- Climb Mount Zeus, the Cyclades’ highest peak, and hike the soaring cliffs ringing Santorini’s caldera.
- Set sail from Náxos on a day-long sailing excursion, and anchor at secluded beaches and inlets.
- Explore whitewashed villages and volcanic seascapes while kayaking the length of Santoríni’s western coast.
- Trace the history of legendary civilizations at the Acropolis in Athens and ancient Thira on Santoríni.
Situated amid the sparkling Aegean, the Cyclades captivate with whitewashed villages, ancient ruins, and craggy hillsides that give way to idyllic beaches. Take to the seas and the trails to experience Greece's mythic islands on a unique adventure. On lush Náxos, spend an exhilarating day sailing to remote beaches and bays, and hike to the highest peak in the Cyclades. Then journey to Santorini to explore the island’s remarkable geological features and timeless villages on a variety of kayaking and hiking excursions. Paddle to crimson-colored volcanic beaches, hike along soaring cliffs, and step back in time amid fascinating archaeological ruins.
Arrive in Athens and meet up in the evening for a guided walk through the city. Later, kick off our adventure with dinner at a traditional Greek tavern in the historic Plaka neighborhood.
Spend the morning at the hilltop complex of the Acropolis, perhaps the greatest ancient monument of the Western world. Explore the Parthenon, built in honor of the goddess Athena, and the New Acropolis Museum. Visit the Panathenaic Stadium, where the first modern Olympic games were held in 1896. This afternoon, travel by high-speed boat to the lush island of Náxos, the largest of the Cyclades.
Take to the sea this morning on a sailing excursion, and explore the secluded beaches for which the Cyclades are known. Depending on conditions, we may set a course for the tiny, rugged islands of the eastern Cyclades or the sheltered coves and sea caves along Náxos’s southern coast. Try your hand at trimming the sails while honing your nautical skills, and drop anchor to swim in crystal-clear waters. Have a picnic lunch on shore.
Today’s hike begins at the foot of Mount Zeus (3,290 feet), the highest mountain in the Cyclades. Set out from the chapel of Agia Marina, following a trail past ancient stone walls and olive groves to the rocky summit. Take in spectacular views during our descent, then transfer to Apiranthos for a free afternoon to explore the village. Take an evening stroll through Náxos Town, crowned by a medieval castle from which the Venetians controlled these islands for centuries. (4 miles hiking, 4 hours)
Catch a morning ferry to Santorini, an archipelago formed from a volcanic cone that erupted in the second millennium B.C., burying the island's Minoan culture and possibly inspiring the legend of Atlantis. After checking in to our hotel and having lunch, embark on a spectacular hike along the rim of the caldera, ringed by soaring cliffs that overlook the cobalt sea below. Beginning just north of Fira, follow the trail to the blue-domed village of Oia, which cascades down a craggy hillside. Explore the town’s mazelike alleyways and take in the island sunset. (5 miles hiking, 3 hours)
Gear up for a leisurely kayak excursion today. After an introductory lesson for beginners, set out from Akrotiri Beach and round the dramatic white crags on the island’s southwest coast. Stop to snorkel at Kambia Beach within view of the crimson cliffs of Red Beach, and then return to Akrotiri for lunch at a seaside taverna. This afternoon, venture into the ruins of ancient Akrotiri, an important Minoan Bronze Age settlement that was buried by volcanic ash around 1450 B.C. In the company of a local guide, examine frescoes and buildings that were remarkably well preserved by the volcanic ash. (6 miles paddling, 4 hours)
Today’s kayaking route gives us the opportunity to visit unique black lava caves and the southern lighthouse of the island—known as Fanari. We then enter the famous Santorinian caldera and paddle towards one of few caldera beaches. After time to snorkel and relax on the beach, we will enjoy a full picnic lunch looking out over the volcanic islands, Thirassia, and the cities of Fira and Oia. After lunch, we will paddle back in time to visit a winery for a tasting or explore on your own before dinner. (6 miles paddling, 4 hours)
At Santorini’s former capital of Pyrgos, explore labyrinthine streets encircling the ruins of a Venetian castle. Then hike to the island’s highest peak, Profítis Ilías (1,857 feet), home to an 18th-century monastery of the same name. Continue on foot to ancient Thira, a fascinating cluster of Hellenistic, Roman, and Byzantine ruins set on a rocky promontory high above the sea. Explore the site and then transfer to a nearby beach to swim. Later, fly back to Athens for a farewell dinner. (4–5 miles hiking, 3 hours)
After breakfast, transfer to the airport for your flight home.