Island Inspiration

Experience Cyclades with Erin Outdoors


The Cycladic islands are the prototypical Greek islands. White-washed houses, turquoise blue seas, olive groves and sun-drenched landscapes. It is here where man lived in harmony with the environment for thousands of years. We believe that island hopping is the best way to connect with this past and get to know the islands, each of them stamped with its own unique character.
The trip starts in Athens, and after visiting the Acropolis and the new Acropolis museum, we will hop in our ferry to Naxos, the biggest and one of the most beautiful islands of the Cyclades, if one can be in position to choose. It is an island with dramatic landscape changes, Venetian castles and traditional villages perched on the cliffs of its mountains.
Our next stop is Santorini. Photos of vibrant blue waters overlooked by whitewashed stone homes nestled above multicolored cliffs are constantly fueling wanderlust around the world, and we’ll be right in the middle of it! Not only is this trip full of adventure, but nightly group sessions ensure that our time together helps us grow as individuals as well. We will leave Greece refreshed, grateful, and ready to take on the challenges in our lives.




Often referred to as the cradle of Western civilization, Athens has been continually occupied by people for the last 7,000 years. You can't move without bumping into an ancient ruin or building, which evokes imagery of the Greek gods or the thoughts of their philosophers.
In the afternoon, we will meet at our hotel for an introductory talk and after a walk around Plaka, the oldest neighborhood of Athens, we will have our first dinner together in a traditional restaurant. Of course, Greek cuisine will play a starring role on our trip!

Overnight in Athens, Athenian Callirhoe (D)

No matter how many photographs you’ve seen, nothing can prepare you for seeing the Acropolis in person, still standing after thousands of years. Alongside a specialized guide, you will explore the site and afterwards we will head towards the long-awaited Acropolis museum.
Early in the afternoon, we will drive to the port of Piraeus and from there we will take the ferry to Naxos. As the ferry arcs toward the island, you catch the first glimpse of the Portara, a marble gateway on the headland, all that remains of an ancient temple to Apollo. This is just the beginning of our adventure here.

Overnight in Naxos, Naxos Beach Hotel (B,L,D)
Driving distance:

Athens center to Piraeus port 10km / 25min
Piraeus port to Naxos 17:30-22:45

Our first hike starts, right next to the place where the two “small” Kouroi (male statues) of Naxos lay down, for 2600 years now. We will continue on to the Upper Castle, the former Venetian stronghold, passing olive groves interspersed with elements of the phrygana and maquis, and we will end up in one of the most beautiful villages of the island, Chalki.
In the afternoon, we’ll set off to explore the old town of Naxos which is regarded to be one of the most beautiful towns in the Cyclades, particularly popular for its fine architecture that is composed of Venetian and Cycladic elements.

Overnight in Naxos, Naxos Beach Hotel (B,L,D)
Hiking distance:
7km / Hiking Duration: 3 hours
Driving distance:

Naxos town to Kouros statue 10km / 30min
Chalki to Naxos town 16km / 40min
Tinos to Naxos 10:55-13:15

The island is home to the highest mountain in the Cyclades, Mount Zeus. The mountain and the hike to the top of it is  the most epic one in the region. Mount Zeus has important historical significance because in ancient times, the local Greeks believed that the cave on the northwest side of the mountain was the birthplace of the god Zeus. When climbing it, you'll get the distinct feeling that Greek mythology is actually rooted in reality. After the hike, we will go for lunch in one of the most beautiful villages of the island, Apiranthos, which seems to grow out of the stony mountains.
In the afternoon, take a swim in the gorgeous sandy beach in front of our hotel. Swimming in the Aegean after a hike helps the body feel refreshed again.

