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Italy – Florence to Siena Tuscany Treasures Bike Tour

5 Nights / 6 Days
Difficulty: Moderate+, 3-4 out of 5
Self Guided Bike Tour
Mar-Nov (July & Aug not recommended)
~40 km/day
+430 to +709 m/day
Hybrid, Road, Gravel & E-bike Rentals

Florence to Siena – Deluxe Tuscany Treasures Self-Guided Bike Tour: Immerse yourself in the essence of Tuscany on this 6-day cycling adventure. Starting from the vibrant city of Florence, our self-guided Italy bike tour takes you through breathtaking landscapes that have inspired countless artists and travelers. Pedal through rolling hills, lush vineyards, and charming medieval villages, blending iconic landmarks with hidden gems. Journey from UNESCO-listed Florence to the enchanting destinations of San Gimignano and Siena, discovering lesser-known Tuscan treasures like Certaldo and Casole d’Elsa. Experience the perfect balance of cycling, relaxation, and cultural exploration as you breathe in the crisp air and cycle past picturesque landscapes. Immerse yourself in local life, savor authentic Tuscan cuisine, and indulge in world-class wine. The tour culminates in the historic UNESCO-listed centre of Siena, where cycling, relaxation, and cultural exploration reach their peak. Whether you’re an avid cyclist or simply seeking an unforgettable adventure, this self-guided Italy bike tour promises a lifetime of captivating memories. Are you ready to hit the trails and create memories that will last a lifetime?

Pro-tip: Book early! Lodging in Tuscany is in high demand, and the boutique hotels along our tour route book up many months in advance. June and September are especially popular. We recommend booking 4-6+ months before your desired travel date.

Get your adventure!

1. Call or email with questions: +1-970-230-5896 or email us.

2. Book the trip, pay a deposit, and get excited about your adventure!

Arrival & Departure Locations

The tour starts in Florence and concludes in Siena. You can depart from Siena by train to Florence, Rome, or elsewhere on your own.

Price Includes

Exclusively Yours: Customize your travel dates to fit your schedule—no need to coordinate with other travelers!
Luxurious Stays: Enjoy 5 nights in boutique, hand-picked 3 & 4-star hotels (with options to upgrade to superior category accommodations or rooms.)
Breakfast Daily: Savor six traditional breakfasts to start your days right.
Personal Welcome: Attend a private orientation meeting to cover route notes, navigation tools, bike setup, and meet your friendly local contact.
Hassle-Free Travel: Enjoy baggage transportation between hotels every day your lodging changes.
Seamless Navigation: Get Pure Adventures GPS route notes and maps for a smooth journey.
Insider Tips: Discover suggested sites to visit, local information, and dining spots curated just for you.
On-Call Support: Access local emergency support throughout your tour during daylight-riding hours.
Comprehensive Prep: Receive a package of pre-travel documents electronically to help you prepare for your adventure.
Advanced Navigation: Benefit from GPX tour files provided in Ride With GPS.
Digital Companion: Carry a digital tour packet with maps, visitation suggestions, and site information.

Not Included:

Our Tuscany self-guided tour has a choice of bike rentals: Hybrid, Gravel, Road, or E-Bike
Extra nights and/or meals outside of the itinerary
Trip insurance

Lodging

Deluxe Hotels – Standard Offer: classic room category

Florence: Hotel Villa Liana *** (1 night)
Certaldo: Hotel Bellavista Toscana (2 nights)
Casole d’Elsa: Casole d’Elsa B&B *** (1 night)
Siena: Hotel Santa Caterina *** (1 night)

Deluxe Hotels – Upgraded Offer: deluxe room category

Florence: Hotel Baglioni **** (2 nights)
Certaldo: Hotel Bellavista Toscana (2 nights)
near Casole d’Elsa: Hotel Borgo San Luigi **** (1 night)
Siena: Certosa di Maggiano **** (1 night)

About the Lodging: Indulge in our deluxe accommodations, featuring private rooms and baths, complemented by a range of standard amenities. While lodging availability is based on your preferred travel dates, we assure you a comfortable stay. Opt for an upgraded room category to enjoy enhanced accommodations, often with breathtaking valley views, available in select locations. Our standard rooms promise a cozy and comfortable experience. Your relaxation and comfort are our top priority!

