6 days
2/4
from April to November
from 1790€

Tuscany – a paradise for cycling enthusiasts!

Rolling hills, legendary Strade Bianche, cypress-lined roads, Chianti wine, the Val d’Orcia, wide open fields, San Gimignano, Siena, Florence — and an incredible 55% of the route on Tuscany’s smooth, scenic gravel roads.

We’ve brought all of this together into an unforgettable four-day cycling adventure designed to inspire and delight.

Our journey begins in San Gimignano, a charming medieval town famous for its striking stone towers. We finish the first day in Siena, arriving at the iconic Piazza del Campo, the very square where the legendary Strade Bianche race comes to an end.

The next day takes us into the breathtaking Val d’Orcia, a postcard-perfect landscape of rolling hills and timeless beauty. We then turn north for a day among the vineyards of the famous Chianti region.

To finish, we roll into Florence, where we explore the highlights of this Renaissance jewel. After such a rich experience, we head home filled with fresh inspiration and unforgettable memories.

On average, we’ll ride 73 km per day with 1,270 meters of elevation gain — the perfect balance of challenge, scenery, and pure riding pleasure.

Day 1

Welcome to Italy!

Your cycling adventure begins in Italy — and we’ll make sure everything is smooth, simple, and stress-free from the moment you arrive. We’ll pick you up at Bologna Airport at 11:00 AM and Florence Airport at 13:00 PM, then head straight into the Sienna, where our hotel will be waiting for us.

Once we check in, you’ll have time to get everything ready for the days ahead — bike setup, gear checks, and final adjustments — so you feel fully dialed in and prepared.

In the afternoon, you’ll have free time to explore Sienna and the surrounding area at a relaxed pace, enjoy the town atmosphere, and settle in before the riding begins.

In the evening, we’ll come together for a group dinner, the perfect chance to get to know each other, enjoy great local food, and kick off the trip the right way.

Day 2 - Cycling from San Gimignano to Sienna

Tuscan Towers, White Gravel & Timeless Evenings!

After breakfast, we’ll transfer to San Gimignano, one of Italy’s most picturesque hill towns, instantly recognizable by its 14 medieval towers—silent witnesses of the wealth and power of historic Tuscan families. After a must-have morning espresso on the main square, surrounded by stone streets and the aroma of fresh pastries, our real adventure begins.

Today brings our first gravel stage—a true Tuscan classic. The route flows through rolling vineyards, cypress-lined roads, and gentle hills, guiding us toward Colle di Val d’Elsa, a town celebrated for its centuries-old crystal craftsmanship and known worldwide as the Crystal City.

We’ll end the day with dinner at one of Siena’s authentic local restaurants, followed by a relaxed evening walk through the historic center, when the city slows down and reveals its most enchanting atmosphere.

⭐ Today’s Must-See Highlights

  • San Gimignano – Iconic medieval towers and timeless Tuscan charm
  • Colle di Val d’Elsa – Historic crystal town with authentic local character
56
Kilometres
770
Elevation metres
4h 20min
Cycling time
Komoot
route tour
Day 3 - Cycling from Sienna to Bagno Vignoni

Tuscany at Its Purest!

After breakfast, we leave our luggage at the hotel — we’ll be back again this evening — and get ready for another unforgettable day on the bike.

Tuscan gravel roads are a feast for both eyes and soul. Smooth white roads winding through vineyards, olive groves, and gently rolling hills feel tailor-made for riders who appreciate an authentic cycling experience, far from traffic and city noise.

Our route leads us toward Murlo, a small hilltop village known for its archaeological sites and remarkably well-preserved Etruscan heritage. Time seems to slow down here. From Murlo, we continue across rolling hills toward the outskirts of San Quirico d’Orcia, a classic Tuscan village where every turn reveals postcard views of cypress trees and endless open fields.

We finish the stage in Bagno Vignoni, a truly unique place famous for its large thermal pool right in the main square — a sight you won’t find anywhere else in Italy. After a short break, we load the bikes into the support vehicles and return to the hotel, where a relaxed evening and a well-deserved dinner await.

