Our trip begins in Catania, Sicily's second-largest city, situated at the foot of Mount Etna. The city has been repeatedly rebuilt, most notably following the devastating 1693 earthquake that led to its stunning Baroque reconstruction. The city's historic center is a UNESCO World Heritage Site, featuring magnificent black lava stone buildings, the grand Piazza del Duomo with its elephant fountain symbol, and the impressive Cattedrale di Sant'Agata. Must-sees in town include an ancient Roman amphitheater and a vibrant fish market, surrounded by an intriguing and diverse variety of restaurants serving fresh-caught seafood.

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We meet in Catania's historic center at 10:00 am and drive north to Aci Castello on the "Cyclops Riviera," where we paddle the Cyclops Islands, named after the mythical Cyclops from Homer's Odyssey. We paddle the crystal-clear waters around the legendary Faraglioni dei Ciclopi - towering basalt rock formations that, according to myth, were hurled by the blinded Cyclops at the escaping Odysseus. After the paddle, we visit Aci Castello, a charming seaside town famous for its Norman castle, built on a dramatic black volcanic rock outcropping that juts into the Ionian Sea. Rejoining our van, we set off towards imposing Mount Etna. Arriving at our agriturismo on the north slope of the mountain, you will have time to relax before an authentic farm-to-table dinner accompanied by local wines.

Overnight: Il Borgo di Alcantara

Meals: Breakfast, Lunch & Dinner

Today's kayaking begins at Giardini Naxos, the first Greek colony in Sicily. We launch our kayaks from a white-sand beach where Greek triremes landed over 2,700 years ago. Paddling through the clear water toward Isola Bella, the mass of Mount Etna is very much present above us, and ancient Taormina beckons from a hilltop ahead. After landing and lunch, we'll take the funicular up to elegant Taormina and visit its crown jewel, the ancient Greek-Roman Teatro Antico, a magnificently preserved amphitheater with breathtaking views of Mount Etna and the Ionian Sea.

Overnight: Il Borgo di Alcantara

Meals: Breakfast, Lunch & Dinner

After a sumptuous breakfast at the agriturismo, we set off up Mount Etna. After passing through the village of Linguaglossa, we climb through a verdant landscape of pine forest, punctuated by stands of white-trunked Etna birch trees and evidence of historic lava flows, before arriving at Piano Provenzana. Here, we board 4x4 vehicles for a trip up to 2,900 meters, led by volcanological guides. The tour offers short hikes and stunning views of the north craters, the famous Valle del Bove, and the coast beyond. Descending through a stark landscape defined by both old and very recent lava flows, we'll be able to reflect on what would entice someone to live on the side of an active volcano. One answer will become apparent when we arrive at Gambino Vini's tasting room and restaurant for wine tasting and lunch at the vineyard. After lunch, we carry on to our accommodations at a seaside villa outside of Syracuse. Dinner this evening is at a restaurant on one of the medieval streets of Ortigia, an enchanting island that forms the historic heart of Syracuse.

Overnight: Villa Sunset

Meals: Breakfast, Lunch & Dinner

Launching at a sandy river mouth, we'll paddle to old Syracuse and the fortified island of Ortigia. Founded by the Greeks, Syracuse was once a city-state to rival Athens. Kayaking along the city wall, we'll have a chance to stop at a beach, explore the warren of narrow streets, have lunch, and sample a refreshing almond granita before carrying on around the city. The snows of Mount Etna and the sugarcane introduced by the Arabs gave rise to the Sicilian taste for things icy and sweet. After a full day in and around Syracuse, we'll drive to our hotel located near Noto and settle in before another spectacular Sicilian dinner.

Overnight: La Corte del Sole Lido di Noto

Meals: Breakfast, Lunch & Dinner

Starting early at Marzamemi, one of the most beautiful coastal towns in all of Italy, which the Arabs founded in the 10th century, we'll set course south along the shore toward Capo Passero and the town of Portopalo. The broad sandy beaches will allow us to stop for lunch and take a swim along the way. After returning to the hotel, you will have time to relax before taking a sunset walk in the Sicilian Baroque masterpiece of Noto, perhaps accompanied by a glass of the local DOC Nero d'Avola, and then enjoy dinner at a family-run trattoria.

Overnight: La Corte del Sole Lido di Noto

Meals: Breakfast, Lunch & Dinner

Today, we'll have a memorable paddle to the golden sand beaches, rock formations, and caves of Punta Cirica. The area provides excellent opportunities for exploration and relaxation and is regarded as one of Sicily's best "secret" beaches. After lunch, we'll drive to Modica, part of the "The Baroque Route," which, along with much of Catania, was rebuilt in the ornate Sicilian Baroque style following the devastating earthquake in 1693. After exploring the winding streets of this architectural gem, we'll sample some of the chocolate that Modica is famous for. Returning to the hotel, we will enjoy a celebratory Sicilian dinner of locally sourced seafood and produce on the terrace, overlooking the Mediterranean, as the sun sets over the nearby Vendicari nature reserve.

Overnight: La Corte del Sole Lido di Noto

Meals: Breakfast, Lunch & Dinner

After breakfast, we will return to Catania, arriving by 11:00 am, with drop-offs available at both the airport and train station. Arrivederci!

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Meals: Breakfast

Tofino Expeditions was the highest rated sea kayaking adventure travel company in a National Geographic Adventure survey of international outfitters based on:

• Quality of Service
• Education
• Sustainability
• Spirit of Adventure