Tuscany Gravel Tour 2026

Ride along Tuscany's white gravel roads through vineyards and olive groves.
Climb gently into cypress-lined hills, medieval villages, and wide, sunlit valleys shaped by centuries of life and light.

April 25 - May 1, 2026

Price: EUR 5495

All-Inclusive
Beautiful 4-star hotels, airport transfers, all main meals, professional guiding, and much more. Full details below.

A 30% deposit is due to secure your reservation. The remaining balance is due 90 days before the start of the tour.

(View the cancellation policy below in the section "Price and Details")

Request to Book

Your Host: Ryan Van Duzer

Ryan has been traveling the world by bicycle for 20 years and documenting his adventures on YouTube. His channel highlights the natural beauty of the world while giving viewers an intimate look into different cultures. His goal is to inspire people to get out and challenge themselves.

Join us in Tuscany for a gravel cycling journey that goes far beyond a typical bike tour.

This is a carefully crafted experience through one of Italy’s most beautiful regions, designed for riders who want more than just great roads. It’s about moving through the landscape at the right pace, riding quiet gravel lanes and rolling hills, and ending each day in exceptional places to stay. The focus is as much on the experience as the riding itself.

The routes are built around classic Tuscan gravel: white roads winding through vineyards, olive groves, cypress-lined ridges, medieval villages, and open countryside. Distances and elevation are thoughtfully balanced to allow time for long lunches, café stops, wine tastings, and unhurried evenings. This is not about racing from point to point, but about riding well and living well.

Accommodation is a key part of the journey. We stay in a handpicked selection of beautiful four-star hotels and atmospheric agriturismos, chosen for their comfort, character, and connection to place. Expect excellent food, warm hospitality, and settings that invite you to truly relax after a day in the saddle.

Tuscany needs little introduction. Its landscapes have inspired artists, writers, and travelers for centuries. For gravel riding, it is close to perfect: endless dirt roads, gentle climbs, big views, and a rhythm that encourages you to slow down and take it all in.

You’ll be traveling with like-minded riders who value quality, connection, and discovery. The result is a gravel journey that feels personal, refined, and deeply rewarding—one that stays with you long after the ride is over.

Why Travel With Us

As a family-run business, we pour our hearts into every detail. We know this is more than just a trip. It is your dream, the effort you have put into preparing, and precious time away from your loved ones.

We are dedicated to creating unforgettable adventures at fair value, ensuring you get the most out of your journey. Your trust means everything to us, and we are honored to be part of your adventure.

Take a look at some reviews from our past guests. We also encourage you to get in touch with them directly to hear about their experiences.

Is This Tour Suitable for Me?

If you are a cyclist who enjoys adventure, gravel paths, Italian food, great accommodation, and the rhythm of long days on a bike, this trip is for you.

Our tours are more than just rides. They are immersive journeys that challenge you physically and reward you with new friends, unforgettable landscapes, and meaningful connections. If you crave movement, exploration, and growth, you have found the right experience.

What Are the Hotels and Agroturismos Like?

This entire tour is based in beautiful 4-star hotels and spectacular agroturismo stays. For more details, please see the Accommodation section below.

How Much Gear Do I Need to Carry on the Bike?

This trip includes luggage transfers between the two base camps. You only need to carry a day pack while riding, whether that is a backpack, frame pack, saddle pack, or a combination.

How Long Are the Daily Rides?

Daily distances vary, and each day you can choose between a shorter and a longer route. The two groups meet for lunch, so you get the shared group experience regardless of which option you choose. Please see the itinerary below for detailed daily distances.

What Is the Pace Like?

Think of this as a weeklong ride with friends. This is not a race, it is an adventure. You do not need to be a professional cyclist or have technical mountain biking skills. However, you should be comfortable spending 5–7 hours in the saddle each day and managing the terrain and distances outlined in the itinerary. The focus is on enjoying the journey, embracing the challenge, and experiencing Tuscany one pedal stroke at a time. We have planned the trip so that after each day of riding, you will have time to unwind. Swim in the pool, enjoy a drink, read a book, and soak in the views.

How Technical Are the Rides?

