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A Timeless Journey through Ancient Sicily and the Aeolian Islands

The largest island in the Mediterranean is arguably the most beautiful and certainly the most dense with history and humanity. Sicily's complex culture is matched only by its stunning natural beauty and the incredible, diverse landscape: rolling hills and valleys swathed in grapevines, miles of aquamarine coastline and a series of archipelagos that can be reached via a quick boat ride. We will pedal back in time to a colorful and enigmatic past that has never left the island. With Tourissimo, you will see (and taste) the real Sicily. This seductive Mediterranean island has lured conquerors and visitors for centuries. Phoenicians, Greeks, Romans, Arabs, and Normans have all contributed to the many layers of its vibrant culture. Focusing on the most alluring sites on the eastern side of the island, we’ll swim in pristine waters, hike the highest volcano in Europe (Etna) and visit one of Italy’s best-kept secrets: the Aeolean Islands.

Sicily is a region renowned for its Baroque and Norman architecture, for its artistic importance (many poets, writers and intellectuals were born here), and of course, its excellent food! The cuisine in Sicily is different from the rest of Italy because of the various cultures it has been exposed to. In addition to its great wines, dinner in Sicily usually consists of vegetables (tomatoes, eggplants, artichokes), plenty of seafood, and yes, lots of pasta and olive oil. Its lemons, oranges, figs, almonds and apricots are among the best in the world.

Not sure if you can do it? Contact us to schedule a call about how demanding the rides and hikes are or about reserving and E-bike.


Relevant Blog: Italy’s Scattered Hotels, the Alberghi Diffusi



• Experience charming Scicli, Ragusa, and Modica (UNESCO World Heritage Sites)

• Savor breathtaking views of the Mediterranean

• Explore the Aeolean Archipelago, a UNESCO World Heritage Site

• Hike the most unusual corners of the islands at a relaxing pace

• Travel by private boat with seafood lunch on board

• Enjoy an authentic Sicilian cooking class

• Walking tour of Ortigia (Siracusa), and Taormina

• Visit a wine producer on the island of Lipari, famous for Malvasia

• Ride the scenic farmland of the southern island dotted by historical sites

• Sample local products only from local producers, such as capers, fruits and vegetables



USD 5,995

Private room (single supplement) USD 695


8 days (7 nights)



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Customize this trip Sicily
AMAZING! Loved the riding, hotels, experiences etc. etc.
Cannot thank you enough!  

Kathy Burges Sicily East Private

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Day by Day

[fa icon="plus"] Day 1

Siracusa - Arrival and warm-up ride - 13 mls - Flat

This morning we will pick you up in Catania and drive to Siracusa-Ortigia. Lunch upon arrival in Ortigia and tour overview.

In the afternoon, we will go over bike fitting in preparation for some stunning rides in the days ahead that will include the Iblei Mountains and the so-called Baroque Triangle. The short ride around Ortigia will afford nice views and the chance the get acquainted with the bikes. Founded by Greek settlers in the 8th century BC, Siracusa grew into an economic and political center in the Mediterranean in the form of a city-state, and as such was at the center of tensions and struggles. The island of Ortigia is the city's most ancient settlement and its most charming part, but also the most exposed to the power of the sea. A walking tour with a local guide will unveil Ortigia for us. 

In the evening, we dine at a typical Sicilian osteria where we get our first taste of some mouth-watering local specialties.

[fa icon="plus"] Day 2

Siracusa - Scicli - 30 or 35 mls ride - Rolling

Today, we have a stunning bike ride that crosses beautiful valleys, green hills, and small canyons. We are entering the Monti Iblei or Hyblaean Mountains, a mountain range in southeastern Sicily. After leaving Siracusa, the landscape gradually changes from gentle hills with mediterranean vegetation to numerous woods which are intermingled with typical dry stone walls. Olive trees, vines, citrus fruit, and almonds, as well as scattered sheep, are part of the local scenery. 

We start with a transfer to Palazzolo Acreide, which is conveniently also the highest point of the ride. Pace yourself and take your time when you come to a peaceful ridge road (around mile 10) with expansive views. We reach Modica, one of the most picturesque towns in Sicily. The arrival is progressively more dramatic as we descend into the baroque architecture-filled center. In Modica, we visit the Bonaiuto chocolate shop, one of the oldest on the island. Modica's chocolate is characterized by an ancient and original recipe using manual grinding (rather than conching), which gives the chocolate a peculiar grainy texture and aromatic flavor. It is one of the specialties of the island.

In a few miles, we find ourselves in Scicli. A little off of the beaten path when compared to Modica and Ragusa, it is one of our favorite places on the island. We spend two nights there.

