Self-Guided Tours & Trips in Tuscany
Explore a wide diversity of self-guided tours through Tuscany. We have 44 adventures that vary from 4 days to 9 days. With the greatest number of departures in April, this is also the most popular time of the year.
10 best self-guided Tuscany tours
Compiled by
MelissaTuscany travel expert at TourRadar
- Tuscany Escape: 7 days Through Art, Wine & Hills, Self-Drive
- 5 Day Florence With Car Rental
- Pearls of Tuscany
- 4 Days in Florence.
- A Taste of Tuscany Cycling
- Grand Tour of Tuscany (7 days)
- Short vacation Tuscany (5 days)
- Picturesque Tuscany - with Charm 8 Days
- Via Francigena - From Chiusi to Città di Castello 6 Days
- Walking in Tuscany
The Tuscan countryside unfolds from Florence's Ponte Vecchio to Chianti's wine routes. Self-drive freedom lets you uncover Siena's Piazza del Campo and San Gimignano's medieval towers. Includes 4-star stays at Grand Hotel Adriatico and Hotel Le Pozze di Lecchi.
Duration 7 days Destinations Florence, Pisa, Gaiole in Chianti, Siena, San Gimignano Age Range All Ages Welcome Operator TUI Italia From $1,285
10% Off- US$1,156You save $128
Create your Tuscan adventure with a rental car and Hotel Luxor Florence base. Freedom to explore the Uffizi Gallery, discover Oltrarno's authentic neighborhoods, and visit local artisan workshops at your own pace.
Duration 5 days Destinations Florence Age Range All Ages Welcome Operator STM Tours LLC From $1,409
30% Off- US$986You save $423
Pearls of Tuscany
“Thank you for a great vacation that someone else planned for us and we didn't have to worry about anything.”
Jaromir, traveled in July
Duration 6 days Destinations Pisa, Massaciuccoli, Tuscany, Siena, San Gimignano, Lucca, Florence Age Range All Ages Welcome Operator Worldee From
30% Off- US$304
Duration 4 days Destinations Florence Age Range Ages 18+ Operator Remaz Tours GmbH From
30% Off- US$1,589
GPS directions guide you through Tuscany from Agriturismo La Pietriccia. Wander Montallese's mountain trails, Radicofani's hilltop views, and Sarteano's medieval center. Features host Stefano's briefings, cooking class, and route planning from Chianciano Terme.
Duration 8 days Destinations Chianciano Terme, Radicofani, Sarteano, Montepulciano, Pienza, Val d'Orcia Age Range Ages 13+ Operator Exodus Adventure Travels From
30% Off- US$2,180
Duration 7 days Destinations Pisa, Casciana Terme, San Gimignano, Siena, Greve in Chianti, Florence Age Range Ages 16+ Operated in Only: German Operator ASI Reisen From
30% Off- US$1,048
Duration 5 days Destinations Pisa, Lucca, Massaciuccoli, Montecatini, Collodi, Pescia, Pistoia, Florence Age Range Ages 16+ Operated in Only: German Operator ASI Reisen From
30% Off- US$742
Duration 8 days Destinations Florence, Greve in Chianti, Tuscany, Castellina in Chianti, Panzano, Siena, Marina di Campo, San Gimignano, Volterra, Marina di Castagneto CarducciSee all destinations Age Range Ages 16+ Operated in Only: German Operator ASI Reisen From
30% Off- US$1,600
Duration 6 days Destinations Chiusi, Chiusi della Verna, Anghiari, Citerna Age Range Ages 16+ Operated in Only: German Operator ASI Reisen From
30% Off- US$679
Duration 8 days Destinations Pistoia, Tuscany, Florence, Vinci, Lucca Age Range Ages 18+ Operator Just You From $2,212
9% Off- US$2,011You save $201
What people love about Self-Guided Tours in Tuscany
We created a self-guided tour starting in Florence through San Gimignano, Siena, Montepulciano and ending in Arezzo. The Cycle Europe team was very helpful in setting things up, recommendations and the delivery and collection of the bikes in different cities. The bikes were excellent, the fitting and service too. I will def use this team again and next time I will use their route planning service but we did not have enough lead-time to do that for this tour. Highly recommend!
