Self-Guided Tours & Trips in Tuscany
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10 best self-guided Tuscany tours
Compiled by
MelissaTuscany travel expert at TourRadar
- Luxury Italy by High-Speed Train
- Italy by High-Speed Train - Mestre
- 5 Day Florence With Car Rental
- Tuscany Thrills: A 3-Day Escape of Wine, Relax, and Fun
- Tuscany Escape, Self-Drive
- Flavor of Tuscany & Cinque Terre 4*
- Tuscan Delights Self-Drive Tour 7days/6nights
- Flavor of Tuscany & Cinque Terre 3*
- 4 Days in Florence.
- Car tour from culture to pleasure in Tuscany
Duration 9 days Destinations Rome, Florence, Castellina in Chianti, Siena, San Gimignano, Venice Age Range Ages 10+ Operator Flag Travel Holidays From
- NZ$8,076
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 Ages 10+ Operator Flag Travel Holidays From
- NZ$2,625
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 $2,346
5% Off- NZ$2,229You save $117
Tuscany Thrills: A 3-Day Escape of Wine, Relax, and Fun
1 Review by TourRadar travelers“The accommodations were full of charm, right in the heart of a historic hilltop town with views that didn't feel real.”
Jane, traveled in June
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 San Gimignano, Ulignano, Tuscany Age Range Ages 18+ Operator Italy on a Budget Tours From
5% Off- NZ$745
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 $2,042
10% Off- NZ$1,838You save $204
Rome's ancient sites await with Hop-On-Hop-Off passes. Visit Florence's Renaissance treasures and Chianti wineries as you wish. The 48-hour Cinque Terre Train Card opens up Monterosso, Vernazza, and Manarola.
Duration 8 days Destinations Rome, Florence, Monterosso al Mare Age Range All Ages Welcome Operator Destination Italia From
10% Off- NZ$2,444
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 All Ages Welcome Operator RANIERI TOUR OPERATOR From
10% Off- NZ$1,572
Your Roman holiday includes a 24-hour Hop-On-Hop-Off pass and Cinque Terre Train Card. Visit Vatican Museums, enjoy Chianti wine tastings, or join cooking classes in Trastevere. 3-star hotels and train connections provided.
Duration 8 days Destinations Rome, Florence, Monterosso al Mare Age Range All Ages Welcome Operator Destination Italia From
10% Off- NZ$1,976
Duration 4 days Destinations Florence Age Range Ages 18+ Operator Remaz Tours GmbH From
10% Off- NZ$2,646
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 All Ages Welcome Operator DERTOUR From
10% Off- NZ$1,484
What people love about Self-Guided Tours in Tuscany
- Tuscany Thrills: A 3-Day Escape of Wine, Relax, and Fun
Authentic, Peaceful, and Absolutely Worth It This trip was the perfect Tuscan getaway. The accommodations were full of charm, right in the heart of a historic hilltop town with views that didn’t feel real. It was quiet, cozy, and felt like stepping back in time in the best way. The wine tastings were a standout. Visiting small, family-run wineries and learning directly from passionate winemakers made it so much more than just sipping good wine; it was an experience. The balsamic and truffle oil tastings were a delicious bonus. I also added an optional activity during my stay, which made it even more memorable. It was nice to have that flexibility to personalize the trip. Everything was beautifully paced, with plenty of room to explore or relax. If you’re looking for a short escape that blends culture, wine, and stunning scenery, this is it.
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
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.