Optional Add-Ons

Extra nights
Siena ride extension
Travel insurance

Guides & Local Support

Local Experts: Meet Maurizio, our dedicated representative in Italy! Born and raised in Val d’Elsa, where his family has deep roots, Maurizio brings unmatched passion and local knowledge to his work every day. A sports enthusiast, Maurizio balances swimming, cycling, and tennis into his routine, embodying the vibrant, active spirit of Tuscany. He looks forward to welcoming you to the place he proudly calls home!

Tour Highlights - Tuscany Self Guided Bike Tour

Flexible Travel Dates: Choose your own departure dates and travel at your convenience.
Scenic Cycling: Ride through serene olive groves, lush vineyards, and the beautiful Tuscan countryside.
Peaceful Routes: Enjoy quiet roads with some challenging connector routes offering stunning vistas.
Explore Florence: Discover the UNESCO-listed birthplace of the Renaissance, with iconic sites like the Duomo, Ponte Vecchio, and Piazza della Signoria.
San Gimignano Adventure: Explore this medieval town and savor a regional wine tasting with a delightful cutting board of local cheeses and salami.
Medieval Hidden Gems: Uncover the lesser-known hilltop towns of Certaldo and Casole d’Elsa, brimming with charm, history, and regional delights.
Cheese Tasting: Enjoy a delicious regional cheese-tasting experience along your route during the Certaldo loop ride.
Culinary Delights: Taste exquisite wines and olive oils in every town, with abundant culinary offerings.
Historical Exploration: Wander through ancient towns and numerous historical sites along the way.
Celebrate in Siena: Conclude your journey in Siena, a UNESCO-listed town, and celebrate in the enchanting Piazza del Campo, the vibrant heart of this historic city.
Easy Navigation: Benefit from GPS-driven navigation with the Ride With GPS app, making route-finding a breeze.

Need to Know:

Tuscany self-guided tour is not recommended for July 16-August 31 due to heat. High season rates will apply, if so.
This tour is a mix of paved and finely crushed gravel surfaces: gravel, hybrid & e-bikes are best suited for the route.
Best times to visit: May, June, September-November.
Travel Insurance is required on all Pure Adventures tours.

Photos

Itinerary - Tuscany Self Guided Bike Tour

Day 1Arrival to Florence

Welcome to Florence, the UNESCO-recognized cradle of the Renaissance, where history, art, and culture converge in breathtaking harmony. Marvel at the iconic Duomo and its sweeping city views, stroll across the charming Ponte Vecchio, and immerse yourself in the vibrant atmosphere of Piazza della Signoria, adorned with magnificent sculptures and the historic Palazzo Vecchio. Explore the world-famous Uffizi Gallery, home to masterpieces by Botticelli, Leonardo da Vinci, and Michelangelo. As twilight descends, savor a delightful Tuscan meal at a cozy local trattoria. Florence is poised to captivate your heart with its timeless charm.

Get ready – your unforgettable cycling adventure begins tomorrow!

Meals: on own
Highlights: Florence exploration
Overnight: Florence

Day 2Florence to Certaldo & Short Loop Ride: 33 km / 20 mi

Your journey begins with a picturesque train ride from Florence to Certaldo (50 minutes), offering the flexibility of hourly departures and leaving you extra time to enjoy Florence. Tickets are easy to purchase at kiosks with English-language options, making the process effortless. Certaldo, a hidden gem of Tuscany, is a quaint hilltop village with a historic center, Certaldo Alto, perched above and reachable by funicular. Take time to explore this enchanting town, steeped in history and authentic Tuscan charm. At 5 PM, meet our local expert for a tour briefing and to receive your bikes, preparing you for the days ahead. In the early evening, enjoy a short test ride featuring a gentle 19 km uphill climb, followed by an exhilarating downhill stretch, perfectly setting the tone for your Tuscan adventure!

Meals: breakfast
Distance: 33 km / 20 mi, +635 m
Highlights: continued Florence exploration, arrival in Certaldo
Overnight: Certaldo

Day 3San Gimignano Loop Ride & Wine Tasting: 41 km / 25 mi

Today, embark on a scenic loop ride from Certaldo to the captivating town of San Gimignano, renowned for its medieval skyline and UNESCO World Heritage status. Ride through Tuscany’s picturesque rolling hills, lush vineyards, and olive groves. Upon arrival, explore San Gimignano’s charming streets, savor a glass of Vernaccia wine, and indulge in award-winning gelato. After a relaxing return to Certaldo, cap off the day with a delightful cutting board of local cheeses and salami, paired with a wine tasting (included.) Today’s journey promises a day filled with beauty, culture, and unforgettable experiences.