⭐ Today’s Must-See Highlights

  • San Quirico d’Orcia – A quintessential Tuscan town surrounded by cypress-lined roads and open countryside
  • Bagno Vignoni – A one-of-a-kind thermal village with a steaming pool at the heart of its main square
84,8
Kilometres
1360
Elevation metres
7h 10min
Cycling time
Komoot
route tour
Day 4 - Cycling from Bagno Vignoni to San Rocco a Pilli

Riding the Soul of Strade Bianche!

We’ll start the stage right where we finished yesterday—in Bagno Vignoni, a small thermal village full of character and timeless charm. The afternoon will once again be dedicated to exploring the streets, history, and atmosphere of Siena.

Today is the longest and most demanding stage of our Tuscan gravel journey—but also one of the most iconic. An impressive 72% of the route runs on gravel, weaving through vineyards, olive groves, and dusty white roads that define classic Tuscan riding.

The opening kilometers are gentle, with rolling terrain guiding us through the most legendary sections of the Strade Bianche race. In recent years, these roads have been dominated by our Tadej Pogačar—and today, we get to experience them ourselves. The soft crunch of gravel beneath the tires, dust hanging in the air, and endless views lined with cypress trees deliver that unmistakable gravel magic.

⭐ Today’s Must-See Highlights

  • Strade Bianche – World-famous white roads and pure gravel heritage
95,9
Kilometres
1660
Elevation metres
8h 15min
Cycling time
Komoot
route tour
Day 5 - Cycling from Sienna to Radda in Chianti

A Final Ride Through Chianti!

After breakfast, we pack our gear and check out of the hotel—today marks the final stage of our Tuscan gravel journey. The route leads us through rolling countryside, framed by vineyards and olive groves, where every village carries its own story and rhythm.

We first ride through Vagliagli, a classic Tuscan village surrounded by vineyards that form part of the legendary Chianti Classico wine route. From there, we continue toward Radda in Chianti, one of Tuscany’s most picturesque stops—a medieval hill town perched on a ridge between two valleys, offering views that make you fall in love with Tuscany all over again.

Our ride concludes in Radda with a short walk through its charming cobbled streets, a perfect way to soak in the atmosphere and mark the end of the journey.

Afterwards, we transfer to Florence, where our final hotel awaits. The afternoon is reserved for exploring the city, and in the evening we come together for one last farewell dinner—closing the trip the Tuscan way.

⭐ Today’s Must-See Highlights

  • Radda in Chianti – Medieval hill town with classic Chianti views
  • Florence – Renaissance masterpieces and timeless Italian elegance
75,3
Kilometres
970
Elevation metres
5h 35min
Cycling time
Komoot
route tour
Day 6

The end!

After a final breakfast, we say goodbye to the Italy. We travel together toward Florence airport, arriving comfortably around 11:00 AM and then to Bologna airport, arriving around 13:00 PM. The drive is a chance to share last impressions, stories from the rides, and a quiet smile at how quickly the week has passed.

At the airport, we say our goodbyes as you continue your journey — richer for an experience that revealed the authentic, green, and cyclist-friendly country. And who knows — perhaps we’ll meet again next year on a new cycling adventure.

What is included in the price?

Our trip includes:

  • Organized transportation on the first day of the trip for you and your bike using the tour operator’s vehicles. Pick-up available at Bologna Airport at 11:00 AM and at Florence Airport at 13:00 PM.
  • Organized transportation on the last day of the trip for you and your bike using the tour operator’s vehicles. Drop-off available at Florence Airport at 11:00 AM and at Bologna Airport at 15:00 PM.
  • 5 nights in 3*** or 4**** hotels with breakfast included.
  • Water and isotonic drinks during the rides.
  • Sweet and salty snacks during the rides.
  • Refreshment stops along the route.
  • Support vehicle accompanying the group during the rides.
  • Emergency bike service if needed throughout the journey.
  • Luggage transfer between accommodations.
  • Travel organization and preparation costs included.
  • GPX routes to download to your navigation devices.
  • A PDF guidebook with highlights and points of interest along the journey.

