Tuscany Gravel Explorer
Where white roads, rolling hills, and earned moments define the ride.
Dates
Mid June 2027
Type
Gravel
Duration
8 days / 7 nights
Rider Level
3/4/5
Starting From
$4995
Gravel cycling. Italian style.
Experience the heart of Italy like few ever do, off the beaten path and onto the iconic Strade Bianche. This trip is a deep immersion into one of the most storied cycling landscapes in the world, where white gravel roads wind through sun-drenched vineyards, ancient olive groves, and preserved medieval hill towns.
This is cycling stripped back to its essence – quiet, rolling roads. Endless ribbons of white gravel. Long, rhythmic climbs that reward patience and pacing. Flowing descents that invite you to let the bike run.
Tuscany is much more than the riding. It’s the moments between the miles that complete the experience. Espresso stops in village piazzas. Long lunches overlooking vineyards. Evenings spent around the table with family enjoying locally sourced cuisine, regional wines, and the camaraderie that comes from shared effort on the road. Hospitality here is not performative; it’s genuine, warm, and deeply rooted in place.
Our routes are carefully designed to showcase both the legendary and the hidden. Think the famous sections of Strade Bianche, balanced with lesser-known farm roads and quiet lanes that few visitors ever find. With expert guidance and full support, you’re free to focus on the ride itself, knowing that every detail has been squared away.
This is a journey that blends grit and grace – demanding yet deeply rewarding. A week of riding that reconnects you to why you fell in love with cycling in the first place, experienced the Avanti way.
Defining Experiences
- Strade Bianche - Iconic Gravel: Follow in the tire tracks of the world’s best as you ride the same white gravel sectors made famous by the Strade Bianche. Each climb, descent, and sweeping corner connects you directly to the rhythm and history of one of cycling’s most revered races.
- UNESCO Heritage Landscape: Cycle through Tuscany’s iconic rolling hills, cypress-lined roads, and timeless countryside. Stunning landscape shaped by centuries of agriculture, where every mile feels cinematic, offering uninterrupted views that are as rewarding as the riding itself.
- Gravel, Perfected: Expertly curated routes inspired by professional racing, balanced with quiet backroads known only to locals. Guided by those who live and breathe these roads, you’ll experience Tuscany not as a visitor, but as a rider welcomed into its rhythm.
- The Heart of Italy: Food, wine, and hospitality from rustic trattorias tucked into hilltop villages to private tastings at family-owned vineyards, every meal becomes part of the journey. Thoughtful cuisine, local wines, and genuine hospitality provide the perfect counterpoint to demanding days in the saddle.
Itinerary
Day 1 – Arrival + Transfers + Bike Fit
Welcome to Tuscany.
We’ll coordinate arrivals from Florence or Rome (via train) and transfer you to our countryside home base at Palazzo a Merse, just outside Siena.
Once settled, we’ll build and fit bikes, dial in equipment, and walk through the week ahead.
No riding today – just logistics, introductions, and an easy first evening together.
Arrival Window: Saturday afternoon/evening
Activity: Airport/train transfers, check-in, bike fitting/build
Evening: Welcome briefing + dinner at the Palazzo
Day 2 – Ride 1: Val di Merse (Local Loop / No Van)
Our first ride stays close to home, easing into the week on quiet roads and classic Tuscan gravel. This is about finding rhythm, confirming setup, and shaking out travel legs.
Short and long options available. Café stop included.
Ride: Val di Merse loop (short + long options) to the San Galgano Abby
Surfaces: Gravel + road
Support: No van (local ride) + coffee stop
Midday: Casual village lunch on return
Evening: Pool recovery + dinner at the Palazzo
Non-Rider Option: Local hike near Sovicille (2–3 hrs) or relaxed morning + pool
Day 3 – Ride 2: Crete Senesi (Local Loop / No Van)
Wide-open landscapes, rolling terrain, and long stretches of white road define today. The Crete Senesi delivers that unmistakable Tuscany feel — quiet, expansive, and deceptively challenging.
Again, short and long options keep the group aligned.
Ride: Crete Senesi loop (short + long options)
Surfaces: Gravel-forward
Support: No van (local ride) + coffee stop
Midday: Lunch stop in Monteroni or Radi
Evening: Dinner at a local restaurant
Non-Rider Option: Siena countryside stroll, markets, cafés
Day 4 – Ride 3: Chianti (Van Day)
We load up and head into Chianti for a bigger, more structured day. Expect longer climbs, ridgeline roads, and classic gravel connectors that reward steady pacing.
