Tuscany Dreams Retreat

8-Night/7-Ride Cycling Tour — Siena (4 nights) → Lucca (4 nights)

Overview (what’s included)

• 8 nights (4 nights Siena, then 4 nights Lucca), 4-star/characterful Tuscan hotels (dinner + B&B).

• Bike rental (choice of gravel or road bikes), daily sports nutrition & mechanical support.

• Group ride leader / guide and sag vehicle as required.

• Transfers: arrival transfer from Florence or Pisa airport on Day 1 (optional), transfer Siena → Lucca (mid-trip), and departure transfer to Pisa/Florence on final day.

• Two cultural outings included: Siena guided visit (cathedral + Piazza del Campo) and Montecarlo winery visit (Lucca hills). 

Nights 1–4: Base — Siena (Piazza del Campo as local hub)

Day 1 — Arrival / shake-out ride (easy)

• Morning/Afternoon: Arrival to Florence or Siena; hotel check-in; bike fitting & brief kit talk.

• Ride: 1.5–2 hr coastal/rolling loop around Siena (20–35 km, 200–400 m climbing). Easy pace, get used to the bikes.

• Evening: Welcome dinner with traditional Tuscan menu (pappardelle, bistecca alla fiorentina options).

Day 2 — Strade Bianche loop (signature day)

• Type: Gravel / mixed

• Distance: ~90–120 km (can be shortened)

• Climbing: ~1,200–2,000 m depending on route variant

• Highlights: White-gravel sectors around Crete Senesi and the Monte Sante Marie gravel sector (famous in L’Eroica / Strade Bianche), finish/ride through the rolling Chianti landscapes and back towards Siena. Includes a classic steep approach that replicates Strade Bianche race feel. 

• Logistics: Sag vehicle support at feed/turnaround options; lunch at a country osteria.

Evening: Recovery dinner in Siena town — slow food, local wines.

Day 3 — Crete Senesi & Monte Sante Marie (gravel classic)

• Type: Gravel-heavy, with technical dirt climbs and descents

• Distance: 60–100 km (route options for different abilities)

• Climbing: 1,000–1,600 m

• Highlights: The lunar clay hills of the Crete Senesi, long white-road climbs (Monte Sante Marie is a standout). This is an L’Eroica style day: dusty, scenic and testing. Route can be shortened for mixed groups. 

Day 4 — Chianti / rolling climbs (road day) + Siena cultural outing

• Morning Ride: Road ride through classic Chianti villages — Castellina, Radda, Greve (50–90 km, moderate climbing) — ideal for pavement speed and classic Tuscan views.

• Afternoon Cultural Option: Guided visit to Siena Cathedral (Duomo di Siena) and Piazza del Campo — interpret history, Palio stories and architecture. (guided walking tour ~1.5 hrs)

• Evening: Relaxed dinner — roast, local olive oil tasting, gelato in town.

Why: A change of surface and effort, plus your first cultural outing in Siena (city highlights). 

Day 5 — Transfer Siena → Lucca (transfer day with short ride en route)

• Morning: Transfer with luggage and bikes (approx. 2–3 hr transfer depending on stops). Rocacorba Atelier handles transfers.

• Optional en-route stop: Light lunch in the Val d’Orcia or a hill village.

• Afternoon: Short “arrival” ride near Lucca (30–50 km, 300–700 m), ease into the Lucca hills.

• Evening: Check in to Lucca hotel; dinner featuring local specialities (stewed meats, castagnaccio if in season).

Nights 5–8: Base — Lucca / Lucca Hills

Day 6 — Monte Serra & Altopascio foothills (road & climb day)

• Type: Road (can include gravel spur)

• Distance: 60–100 km

• Climbing: 900–1,600 m

• Highlights: Monte Serra approaches and foothill climbs overlooking the Lucca plain and sea views in the distance. A classic testing day with long sustained climbs and rewarding descents. Routes around Monte Serra and Altopascio give a good mix of gradients and scenic overlooks. 

• Evening: Dinner back in Lucca — try local olive oil–heavy dishes and Tuscan seafood options.

Day 7 — Apuan Alps / Garfagnana (big climbing day)

• Type: Road (steep mountain climbs)

• Distance: 70–120 km (route variants)

• Climbing: 1,500–2,500 m (choose shorter option for mixed groups)

• Highlights: The Apuan Alps north of Lucca deliver steep, dramatic climbs, quiet traffic-light roads, and big panoramic descents. This is the day for riders who want serious vertical metres and alpine scenery near the coast. 

Day 8 — Montecarlo wine valley & easy social ride + winery visit (cultural day)

• Morning Ride: Gentle social loop through the Lucca hills to Montecarlo di Lucca (40–60 km, comfortable climbing).

• Winery Visit: Afternoon Montecarlo winery tasting (guided tasting / cellar tour; options include Tenuta del Buonamico, Fattoria Carmignani or similar — half-day experiences and lunches available). This is your included winery cultural outing. 

• Evening: Farewell dinner — multi-course Tuscan tasting paired with local wines.

Day 9 — Departure day (transfer to Pisa or Florence)

• Morning: Optional short ride on the Lucca city walls (a flat spin) or a final coffee in Piazza Napoleone. Transfer to Pisa or Florence airport per flight schedule.