Grand Cycling Tour of Sicily

Explore both coasts of Sicily on our guided bike tour in Sicily
  • Length 14 days
  • From USD$6850
  • Style/Level Classic 3.5
  • Countries Italy
  • Begin/End Siracusa (Syracuse in English) / Trapani
See related tours

This bicycle tour of Sicily explores traditional southern Italy and the heart of ancient Magna Grecia. Beginning in Siracusa (Syracuse), a UNESCO World Heritage Site with over 3,000 years of Mediterranean history you’ll discover the interior towns in the Valle di Noto. You’ll visit four of them, Ragusa, Scicli, Modica and Valle di Noto. All four are listed on the UNESCO list of World Heritage Sites and each one is spectacularly beautiful. Your journey will continue to the coastal town of Trapani known for its seaport and tuna fishing. Explore the medieval village of Erice with its narrow stone alleyways, and the hilltop town of Caltabellotta. You’ll also visit Marsala and sample its fortified wines, and discover some of the finest classical Greek temples still in existence at Selinunte and Agrigento. The diverse terrain offers a rewarding cycling journey through beautiful regions rich in vineyards and agriculture, and picture perfect coastal views.

***If this sounds great but you don’t have time for the full 14 days, check out either the 8-day Bicycle the Baroque Towns of Southeastern Sicily, or the 7-day Cycling Southwestern Sicily’s Ancient Mediterranean Cities tours.***


  • UNESCO World Heritage Sites in the valle di Noto, Syracuse, Rural countryside accommodations with pools, Olive oil tasting, Beaches and swimming opportunities, Agrigento, Lunch at Caltabellotta, Guided walk of Selinunte, Marsala wines, Erice, Trapani, Archaeological site of Cava d’Ispica.


  • 14 days, 13 nights accommodation

  • meals as noted in itinerary

  • olive press visit and tasting

  • guided walk of Valle dei Templi and Selinunte

  • wine tasting

  • Marsala wine tasting

  • All Classic tour inclusions

Keep in mind

We work hard to maintain consistency across all of our tours, but some trips have unique differences. Here are some things to keep in mind about this tour.

  • We recommend not drinking the tap water in Sicily. While tap water in Europe is generally safe to drink, Sicily is different. We will provide bottled water on tour. If you arrive early, we recommend you drink bottled water also.
  • We will have a free night in Ragusa on Day 5, where you can choose to dine at Michelin restaurants if you wish. If you’d like to enjoy an evening at either Locanda don Serafino (1 Michelin star) or Ciccio Sultano Duomo (2 Michelin stars), we recommend you make reservations online in advance. 

Date Price Private room fee Note
Sep 28-Oct 11, 2024 USD$6495 USD$650 Sold out – waitlist available
May 3-16, 2025 USD$6850 USD$650 Book Now and Save $200 per person.
Sep 27-Oct 10, 2025 USD$6850 USD$650 Book Now and Save $200 per person.
DateSep 28-Oct 11, 2024
Private room feeUSD$650
NoteSold out – waitlist available
DateMay 3-16, 2025
Private room feeUSD$650
NoteBook Now and Save $200 per person.
DateSep 27-Oct 10, 2025
Private room feeUSD$650
NoteBook Now and Save $200 per person.

Download Itinerary

We’ll send you a link to a full day by day tour itinerary that can be downloaded and printed so you can review all the details online and offline. This packet also includes details about what to expect on tour and arrival and departure details.
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  • Total distance 709km (438 miles)
  • Average daily distance 64km (40 miles)
  • Tour style Classic
  • Tour level 3.5

Highlights: Ancient Siracusa, one of the oldest Greek settlements in Magna Grecia

Arrive today in Siracusa or “Syracuse” in English. The Greek “Syrakousai” was one of the first Greek colonies in the western Mediterranean, founded in 734 BC by colonists from Corinth. By the mid-5th century BC it rivaled Athens for supremacy with a population of a quarter of a million people. Home to Archimedes (of Archimedes Principle fame) Siracusa has a wealth of ancient Greek ruins and the largest Greek theater from the 5th Century BC. Our hotel is in the center of ancient Ortigia. Enjoy a test ride around the ramparts before our special welcome dinner tonight.

