7 days
2/4
from May to October
from 2588€

Elba Island & Tuscany – Cycling Between Vineyards, Coastlines, and Rolling Italian Hills!

Our adventure kicks off on Elba Island, where smooth roads, winding switchbacks, and wide-open views instantly push motivation into high gear. Over two days, we’ll explore the very best of the island — from scenic coastal climbs to fast descents cutting through pine forests.

From Elba, we take the ferry from Piombino back to the mainland and ride straight into the heart of Tuscany.

Ahead of us lie Buonconvento, Montepulciano, Siena, and San Gimignano — a region cyclists love for its flawless asphalt, steep vineyard-covered hills, and roads where the climbing never truly lets up.

This tour blends sea views, hill climbs, iconic Italian roads, and outstanding local cuisine into one unforgettable cycling experience. If you’re looking for a trip with carefully designed routes, action-packed days, and relaxed Italian evenings, this is it. Come ride with us.

On average, we’ll ride 97 km per day with 1,694 meters of elevation gain.

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 Pisa Airport at 13:00 PM, then head straight into the city, 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 Pisa 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 Portoferraio to Cavo and back

From Ferry to First Pedal Strokes!

The day begins in Piombino, where we board the ferry for a smooth one-hour crossing — just enough time to take in the sea air before the cycling action begins. We clip in for the first time in Portoferraio, once Napoleon’s place of exile and today the starting point of one of Elba’s most scenic island stages.

The route follows the coastline toward Porto Azzurro, passing turquoise bays and short, punchy ramps that keep the ride playful and engaging. From there, we roll over gently undulating terrain to Rio Marina, a former mining village where the island’s iron-rich history is reflected in the striking reddish landscape.

What follows is a true island classic: the road constantly rises and falls, pine forests provide welcome shade, and wide-open sea views lift the pace and the mood. On Elba’s northeastern edge, we reach the peaceful village of Cavo. From here, the route turns back along the coast, finishing just outside Portoferraio, where our hotel and a well-earned recovery await.

⭐ Today’s Must-See Highlights

  • Portoferraio – Historic harbor town and Napoleon’s former refuge, full of character and sea views
  • Cavo – Quiet coastal village on the island’s northeastern tip, perfect for a calm seaside finish
56,3
Kilometres
1010
Elevation metres
3h
Cycling time
Komoot
route tour
Day 3 - Cycling from Portoferraio to West Coast Road

Elba at Its Finest!

Day three is the ultimate Elba cycling highlight — long, varied, and packed with views you won’t forget. We roll out from Bagnaia, head toward Portoferraio, and continue to Procchio, where one of the island’s most iconic stretches of road begins.

From here, the climb takes us through Sant’Ilario and Poggio, winding past vineyards and chestnut forests all the way to Marciana. Nestled beneath the dramatic slopes of Monte Capanne, this is Elba as cyclists know it best — sustained climbs paired with views that reward every meter gained.

The ride continues along a spectacular ridge road toward Colle d’Orano, before dropping down to the island’s western side. Here, the landscape opens up into its wildest, most untouched form. Following the coastline, we reach Marina di Campo, home to the island’s largest bay, before rolling back across gently undulating terrain past Lacona and returning toward Portoferraio.

⭐ Today’s Must-See Highlights

  • West Coast Road – A dramatic coastal stretch with raw landscapes, open views, and a true sense of Elba’s wild side
  • Marina di Campo – The island’s largest bay, known for its long beach, relaxed seaside vibe, and stunning setting
94,9
Kilometres
2150
Elevation metres
5h 25min
Cycling time
Komoot
route tour
Day 4 - Cycling from Piombino to Buonconvento

Rolling into the Heart of Tuscany!

We start the day with a ferry back to the mainland, then clip in once again in Piombino and head straight toward the Tuscan interior. The opening kilometers toward Riotorto follow the sea, before the road turns inland and the scenery shifts into classic Tuscany — forests, rolling hills, and quiet rural stretches leading us to Massa Marittima.

Widely considered one of Maremma’s most beautiful medieval towns, Massa Marittima impresses with its Romanesque cathedral and deep-rooted mining heritage — a place that truly rewards experiencing it in person.

From there, we continue along peaceful country roads via Palazzetto toward Monticiano. Pine forests, scattered Tuscan villas, and perfectly rolling terrain make this a dream stretch for cyclists. The road gently rises and falls all the way to Vescovado, a classic settlement along the historic Via Francigena.

