Island hopping through the Dodecanese

GENERAL INFO

Scattered across the southeastern Aegean, the Dodecanese form a remarkable chain of islands stretching along the coast of Turkey. Although they share a common history, each island has developed its own distinctive personality. Ancient ruins, Byzantine churches, medieval castles and Italian architecture tell the story of centuries of changing rulers, while traditional villages and quiet harbors still preserve the relaxed rhythm of island life.
Our journey takes us across some of the most fascinating islands in this corner of Greece, traveling by ferry and using each island as a base for exploration. We’ll begin with three nights on Kos, combining cultural discoveries and hikes with a full-day excursion to the volcanic island of Nisyros. From Kos, we’ll continue to Tilos for one night, spending an afternoon exploring its rugged landscape and abandoned medieval settlement before continuing on to Rhodes.
We’ll finish with three nights on Rhodes, beginning with a walk through its atmospheric medieval Old Town, one of the best-preserved medieval cities in Europe. From there, we’ll take a ferry to nearby Symi, one of the most picturesque islands of the Dodecanese, known for its colorful neoclassical harbor and crystal-clear waters. We’ll round out our time on Rhodes with a day of sea kayaking, exploring the island’s beautiful coastline from the water.
Along the way, there will be plenty of opportunities to walk, swim, explore and, of course, eat well. Rather than simply ticking off islands, this trip is about experiencing the different faces of the Dodecanese, from volcanic landscapes and mountain trails to turquoise waters, lively harbors and ancient sites, and enjoying the journey between them.

DAILY ITINERARY

Kos, the third largest island of the Dodecanese after Rhodes, is a fascinating blend of ancient history and more recent influences. Its harbor is dominated by the imposing Castle of the Knights of St. John, while in the town, Ottoman mosques stand alongside austere Italian buildings from the fascist period, and extensive Hellenistic and Roman remains lie scattered among the public gardens.
In the afternoon, we will meet at our hotel for an introductory talk before setting out on foot to explore the town and discover some of its fascinating history. We’ll then head to dinner, where Greek cuisine will take center stage. Of course, we have spent many hours sampling countless delicacies while researching this important aspect of the trip, and tonight we’ll put that research to good use over our welcome dinner!

Overnight in Kos in a boutique hotel
Dinner included

The tiny, round island of Nisyros is one of the most fascinating islands of the Dodecanese and a UNESCO Global Geopark, recognized for its exceptional volcanic landscape and geological heritage. With just four villages, Mandraki and Pali on the coast, and Emporeio and Nikia perched on the slopes of the volcano’s caldera, it feels worlds away from the larger islands.
In the morning, we’ll take a boat from Kos to Nisyros and, upon arrival, transfer to the whitewashed village of Nikia, perched dramatically on the edge of the island’s 4-km-wide caldera. From here, we’ll hike down towards the floor of the caldera and into Stefanos Crater, the largest and most impressive of Nisyros’ volcanic craters. Walking inside an active volcanic crater is a truly unique experience; with its steaming vents, barren landscape and striking mineral colors, the scenery feels almost otherworldly.
After exploring Stefanos Crater, we’ll drive back to Mandraki, the island’s charming main village. Here, we’ll take some time to explore its narrow streets, traditional whitewashed houses and waterfront before sitting down for lunch at a local taverna. After lunch, we’ll return to the port and catch the boat back to Kos, arriving in the afternoon.

Overnight in Kos in a boutique hotel
Breakfast and lunch included
Hiking distance:
4km / Hiking Duration: 2 hr
Elevation loss: 
260 m
Driving Distance:
Kos to Kardamaina 28 km / 40 min
Kardamaina to Kos 28 km / 40 min
Ferry:
Kos to Nisyros 9:00-10:00
Nisyros to Kos 15:30-16:30

Today we leave the coast behind and head into the mountains to explore the wild side of Kos. Our hike begins near the picturesque mountain village of Zia, the highest village on the island, surrounded by pine forests and offering wonderful views across the Aegean. From here, we follow a mountain trail through fragrant pine and oak woodland, gradually climbing higher towards the summit of Mount Dikaios, the highest point on Kos at 846 meters.
As we gain elevation, the landscape opens up and the views stretch across the island and, on a clear day, towards the neighboring islands and the coast of Turkey. Near the summit, the trail becomes more rugged as we make our way towards the small chapel of Christos, perched just below the highest point. After taking some time to enjoy the spectacular panorama, we descend back towards Zia, where we’ll stop for lunch and enjoy some well-earned local specialties before returning to our hotel in Kos.