This is a true camp day — beautiful, demanding, and memorable.
Ride: Chianti route (short + long options)
Surfaces: Gravel + road
Support: Full van support + coffee stop
Midday: Winery or village lunch stop
Evening: Pool recovery + dinner out
Non-Rider Option: Truffle hunting & cooking class or guided wine tour (Chianti/Montalcino)
Day 5 – Rest Day + Siena (Group Day)
Midweek reset.
This is the one day we’re all on the same schedule — riders and non-riders alike.
Sleep in, enjoy a slow morning, then head into Siena for an afternoon walking tour and Contrada museum visit. A perfect cultural counterbalance to the riding.
Activity: Rest + shared group experience
Morning: Relax, optional light walk, coffee, pool
Afternoon: Siena walking tour + Contrada museum
Evening: Group dinner in Siena
Day 6 – Ride 4: San Gimignano (Van Day)
Back on the bikes for a scenic and satisfying ride toward San Gimignano. Rolling terrain, gravel sectors, and postcard views all day long.
This is one of the most visually striking rides of the week.
Ride: San Gimignano route (short + long options)
Surfaces: Gravel + road
Support: Van support + coffee stop
Midday: Agriturismo or village lunch
Evening: Dinner at Bandierino, Piazza del Campo
Non-Rider Option: Vintage car tour + picnic or Florence day trip
Day 7 – Ride 5: Val d’Orcia (Van Day / Queen Ride)
The closer — and the emotional high point of the week. Val d’Orcia delivers long gravel stretches, cypress-lined climbs, and the Tuscany you’ve imagined for years.
Steady pacing, full support, and time to take it all in.
Ride: Val d’Orcia route (short + long options)
Surfaces: Predominantly gravel
Support: Full van support + coffee stop + mid-ride nutrition
Midday: Winery lunch option
Evening: Final dinner at the Palazzo
Non-Rider Option: Val d’Orcia hot springs + villages (spa-focused day)
Day 8 – Departure Day (Arriverderci Toscana!)
Private transfers back to Florence or train connections based on flight schedules.
Dusty bikes, tired legs, and a full memory bank.
Activity: Departures + transfers
Where we'll ride
Where We Stay
Palazzo a Merse – Siena
The B&B Palazzo a Merse is a historic 18th-century farmhouse located in Tuscany, just 10 km from Siena, in the green countryside of the Val di Merse.
The carefully renovated farmhouse, built around an old 13th-century mill, offers a spacious, shaded garden with a swimming pool and barbecue. The apartments, which sleep 2-6, retain their period features and are carefully furnished.
They offer independent heating, fully equipped kitchens, and TVs. The large garden is perfect for enjoying the delicious breakfasts the owners prepare for their guests, dining, savoring the excellent Tuscan wines, or relaxing around the pool.
What our clients are saying
Trip Inclusions
- 8 days/7 nights accommodations (double occupancy).
- Logistics like airport transfers and safe bike storage.
- Carefully curated guided rides and on-road support
- Stays - Your Second Home: Handpicked, comfortable, and locally rooted stays. From ancient farmhouses to family-run guesthouses, offering both cultural immersion and optimal recovery bases.
- Gear - Bike Rental: High-quality, well-maintained bicycles suitable for the local terrain and your skill level.
- Meals - Breakfast and Dinner: Delicious and locally-sourced ingredients, designed to fuel your rides, your soul, and offer a taste of the local cuisine.
- Support: Experienced bilingual guides, dedicated support and transportation, detailed logistical planning, etc. Everything required to ensure your comfort and safety.
- Airfare: International or domestic flights to and from the tour starting/ending points.
- Supplemental Snacks: Additional snacks or beverages beyond the provided breakfast, lunch, and dinners.
- Extracurricular Alcohol: Some excursions include drinks. Otherwise, you will be billed individually for your choice of "recovery" beverage.
- Spa Services and Optional Excursions Not Outlined in the Itinerary: Any personal spa treatments, massages, or optional activities and excursions not explicitly detailed in the tour itinerary.
- Tips for your Tour Guides: Gratuities for your tour guides and support staff are not included in the tour price.