Classic Tuscany - Cycling from Florence to Pisa - Classic Self Guided
- Postcard Southern Tuscany - Cycling Cortona, Montalcino, Siena - Classic Self Guided
Although the route was very hilly, we loved everything about our self-guided tour. The itinerary kept us on less-traveled roads as much as possible, and took us through small scenic towns with gorgeous views. We also appreciated the opportunity to tour several monasteries and scenic spots along the way. Our accommodations were very good and we had a hearty, tasty breakfast every morning. The combination of paper maps with precise directions and GPS ensured that we were hardly ever lost. We were also impressed with the quality of the bikes and the expert fitting and orientation we received before we set out. I'd highly recommend this tour for bikers who don't mind lots of elevation change!
What our customers ask about Self-Guided Tours & Trips in Tuscany
What's the best time of year for a self-guided tour in Tuscany?
The prime months for exploring Tuscany on your own are April through October with May and September offering the most balanced conditions. Spring sees temperatures around 20°C (68°F) and countryside dotted with wildflowers near San Gimignano while fall brings grape harvests and clear skies perfect for photography. Tour data shows the highest concentration of departures in May and September with most accommodations operating at full capacity during these months. The shoulder seasons also mean shorter lines at popular sites like the Uffizi Gallery and more availability at local restaurants.
What are the best areas to stay in Tuscany for a self-guided tour?
Three key locations serve as ideal bases: Montecatini Terme Florence and Siena. Each offers distinct advantages for independent travelers. Montecatini Terme with its central location puts you within an hour of both Pisa and Florence. The Grand Hotel Croce di Malta here provides easy access to lesser-known towns like Vinci. In Siena the Hotel Italia positions visitors perfectly for exploring the Val d'Orcia region while Florence serves as an excellent starting point for day trips throughout the region.
How much time should I allow for a comprehensive self-guided tour of Tuscany?
Seven to eight days allows for a well-paced exploration of Tuscany's main regions. Most successful itineraries dedicate 2-3 days to Florence followed by 2 days in the Chianti region and 2-3 days in Siena and its surroundings. This timeline lets travelers explore major sites while leaving room for spontaneous discoveries such as local festivals or markets. Properties like Hotel Francia & Quirinale in Montecatini serve as comfortable bases between destinations.
What are the must-visit wineries and food experiences for self-guided travelers in Tuscany?
The Chianti Classico region between Florence and Siena offers excellent wine tasting opportunities while Montepulciano's Vino Nobile producers provide insights into traditional winemaking. Local hotels like Hotel Manzoni can connect visitors with family-run olive oil producers and authentic restaurants. The self-guided format allows for extended tastings and unplanned stops at small producers particularly in lesser-known areas of the Chianti region.
How can I combine coastal and inland exploration on a self-guided Tuscan tour?
Begin in either Florence or Pisa then create a route that connects inland towns with coastal areas like the Maremma region. Consider staying at Hotel Repubblica Marinara in Pisa for seaside access before moving to inland properties such as Hotel Italia in Siena. This approach allows travelers to experience both Tuscany's medieval hill towns and its Mediterranean coastline while maintaining flexibility in the schedule.
What should I budget for a self-guided tour in Tuscany beyond the basic package?
Plan for daily expenses beyond the base tour cost of 160-180 USD. This includes meals (30-50 USD per person) local transportation (15-20 USD daily) and attraction entrance fees (10-15 USD each). Properties like Hotel De La Pace in Florence or Hotel Italia in Siena may have additional city taxes. Factor in extra funds for spontaneous activities such as cooking classes or private wine tastings.
What level of physical fitness is required for self-guided tours in Tuscany?
Self-guided tours typically require moderate fitness with daily walking distances of 13-24km or cycling routes of 40-65km. The Via Francigena route from San Miniato to Buonconvento features 4-7 hour walks through rolling terrain. Hotels like La Luna in Lucca provide comfortable rest stops between active days. Most routes follow well-marked paths through vineyards and medieval towns with options to shorten or extend based on energy levels.