Discover Greek Islands – Santorini & Crete
9 days
From $ 4599
Duration9 days

Immerse yourself in culture, must-see sights and plenty of relaxation on this 9-day Grecian adventure. Santorini and Crete truly embody some of Greece’s finest aspects—culture, cuisine, coast, countryside and all-encompassing, awe-inspiring beauty. This trip provides the perfect balance between relaxation and activity. Hike, kayak and swim; no matter your mode of travel, Greece is a destination that never stops giving. We’ll experience each moment through the eyes of local guides and alongside similarly adventure-loving travelers. See Santorini by sea, then kayak the Cretan coast, stopping to dip your toes in the sand or float in warm, clear waters. Hike along a crater’s edge with unbelievable sea views and winding coastal paths. Take in the sun-soaked countryside and expansive fields of olive groves and grapevines. Sample local wines and fresh cuisine while picking up some culinary pointers in a Greek cooking class. Enjoy the perfect blend of rewarding activity and sublime relaxation on this multisport adventure to two of Greece’s most beautiful islands, taking unforgettable memories and great friendships back home with you. This is a great trip for adults and fit, older teens. If you're traveling with younger children, check out our Greek Islands Family Adventure.

This tour is operated by

  • Duration: 9 days
    Service level: Standard
  • Physical Grading: Light
  • Ages: 18+
Discover Greek Islands – Santorini & Crete - Tour Map