Meals: breakfast & wine tasting w/light snack
Distance: 40 km / 25 mi, +708 m
Highlights: cycling lush rolling hills, olive groves, UNESCO San Gimignano, gastronomic delights
Overnight: Certaldo

Day 4Certaldo to Casole d'Elsa & Cheese Tasting: 44 km / 27 mi

Today’s bike ride will take you from Certaldo to the charming hilltop village of Casole d’Elsa. Pedal through Tuscany’s idyllic countryside along quiet, winding roads framed by vineyards, olive groves, and cypress trees, capturing the quintessential beauty of the region. Pass through charming hamlets and rolling hills, with breathtaking views at every turn. As you approach Casole d’Elsa, the landscape becomes even more enchanting. This picturesque medieval village, known for its artistic heritage surrounding crystal making and panoramic vistas, invites you to pause, explore its medieval streets, and immerse yourself in the tranquil surroundings. Along the way, stop at one of our favorite places for a sampling of delicious local cheese – a highly authentic experience!

Meals: breakfast & cheese tasting
Distance: 44 km / 27 mi, +699 m
Highlights: vineyards, olive groves, cypress trees, medieval streets of Casole d’Elsa
Overnight: Casole d’Elsa

Day 5Casole d'Elsa to Siena: 39 km / 24 mi

Embark on your final bike ride from Casole d’Elsa to Siena, a breathtaking journey through Tuscany’s heart. Pedal along gently rolling hills and quiet country roads, with sweeping views of vineyards, golden fields, and rustic farmhouses dotting the landscape. As you near Siena, the scenery becomes even more dramatic. Iconic cypress-lined roads guide you towards this remarkable medieval city. The final stretch builds anticipation as Siena’s historic skyline comes into view, crowned by the stunning Torre del Mangia and the magnificent Duomo. Your ride concludes in Siena’s UNESCO-listed old town, where you can celebrate the end of your journey in the enchanting Piazza del Campo, the vibrant heart of this historic city.

Meals: breakfast
Distance: 39 km / 24 mi, +430 m
Highlights: cycling scenic landscapes, Siena landmarks & exploration
Overnight: Siena

Day 6Departure Day or Extend

Departure Day – unfortunately, your amazing Tuscan cycling adventure has to end but your time in Italy can continue! If you have time, we can help arrange a stop in Florence, Rome or other onward travels. Trains from Siena to Florence are possible. Take your time and enjoy your last morning in Siena before checking out.

Pro Tip: Extension options include a gorgeous 33 km or 69 km loop ride from Siena. The longer route goes into Chianti! Please inquire!

Meals: breakfast

Map

Dates & Rates: Tuscany Self Guided Tour

Dates: Plan your trip at a time that best fits your schedule! Pure Adventures tours have flexible start dates.

2025 Tour Rates: (based on double occupancy)

Standard Lodging: see Lodging section for details

2 persons: 1,795 euros/person
4 persons: 1,760 euros/person
6 persons: 1,715 euros/person
Single Supplement: 479 euros/person
(applies when 2 or more traveling but in separate single-use rooms)

Upgraded Lodging: see Lodging section for details

2 persons: 2,160 euros/person
4 persons: 2,110 euros/person
6 persons: 2,085 euros/person
Single Supplement: 888 euros/person
(applies when 2 or more traveling but in separate single-use rooms)

Hybrid Bike Rental: 230 euros
Road Bike Rental: 260 euros
E-bike Rental: 260 euros
Bike Rental Details Page

Need to Know:

Not recommended July 16-August 31. High season rates will apply, if so.
BEST times to visit: May, June, September-November.

New! Travel Insurance is now required to participate in this tour. You can book through our preferred vendors or your own. Proof of coverage will be required.

How do our tours compare to similar trips? You Get More! We are much less than guided trips with similar experiences if you compare prices. In our private, independent format, you get much more than what most traditional self-guided tours offer, plus it’s a better experience! Our team has gone to great lengths to build and create exceptional tours worldwide, vacations that will give you lifelong memories. From the accommodations to the bikes to the routes themselves, we hold each component of our tours to a very high standard. We are dedicated to empowering people through travel! Why travel with us? Read more!

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