Florence to Siena and Monteriggioni: Private day trip
Private ride with a local driver
8hRound tripPrivate driver
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About your trip
Leaving Florence, the roads slip into vineyard-draped hills along the Chiantigiana—Tuscany’s “Liquid Gold” road. Pause at family-run cellars for a barrel-side sip, then roll into Siena, where Gothic towers rise above honeyed rooftops. After exploring its fierce contrade spirit, end in Monteriggioni, a perfect medieval crown perched above the Valdelsa Valley.
Exclusively yours: private vehicle and professional driver
Discover local insights you won't find in guidebooks
Experience the freedom to explore at your own speed
Perfectly planned for families, friends, or solo travelers
What to expect
Your day trip begins wherever you are
Meet our professional driver right where you prefer in Florence whenever suits you best. No time wasted getting to the pickup point, grab your bag and start your trip right away.Discover more with local expertise
Your driver’s local insights will set the tone for your day trip. A hidden café here, a must-try restaurant there; insider tips you’ll love sharing later. This isn’t a guided tour but your ride will be rich with stories and discoveries along the way. And throughout the day, your driver will be available for you as needed, ready to assist, happy to help, making your trip stress-free.Explore at your own pace
After arriving in Siena, you'll have the freedom to explore the historic Gothic towers of this hilltown before continuing to Monteriggioni, where you can admire the views of the region, all at your leisure. Meanwhile, your driver will wait for you nearby, ensuring a stress-free return trip.
Perfect for any private group
Whether you're traveling solo, as a family with kids, or as a large group, this service is tailored for your comfort and flexibility. It's the ideal option especially if you have limited time or a busy schedule.Good to know
- Two-way private car transfer
- Air-conditioned vehicle
- Personalized pickup and drop-off
- Professional English-speaking driver
- Complimentary bottled water
- Free cancellation 24 hours before departure
- Entry/Admission tickets to paid attractions in Siena and Monteriggioni should be purchased separately unless specified otherwise
- Meals, snacks, and gratuity are not included
From €237
per person
Select date and travelers
Free cancellation up to 24 hours before your pickup time.
For a group of 1-3 travelersTotal€711
Your trip at a glance
Your trip at a glance
Start in Florence
You choose the pickup spot.
1
Siena
Feel free to explore at your own pace and discover
Stop: 3 h 30 min - admission not included






2
Monteriggioni
Feel free to explore at your own pace and discover
Stop: 2 hours - admission not included






Back to Florence
We’ll take you back to your starting point.
Duration of the stops can be changed upon request after booking
Have questions or need help?Contact our Customer Support. We are available 24/7
Daytrip is loved all around the world. Here's why.
Know more about your day trip
During your 3.5-hour visit to Siena, prioritize the magnificent Piazza del Campo with its distinctive shell shape and Torre del Mangia offering panoramic views (climb the 400 steps if time permits). Visit the stunning Duomo (Cathedral) with its incredible marble floor, Piccolomini Library frescoes, and works by Michelangelo and Donatello. Don't miss the historic Palazzo Pubblico housing the Civic Museum with Lorenzetti's famous "Good and Bad Government" frescoes. Walk the atmospheric contrade (districts) identified by animal or mythological symbols that compete in the famous Palio horse race.
Monteriggioni presents one of Italy's most perfectly preserved medieval fortified villages, appearing largely unchanged since its construction in the early 1200s. During your 2-hour visit, walk the complete circuit of its intact circular walls with 14 imposing towers mentioned by Dante in the Divine Comedy. The tiny village within contains just a handful of streets surrounding a central piazza with a Romanesque church. This compact defensive structure offers an authentic glimpse into medieval military architecture and provides excellent photo opportunities of the surrounding Tuscan countryside.
The Palio isn't merely a horse race but Siena's cultural cornerstone, held twice yearly (July 2 and August 16) in Piazza del Campo. The event sees the city's 17 historic contrade (districts) compete in a bareback horse race circling the piazza three times. Year-round, you'll notice contrada flags and symbols throughout neighborhoods, reflecting intense local loyalties passed through generations. During your visit, look for contrada museums displaying historical costumes and Palio victories, and notice boundary markers on buildings showing district territories that shape residents' identities to this day.
For iconic views of Siena's skyline dominated by the Duomo and Torre del Mangia, visit the elevated Bastion of San Domenico accessible from Via Camporegio. Within the city, climbing the Torre del Mangia (400 steps) rewards with spectacular panoramas across terracotta rooftops to the surrounding countryside. For photographing the distinctive shell-shaped Piazza del Campo, the terrace of the Civic Museum offers excellent elevated perspectives. Early morning or late afternoon light bathes the city's warm-toned buildings in golden light, creating particularly photogenic conditions.
Siena is approximately 75 kilometers (47 miles) south of Florence, with a driving time of about 1 hour 15 minutes. Monteriggioni is roughly 15 kilometers (9 miles) north of Siena, positioned conveniently between Florence and Siena. Your private Daytrip driver handles all transportation through the scenic Chianti countryside, with its characteristic vineyards, olive groves, and cypress-lined roads. This efficient route allows you to experience both the major cultural center of Siena and the perfectly preserved medieval fortress town of Monteriggioni in one day.
In Siena, sample traditional ricciarelli (soft almond cookies), panforte (dense fruit and nut cake), and pici (thick hand-rolled pasta) with ragu or cacio e pepe sauce. Look for truffles, wild boar, and Chianina beef dishes reflecting the region's hunting tradition. In Monteriggioni, smaller trattorias serve authentic Tuscan cuisine. Both locations offer excellent opportunities to taste Chianti Classico wines. For quick authentic bites, visit Siena's historic Antica Pizzicheria al Palazzo della Chigiana, a traditional delicatessen operating since 1935, for local cheeses and charcuterie.
April through October offers pleasant conditions for exploring, with spring (April-June) and early fall (September-October) providing ideal temperatures and fewer tourists than summer months. Summer brings the excitement of Palio season but also peak tourist numbers and heat that can make midday exploration challenging. Winter offers peaceful visits with virtually no crowds, though some attractions may have reduced hours. If possible, visit Siena midweek to experience the magnificent Duomo and climb the Torre del Mangia without long lines.
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Frequently Asked Questions
If you have any questions, here are the answers.Day trips offer travelers private round-trip transportation to popular sightseeing locations. One of our professional drivers will pick you up in a luxurious, climate-controlled car, take you to the site of interest, and wait for you while you explore before driving you back to your hotel.
Yes! You’re free to choose the pickup and drop-off times that work best for you. However, the time spent at the destination is fixed and cannot be changed.
Each sightseeing stop has a recommended duration that includes plenty of time to explore. However, it is possible to customize the time spent at each sightseeing stop at a later stage in the booking process to best fit your unique schedule.
Your Daytrip driver will wait for you nearby for the duration of your exploration, meaning you’ll never have to wait for your return trip transportation to arrive. Your comfort and convenience are our top priorities, and we aim to close out your day trip with a return on your schedule.
The price of a day trip does not include any entrance tickets, guided tours, or meals you may partake in at your destination. The price covers round-trip transportation in a luxury vehicle with a professional driver who can provide local insights en route.
Day trip bookings can be canceled up to 24 hours before your trip for a full refund, no strings attached. While the destination and stops are predetermined, it is possible to change your pick-up point, whether it is at your hotel or some other location within the city.
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