The September 14 and 28, 2024 departures are staying at Palazzo Salomone.

Meals : Dinner
Lodging : Henry’s House , Palazzo Salomone

Highlights: UNESCO town of Noto, country resort near the world famous Vendicari nature reserve

Your first ride in Sicily has you pedaling through small beach and fishing towns, passing an abandoned “tonara” or tuna canning factory which was one of the biggest economic drivers of the island in the late 18th and 19th centuries. The route takes us inland to the imposing town of Noto, one of the many towns in this region rebuilt (in a new location) in the grand baroque style after the earthquake of 1693. The striking white town is perched above the valley and makes for an impressive destination as you pedal towards it. Enjoy a walk in Noto before heading to our destination tonight, a splendid old farmhouse renovated into lodging with a swimming pool and particularly lovely grounds.

Meals : Breakfast, Dinner
Lodging : Hotel Corte del Sole

Highlights: Fishing port of Marzamemi, coastal scenery and beaches, wine tasting

Take your swimming suit along today as there are plenty of opportunities to find an isolated beach to take a refreshing dip. You’ll pass through the fishing village of Marzamemi, a village built up around the ancient tonara. The red tuna from this area are still prized in Japan for sushi. While the tonara here is no longer working, the quaint fishing village has maintained its charm with quaint buildings, restaurants, cafés and stores. From here you can opt to continue your ride along a quiet coastal road to Capo Passero, which is the furthest southeastern point in Sicily. This evening we’ll enjoy a wine tasting before dinner together.

Meals : Breakfast, Dinner
Lodging : Hotel Corte del Sole

Highlights: Cavagrande del Cassibile, lunch together with pool and sea view, lovely farm hotel amid almond and olive groves

Your ride today takes you to the interior of the island through olive and almond groves. An impressive climb of approximately 400 meters (1,300 feet) up a narrow canyon that delivers stunning views into the deep canyon and far out to the sea as you summit on the plateau. Reward yourself with a pool side lunch (and perhaps a dip in the pool!) before continuing along the plateau to reach our quiet country lodge immersed in the hills and close to the expansive ruins of the old city of Noto destroyed in the earthquake of 1693. A brief stroll through Noto Antica’s ruins allows you to travel back in time and imagine the large city that once dominated the area. All that remains today is scattered stones, crumbling buildings and tower ruins.

Meals : Breakfast, Lunch, Dinner
Lodging : Kallikoros

Highlights: Country roads, the new and old cities of Ragusa

You are primarily on country roads today as you pedal west to Ragusa. Stop and visit an olive oil press to learn about the local olives, the local farmers, and the business of making olive oil. From there you’ll continue to Ragusa which, like Noto, was rebuilt in the 17th century after the massive earthquake. Uniquely though, Ragusa was not moved to a new site. The result is a new baroque town on a ridge top next to the ancient town clinging to a narrow ridge and the valley below.

Meals : Breakfast
Lodging : Hotel San Giorgio

Highlights: Lands once occupied by Greeks, Romans, Arabs, Normans and Italians; water mill; archaeological site of Cava d’Ispica; picnic

The timeless landscape of southeast Sicily comes to life today as you pedal ridges and hills toward the famous archaeological sites of Cava d’Ispica, a narrow gorge filled with grottoes which were used since Neolithic times for lodging. Enjoy a picnic lunch near a unique water mill built in a cave before continuing on to the delightful town of Scicli. Scicli is the set for the TV film series Inspector Montalbano, based on the fictional town of Vigáta. Tourism to the area has boomed thanks to this popular TV series although a walk through town will highlight much more than a mere TV set! *The May 4 departure will stay at Palazzo Conti.

Meals : Breakfast
Lodging : Hotel Novecento , Scicli Albergo Diffuso , Palazzo Conti

Highlights: Famous chocolate town of Modica and to the seaside town of Donnalucata

We’ll mark two loop rides today to nearby Modica and to the seaside at Donnalucata. Donnalucata is the site of a decisive battle in 1091 between the Normans and the moors. It was also central to the allied invasion of Sicily in July 1943. It also offers a chance for a little beach time for those so inclined. Modica is another town rebuilt after the earthquake of 1693 but, as it sits astride the Modica River, it also suffered from devastating floods at the beginning of the 19th century. Modica is also famous for retaining the original Aztec recipe for chocolate imported by the Spaniards in the 16th century. We’ll enjoy a special visit and tasting at the Bonajuto chocolate shop which touts six generations of artisan confectioners. *The May 4 departure will stay at Palazzo Conti.