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Day 1: Welcome to Santorini! Enjoy an afternoon walk and local wine.
Arrive in Santorini, Greece, and meet at our host hotel by 3pm. After introductions we transfer to a local winery near Oia to learn about wines made from grapes grown in Santorini's volcanic soil. We see the unique grapevine cultivation process of weaving the vines into baskets to capture the air’s humidity for water. We sample local, award-winning wines and enjoy mezze, small plates of local cuisine. We transfer to a restaurant with sweeping caldera views for dinner and return to our hotel. Afternoon snack and dinner included.
Meals: D
Day 2: Hike Santorini’s iconic crater rim and spend an evening at sea.
We set out for Oia along the Santorini volcanic crater rim. The trail is set high above the sea and follows the edge of the caldera, rewarding us with extraordinary views. There is free time in Oia to enjoy lunch on your own and soak in the atmosphere. Later this afternoon we board a boat at Ammoudi Bay to explore the beauty of the island from the sea. We follow the steep coastline of the caldera past Armeni Bay and the church of Efta Paides. A warm-water swim at the volcanic hot springs of Palaia Kammeni is followed by a freshly prepared dinner onboard. We continue our cruise as daylight fades into a colorful, dramatic sunset. Breakfast and dinner included.
Hiking: 6.6 miles, 4.5 hours, elevation gain 1,100'/ loss 1,800'; Boat tour: 5 hours with stops.
Meals: D
Day 3: Explore ancient Akrotiri and a nearby beach, then ferry to Crete.
We tour a former tomato factory and make our own tomato paste for a hands on taste of agrarian life on Santorini. From there, we hike along the beach between lapping waves and towering cliffs of stunning volcanic ash formations. Turning uphill on a coastal path, we reach vistas of the countryside before descending to a black sand beach. Dorians, Venetians and Turks occupied Santorini, but its most influential inhabitants were the Minoans that lived here in 3000 BC. Akrotiri, known as the Greek Pompeii, became a flourishing Mediterranean trading center before its abrupt destruction by the volcanic eruption. After lunch, we tour the streets and squares of the city, which were buried in volcanic ash and frozen in time. Later this afternoon we say goodbye to Santorini and board our high-speed ferry to Crete. We arrive in Heraklion, transfer to our accommodations and enjoy our first Cretan dinner. All meals included.
Hiking: 3.1 miles, 2 hours, elevation gain 250'/ loss 250'; Ferry: 2 hours.
Meals: B, L, D
Day 4: Discover the Cretan countryside and visit Knossos Palace.
A visit to the archaeological museum of Heraklion showcases finds from all over Crete, spanning 5,500 years of the island’s history. Next, we transfer to Crete’s most important wine-making region, hiking along charming villages, vineyards and olive groves. We start in Houdetsi, a Middle Eastern music pilgrimage site, and hike the Spiliotissa valley. The well-maintained trail passes through dense vegetation and a series of byzantine churches. Inside the valley, we encounter the monastery of Panagia Spiliotissa, built partly into a cave. We complete our hike in the 15th century village of Agios Vasileios and transfer to Lyrarakis, one of Crete’s best wineries, where we enjoy a vineyard tour, wine tasting and lunch. In the evening we visit the archaeological site of Knossos. Knossos is considered Europe’s oldest city and the site of King Minos' mythological labyrinth. The rest of the evening is free to see the sights in Heraklion and dine on your own. Breakfast and lunch included.
Hiking: 1.1 miles, 1 hour, elevation gain 70'/ loss 350'.
Meals: B, L
Day 5: Kayak along the spectacular Cretan southern shore.
Early in the morning we head towards the rugged southern part of Crete, passing through mountains and ending at panoramic views of the Libyan Sea. We arrive in Chora Sfakion and set out in our sea kayaks to explore one of the most protected and stunning areas in Crete. Paddling the clear blue Mediterranean waters to Sweetwater Beach, we discover sea caves and admire the spectacular coastline. After a relaxing beachside lunch, we continue our paddle to Loutro. The village lays in the embrace of a cliff which towers nearly 2,000 feet above its inhabitants. Loutro is unique in that it is accessible only by small boat or foot and contains eye-catching white buildings with blue shuttered windows, all just feet from the calm water’s edge. We settle into our hotel and later this evening enjoy dinner at a local restaurant. All meals included.
Kayaking: 5 miles, 2.5 hours; Transfer: 3 hours with stop.
Meals: B, L, D
Day 6: Hike a scenic coastal path; take a refreshing swim in the sea.
Our hike follows the scenic E4 Coastal Trail. From Loutro we reach castle ruins perched on the hillside and a sweeping view of the sea. Ringing bells reveal nearby goat herds as we continue through small settlements and along the rugged, rocky coastline. We arrive at the entrance of Aradena Gorge and enter, experiencing vertical cliff walls surrounding a rocky footpath and rare indigenous plants. We return to Marmara Beach, which means “marbles” and refers to the marble sea caves located next to the beach. The stones’ minerals lend the water an incredible hue, from turquoise to emerald green. We have free time to enjoy the beach and swim, exploring the sea caves in calm winds. We enjoy lunch at a taverna overlooking the beach and return by boat to our hotel in Loutro. The rest of the afternoon and dinner is free for you to explore on your own. Breakfast and lunch included.
Hiking: 3.3 miles, 2.5 hours, elevation gain 720'/ loss 720'; Swimming/beach time: 1.5 hours.
Meals: B, L
Day 7: Cruise along stunning gorges and beaches; hike the Agia Irini Gorge.
We travel by private boat early this morning to Sougia, with views of immense gorges and tranquil beaches. We begin our hike into the Agia Irini Gorge, renowned for its biodiversity. As we descend into the gorge, we see an amazing array of trees, brush woods, fine herbs and perhaps even endangered wild goats and Cretan vultures. In this historically significant area, we listen to our guides’ tales of rebels’ narrow escapes. Emerging from the gorge, we transfer to Chania with a stop for lunch in a small mountain village. This evening, settle into our hotel and enjoy a city walking tour before another wonderful dinner together. All meals included.
Hiking: 4.7 miles, 3.25 hours, elevation gain 300'/ loss 1700'; City walking tour: 1.6 miles, 1.25 hours; Transfers: 2.75 hours; Cruise: 1 hour.
Meals: B, L, D
Day 8: Enjoy the tranquil waters of Balos Beach and a Greek cooking class.
We set out early this morning to visit the iconic lagoon of Balos Beach. Balos is famous for its turquoise waters and pink sands, the hue derived from broken coral raised from the seabed by ancient tectonic activity. We time our visit to relax and swim without the crowds that come later in the day. After a sun-and-sand-filled morning, we return to Chania for a free afternoon. Later in the day, we transfer to the picturesque settlement of Litsarda. Among olive trees and an organic farm, we have a traditional Greek cooking lesson and dine on our edible accomplishments. Our farewell celebration is accompanied by live local folk music. Breakfast and dinner included.
Hiking: 1.8 miles, 1 hour, elevation gain 550'/ loss 550'; Swimming/beach time: 1.5 hours; Transfers: 4 hours.
Meals: D
Day 9: Free time to explore the Venetian town of Chania before departing.
The trip concludes after breakfast at our hotel. Schedule your departing flight any time this day or continue to explore Greece on your own. Breakfast included.
Meals: B



  • Accommodations and meals as noted in the itinerary
  • skilled bi-lingual guides
  • all kayaking gear
  • island ferry
  • two wine tastings
  • Akrotiri, Archaeological Museum of Heraklion and Knossos Palace entrance fees
  • Accommodation

    Hotels, 8 nights

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