A cycling tour that showcases the very best of Eastern Sicily, combining magnificent Baroque towns, UNESCO World Heritage Sites, breathtaking coastal scenery, and the spectacular landscapes of Mount Etna. Carefully designed for cyclists, this itinerary blends enjoyable daily rides with the discovery of the island's rich history, culture, and outstanding food and wine traditions.
The route takes you from Syracuse to Ragusa, through the remarkable Villa Romana del Casale in Piazza Armerina, before climbing towards Mount Etna and ending in the charming town of Taormina. With well-balanced daily stages and scenic roads, this tour offers an active, authentic, and unforgettable cycling experience through some of Sicily's most iconic landscapes.
The tour will also include authentic experiences focused on Italian wine and cuisine. After the daily rides, you will discover the flavors of the region through local wine tastings, traditional products, and unforgettable moments celebrating Italy's rich food and wine culture. A perfect balance of cycling, culture, and lifestyle — experiencing not only Italy's most beautiful roads, but also its unique dolce vita.
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Day by Day Itinerary
Sunday · Arrival, Catania
Welcome at Catania Airport. Transfer to the hotel in Siracusa. Meet your guide Raffaele and your Hersh ORO bike — fitted and ready. Optional short test ride, then dinner together to kick off the adventure.
Monday · Siracusa → Marzamemi
Discover the magic of the south-eastern coast of Sicily, heading to the charming seaside village of Marzamemi. Breathtaking landscapes, crystal-clear waters, authentic local traditions.
Tuesday · Siracusa – MAT – Ragusa
Departing from Syracuse, stop at the MAT (Anthropological Museum), then on to the Baroque city of Ragusa — historic centre and panoramic views.
Wednesday · Ragusa – Donnafugata wine experience
Via Modica, the city of chocolate, along the coast to Marina di Ragusa, then on to the Donnafugata wineries.
Thursday · Ragusa – Piazza Armerina
Caltagirone, world-renowned for its ceramic tradition and Baroque heritage — the Staircase of Santa Maria del Monte, artisan workshops. Then Piazza Armerina and the Villa Romana del Casale mosaics.
Friday · Mount Etna ⭐
From Piazza Armerina to the slopes of Mount Etna, the highest active volcano in Europe — lava flows, unspoilt nature. Finale in Taormina.
Saturday · Farewell & Departure
Transfer to Catania Airport. Arrivederci — see you next time in Italy.
Pricing
| Standard price | $6,250 per person (double room) |
| Early Bird | $4,990 per person — book by November 30, 2026 |
| Single supplement | +$500 (single room, 6 nights) |
| E-bike upgrade | Available at supplemental cost — ask on booking |
| Deposit | $550 to confirm your place |
| Balance due | January 31, 2027 |
Included
- 7 days / 6 nights double hotel accommodation
- Daily breakfast + 6 dinners (half board)
- All carbon road bikes Hersh ORO (e-bikes at supplement)
- All airport transfers within Italy
- Luggage transportation throughout the trip
- Private support vehicle on all rides
- Expert guides
- Free commemorative Hersh Bike Jersey
- Farewell dinner at a surprise location
- Daily safety meetings before each ride
- Water & electrolytes on rides
- Mechanical assistance
Not included
- International flights and personal travel insurance
- Lunches (bring euros for lakeside cafés and mountain stops)
- Mini-bar and personal hotel expenses
- Gratuities for guides
- Optional photographer
- Extra rentals
- Tourist tax
- Drinks and alcoholic beverages
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Ready to ride?
This tour is booked through our partner Bravo Bike Tours — 7 days · 6 nights.
$4,990 per person — book by November 30, 2026 Early Bird price
Book with Bravo Bike ToursPayment via email, PayPal or Zelle — arranged directly with Bravo Bike Tours, our confirmed booking partner for this tour. Questions about the itinerary? Email Hersh.
Frequently Asked Questions
Are flights included?
No — international flights and personal travel insurance are not included. Airport transfers within Italy on arrival and departure days are covered.
Is a single room available?
Yes — a single supplement of +$500 covers a single room for all 6 nights.
Can I upgrade to an e-bike?
Yes, an e-bike upgrade is available at a supplemental cost — just ask when booking.
How do I secure my place?
A $550 deposit confirms your booking. The balance is due by January 31, 2027.
What fitness level do I need?
This is an active road cycling holiday with daily rides up to 62 miles and climbs up to nearly 6,900 ft of elevation gain (Mount Etna day) — see the day-by-day itinerary above for each day's distance and elevation. A good baseline road cycling fitness is recommended.