We finish the stage in Buonconvento, one of the region’s best-preserved medieval towns, enclosed by striking 14th-century red brick walls. This is where we wrap up our first day on the mainland — fully immersed in the Tuscan rhythm, surrounded by history, vineyards, and capped off with an excellent local dinner.

⭐ Today’s Must-See Highlights

  • Massa Marittima – A stunning medieval town in Maremma, known for its Romanesque cathedral and historic mining legacy
  • Buonconvento – A beautifully preserved walled town, offering an authentic Tuscan atmosphere and timeless charm
124
Kilometres
1780
Elevation metres
6h 5min
Cycling time
Komoot
route tour
Day 5 - Cycling from Buonconvento to San Rocco

Postcard Tuscany!

Day four takes us through one of Tuscany’s most iconic landscapes — rolling hills lined with cypress trees, medieval towns, and views that feel like a living postcard at every turn. We leave Buonconvento and climb toward Torrenieri, continuing on to San Quirico d’Orcia, set along the ancient Roman Via Cassia. This stretch of Val d’Orcia is UNESCO-protected, and once you ride through it, it’s easy to see why — this is Renaissance landscape design at its purest.

Just a few kilometers downhill lies Bagno Vignoni, a unique spa village famous for its “main square,” which is actually a large thermal pool. From here, the route continues over short but scenic climbs toward Monticchiello, and onward to Montepulciano — a town of palaces, narrow streets, and the legendary Vino Nobile. This is Tuscany at its most atmospheric, where every building and every view tells centuries of history.

In the afternoon, the route winds through Trequanda, across rolling countryside toward Asciano and Arbia, where the hills around Siena begin to appear on the horizon. We skirt the city center on beautiful country roads before finishing in San Rocco a Pilli, a quiet village just south of Siena.

This is one of the most scenic stages of the entire trip — a day spent riding through landscapes most people know only from photos, while we experience them the best way possible: from the saddle.

⭐ Today’s Must-See Highlights

  • San Quirico d’Orcia – A historic town on the Via Cassia, set in the heart of UNESCO-listed Val d’Orcia
  • Montepulciano – A hilltop wine town famous for Vino Nobile, grand palaces, and timeless streets
  • Siena – One of Italy’s great medieval cities, instantly recognizable by its skyline and rich history
122
Kilometres
1920
Elevation metres
6h 5min
Cycling time
Komoot
route tour
Day 6 - Cycling from San Rocco to San Gimignano

One Last Ride!

The final cycling day begins with quiet kilometers through Tuscan forests, heading toward Ancaiano and on to Pievescola, where the road starts to rise gently through vineyard-lined slopes. Before long, we reach Casole d’Elsa, a fortified hill town whose walls once controlled key routes between Siena and Volterra back in the 13th century.

From here, we tackle one of the most beautiful climbs of the entire trip: a series of sweeping switchbacks leading up to Volterra. With its deep Etruscan roots and towers watching over the surrounding hills for nearly three thousand years, Volterra feels timeless. Remains of Etruscan city walls and a Roman theater make it clear just how important ancient Velathri once was.

After a short break, the route continues over rolling Tuscan countryside toward our final destination: San Gimignano, often called the “Medieval Manhattan” thanks to its unmistakable skyline of towers. We take time for a relaxed ride-through visit, with Via San Matteo almost always welcoming us with the unmistakable aroma of Vernaccia di San Gimignano wine.

A perfect finale — history, vineyards, iconic climbs, and one last unforgettable Tuscan backdrop experienced the best way possible: on two wheels.

⭐ Today’s Must-See Highlights

  • Volterra – An ancient Etruscan city with Roman ruins and sweeping views over the Tuscan hills
  • San Gimignano – The famous “Medieval Manhattan,” known for its tower-filled skyline and Vernaccia wine
87,4
Kilometres
1620
Elevation metres
4h 35min
Cycling time
Komoot
route tour
Day 7

The end!

After a final breakfast, we say goodbye to the Italy. We travel together toward Florence airport, arriving comfortably around 10:00 AM. 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 Pisa 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 10:00 AM.
  • 6 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. Hotel Repubblica Marinara 4****, breakfast included, twin rooms with separate beds.
  2. Hotel Airone isola d’Elba 4****, breakfast included, twin rooms with separate beds.
  3. Hotel Airone isola d’Elba 4****, breakfast included, twin rooms with separate beds.
  4. Agriturismo Percenna, breakfast included, twin rooms with separate beds.
  5. Tuscasì Aparthotel 3***, breakfast included, twin rooms with separate beds.
  6. Hotel Le Colline 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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