Self-Guided Tours & Trips in Tuscany
4.6 stars on(9,010 reviews)- Choose from 25 Tuscany tours
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10 best self-guided Tuscany tours
Compiled by

MelissaTuscany travel expert at TourRadar
- Pearls of Tuscany
- 5 Day Florence With Car Rental
- In the Heart of the Renaissance: Pisa & Florence
- Luxury Italy by High-Speed Train
- Italy by High-Speed Train - Mestre
- 4 Days in Florence.
- Flavor of Tuscany & Cinque Terre 4*
- Flavor of Tuscany & Cinque Terre 3*
- Tuscan Delights Self-Drive Tour 7days/6nights
- Tuscany’s Most Beautiful Stops
Pearls of Tuscany
3 Reviews by TourRadar travelers“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
- NZ$445
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 $2,375
5% Off- NZ$2,256You save $119
Duration 5 days Destinations Pisa, Florence Age Range All Ages Welcome Operator Worldee From
5% Off- NZ$396
Duration 9 days Destinations Rome, Florence, Castellina in Chianti, Siena, San Gimignano, Venice Age Range Ages 10+ Operator Flag Travel Holidays From
5% Off- NZ$9,640
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
5% Off- NZ$3,057
Duration 4 days Destinations Florence Age Range Ages 18+ Operator Remaz Tours GmbH From
5% Off- NZ$2,678
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
5% Off- NZ$2,780
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
5% Off- NZ$2,202
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
5% Off- NZ$1,722
Duration 6 days Destinations Florence, Tuscany, Fiesole, San Miniato, Lucca, Pietrasanta, Viareggio, Pisa, Volterra, San GimignanoSee all destinations Age Range All Ages Welcome Operator Worldee From
5% Off- NZ$575
What people love about Self-Guided Tours in Tuscany
- Pearls of Tuscany
We used Worldee for info for our trip in Tuscany. By their advice we tried ice cream in San Gimignano, awarded as best in the world, and it was really true. Thanks for the tips.
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.