Overnight in Naxos, Naxos Beach Hotel (B,L,D)
Hiking distance: 5km / Hiking Duration: 3 hours
Driving distance:
Naxos town to Agia Marina 23km / 50min
Agia Marina to Apiranthos 5km / 15min
Apiranthos to Naxos town 26km / 55min

Santorini will take your breath away. It is dramatic and unique, formed from the remains of a volcanic crater. In the morning we will catch the ferry there, and after settling into our hotel we will hike the picturesque trail between Fira and Oia, one of the best things to do on the islands. With breathtaking views and stunning vistas at every turn, the trail is guaranteed to be one of the prettiest you’ve ever hiked.

Overnight in Santorini, Fenix Collection (B,L,D)
Hiking distance:
10 km / Hiking Duration: 3h 30min
Driving distance:
Santorini Port to Fira town 8km / 25min
Oia to Fira town 10km / 20min
Naxos to Santorini 11:00-12:20

In the morning we will head towards Akrotiri, Santorini’s principal archaeological wonder: a town preserved under layers of lava. There we will enjoy our guide’s insight on the history of the area. Right afterwards, we will put on our bathing suits and sea kayak into one of the most scenic areas of the island. Kayaking offers a wonderful way to explore the dramatic coastline of Santorini– expect high red cliffs and smooth pebbles under clear water. In the afternoon we will have time to stroll in Fira town before our farewell dinner overlooking the Caldera

Overnight in Santorini, Fenix Collection (B,L,D)
Sea kayaking duration:
2 hours
Driving distance:
Fira to Akrotiri 12km / 20min
Akrotiri to Imerovigli 12km / 20min

Hopefully with a slight sense of nostalgia which comes when a nice experience has to come to an end, here your trip with Tripin Adventures 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.




Erin Sullivan, aka Erin Outdoors, is an adventure guide turned blogger and photographer. After spending six years as a wilderness and adventure travel guide worldwide, Erin turned her experiences into a blog with the goal of helping people to find adventure in their own lives. Erin connects with thousands of people online every day through her writing and photography, centered around personal development and living with purpose. She is thrilled to invite you on a journey of exploration, growth, and self-discovery.


Having already been to more than forty countries with his backpack, travelling is a way of life for him and although he studied to be an engineer, he decided that sharing his passion with others is much more vital, because interacting with people has always been an inspiration. He loves the outdoors, especially rock climbing and hiking and when he is not guiding he is probably off somewhere on his bike.
He worked as a guide for 10 years, leading trips for the largest companies of the world such as National Geographic and Mt Sobek, received the prestigious REI Top Guide Award for 2013 and actively designed adventure trips throughout Greece. Establishing his own adventure travel company was simply the next step, because showing people, Greece off the beaten track, is his dream job...


I met Dimitris in the summer of 2012. I was leading a 3-week trip in Greece for teenagers, and Dimitris was our Greek guide. It was one of those things that feels random at the time, but I can tell you now that I was extremely lucky to meet him! In fact, Dimitris is the subject of one of my first blog posts. I'll give you a summary. We were floating in the Adriatic sea while the kids had some free time. I was 22 and newly graduated from college, and I felt really insecure about my decision to be a guide for the summer. I didn't know where I was going from there, and sure, while that was a fun job, I didn't have a sense of direction. I told Dimitris I probably would have to go home and find a "real job." Dimitris looked surprised. He asked me, "Is this not a real job? Is this not your real LIFE?!" And I never looked back. Yes, this is real life. I hope you can join us.



  • 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 to the Acropolis archaeological site and the Acropolis museum
  • Entrance fees to the Akrotiri archaeological site
  • Tourist guide for the archaeological sites of Acropolis and Akrotiri and for the Acropolis museum
  • Services of a guide throughout the tour
  • Transport and handling of one reasonably sized suitcase and one carry-on per person


  • Domestic and/or international air fare
  • Medical expenses
  • Transfer to and from the airport/port
  • Travel or emergency evacuation insurance
  • Gratuities for leader/guide or driver
  • Alcoholic beverages and meals other than outlined in itinerary
  • Visas if needed
  • Other items of a personal nature
  • Αnything 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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