am is a genuinely different town from the midday version; the towers and the Piazza della Cisterna in that first quiet hour are the site at its most atmospheric. Siena's Piazza del Campo quiets significantly after 3pm when the main day-trip groups return northward; that late afternoon shadow of the Torre del Mangia crossing the terracotta brick is the version that makes the medieval geometry of the campo fully visible, and it's worth timing the stay to experience it.
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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.
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.
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 personAccommodations
Transportation
24/7 support
Activities
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Tourlane App
Travel plan
Flights
Flexible cancellation policies
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Why plan with an 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
Three nights in Florence followed by three in Siena, with the rental car bridging them through the Chianti hills — six days in Tuscany that cover the region's two great medieval cities and the landscape between them. Picking up the car in Florence and driving south through the vineyards and the ridge roads of the Chianti Classico zone is the experience that ties the two halves together, and it is worth taking slowly rather than treating as a transit.
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What I always tell people about the drive south: the road between Greve in Chianti and Panzano passes through the heart of the Classico zone, and a stop at a small producer — found on an unmarked side road — is more rewarding than any official cellar tour. Ask in the village for a family estate that sells direct. The conversation over a tasting there is more honest than anything organized.
Florence across three days with the Duomo, the Ponte Vecchio, the museum visits, and the local markets fills the time without effort. The B&B Hotel Firenze Pitti Palace al Ponte Vecchio sits on the Oltrarno side of the river — the quieter and more residential half — which gives the evenings a different character from the tourist-facing streets across the Arno. In Siena, the Piazza del Campo and the Gothic cathedral are the two things that define the city visually, but the lanes behind the Terzo di San Martino — away from the main tourist circuit — are where the city's daily character lives, and they reward an afternoon without a destination.
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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.
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.
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.
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.
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