[fa icon="plus"] Day 3

Scicli - Punta Secca loop - 34 or 38 mls ride - Rolling

We start today’s ride with a pleasant downhill from the Altopiano Ibleo toward the coast. The landscape sees tiny farms, pastures, and greenhouses. The economy here is all about agriculture (including winemaking). The lush vegetation is quintessentially mediterranean and comprised of agave, eucalyptus, carob trees, and olive trees. After a stretch along the coast, we reach Punta Secca. If you are familiar with the literary phenomenon that is Commissario Montalbano (Inspector Montalbano) by Camilleri (also a TV series), take note of Montalbano's home facing the water. His meditative swims were made legendary by the pen of the author. Did you bring your swimming gear?

After lunch, we climb back up the valley with great views of the Irminio River Canyon.

Scicli, is another great example of baroque reconstruction (it was destroyed by the 1693 earthquake). Our charming "albergo diffuso" (scattered hotel) - see blog link on this page - sits above the San Bartolomeo church, which deserves a visit. 

In the evening enjoy a stroll through Scicli with dinner featuring an Italian staple no matter the latitude: pizza!

[fa icon="plus"] Day 4

Scicli - Zafferana Etnea -  30 or 40 mls ride - Rolling

After breakfast, we will set off to reach Vizzini and from there we will transfer to Mount Etna. It’s our last bike ride and tonight, we’ll shift into hiking mode. The volcanic soil of the Etna slopes (and of most of Sicily for that matter) and the mild, dry climate allow for wine production that all experts agree is among the most unique yet underrated. The highlight of the ride is the stop at Ragusa-Ibla. Ibla is the old town and an architectural treasure (but also a chance for a morning cappuccino in the Piazza del Duomo). All of the buildings are adorned in typical Sicilian Baroque (UNESCO World Heritage Site). Check out the palaces, their doorways, and balconies, before heading into the Duomo. 

After 15 miles slightly uphill we reach our lunch stop. Guides will load the bikes for the transfer to Zafferana Etnea (fast riders can go farther and be picked up in Vizzini). 

At dinner, we’ll cover tomorrow’s logistics and options for the Etna excursion.

[fa icon="plus"] Day 5

Mount Etna - 2.5 - 5 hr hike

This day will be entirely dedicated to Etna. Accompanied by an alpine-volcanology guide, and depending on wind and weather conditions, we will set off on a full-day hike experience on this marvelous and complex volcano. We start with a transfer with a special vehicle suited to climb on unpaved roads consisting of volcanic ashes. As we gain elevation, the views become more and more majestic, and the vegetation almost fades; it's not unlikely to find snow near the top. Smoke and ashes from the crater fill the air while the deep blue Mediterranean is in the distance appearing both near and far. 

In the afternoon we will return to our hotel and take part in a Sicilian cooking lesson. 

[fa icon="plus"] Day 6

Lipari - 4 hr hike

After breakfast, we will head by hydrofoil to the main island of the Aeolian archipelago: Lipari. Its volcanoes are considered active, and steaming fumaroles and hydrothermal activity can still be seen everywhere on the island. Inhabited since 5,000 B.C, it has been considered a rich island since antiquity because it was one of the few centers in the Mediterranean for trading obsidian, a hard black volcanic glass prized by Neolithic people for the extremely sharp cutting edges that can be achieved. Throughout its history, Lipari has been conquered and inhabited by Arabs, Normans, Greeks, Romans, Spanish and pirates. Particularly impressive is the old Greek Acropolis overlooking the main town, a mighty fortress still standing today.

Our day will be dedicated to hiking and exploring the island and visiting the main town of Lipari. We’ll also enjoy a wine tasting at Cantina Castellaro. Breathtaking views throughout the day will make this a memorable day. 

[fa icon="plus"] Day 7
Vulcano - 3 hr hike
After breakfast we set off by private boat to explore the island of Vulcano. We will hike up and around its grandiose crater and then experience a scenic lunch onboard and snorkeling in the pristine water. Our captain, Nando, will take us to his favorite corners and will share how life is as a fisherman in the Aeolean Islands. Return to Lipari in the afternoon and free time before dinner.
[fa icon="plus"] Day 8

Taormina - 2 hr walk (optional)

Today we say goodbye to the Aeolean archipelago and head back to the main island of Sicily. Our tour would not be complete without the charming town of Taormina, famous for its medieval alleys and its Greek theater which hosts the most amazing scenographic background in the world: the Sicilian blue coastline and the whole greatness of the Etna volcano. In the 20th century, Taormina became a colony of expatriate artists, writers, and intellectuals, attracted by its mild climate and luscious landscape, who built their magnificent villas around its promontory and helped intensify its reputation as one of the most glamorous towns in Italy.