The route includes some of the best gravel Tuscany has to offer. While it is not a technical singletrack challenge, it is a true backcountry adventure that requires endurance, confidence, and comfort on varied terrain. You will not need advanced mountain biking skills, but you should be comfortable riding on uneven surfaces and prepared for long days. In short, the trip is not highly technical, but it is physically demanding. The reward is stunning, raw Italian landscapes and the deep satisfaction of riding it all under your own power.

What Type of Bike Is Recommended?

This is entirely up to you, but we recommend a drop-bar gravel bike, a flat-bar adventure bike, or a touring bike.

Tires: Aim for tires starting at 35mm (1.4") wide. Wider tires of 1.8–2.4", will add comfort and control on rougher surfaces. Good tread is essential for the mix of gravel, asphalt, and occasional singletrack.
Gearing: A wide-range drivetrain with low gearing is highly recommended for the climbs.
Packs: Since your main luggage is transferred, you only need a day pack while riding.
Suspension: Suspension is not necessary in Tuscany. A rigid fork is perfect, but a bit of suspension is not wrong either.

Road bikes are not suitable for this journey. You will need a bike with clearance for wider tires to ride comfortably and confidently.

E-bikes: We love the simplicity and rhythm of traditional bikes. A big part of what makes these journeys special is the shared pace and the effort it takes to reach each place. For that reason, we do not recommend e-bikes. That said, if you feel you need one to participate, you are still welcome to join. Please note that e-bike battery packs are generally not allowed on flights.

Bike Rentals

We can help you find the right rental bike if you would rather rent a bike than travel internationally with your own. Bike rentals typically start at 300 euros for the tour. Please send us an email if you would like to rent a bike.

What Is the Weather Like?

Late April in Tuscany sits perfectly between spring and early summer and offers excellent conditions for gravel riding.

Days are generally mild, green, and bright, with long daylight hours and comfortable temperatures. Mornings are often cool and clear, while afternoons warm up without the intense heat of summer. Extended periods of rain are uncommon.

In the valleys: Daytime temperatures typically range from 20 - 25°C (68 - 77°F). Rain showers are possible but usually brief. Evenings are pleasant and cooler.
In higher terrain: Temperatures are slightly cooler, often between 15°C - 20°C (59°F to 68°F). Conditions can change quickly with clouds or wind, especially on ridgelines.

Layering is recommended. Overall, expect stable and enjoyable riding weather, with the flexibility to adapt to occasional spring changes.

What If I Am Traveling Solo?

Around 40% of our guests travel solo. One of the most rewarding aspects of these trips is the strong sense of connection that forms along the way.

I Am a Woman Traveling Solo

You do not need a partner or group of friends to join this trip. Traveling solo can feel intimidating, but many of our tours have a close to 50/50 gender balance.

Take the leap. You will feel supported, empowered, and surprised at how quickly a sense of community forms.

Guides

You will be guided by two highly experienced, fully certified local guides who know Tuscany inside and out. They are passionate about their work and committed to your safety and enjoyment throughout the journey. In addition to our local guides, you will have a Vagabond Trails tour leader and, of course, Ryan himself on the tour. Your well-being and enjoyment is always our top priority.

Please ensure that your physical condition aligns with the itinerary below. If you have any questions, do not hesitate to contact us.

Itinerary

7 Days

Total Riding Distance: 283 miles / 454 km (approx.)

Total Elevation Gain 42500 ft / 13000 m (approx.)

Base Camp Tour

This bike tour uses a base camp model, designed for comfort, flow, and daily exploration.

Instead of moving hotels every night, we stay in two carefully selected 4-star hotels, spending three nights at each. This allows you to ride light, settle in, and fully experience each region. Your main luggage stays put, while you head out each day on loop rides or point-to-point routes with support.

The result is less packing, better recovery, and more time to enjoy the riding, the surroundings, and the people you’re sharing the journey with.

Two Daily Distances

Each riding day offers two distance options: a shorter route and a longer one. Both are fully guided and adapted in real time to the group’s fitness, energy, and preferences as the tour unfolds. This flexibility allows everyone to ride at the right pace, whether that means pushing a little farther or keeping things relaxed, while still sharing the same experience and support throughout the journey.