Overnight in Kos in a boutique hotel
Breakfast, lunch and dinner included
Hiking distance:
7,1 km / Hiking Duration: 4 hr
Elevation gain & loss:
480 m & 480 m
Driving Distance:
Kos to Zia 15 km / 30 min
Zia to Kos 15 km / 30 min

In the morning we take the ferry from Kos to Tilos, one of the smallest and least inhabited islands of the Dodecanese. Upon arrival, we’ll have a hike through the island’s rugged and peaceful interior. We walk along old stone paths and ancient terraces, surrounded by olive and carob trees, as the trail winds its way towards the abandoned medieval settlement of Mikro Chorio. Once home to around 220 houses, the village is now a haunting collection of impressive stone ruins, with old threshing circles, olive-pressing stones and cisterns still bearing witness to Tilos’ intense agricultural past. As the afternoon light falls across the deserted settlement and the surrounding hills, it is easy to imagine the village as it once was. After our hike, we return to the coast and enjoy a well-deserved dinner before spending the night on Tilos.

Overnight in Tilos in a boutique hotel
Breakfast and dinner included
Hiking distance:
8 km / Hiking Duration: 3 hr
Elevation gain & loss: 350 m & 350 m
Ferry:
Kos to Tilos 7:30-10:30

After breakfast, we will take the ferry from Tilos to the island of Rhodes, the fourth largest island in Greece and the historic capital of the Dodecanese, where Byzantines, Venetians, Turks and Greeks have all left their mark. Upon arrival, we’ll check into our hotel and have some time to relax and settle in before heading out in the afternoon to explore the magnificent medieval town of Rhodes. A UNESCO World Heritage Site and one of the largest and best-preserved medieval settlements in Europe, the Old Town is a maze of atmospheric cobbled streets, imposing fortifications and remarkable historic buildings.

Overnight in Rhodes in a boutique hotel
Breakfast, lunch and dinner included
Ferry:

Tilos to Rhodes 10:40-14:40

Today we take the ferry from Rhodes to the enchanting island of Symi. The first sight of Gialos harbor is unforgettable, with its two-story, pastel-colored neoclassical houses rising amphitheatrically from the water and covering the surrounding hillsides.
We’ll explore the picturesque town on foot, wandering through its narrow streets and discovering the island’s distinctive architecture and maritime heritage and from there we will hike to Emporeios to meet a local family for a very special cooking experience. Here, we’ll step back in time and experience the warmth of Greek hospitality while learning the secrets of traditional Symian cuisine. Our hosts will share family recipes as well as stories of island life and their family’s long connection with sponge diving and shipping, two industries that played an important role in Symi’s history. Together, we’ll prepare traditional dishes such as tzatziki, stuffed tomatoes and spinach pie, before sitting down to enjoy the fruits of our work over a delicious homemade lunch.

Overnight in Rhodes in a boutique hotel
Breakfast and lunch included
Hiking distance:
8 km / Hiking Duration: 3 hr
Ferry:
Rhodes to Symi 8:00-9:40
Symi to Rhodes 17:40-19:00

Today we discover the beautiful east coast of Rhodes from a completely different perspective! We’ll set out by sea kayak from Kathara Beach in Faliraki, paddling along a spectacular stretch of coastline dotted with secluded beaches, dramatic rock formations and hidden sea caves. Our route takes us past some of the island’s most beautiful coastal spots, including Anthony Quinn’s Bay, Ladiko and Traounou Beach. Along the way, we’ll have plenty of opportunities to explore the caves, swim and snorkel in the crystal-clear Aegean waters, and enjoy the peaceful feeling of being away from the crowds. We’ll stop at a secluded beach for a traditional homemade Greek picnic before paddling back along the coast to Faliraki.

Overnight in Rhodes in a boutique hotel
Breakfast, lunch and dinner included
Paddling distance:
9 km / Paddling Duration: 4 hr
Driving Distance:
Rhodes town to Faliraki 15 km / 25 min
Faliraki to Rhodes town 15 km / 25 min

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. Continue independently and spend some days in Rhodes, or return to Athens to catch your flight home.

Breakfast included

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WHAT'S INCLUDED

PRICE INCLUDES

  • All accommodations based on double occupancy
  • Hotel taxes and service charges
  • All transportation during the trip
  • All activities mentioned in the program
  • Entrance fees to the Grand Master's Palace of Rhodes
  • Tourist guide for the city tour of Rhodes town
  • Services of a guide throughout the tour
  • Ferry tickets
  • Transport and handling of one reasonably sized suitcase and one carry-on per person

NOT INCLUDED

  • 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

INCLUDED MEALS

  • Breakfast
  • Lunches and dinners as indicated in the itinerary

ITINERARY CHANGES

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.

TRIP NOTES

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