What is not included in the trip price and possible supplements:

The basic price of the trip does not include:

  • Tips are not included.
  • Cost of drinks on all days of the trip.
  • There are many opportunities for individual sightseeing during the trip. Entrance fees are not included in the price.

Extra charges may apply:

  • Single room (You can select it during registration)
  • road/gravel or electric bike rental (You can select it during registration)
  • cancellation risk cost (Arrange it with your local providers)
    – basic cover
    – extended cover
  • cost of accident insurance (Arrange it with your local providers)

Map of the entire journey

Where do we stay?

  1. TuscaSì ApartHotel 3***, breakfast included, twin rooms with separate beds.
  2. TuscaSì ApartHotel 3***, breakfast included, twin rooms with separate beds.
  3. TuscaSì ApartHotel 3***, breakfast included, twin rooms with separate beds.
  4. TuscaSì ApartHotel 3***, breakfast included, twin rooms with separate beds.
  5. Hotel Villa Bonelli 3***, breakfast included, twin rooms with separate beds.

In the event of unforeseen changes, we reserve the right to provide alternative accommodation of equal or higher quality than originally planned.

How do I apply?

Signing up is quick and easy – just follow these 3 simple steps!

Fill in the registration form

Fill in your details on the online registration form, submit it and you’re on your way to an unforgettable cycling adventure!

Payment

Confirm your registration by simply paying 25% of the trip. Hurry, places are limited!

What's next?

After payment, we will send you a confirmation and an invoice. 60 days before departure, you will receive detailed instructions to make sure you are ready to go.

Log in

Don’t delay – apply now and be part of an unforgettable journey that will inspire you with breathtaking views, new friendships and moments you’ll remember for a long time.

No. of applicants:

Log in

FAQ

Together for the best cycling experience!

1. Booking & Payment

1.1 How do I register for a cycling trip?

At the bottom of every trip page, you’ll find a registration form. Take a moment to read it carefully and fill in all required fields, including any optional add-ons. Once you submit the form, you’ll receive an email with a PDF summary of your registration along with the payment details.

1.2 When and how do I pay the deposit or full amount?

During registration, you can choose to pay a 25% deposit or the full trip price. We recommend completing your payment as soon as possible, as this final step officially secures your spot. After registering, you’ll receive an email with all instructions and payment information.
The full balance must be paid no later than 30 days before departure.

1.3 What happens if I need to cancel? Are there cancellation terms?

Refunds are issued according to our Terms & Conditions. You can review the full cancellation policy here.

1.4 Can I change my travel date or package after registering?

Yes — changes are possible by agreement, up to 30 days before departure.
For details, contact us at info@gobiketravel.com

2. Bikes & Equipment

2.1 Do I need to bring my own bike, or can I rent one?

Whichever suits you best. You’ll indicate your choice in the registration form.
If you bring your own bike, we’ll reserve space for it in the airport shuttle.
If you choose to rent, simply submit the required details, and your bike will be waiting at your hotel before the first ride.

2.2 What types of bikes are available for rent?

You can choose from:

  • Road Bike
  • Mountain Bike
  • Gravel Bike
  • Electric Hardtail MTB
  • Electric Full-Suspension MTB
  • Electric Road Bike

2.3 Am I responsible for damage to a rental bike?

Yes. In case of major damage, repair costs must be covered by the renter.

2.4 What equipment is included with the bike?

You’ll receive water bottles and your chosen pedal type. Available options include Look pedals, Shimano SPD, Shimano SPD-SL, or MTB flat pedals. You’ll also get a basic repair kit with essential tools and a spare tube for emergencies.

2.5 What if my bike breaks during the trip?

On Supported or Supported & Guided trips, our support vehicle provides basic on-the-spot repairs. For damage requiring a bike shop, we will help you reach the nearest service center (repair costs are covered by the rider).
On Self-Guided trips, you are responsible for carrying basic tools and handling minor repairs on your own.