Day 1 | Arrival Day | Florence Airport (Amerigo Vespucci Airport)

You arrive in Florence and are transferred straight into the Tuscan countryside. Almost immediately, the pace shifts. Vineyards replace traffic. Olive groves roll past the windows. Our first base is a handpicked four-star hotel, chosen as much for its setting as its comfort.

Bikes are assembled and checked in the afternoon. There is no rush. Just enough time to settle in, stretch the legs, and let the place work its quiet magic. Depending on your arrival time, you may have time for a short ride to loosen up. In the evening, we gather for a welcome dinner. Good food, good wine, introductions, and a sense of what the week ahead will hold. This is where the group begins to form.

Ride: A spontaneous short ride may take place in the afternoon for early arrivals.

Day 2 | White Roads and Rolling Hills

Today is your introduction to classic Tuscan gravel. We roll out onto smooth white gravel roads that thread through open countryside, vineyards, and gently rising hills. The riding feels immediately right. Engaging, but never frantic. The terrain undulates naturally, offering steady climbs and long, flowing descents that invite you to settle into a rhythm.

This area around Siena is iconic for a reason. Medieval villages appear on ridgelines. Cypress trees punctuate the landscape. Ancient abbeys and stone farmhouses sit quietly in the fields, unchanged for centuries.

We ride, stop when something catches the eye, and ride again. Lunch is unhurried. The afternoon is relaxed. When the bikes are put away, there is time to simply be here. Swim. Read. Sit with a drink and watch the light change.

Short ride: 37 km (23 mi) | +837 m (2,745 ft)
Long ride: 72 km (45 mi) | +1,424 m (4,670 ft)

Day 3 | Villages, Vineyards, and Quiet Roads

Today takes us into Val di Merse, a wilder and less-traveled corner of Tuscany. The roads narrow. Forests close in. Gravel lanes weave through rolling hills and along clear rivers. This is a quieter day, not in effort, but in atmosphere. Villages feel lived-in rather than visited. Abbey ruins rise unexpectedly from fields of wildflowers. Birdsong replaces traffic noise.

The riding is relaxed and immersive, with gentle gradients punctuated by climbs that open wide views over green valleys. Stops at small osterias offer local cheese, honey, and espresso. Simple things, done well. This is a turning point, where the mind really slows down.

Short ride: 37 km (23 mi) | +537 m (1,760 ft)
Long ride: 60 km (37 mi) | +833 m (2,730 ft)

Day 4 | Recovery Ride, Transfer, and Wine

After two solid days in the saddle, today is deliberately lighter. We begin with a gentle recovery loop around Siena. Short, scenic, and relaxed. Just enough to keep the legs moving and enjoy the morning air. No pressure. Plenty of time for conversation and a coffee stop.

Back at the hotel, we pack up and transfer to our second base deeper in Tuscany. A new landscape, a new feel. In the afternoon, we shift gears completely with a guided wine tasting at a local estate. Stories, flavors, and a deeper connection to the land we have been riding through. It is a reset day, physically and mentally.

Recovery ride: 32 km (20 mi) | +467 m (1,530 ft)

Day 5 | Remote Gravel and Big Views

Montalcino delivers one of Tuscany’s most rewarding riding days. The gravel winds through vineyards and quiet country lanes, climbing steadily toward wide, open views across the Val d’Orcia. Cypress-lined roads stretch ahead. Stone farmhouses sit perfectly placed in the landscape. The riding feels purposeful, honest, and deeply satisfying.

Climbs are earned. Descents are smooth and fast. The town of Montalcino itself, crowned by its medieval fortress, feels like a reward rather than a destination. A coffee stop here lingers. Nobody rushes it.

Short ride: 43 km (27 mi) | +745 m (2,445 ft)
Long ride: 70 km (44 mi) | +1,336 m (4,385 ft)

Day 6 | The Best of Tuscany

This is the day that tends to stay with people the longest. Val d’Orcia unfolds in a series of near-perfect scenes. Rolling hills. Green fields. Cypress-lined ridges. Quiet strade bianche that seem to exist solely for cycling. Each turn feels composed, yet completely real.

We ride past places known for their Renaissance beauty and pecorino cheese. The terrain flows. The views open. The effort feels meaningful but never forced.

The final lunch is long, relaxed, and celebratory. The riding ends, but the experience does not. In the evening, we come together one last time for a farewell dinner. Tired legs. Full hearts. Shared stories.

