Self-Guided Tours & Trips in Tuscany
4.5 stars on(8,460 reviews)- Choose from 21 Tuscany tours
- 22 verified reviews from TourRadar travelers
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10 best self-guided Tuscany tours
Compiled by
MelissaTuscany travel expert at TourRadar
- Tuscany Thrills: A 3-Day Escape of Wine, Relax, and Fun
- 5 Day Florence With Car Rental
- Luxury Italy by High-Speed Train
- Tuscany Escape, Self-Drive
- Tuscan Delights Self-Drive Tour 7days/6nights
- Italy by High-Speed Train - Mestre
- Car tour from culture to pleasure in Tuscany
- Classic Tuscany - Cycling from Florence to Pisa - Classic Self Guided
- Postcard Southern Tuscany - Cycling Cortona, Montalcino, Siena - Classic Self Guided
- 4 Days in Florence.
Your Tuscan adventure awaits at approx. $140 daily, with accommodations near San Gimignano and Chianti wine tastings. Add optional €100 Vespa rentals or €120 horseback rides while roaming independently.
Duration 3 days Destinations Tuscany, San Gimignano Age Range 18 to 99 year olds Operated in English, Italian Operator Italy on a Budget Tours From
- NZ$760
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 up to 99 year olds Operator STM Tours LLC From $2,281
5% Off- NZ$2,167You save $114
Duration 9 days Destinations Rome, Florence, Castellina in Chianti, Siena, San Gimignano, Venice Age Range 10 to 80 year olds Operator Flag Travel Holidays From
5% Off- NZ$7,852
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 up to 80 year olds Operator TUI Italia From $1,985
15% Off- NZ$1,688You save $298
Tuscany's treasures await as you drive from Florence's historic center to Pisa's Leaning Tower. Visit Volterra's Etruscan ruins, stop at Bolgheri's prestigious wineries, and discover Montepulciano's authentic farms. Pre-arranged tastings and 3-4 star hotel stays included.
Duration 7 days Destinations Florence, San Gimignano, Siena, Montepulciano, Volterra, Bolgheri, Pisa Age Range 1 to 99 year olds Operator RANIERI TOUR OPERATOR From
15% Off- NZ$1,529
Navigate independently between Hotel Empire Rome and UNA Vittoria Florence via high-speed rail. Explore Vatican Museums with skip-the-line access, discover Chianti vineyards, and wander Venice's hidden calli. Optional afternoon tours available at Doge's Palace.
Duration 7 days Destinations Rome, Siena, Castellina in Chianti, San Gimignano, Florence, Venice, Mestre Age Range 10 to 80 year olds Operator Flag Travel Holidays From
15% Off- NZ$2,552
From Florence's Uffizi Gallery to Pisa's Square of Miracles, Tuscany's treasures await. Self-drive adventures lead to Volterra's alabaster workshops and Certaldo's hilltop castle, complemented by wine tastings in Montecarlo and traditional pastry sampling in Siena's historic center.
Duration 8 days Destinations Florence, San Gimignano, Volterra, Certaldo, Siena, Monteriggioni, Pisa, Lucca, Montecarlo Age Range up to 99 year olds Operator DERTOUR From
15% Off- NZ$1,443
Classic Tuscany - Cycling from Florence to Pisa - Classic Self Guided
5 Reviews by TourRadar travelers“We completed a self-guided route and it felt like a completely independent trip, but we never had to consider a single logistical hurdle.”
Jeff, traveled in May
A 326km route winds through Tuscany's finest landscapes. Detailed GPS routes lead from Florence through Chianti wine country to Pisa. Carefully selected properties like Hotel Il Chiostro del Carmine serve as bases for independent adventures.
No departure dates availableDuration 8 days Destinations Florence, Radda in Chianti, Siena, San Gimignano, Vinci, Lucca, Pisa Age Range 3 to 99 year olds Operator BikesPlus Travel Postcard Southern Tuscany - Cycling Cortona, Montalcino, Siena - Classic Self Guided
2 Reviews by TourRadar travelers“The bikes were titanium bikes, with quality components. The routes they planned was perfect, and the hotels were fabulous.”
Michael, 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.
No departure dates availableDuration 9 days Destinations Cortona, Lake Trasimeno Regional Park, Montepulciano, Pienza, Val d'Orcia, Montalcino, San Quirico D'orcia, Bagno Vignoni, Siena Age Range 3 to 99 year olds Operator BikesPlus Travel 
No departure dates availableDuration 4 days Destinations Florence Age Range up to 99 year olds Operator Remaz Tours GmbH
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
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.
- Tuscany: hilltop towns of Val d’Orcia & Siena (Self-guided Walking Tour)
We enjoyed our trip & most all of the hotels & breakfasts. The walk was a lot harder than anticipated; what was described as an easy walk turned out to be a lot of steep uphill terrain. We thought the price was great & we always received our luggage on time. Having to confirm our transfers was a problem as no one spoke English & they didn’t understand my Italian. All in all we had a great time & found the navigation APP helpful. We saw some beautiful landscapes & scenery but were so tired by the time we got to town we didn’t really get to enjoy the towns as we would have liked.
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.