The Dodecanese trio of Rhodes, Symi and Tilos encompass everything that people love about the Greek islands: picturesque hikes, towns shaped through the centuries, and, of course, a deep love for food and wine. Guided by an expert tour leader, we explore it all on a well-balanced hiking adventure, taking gentle coastal and in-land trials and going deep into the local culture. There’s also time for a guided wine-tasting session, a barbecue on a traditional kaiki cruise, and plenty of moments to relax on the beach or choose your own adventure.
Activity Areas
Coastal Walks
New Walking Holidays
Walking & Trekking
Region & Country & City
Europe: Greece, Greek Islands
Included in the Price
— All breakfasts, four lunches
— All accommodation
— All transport and listed activities
— Tour leader throughout
— Group arrival and departure transfers available
Not Included In The Price
— Travel insurance
— Single accommodation (available on request)
— Visas or vaccinations
— Tourist tax (paid locally)
Accommodation Information
— Accommodation: 7 Classic nights (hotels)
— Travel by public transport, boat/ferry, and minibus
Map
Itinerary
Day 1 Adventure starts in Rhodes
Our adventure begins in Rhodes, the largest of the Dodecanese islands.
Around 6pm, say yassou (hello) to your tour leader and fellow travellers, when we gather as a group for the first time to get to know each other and learn more about the adventures ahead.
Your tour leader then ensures a big Greek welcome by arranging an optional group dinner at a nearby restaurant (this will be included for all in 2026).
Want to explore Rhodes further? Secure pre-tour hotel nights through your sales representative.
Accommodation: STAY Hotel (or similar)
Day 2 Discover traditional Greek foods and enjoy a wine-tasting experience in Apollona
Dive deep into Greek culture, food and wine in the traditional hillside village of Apollona.
First on the list is Apolloniatisses, an entrepreneurial co-op where local women preserve local recipes and delicacies such as melekouni, an energy bar made of honey, sesame and cinnamon.
Then, we continue our exploration of Greek food and drink with a visit to a winery, where we sample six different wines, all produced from locally grown grapes. Later, we learn how to cook various Greek and Rhodian dishes and, of course, enjoy our creations!
Finally, we taste traditional Greek coffee in a historic kafenio (café).
The afternoon is free to explore Rhodes town, go for a swim or relax under the Rhodian sun. Other optional excursions include an e-bike tour, sea kayaking, visit to the Old or New Town, or an exploration of Lindos, a hillside village of whitewashed houses, crowned by a clifftop acropolis.
Accommodation: STAY Hotel (or similar)
Day 3 Ferry to Symi • Hike up the Kali Strata to Chorio
Checkout and take the fast ferry to Symi, known as the Princess of the Dodecanese. Here, brightly decorated houses wrap around Gialos Bay, providing a picturesque view.
To discover the secrets of Symi, we walk through Gialos town towards Pedi village, hiking up the Kali Strata, a unique staircase leading to the upper village of Chorio, which is known for its beautiful aristocratic mansions. Our hotel is on Pedi Beach, a quiet bay, ideal for relaxing moments and unforgettable sunrises.
The afternoon is free to explore Symi town, swim, visit a local museum or relax on the beach.
Accommodation: Pedi Beach Hotel or Niriides Hotel (or similar)
Day 4 Pine forest hike • Board a traditional kaiki for a barbecue and cruise
Take a bus from Pedi to the 15th-century Roukouniotis Monastery, which we explore before beginning our hike. Our trail takes us through a pine forest of aromatic herbs and small chapels to sea level, where Saint Emilianos Church overlooks the Turkish coastline.
There’s time to swim in the refreshing Aegean waters and enjoy a barbecue lunch with Greek mezedes on a kaiki, a traditional wooden boat. The captain and crew will have the meal ready and later take you on a scenic cruise back to the hotel.
Accommodation: Pedi Beach Hotel or Niriides Hotel (or similar)
Day 5 To Tilos • Coastal hike and exploration of the Mikro Chorio ghost village
Say goodbye to Symi and set off for Tilos on a short ferry ride. Dropping luggage at the hotel, we hike a trail which starts from the beautiful seaside village of Livadia and leads us along the coastline to lovely beaches, including one with red sand.
Reaching the tree-lined Lethra Beach, we begin the ascent towards Mikro Chorio (meaning small village). Once highly populated, it is now deserted. The houses remain along with narrow alleys, green courtyards and the few present inhabitants: goats.
During summer, a bar operates here, and you can stroll around this unique ‘ghost’ settlement. After, we start our descent back to our starting point, Livadia.
The afternoon is free to enjoy this seaside village, perhaps relaxing on the beach.
Accommodation: Irini Hotel (or similar)
Day 6 Hike to Megalo Chorio, the capital of Tilos
We start at Agios Panteleimonas, a monastery built by a sailor in 1531 to honour the saint who saved him from a shipwreck. It stands imposingly on top of a mountain slope, surrounded by maple trees, a juxtaposition to the harsh surroundings.
Our hike starts on the outskirts of the monastery and leads to the small harbour of Agios Antonios, which has fantastic views of the nearby volcanic island of Nisiros.
After, we ascend to Megalo Chorio (big village), the capital of Tilos. Built under the protection of a medieval castle, it overlooks Eristos, the biggest beach on the island.
The afternoon is free to enjoy more of Tilos.
Accommodation: Irini Hotel (or similar)
Day 7 Return to Rhodes
After an easy morning, we set off for Rhodes in the early afternoon. As a group, we enjoy an evening together in Rhodes town, sharing memories of the adventure and, perhaps, planning the next!
Accommodation: STAY Hotel (or similar)
Day 8 Adventures ends in Rhodes
After breakfast, we begin our return journeys home. If you’d like more time in Rhodes speak to your sales representative about extending your stay.
