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 May, this is also the most popular time of the year.
10 best self-guided Tuscany tours
Compiled by
MelissaTuscany travel expert at TourRadar
- Postcard Southern Tuscany - Cycling Cortona, Montalcino, Siena - Classic Self Guided
- Tuscany Absolute
- Tuscany Escape: 7 days Through Art, Wine & Hills, Self-Drive
- 5 Day Florence With Car Rental
- In the Heart of the Renaissance: Pisa & Florence
- Pearls of Tuscany
- Luxury Italy by High-Speed Train
- 4 Days in Florence.
- Tuscany based in one hotel
- A Taste of Tuscany Cycling
Postcard Southern Tuscany - Cycling Cortona, Montalcino, Siena - Classic Self Guided
2 Reviews by TourRadar travelers“We loved everything about our self-guided tour. The itinerary kept us on less-traveled roads as much as possible.”
kathysteinberger, traveled in July
GPS navigation guides cyclists through Tuscany's heart. Daily rides of 22-67km connect Cortona to Siena, with stays at Hotel S. Luca and Hotel dei Capitani. Brunello wineries and UNESCO landscapes unfold at your chosen pace with included luggage transfers.
Duration 8 days Destinations Cortona, Lake Trasimeno Regional Park, Montepulciano, Pienza, Val d'Orcia, Montalcino, San Quirico D'orcia, Bagno Vignoni, Siena Age Range All Ages Welcome Operator BikesPlus Travel From
- US$1,726
Tuscany Absolute
12 Reviews by TourRadar travelers“The hotels were great, especially the picturesque Montepulciano one nestled in the countryside—a true Tuscany gem.”
Borna, traveled in August
Florence's Hotel Executive welcomes you to discover Accademia Gallery and Ponte Vecchio independently. Move on to Montepulciano's Villa Cicolina, exploring Siena's medieval streets and Piazza del Campo. Flexible itinerary includes breakfast and private transfers.
Duration 7 days Destinations Florence, Siena, San Gimignano, Castellina in Chianti, Montepulciano Age Range All Ages Welcome Operator Flag Travel Holidays From $3,053
20% Off- US$2,442You save $611
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 $1,278
15% Off- US$1,086You save $192
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 $1,401
35% Off- US$911You save $490
Navigate Tuscany at your own pace through the Worldee App Guide, starting at Piazza dei Miracoli in Pisa where you'll photograph the iconic 12th-century Leaning Tower before traveling to Florence. See Renaissance masterpieces by Botticelli at the Uffizi Gallery, admire Michelangelo's David at Galleria dell'Accademia, and wander through Boboli Gardens behind Palazzo Pitti. Stay at Le Cascine in Pisa (rating 8.2/10) and Hotel Balcony in Florence (rating 8.2/10), located just 400 meters from Santa Maria Novella station.
Duration 5 days Destinations Pisa, Florence Age Range All Ages Welcome Operator Worldee From
35% Off- US$378
Pearls of Tuscany
“I will definitely recommend and I will use these services again next time.”
Michaela, traveled in May
Duration 6 days Destinations Pisa, Massaciuccoli, Tuscany, Siena, San Gimignano, Lucca, Florence Age Range All Ages Welcome Operator Worldee From
35% Off- US$311
Duration 9 days Destinations Rome, Florence, Castellina in Chianti, Siena, San Gimignano, Venice Age Range Ages 10+ Operator Flag Travel Holidays From $5,081
20% Off- US$4,065You save $1,016
Spend 3 nights at River Hotel & Spa Firenze with convenient airport transfers from Florence Municipal Airport included. The UNESCO-listed historic center is yours to see at your own pace, with optional skip-the-line access to the Accademia Gallery where you'll find Michelangelo's David plus masterworks by Giotto and Bernardo Daddi. The self-guided package works for groups of 10-90 travelers aged 18+ and includes daily breakfast. You're free to wander Florence's art-filled streets - the Duomo, Ponte Vecchio, and beyond - completely on your own schedule.
Duration 4 days Destinations Florence Age Range Ages 18+ Operator Remaz Tours GmbH From
20% Off- US$1,580
Duration 8 days Destinations Montecatini, Pisa, Florence, San Gimignano, Vinci, Lucca Age Range All Ages Welcome Operated in English, German Operator Eurobike From
20% Off- US$1,169
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
20% Off- US$2,180
What people love about Self-Guided Tours in Tuscany
- Tuscany Absolute
My group of 4 couples had a wonderful time with the tour that was arranged for us. 4 days in Florence, 2 nights in Sienna and 2 nights in Montepulciano! We loved the cooking classes, wine tours, city tours - all of it. Hotels were outstanding also. Great time - loved it.
- Classic Tuscany - Cycling from Florence to Pisa - Classic Self Guided
Cycle Europe makes bicycle tourism easy and fun. We completed a self-guided route and it felt like a completely independent trip, but we never had to consider a single logistical hurdle. Everything went smoothly, the routes were incredible, and the overnight stays gave us the opportunity to truly explore Tuscany. Just a brilliant tour!
- Postcard Southern Tuscany - Cycling Cortona, Montalcino, Siena - Classic Self Guided
From beginning to end, Cycle Europe was fantastic. The pre-planning and communication was incredible. The bikes were titanium bikes, with quality components. The sent staff members to expertly fit the bikes, the routes they planned was perfect, and the hotels were fabulous. On top of everything else, they were willing to help us for our entire vacation. They helped set up a cooking class for us in Lucca, helped arrange a special ceremony for our parent's 50th anniversary, and helped arrange our private transfer. They were really amazing.
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.