3. The Cycling Trip Experience

3.1 What’s the difference between Self-Guided, Supported, and Supported & Guided trips?

Self-Guided: We take care of logistics (hotels, airport transfers, luggage transport), while you ride independently.

Supported: Everything from Self-Guided plus a support vehicle offering drinks, snacks, emergency repairs, and refreshment stops.

Supported & Guided: Full support plus a professional cycling guide riding with you — navigation, insights, assistance, photos, and on-the-road support.

For a more detailed explanation of how the trip types differ, click HERE.

3.2 Are the routes suitable for beginners or experienced cyclists?

Routes are designed for the average recreational cyclist. These are not races — the goal is enjoyment. Each trip includes a difficulty rating listed at the top of the trip page.

3.3 How many kilometers do we ride per day?

It depends on the trip. Daily distances are listed in the itinerary. You can shorten a stage using the support vehicle or extend it with an optional climb or loop.

3.4 Can I ride at my own pace and stop whenever I want?

Absolutely. Our trips encourage riding at your own speed and taking breaks whenever something catches your eye. Guides are happy to wait for you.

3.5 What is the best time of year for cycling?

Trips are scheduled during optimal cycling months. Daily riding usually begins around 10:00 AM, but this can be adjusted with your guide.

3.6 What if it rains?

Self-Guided: You’ll need to wait for the storm to pass.

Supported / Supported & Guided: The support vehicle is always available. In severe weather, we can adjust the route or departure time.

3.7 Can stages be shortened or extended?

Yes — shorten a stage using the support vehicle or extend it with an additional climb.

3.8 Can we travel on dates that are not listed?

Yes, for groups of several cyclists we can arrange custom departure dates.
Contact us at info@gobiketravel.com
.

4. Accommodation & Meals

4.1 What types of hotels do you use?

We typically book 3- and 4-star hotels with breakfast included. Rooms are double with separate beds. In rare cases, if hotels are fully booked, you may receive a shared double bed — this will always be clearly stated in the trip details.

4.2 Are meals or drinks included in the price?

Breakfast is always included; dinner is sometimes included and noted in the itinerary. Drinks are never included.

4.3 Is luggage transferred between hotels?

Yes. All trip types include daily luggage transfers. You carry only what you want for the ride.

5. Logistics & Support

5.1 Is a support vehicle available?

Support vehicles are included on all Supported and Supported & Guided trips.

5.2 What does support during cycling include?

You’ll have a support driver nearby at all times, refreshment stops every 20–25 km, water, isotonic drinks, snacks, and basic emergency bike service (e.g., flat tires).
Support can also help shorten a stage if needed.

5.3 How do I receive the GPX routes?

You’ll receive GPX files by email approximately 14 days before departure. Simply upload them to your navigation device.

5.4 Do you offer airport transfers?

Yes. Every trip includes airport transfers from and to designated airports.
If you arrive at a different airport or at another time, we can arrange a private shuttle for an additional fee.

6. Safety

6.1 What happens in case of an accident or injury?

On Supported and Supported & Guided trips, we provide first aid and transport to a hospital if safe. On Self-Guided trips, you must manage this independently.

6.2 Are the trips suitable for children or families?

Somewhat. They are suitable for families familiar with cycling together.
Children must be able to ride safely in traffic, and parents should consider distance and elevation. We can also create a custom, easier itinerary for families upon request — contact us at info@gobiketravel.com

6.3 Do I need travel or accident insurance?

We strongly recommend arranging accident or travel insurance with your local provider. It can significantly reduce medical and transport costs in case of an emergency.

What do our cycling journeys look like?

We take care of everything so you can focus on enjoying yourself – from the moment you check in until you return home. With us, cycling trips are more than just sport – they’re stories you’ll tell for a long time to come.

Read more

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Do you have your own team of cycling enthusiasts?

We organise unforgettable cycling experiences for groups – we can tailor the dates and the trip to your wishes! Send us an enquiry and together we’ll create the perfect adventure for your team!”

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