Gran Fondos

The Strade Bianche Experience 2027

Difficulty:

Thu, Mar 4 - Mon, Mar 8, 2027

5 days, 4 nights

Italy

Only 12 places available

From £4430 pp

Five days in Tuscany built around white roads, race atmosphere and repeated punchy efforts. At 402 km and 6140 m of climbing, this is not the hardest trip in the programme, but it is still a serious cycling weekend rather than an easy Italian escape.

Join us for an extraordinary 5-day cycling adventure in the heart of Tuscany, centred around the legendary Strade Bianche race.

This event is designed for cycling enthusiasts eager to experience the challenge of the white gravel roads and ride through the stunning landscapes that make this race one of a kind.

Difficulty: 3/5 - Hard

Gravel sectors, sharp climbs, unpredictable spring conditions, and event intensity make this ride harder than the elevation stats alone suggest. You don't need to be a pure mountain goat, but you do need genuine fitness and confident bike handling to stay safe and enjoy the challenge.

Dining: Meals feature generous, local Tuscan flavors, but lunches and ride stops are strictly scheduled around timing and fueling requirements.

Who this is for: Best for riders who like punchy terrain, race build up and mixed road surfaces. Not for guests booking mainly for Siena, wine and gentle rolling rides.

Arrival Airport

Florence, Italy

Departure Airport

Florence, Italy

Start Location

Sienna, italy

Finish Location

Sienna, italy

Total Distance

402 km

Total Elevation

6140 m

Longest Day

Day 4 – 138 km

Biggest Climbing Day

Day 4 – 2080 m

Day by Day

You arrive in Siena on Thursday and settle into the city’s quiet anticipation. Those who land around lunchtime head out for a gentle 20km spin to wake the legs and shake off the travel.

As evening falls, everyone gathers at Nonna Gina for a first taste of Tuscan cooking and a detailed briefing over dinner, the weekend starting to take shape around the table.

Friday opens with a guided ride into the Tuscan hills. The day’s route threads together 101 km of mixed terrain and 1510 metres of climbing, with long views, white gravel and that familiar Strade Bianche camber under your tyres.

The afternoon slows into local rhythm, with time to taste wine or wander a nearby medieval village. Dinner at Al Mangia closes a day that moves neatly from effort to easy indulgence.

Saturday belongs to the professionals. You roll out for 56 km and 1000 metres of climbing, hopping between prime viewing spots on the course, close enough to feel the peloton hammer past on the gravel sectors.

Siena is alive when you return. The evening builds into a dinner at Osteria La Sosta di Violante where the day’s best moments bounce around the room.

Saturday: Watch The Strade Bianche Pro Race

Sunday is your race. The Gran Fondo Strade Bianche sends you onto the same legendary roads as the WorldTour, with various course lengths to match your ambition.

Your start comes with priority bib numbers right at the front, among the opening wave of 300 to 500 riders in a mass of 6000. The full loop runs to 138 km and 2080 metres of climbing, sweeping through vineyards, cypress‑lined lanes and historic towns before you drop back into Siena.

A post‑race meal at Antica Ostereria da Divo waits at the finish along with a proper debrief from the Rouleur team.

Monday riders will bid a bittersweet farewell to Siena, leaving with dust in their kit and Strade Bianche pressed firmly into memory. If you've travelled from further afield and would like to extend your stay, just let us know, we're happy to help arrange additional nights.

What's Included

Hotel stays

Reside in the heart of one of Italy's oldest cities.

Entry to the Gran Fondo Strade Bianche

Ride one of Europe's most prestigious events with guarunteed access in the first wave 0 - 300 of the 6000 participants.

Meals

Substantial breakfasts, practical ride day meals, local Tuscan dinners.

Ride support

Become of the team with support from our experienced ride leaders.

Watch the Strade Bianche pro race

Up-close access and prime viewing areas.

Mechanical help

Pro-level mechanics and vehicles escorting you throughout the day

INCLUDED

Lodging
Meals
Selected beverages (non‑alcoholic unless stated)
Hydration & nutrition on‑road
Pro guides
Mechanic & support vehicle
Partner kit on arrival (where specified)
Gran Fondo entry ticket

NOT INCLUDED

Flights
Travel/bike insurance
Personal expenses
Alcohol unless specified
Optional upgrades (transfers, daily laundry, e‑bike, single‑room supplement)

Accommodation & Transport

Set in the middle of Siena’s old town, our chosen hotel occupies a 14th‑century palazzo that once sheltered noble families through the Renaissance.

The restoration keeps the building’s medieval character intact while folding in modern comforts with a light touch, so nothing feels forced or overdone. Step in through the arched stone entrance and the city’s noise drops away into vaulted ceilings, original frescoes and cool terracotta underfoot.

The place carries its history lightly, with just enough patina to hint at merchants, artists and pilgrims who’ve moved through the same corridors on their own journeys – and where you’ll now be adding your own.

The Strade Bianche Experience 2027

From £4430 pp

Thu, Mar 4 - Mon, Mar 8, 2027

Italy

Only 12 places available

"Cycling through the legendary Strade Bianche with the Rouleur team was an unforgettable experience! The 4-day adventure in the heart of Tuscany brought together everything a cycling enthusiast could dream of—epic white gravel roads, breathtaking landscapes, and the thrill of riding a route steeped in history. Every moment was filled with excitement, challenge, and camaraderie. Truly a one-of-a-kind journey for anyone passionate about cycling!"

Tris - Head of Rouleur Travel

MORE THAN CYCLING

FROM THE TEAM BEHIND THE MAGAZINE

We, as cyclists, naturally love Italy. But with over 20 years experience covering the professional peloton, testing iconic brands and hosting events, we've grown to know Italy too.

Bikes

Discover the freedom of two wheels with our bicycle rental service.

Enjoy comfort, performance, and convenience throughout your journey.

The rental rate is £120 per day.

Pinarello DOGMA F

Engineered for pure speed and sculpted with obsessive detail, this is the kind of race bike that turns every climb, corner and descent into a masterclass in performance.

Pinarello DOGMA X

Built for the long days that demand both pace and poise, this endurance thoroughbred delivers race-ready performance with a level of comfort that keeps the joy in every kilometre.

Pinarello X7

Crafted for riders who want comfort without compromise, this endurance machine blends smooth compliance with lively speed, keeping every kilometre controlled and genuinely enjoyable.

Impressions of the Rouleur Travel experience

Anthony L

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We loved the trip. Food and accommodations were fabulous. Loved the rides and the support and all the people. The Maratona is a spectacular event. Looking forward to next year!

Andrew W

Rouleur Pacific Northwest - Seattle to Whistler

This was my first trip with Rouleur, and the first of many I hope. Fantastic people to cycle with and exceptional hosting skills from Tris and Frances.

Matt S

Rouleur Pyreneese: Climbing Giants

This was my second trip with Rouleur Travel and it would be difficult to imagine better cycling experience. The routes chosen, some of the most difficult climbs in the Pyrenees, were fabulous - and wonderfully difficult. Tris and Frances left no detail unattended to and are great good fun to ride with. I’ll go again.

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The Strade Bianche Experience 2027

Day by Day

Hotel stays

Entry to the Gran Fondo Strade Bianche

Meals

Ride support

Watch the Strade Bianche pro race

Mechanical help

INCLUDED

NOT INCLUDED

FROM THE TEAM BEHIND THE MAGAZINE

Bikes

Impressions of the Rouleur Travel experience

Anthony L

Andrew W

Matt S

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