Whether you've seen them in the movies or simply heard a friend speak about them after returning from holiday, the Greek islands are likely to have flirted with your imagination. With so many gorgeous islands scattered throughout Aegean Sea, you may feel like a kid in a candy shop, unable to choose which ones to try. This trip combines probably the two most beautiful: The spectacular Crete and the precious gem of the Aegean, Santorini.
Your trip starts in Crete. Placed midway between Africa and Europe, Crete is a world unto itself. Landscape and history have collaborated to make it one of the most evocative and multi-faceted of the Greek islands, with a rich tapestry of canyons, mountains and, of course, blissful beaches. Afterwards we take the ferry to the world-famous destination of Santorini. It is dramatic and unique, formed from the remains of a volcanic crater and even the most jaded traveler succumbs to the spectacle of this surreal landscape. During the days that will follow, we will explore the island from one end to the other.


Located in the center of the island, the sprawling city of Heraklion is home to a magnificent archaeological museum and lies just few kilometres from Knossos, the greatest of the Minoan palaces. You will find other reminders of history all over Crete, but the best known are mostly here, near the heart of the island.
In the afternoon we will meet at our hotel and after a brief orientation meeting, we'll set off to explore the old part of this lively city. To conclude the night, we will have our first dinner together in a traditional Cretan restaurant while getting to know each other in eager anticipation of our adventure.

Overnight in Heraklion, Olive Green Hotel (D)

You will start your day visiting the Archaeological museum of Heraklion, with the finest collection of Minoan artifacts in the world, and a brand new setting to do them justice. It's a great introduction to Crete's biggest attraction, the 3500-year-old Minoan palace of Knossos, a sprawling maze of royal chambers, grand staircases, storerooms, and workshops.
After lunch we will head towards the wine country of Heraklion. Locals claim, with some justification, that wine has been being made in the area for four thousand years, probably using grape varieties not far removed from the ones that you are going to try today. Our day ends at the city of Rethymnon, the island's intellectual and cultural capital, which is going to be our base for the next days.

Overnight in Rethymno, Pepi Studios (B,L,D)
Driving distance:

Heraklion to Knossos 5km / 15min
Knossos to Winery 15km / 25min
Winery to Rethymnon 100km / 2hours

Ancient Eleftherna, a Dorian built settlement, lies in the foothills of Psiloritis, the highest mountain of Crete. The Archaeological Institute of America included Eleftherna archaeological site in its top discoveries of 2009. We start our hike from the ancient Acropolis, and on our way we will pass the remarkable Roman cisterns, which are carved into the hill's west side, the Necropolis and a 3rd century BC ancient bridge.
Our hike finishes in the tiny village of Margarites, known for its pottery. Learn about the traditional techniques from a local potter who derives inspiration for his ceramics from Minoan and Byzantine originals.
In the afternoon we will have time to explore the labyrinthine lanes of the historic quarter of Rethymnon which still preserves much of its Venetian and Ottoman appearance.

Overnight in Rethymnon, Pepi Studios (B,L,D)
Hiking distance: 8km / Hiking Duration: 3 hours
Driving distance:
Rethymnon to Ancient Eleftherna 30km / 45min
Margarites to Rethymnon 30km / 40min

To go to Crete without entering a gorge would be a missed opportunity for an incredible experience, and at the southern slopes of White Mountains there is one of the most fascinating.
The pine tree-lined Imbros gorge, is not as famous as Samaria but is in physical terms as impressive and much less crowded. Enjoy this wonderfully quiet walk, narrow and stiflingly confined in places, speckled with caves in others and at one point passing under a monumental natural stone archway. At the end of the gorge we will hop in our bus for a short ride to Frangokastello, a striking 14th century Venetian fortress on a fine stretch of a beach. Here we can wash off the gorge’s dust and enjoy our lunch overlooking the Libyan sea.

