Day 1-2 - Athens, Greece

Fly overnight to Athens and transfer to your centrally located hotel. Gather for a short orientation walk in the vibrant Plaka neighborhood, admiring the city’s iconic sites. This evening, get to know your trip leader and fellow travelers at a welcome dinner at a restaurant with views of the Acropolis. (D)

Walking: 1-2 miles over paved city streets

Day 3 - Athens to Naxos

Take an early ferry to Naxos, the largest island in the Cyclades. Arrive in time for lunch at a local restaurant and then set out on a walking tour of the old town, or Chora, with your guide. Filled with architectural gems, the old town reveals layers of history, from the myth-infused sites of the ancient Greeks to the Venetian conquest in the 13th century. Ascend cobbled streets to Kastro, the town’s castle district, once home to the island’s nobility. Learn about local legends and customs as you meander its narrow lanes, and end your walk at the Portara, a massive marble doorway that is all that remains of a sixth-century Temple of Apollo. The site offers a stunning vista of the town and the Aegean Sea beyond. (B, L)

Walking: 1-2 miles over paved and uneven cobblestoned streets

Day 4 - Naxos

Venture into the beautiful interior of Naxos for a hike along the Seven Villages loop trail. Beginning in the village of Kourounochori, head into verdant hills and valleys on paths that weave through the remote villages, passing olive groves and timeless scenes of rural life. Along the trail, stop to admire marble kouros statues that date back to the ancient Greeks, and visit the enchanting ruins of a 17th-century Jesuit monastery. Return to Chora after lunch and enjoy a free afternoon to take a walk to the beach or relax at a waterfront café. (B, L)

Hiking: 7 miles (5-6 hours with stops) on stone and dirt paths, village lanes, and small roads with mild elevation gain.

Day 5 - Santorini

Board a morning ferry to Santorini and transfer to your hotel on arrival. Explore the island on foot, taking in the dramatic vistas of the cliffs topped with whitewashed villages curving along the edge of an immense volcanic caldera. Later, head to Akrotiri beach for a sunset sea-kayaking excursion. Paddle along the island's southern coast toward the famed Red, Kambia, and White beaches while admiring the sunset over the sea. Stop for a picnic of local fruits and snacks along the way. Alternatively, stay on land and hike from Red Beach to the Akrotiri Lighthouse, following a path along the southernmost tip of the island and arriving in time to catch the sunset. (B, L)

Walking: Brief orientation walking tour 

Afternoon Option 1: Hiking: 4 miles (3 hours) on paved or dirt roads with mild elevation gain
Afternoon Option 2: Sea Kayaking: 3 hours

Day 6 - Santorini

Set out on a half-day hike from Fira to Oia, following the cliff on a trail shaped by the caldera itself. Your route affords spectacular views every step of the way, winding through the picturesque villages of Firostefani and Imerovigli, perched high above the sea. Arrive in Oia and take a guided walk before lunch on your own. Later, head to the Akrotiri Archaeological Site to tour its Minoan ruins, which date back to 5,000 BC, with a local expert. Gather tonight for dinner with the group. (B, D)

Hiking: 6-7 miles (4 hours) on paved and dirt roads and village lanes, with a gradual ascent

Day 7 - Santorini to Crete

The morning is yours to explore Santorini at your leisure. After lunch on your own, transfer to the port to catch a ferry to the island of Crete. Arrive in Heraklion by late afternoon and check in to your hotel. In the evening, set off on a culinary walk with a local guide, sampling local specialties at traditional shops and food producers. Taste local made cheeses and honey, learn about the diverse uses and varieties of herbs on the island, and stop in at a bakery to sample pastries such as kalitsounia and ladokouloura. End the tour at a restaurant on the harbor, savoring Cretan seafood dishes accompanied by raki, a traditional Cretan welcome drink. (B, D)

Walking: 2 hours on paved or cobblestoned city streets

Day 8 - Crete

After breakfast, travel to the town of Elounda on the eastern coast. Today’s trail brings you past the Elounda salt pans and along a narrow causeway that separates the Spinalonga Peninsula from the mainland of Crete. Hike along the peninsula’s rugged coast, taking in panoramic views of Crete, before turning inland to explore the hilly interior. Head back to Heraklion with lunch enroute at a local restaurant. During a free afternoon in Heraklion, consider visiting the impressive Heraklion Archeological Museum or the Bronze Age Palace of Knossos. (B, L)

Hiking: 4-5 miles (2.5 hours) on mostly flat dirt and gravel trails

Day 9 - Crete

Embark on a full-day, back-country excursion, exploring Crete by 4x4 jeep and by foot. Immerse yourself in the island’s rich history and culture, exploring traditions and everyday life from the era of the ancient Minoans to today. Your journey begins at sacred Mount Juktas, known in Greek mythology as the resting place of Zeus. Visit the Church of Christ Savior, poised on a rocky outcrop, and take in 360-degree views from the mountaintop. Continue by jeep along country roads and sample its renowned olive oils and wines. Visit one of Europe’s oldest wine presses at the ancient site of Vathypetro and witness how local olive oil has been produced here since 3,500 BC. Learn about Cretan cuisine—and the fresh ingredients that go into it—over a delicious three-course lunch. Then step into a pottery workshop to watch artisans plying their ancient craft. Tonight, toast your Greek Isles adventure at a farewell dinner. (B, L, D)

Hiking: 1-2 miles of short hikes during 6-hour jeep safari

Day 10 - Crete

After breakfast at the hotel, transfer to the airport in time for your flight home. (B)