Sicily: La Bella Sicilia

Sicily’s Ancient Mainlands Meet the Legendary Aeolian Islands

Bike in the Aeolian Islands from ciclismo classico on Vimeo.

A distinct yet indescribable island, Sicily has withstood centuries of tyranny and upheaval to emerge as a vital and varied cultural region. Contained by the Mediterranean’s largest island, Sicily’s soil and architecture reveal layer after layer of intriguing history and rule by Arabs, Greeks, Romans, Saracens, French, Spanish, and Bourbons. Home to some of the finest examples of Greek architecture in the world, Sicily is an archaeologist’s paradise.

Focusing on the lush green spectacle in springtime and on the vast golden stage in autumn, this itinerary pedals the southern and northeastern tip of the island to beautiful and historic areas overlooked by the masses of tourists. We begin in the ceramic town of Caltagirone, then via olive groves and tiny mountain villages we reach Ragusa Ibla and follow the route to Siracusa, a Greek town filled with archaeological treasures. Our journey includes a hike up Mt Etna, the highest volcano in Europe, and reaches its apex on the dreamy, volcanic Aeolian Islands, each with its own distinct character and charm. We hike, swim, and bike where the movie “Il Postino” was filmed.  Along the way we enjoy traditional food, wine and music.  Come with us on this unique trip and enjoy Sicily’s rich culture!

Want less cycling? Check out our 6-day La Bella Sicilia Mini.


  • Witness views of Europe’s highest volcano, the Mount Etna
  • Two days on exotic Aeolian islands
  • Learn more about the Baroque Ragusa and the Greek monuments of Siracusa
  • Visit to a Slow Food presidia of capers, olive oil and Malvasia wine in Lipari
  • Stay in luxury hotels and enjoy delicious Sicilian feasts including fresh seafood and vegetables
  • Immerse yourself in the Sicilian culture with the local music and the warm people of the Island

Trip Details:

Biking Walking Multi-

Price: $5,195

Single Supplement: $900

Length: 9 days / 8 nights

Level: Intermediate

Total Mileage: 221 miles

Daily Average: 28 miles

Terrain: Rolling and hilly, 4-6 hour hike

Start/End Locations: Caltagirone/Lipari

Trip Dates:

  • 05/01/15 - 05/09/15
  • 05/24/15 - 06/01/15
  • 09/18/15 - 09/26/15
  • 10/09/15 - 10/17/15
  • 10/23/15 - 10/31/15

= Sold Out

Make this tour Private or for more information, call:


Day by Day


Today take our group shuttle at 11:30 am at Catania airport and meet us at the hotel around 1 pm for a light lunch and introductions, followed by a warm-up ride around Caltagirone.

Caltagirone to Ragusa

After an easy start, the traffic-less road begins to undulate and sports three major climbs and several roller coasters; the last part is almost completely downhill before entering Ragusa. In the afternoon, we’ll reach the fascinating Ragusa Ibla (the lower and older part of town), a vestige of the Baroque period.

Ragusa Loop to Donnafugata and Scicli

We start today’s ride with a pleasant downhill toward the coast. We stop for a visit at the beautiful Villa Donnafugata, the rural summer vacation house of the Arezzo family. After lunch we climb back through the valley with great views of the Irminio river canyon. In the evening we’ll enjoy a walking tour of ancient Ragusa Ibla.

Ragusa to Siracusa

Today’s ride takes us up into the Altopiano Ibleo, a remote and beautiful area where shepherds are the only inhabitants and continue on to Siracusa. In the evening, we dine at a typical Sicilian restaurant where we get our first taste of some local specialties.

Siracusa to San Giovanni la Punta

Bike in one of Sicily’s most fascinating archaeological reserves and nature sites. Today’s highlight is a pleasant ride on quiet roads with the impressive Etna right in front of us. Tonight a musical surprise will showcase the genuine Sicilian spirit and way of life that make the inhabitants of this island so warm and welcoming!

Hike Etna

Take an early van ascent up Mt Etna to hike and enjoy the magnificent views of the volcanic area. On a clear day, you can see all of Sicily. In the afternoon, we go to Taormina, where you'll have the rest of the day free to explore the town and to shop. Important information regarding equipment is on the detailed itinerary.

The Aeolian Island Lipari

Geologically, the island of Lipari is quite rugged with deep caverns, steep cliffs, and splendid views. If you love coastal views, the entire ride is one highlight after another. One of the highlights today will be a visit to a local Slow Food presidia famous for the production of capers, olive oil and Malvasia wine.

The Aeolian Island Salina

Today we take a private boat to Salina. On our bikes, we explore Salina’s beauty as well as its fascinating ancient history. After our small bike ride, we are off to the cove of “Il Postino.” In Salina, we’ll have a Aeolian lunch and the best granita!


Around 8:30 am after breakfast we leave from the island of Lipari and offer a group hydrofoil (1 hour) to Milazzo, followed by a group shuttle (2 hrs) to Catania airport for international connections or to continue your travels to Italy and beyond.

What's Included

Trip Planning

  • Bike rental equipped with odometer, map case, handlebar and seat bags and bike pump
  • Ciclismo jersey and water bottle
  • Shuttles at beginning, during and end of the tour

On The Tour

  • 2 wine tastings
  • Hike up Mt. Etna
  • Visit to Siracusa and guided walking tour of Ragusa, a UNESCO World Heritage site
  • Boat ride with locals to remote turquoise coves
  • Music by local Musicians

Accommodations & Meals

  • All accommodations
  • All breakfasts
  • 6 dinners
  • 2 lunches
Here’s a sampling of some of the amazing places you’ll stay on your journey.

For a full listing, request a detailed itinerary!

Locanda don Serafino

The 4-star Locanda don Serafino is situated right in the heart of baroque Ragusa Ibla in a 19th-century mansion that has been tastefully renovated: it offers ten elegant and comfortable rooms for an unforgettable stay. Their restaurant is one of the best in Sicily for its food and wines.
View their website

Grand Hotel Ortigia

Offering a rooftop terrace and glass elevator with sea views, the 5-star Grand Hotel Ortigia is located on the natural island of Ortigia. Rooms are spacious, and offer free Wi-Fi access, a flat-screen TV, and air conditioning. The Spa is a friendly and welcoming.
View their website

Hotel Villa Diodoro

The 4-star Hotel Villa Diodoro boasts a hillside position and an outdoor pool with panoramic sea views, a 5 minute walk from the historic center of Taormina. Rooms are air conditioned and bright.
View their website

Meet the Guides