Overnight in Rethymnon, Pepi Studios (B,L,D)
Hiking distance: 8km / Hiking Duration: 3 hours
Driving distance:
Rethymnon to Entrance of the gorge  50km / 1h30min
Frangokastello to Rethymnon  50km /1h20min

One of the delights of travelling through Crete is food. The local cuisine has its own distinct identity within Greek cooking and great claims are made for the Cretan diet. After breakfast we will drive toward the quaint village of Vamos for a cooking class which takes place in an old olive press dating from 1846. In a unique setting we will take a ride on a "journey" into the aromas and tastes of traditional Cretan Cuisine.
Early in the afternoon, we will drive to Chania. Littered with remnant from its Turkish and Venetian past and bustling with harbor-side life, Chania is one of the most beautiful towns of Crete. Take a walking tour and enjoy our guide's insight on the history of the area

Overnight in Rethymnon, Pepi Studios (B,L,D)
Hiking distance: 7km / Hiking Duration: 3h 30min
Driving distance:
Rethymnon to Vamos 33km / 40min
Vamos to Chania 30km / 50min
Chania to Rethymnon 60km / 1h 10min

Today we will catch the morning ferry to Santorini which was the site of one of the largest volcanic eruptions of all time. Here everything is brighter: the whitewashed cube-shaped houses, the lapis lazuli sea and the sunsets that light up the caldera.
After settling in our hotel, we will be transferred to the modern capital of the island, Fira. From there, we will hike towards picturesque Oia, the most beautiful village of the island if not the whole Aegean Sea. The cobblestone trail follows the rim of the Caldera, taking you away from the crowds, permitting you to admire the power of the natural forces that shaped this amazing environment.

Overnight in Megalochori, Grand View (B,L,D)
Hiking distance: 10km / Hiking Duration: 4 hours
Driving distance:
Santorini port to Megalochori  5km / 20min
Megalochori to Fira  7km / 15min
Oia to Megalochori  16km / 25min

Dorians, Venetians, and Turks occupied Santorini, but its most influential early inhabitants were Minoans. They came from Crete sometime between 2000 BC and 1600 BC and the settlement of Akrotiri, dubbed as the Greek Pompeii, dates from the peak years of their civilization. Alongside with a guide you will have the opportunity to walk along the streets and squares of the city, which was buried in volcanic ash after the eruption of the volcano and frozen in time.
After the tour, it is time for kayaking. We will explore the south side of the island as few people do. Seeing Santorini from the sea level is a real treat, plus paddling gives your upper body a bit of exercise. We will paddle by the Red and White beach with stops on the way for swimming and snorkeling.

Overnight in Megalochori, Grand View (B,L,D)
Sea kayaking duration: 2 hours
Driving distance:
Megalochori to Akrotiri 5km / 10min
Kayak base to Megalochori 5km / 10min

Medieval Santorini comes to life in the lovely village of Pyrgos, which used to be the capital of the island. Here Cycladic houses blend harmoniously with the Venetian manors and the few remaining old stores. This will be the start of our hike, which takes us to the highest point of Santorini, and from there to the ruins of Ancient Thira, located on a headland between the two popular beaches of Kamari and Perissa with dramatic cliffs plunging into the blue waters of the Mediterranean. The change of scenery will make you feel like you are on a mountain, and you will fully experience the diversity and beauty of this amazing island.

Overnight in Megalochori, Grand View (B,L,D)
Hiking distance: 8km / Hiking Duration: 3 hours
Driving distance:
Megalochori to Pyrgos  3km / 10min
Kamari to Megalochori  8km / 20min

Breakfast is at your leisure at the hotel and following that, your Tripin Adventures trip in Greece concludes. Transfer independently from our accommodations in Santorini to the international airport of the island for return flights home or continue your explorations of this marvelous region of Greece.




  • All accommodations as listed (or similar) based on double occupancy
  • Hotel taxes and service charges
  • All transportation during the trip
  • All activities mentioned in the program
  • Ferry tickets
  • Entrance fees for the Archaeological site of Knossos, the Archeological museum of Heraklion and Akrotiri Archaeological site
  • Tourist guide for the Archaeological site of Knossos, the Archeological museum of Heraklion and Akrotiri Archaeological site
  • Services of a guide throughout the tour
  • A bottle of water per day
  • Transport and handling of one reasonably sized suitcase and one carry-on per person


  • Domestic and/or international air fare
  • Medical expenses
  • Travel or emergency evacuation insurance
  • Gratuities for leader/guide or driver
  • Alcoholic beverages and meals other than outlined in itinerary
  • Visas if needed
  • Transfer to and from the airport/port
  • Other items of a personal nature
  • Anything not mentioned in above program


  • Breakfast
  • Lunches and dinners as indicated in the itinerary
  • Snacks during activities


We are constantly updating our unique itineraries based on new information and experiences available. The walks, accommodations, and visits listed may be adjusted. The itineraries presented are subject to modification and change by Tripin Adventures. We reserve the right, without penalty, to make changes in the published itinerary whenever, in our judgment, conditions warrant, or if we deem it necessary for the comfort, convenience, or safety of participants, anything not mentioned in above program.


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