Short ride: 38 km (24 mi) | +711 m (2,330 ft)
Long ride: 60 km (37 mi) | +1,033 m (3,390 ft)

Day 7 | Departure

After breakfast, transfers take you back to Florence Airport.

Legs are tired in the best possible way. The dust has settled, but the memories have not. Long roads. Long lunches. Quiet moments that continue to echo well beyond Tuscany.

Accommodation

For this journey, we stay in two handpicked, beautiful four-star hotels, chosen for their comfort, character, and connection to the Tuscan landscape. Both feature pools and peaceful outdoor spaces, perfect for unwinding after a day on the bike.

Our accommodations are places you’ll genuinely look forward to arriving at each afternoon. Expect warm hospitality, excellent local food, and settings surrounded by vineyards, olive groves, and rolling hills. Rooms are comfortable shared twin rooms (or doubles for couples), offering a high standard of rest and privacy. Single occupancy may be an option, subject to availability.

These stays are an essential part of the experience. They provide not just recovery, but a sense of place and calm that complements the riding perfectly, allowing you to slow down, relax, and fully absorb the rhythm of Tuscany.

How Challenging ?

This expedition has a Medium effort rating. It is a challenging adventure where we can expect 18 - 52 miles / 30 - 85 km daily, 6 - 8 hours of biking per day, with up to +4265ft / +1300m of elevation gain. This trip is not a race; we will ride at a fun social pace. But make no mistake, the daily distances and some sustained climbs will make this a challenging but rewarding ride. Previous multiday biking experience and a good level of riding fitness are recommended.

Each day will offer two different riding distances to accomodate a variety of riders!

Price and Details

The tour includes:

Everything described in the itinerary
All of the scheduled activities
Transport from Florence Airport (“Aeroporto di Firenze” or "Amerigo Vespucci Airport") to the first hotel (including transfer of bike bags)
Transport from the last hotel to Florence Airport – “Aeroporto di Firenze” (or Amerigo Vespucci Airport) (including transfer of bike bags)
All accommodations during the tour in twin rooms (or double if you travel as a couple)
Luggage transfers between accommodations
Use of the backup vehicle in case of a mechanical breakdown
All main meals during the tour (starting with dinner on Day 1 and finishing with breakfast on Day 7)
Online Safety Briefing before the tour
Personal attention before and during your tour
Packing List
Guiding by two certified local cycle guides
Amazing gravel & beautiful landscapes

The tour excludes:

Flights or orther travel to Florence Airport (“Aeroporto di Firenze” or "Amerigo Vespucci Airport")
Any fees associated with Visa applications
Single room supplement
Insurance. All participants are required to have their own insurance appropriate for outdoor sports, such as health, accident, rescue, repatriation, tour cancellation, tour interruption, personal liability, etc.
Alcoholic and non-alcoholic beverages
Expenses for extra activities, such as massages and spas
Gratuity for the local guides
Bike rental (if you're not bringing your own bike)

Price: EUR 5495

A 30% deposit is due to secure your spot, the remaining balance is due 90 days before the start of the trip. Once the trip is confirmed, your deposit is non-refundable, however, it can be transferred to any other trip until 90 days before the start.

Participants:

Minimum 8 - maximum 14

Start: April 25, 2026, all day pick-up, at Aeroporto di Firenze (or Amerigo Vespucci Airport). Please arrive before 2 PM to be able to join the welcome dinner at 7 PM.

End: May 1, 2026, around 1 PM, at Aeroporto di Firenze” (or Amerigo Vespucci Airport)

This tour is operated by Terra Expeditions AB and governed by the Terms and Conditions

Tour Status: Pending!

Cancellation policy:

Trip pending: the 30% deposit payment is fully refundable
Trip confirmed: The 30% deposit payment and 70% balance payment are now non-refundable. You can transfer them to another trip within the next year, as long as it's more than 90 days before your original trip's start date.
90 days or less before the trip starts: no refunds and no transfers.

Travel insurance is required for all of our trips. Make sure that your insurance covers trip cancellation and trip interruption (in case of any unforeseen circumstances)

We reserve the right to change the itinerary without prior notice due to weather conditions and unforeseen circumstances.