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 mythical 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 Santoríni 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.


Trip Highlights

  • Climb Mount Zeus, the Cyclades’ highest peak, and hike the soaring cliffs ringing Santoríni’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.


Activity Level: Moderate

This trip is suitable for beginner and expert kayakers; no previous experience is needed. We will be paddling stable, two-person kayaks for an average of 4 hours (6 miles), and will be hiking 3 to 5 hours (up to 5 miles) on moderate to steep grades at low elevations. During hikes, vehicle support is provided at various points. While kayaking, boat support will not be available. Participants always have the option to rest a day.


Itinerary - 9 Days

Day 1 — Athens, Greece
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.
Hotel Divani Acropolis (D)


Day 2 — Athens/Náxos
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. Porto Naxos Hotel (B,L,D)


Day 3 — Exploring 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. Porto Naxos Hotel (B,L,D)


Day 4 — Náxos/Mount Zeus
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 and during our descent, pause for a light lunch. Continue to the ancient stone village of Danakos, then transfer to Apiranthos for a full lunch and 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. (5 miles hiking, 4 hours) Porto Naxos Hotel (B,L,D)


Day 5 — Santoríni
Catch a morning ferry to Santoríni, 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 into 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) Rocabella Santorini Resort and Spa (B,L,D)


Day 6 — Santoríni/Akrotiri
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) Rocabella Santorini Resort and Spa (B,L,D)


Day 7 — Santoríni
Today, launch your kayak from Balos Beach, tracing the inside of the caldera and learning about the island’s geology as we skim beneath the cliffs. Take out at the secluded pebble beach below the village of Megalochori. A short climb brings us to a church carved into the rock face that offers an incredible view of the caldera. After a picnic lunch, paddle back to Balos Beach and enjoy time before dinner to visit a winery for a tasting or explore on your own. (6 miles paddling, 4 hours) Rocabella Santorini Resort and Spa (B,L,D)


Day 8 — Pyrgos/Ancient Thira/Athens
At Santoríni’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 with a local antiquities expert and descend to a nearby beach to swim. Later, fly back to Athens for a farewell dinner. (4–5 miles hiking, 3 hours) Hotel Divani Acropolis (B,L,D)


Day 9 — Athens/U.S.
After breakfast, transfer to the airport for your flight home. (B)



Pricing starts at $6,200 per person, double occupancy. For a single room, add $600. International airfare to/from Athens and airfare within Greece are not included in the adventure cost. The group flight within Greece is approximately $300 (subject to change).

Group Size: 8–16


Solo Travelers

Accommodations (hotels, tents and cruise cabins) are based on double occupancy. If you prefer single accommodations, and if such are available, you can pay a single supplement fee. If you are traveling alone and wish to share accommodations, we can assign a roommate of the same gender. If there is no one with whom you can share, a single supplement fee will apply.


See special terms and conditions for this adventure.

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Group or Custom Journeys

Starting at $6,200 Per Person

Greek Islands Adventure