We’ll offer a cultural walk of town with its elegant buildings and 3rd century BC Greek amphitheater, still in use today for concerts. Farewell dinner and celebrations at the Michelin-starred restaurant housed in our beautiful hotel Ashbee.

[fa icon="plus"] Day 9

After breakfast you will be transferred to the Catania airport according to your travel plans and flight schedule.


What's Included

Bianchi Intenso Ultegra-105

Bianchi Via Nirone SBianchi Via Nirone S

• Two professional tour guides throughout the program

• All accommodations with breakfast

• Hydrofoil ride to Lipari (round-trip)

• Wine and beer with meals, coffee, cappuccino, and gelato stops

• Wine tasting

• Walking tour of Ortigia 

• Cooking demonstration with a local chef

• Logistical support during the tour and luggage transfer

• Hire of volcanology-trekking guide

• Shuttle at the beginning and at the end of the tour

• All activities mentioned in the day-by-day description

• Bianchi bike rental with GPS navigation



• Airfare
Pre-tour hotel stays and post-tour hotel stays
• E-bike upgrade
• Guide gratuity






Mea Lipari


Borgo Hedone Tourissimo Sicily East


Ashbee Taormina Tourissimo Sicily East


More Info

Food and Wine

Sicilian cuisine shows traces of all of the cultures which established themselves on the island over the last two millennia. Although its cuisine has a lot in common with mainland Italian cuisine, Sicilian food also has Greek, Spanish, French and Arab influences. The use of apricots, sugar, citrus, sweet melons, rice, saffron, raisins, nutmeg, clove, pepper, pine nuts, cinnamon (along with fried preparations) is a sign of Arab influences from the Arab domination of Sicily in the 10th and 11th centuries. Normans influences are also found, such as in the fondness for meat dishes. Later, the Spanish introduced numerous items from the New World, including cocoa, corn, peppers, and tomatoes. In Catania, on the east coast, initially settled by Greek colonists, fish, olives, broad beans, pistachio and fresh vegetables are preferred instead. Much of the island's cuisine encourages the use of fresh vegetables such as eggplant, peppers, and tomatoes, and fish such as tuna, cuttlefish, and swordfish. In Trapani, in the extreme western corner of the island, North African influences are clear in the use of couscous. Sicily is a wine-lover's paradise, such is the variety, complexity and abundance of Bacchus' unique gift! There are 23 DOC zones in Sicily: Alcamo,Contea di Sclafani, Contessa Entellina, Delia Nivolelli, Eloro, Erice, Etna, Faro, Malvasia delle Lipari, Mamertino di Milazzo, Marsala, Menfi, Monreale, Moscato di Noto, Moscato di Pantelleria, Passito di Pantelleria, Moscato di Siracusa, Riesi, Salaparuta, Sambuca di Sicilia, Santa Margherita di Belice, Sciacca and Vittoria. Many grape types are grown, used either in purezza (single grape variety wines), or blended. Some have been around for centuries while others are more recent imports. The following are some of the main varieties: red grapes - Nero D’Avola, Nerello Mascalese, Nerello Mantellato, Perricone, Frappato, Calabrese and the more recently introduced Merlot, Cabernet Sauvignon, Cabernet Franc and Shiraz (Syrah); white grapes - Cataratto, Grecanico, Grillo, Inzolia, Zibibbo, Damaschino, Trebbiano, Ausonica, Moscato Bianco, Carricante, Corinto Nero and the more recently introduced Chardonnay, Viognier and Fiano. Sicily has the most Slow Food Presidia (local projects) of all of the Italian regions. That means that the island has lots to offer in terms of gastronomical discoveries ranging from greens and vegetables to cheese and artisanal bread. Among a few that we will experience are Trapani Sea Salt, The Menfi Artichoke and the Belice Vastedda that is Italy’s only stretched-curd sheep’s milk cheese.

Mount Etna

Etna, also known by Sicilians as ‘Mongibello’ (The Beautiful Mountain), is located on the east coast of Sicily, in the province of Catania. It is the highest volcano in Europe at more than 11,000 feet (3,350 meters). It erupts from the four main summit craters, and has an activity which is both effusive (with liquid magma flows) and explosive: not infrequently, it can "spit" dense columns of ash and gas visible even from space satellites, launching the rocks produced by its eruptions into the surrounding areas. For this reason the region is particularly fertile and the cheeses and wines we will savor will confirm that Sicily is a small piece of paradise.


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