Meals : Breakfast, Dinner
Lodging : Hotel Novecento , Scicli Albergo Diffuso , Palazzo Conti

Highlights: Agrigento, guided visit Valle dei Templi

Agrigento features one of the finest collections of ancient Greek temples anywhere in the Mediterranean basin. Our hotel is not far from the ruins and we’ll take a guided visit at the Valle dei Templi as the setting sun turns the limestone columns a golden color. We will have dinner together this evening.

Meals : Breakfast, Dinner
Lodging : Colleverde Park Hotel

Highlights: Sciacca

Your ride today offers a lovely combination of terrain as you head inland through wheat fields, and vineyards towards the village of Cattolica Eraclea. When the sweet scent of oranges envelopes you, you will know that you are approaching the town of Ribera famed for – you guessed it – orange (and olive) groves! The landscape changes again as you enter a magical area filled with whimsical geologic formations just before you enter Ribera. Our destination today is Sciacca.

Meals : Breakfast
Lodging : Domus Maris

Highlights: Extraordinary lunch at Caltabellotta, swimming pool

Today you’ll enjoy a gorgeous and challenging ride (or shuttle in the van) to Caltabellotta where you’ll feast on a lunch of Sicilian specialties. This hilltop village is nestled on a limestone perch three thousand feet above Sciacca. After lunch the rest of the ride is a feast for the senses as you spin through aromatic citrus and olive groves on your way to our elegant lodge tonight. Enjoy a refreshing dip in the swimming pool, and the spectacular views.

Meals : Breakfast, Lunch, Dinner
Lodging : Il Vigneto

Highlights: Selinunte, optional ride to the beach

Enjoy a ride to Selinunte where we’ll have a guided walk through some of the most spectacular ruins in Sicily. The Greek ruins are divided between two ridges, one features temples and the other the remnants of the ancient city. Take an optional ride to the beach at Porto Palo if you’d like a little extra mileage and the chance for a swim. Tonight we’ll enjoy a special dinner in a local winery, wine tasting and visit.

Meals : Breakfast, Dinner
Lodging : Il Vigneto

Highlights: Castelvetrano, vineyard landscapes, Marsala and its wines

A beautiful ride is on tap for today. Fall in love with typical Sicilian landscapes that feature rolling hills covered in vineyards. This spectacular ride leads you to Castelvetrano and stop to admire its beautiful square. Next up is Mazara del Vallo where you’ll have the chance to explore examples of Muslim architecture and enjoy fresh fish from one of the largest fishing ports in Italy before riding back along the shore to Marsala. This afternoon we’ll sample the famous, fortified Marsala wines.

Meals : Breakfast
Lodging : Hotel Carmine

Highlights: Bike to Erice and Trapani

You ride west today, partially along the coast and then up to the hilltop village of Erice. Erice was a Greek town and important medieval fortress that maintains its original ambiance. The end of the bike ride takes you to the coastal town of Trapani for a celebratory dinner together.

Meals : Breakfast, Dinner
Lodging : La Gancia

Highlights: Trapani

There is plenty of history in Trapani as its strategic position on a slip of land saw Carthaginians, Normans, Arabs, Spanish, and Bourbons walk its streets before the unified Republic of Italy was formed in 1861. If you spend a few days here we recommend a boat excursion and head off to the nearby island of Favignana. Join us again sometime soon!

Meals : Breakfast

Visit our Tour Level page to learn more about terrain levels and how we determine day and tour levels.

Pre-trip planning checklist

Italy travel planning page

  • Wonderful food, great cycling, fascinating history and tour leaders who are friends.

    Dennis D., Calgary, Canada – September 2023
  • Great cultural experience at an affordable price. Rich understanding of many of the aspects of the culture through your the trip

    Ron C., Calgary Canada – September 2023
  • Fun, challenging riding with lots of cultural experiences & fantastic food & wine. The guides are the best & lots of fun!!

    Nancy J., Belfast, MA – September 2023