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Sailing and Hiking the Dodecanese Islands

Highlights

  • Walk inside the dramatic volcanic crater of Nisyros for a truly once-in-a-lifetime experience
  • Hike Tilos’ stunning coastline and red-sand beaches, discovering the atmospheric abandoned village of Mikro Chorio on one of the Mediterranean’s most awarded islands for sustainability and renewable energy
  • Discover Symi’s fragrant pine trails, historic monasteries, and breath-taking views toward the Turkish coastline
  • Immerse yourself in local culture with a guided town walk and hands-on Greek cooking class in Symi
  • Sail into Rhodes’ iconic Mandraki Harbor, framed by medieval walls, to conclude an unforgettable island journey
From £3659 pp*

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What you'll do

Overview

Embark on a wonderful few days sailing, calling at beautiful unspoilt islands, travelling across the deep blue Adriatic sea. The Dodecanese Islands are the ideal sailing destination, with perfect weather conditions throughout the summer. You'll sail on your own chartered boat from Kos to Rhodes. Every island has a unique character and your guide will ensure you make the best of this amazing sailing experience.

Route Summary:
Day 1: Kos to Nisyros & Volcano Visit
Day 2: Nisyros to Tilos Hike
Day 3: Tilos to Symi & Hike
Day 4: Symi walk and cooking class
Day 5: Symi to Rhodes

 Read More

Embark on a wonderful few days sailing, calling at beautiful unspoilt islands, travelling across the deep blue Adriatic sea. The Dodecanese Islands are the ideal sailing destination, with perfect weather conditions throughout the summer. You'll sail on your own chartered boat from Kos to Rhodes. Every island has a unique character and your guide will ensure you make the best of this amazing sailing experience.

Route Summary:
Day 1: Kos to Nisyros & Volcano Visit
Day 2: Nisyros to Tilos Hike
Day 3: Tilos to Symi & Hike
Day 4: Symi walk and cooking class
Day 5: Symi to Rhodes

This Sailing & Hiking trip from Kos to Rhodes, blends relaxed island cruising with rewarding walks & hikes across volcanic landscapes, pristine beaches, and historic villages.

From exploring an active volcanic crater on Nisyros to hiking coastal trails and pine forests on Tilos and Symi, each day balances time at sea with immersive experiences on land.

Swimming in secluded bays, enjoying fresh meals on board, and discovering authentic island culture create a perfectly paced journey.

The trip culminates in Rhodes, where medieval history and grand harbour views provide a memorable finale.

Ideal for travellers seeking nature, culture, and comfort in equal measure.

Please click here for more Greek island hopping trip. 

Arrival Day

Once you arrive in the beautiful island of Kos, it’s time to meet the crew who warmly welcome us on board the sailing boat and our home for the next few days.

After they give us all the information we need to know, it’s time to set off for day one of our exciting adventure –Sailing & Hiking the Dodecanese Islands.

First stop on our Sailing and Hiking Tour is the magical island of Gyali, close to Nisyros. Both islands belong to the volcanic arch of the Aegean, so the colour of the land there is without a doubt unique. We enjoy some time swimming and snorkeling in Gyali’s crystal clear waters and then enjoy a reviving lunch on board. In the early afternoon we dock in the port of Nisyros, Paloi, and we set off for our first walk – to the volcano! The experience of walking through a volcanic crater is enough to take your breath away and can only be described as a one-of-a-kind experience.

In the evening, free time for dinner or stargazing on board!

Sailing: 26 N.Miles (approximately 4 hours)

Walking: Within Stefanos’ crater (approximately 1 hour)

Meals: Lunch on board

 

Nisyros to Tilos & Hike

Our next destination on Sailing & Hiking the Dodecanese Islands is Tilos, an island that has recently been given an award and the title of the Environmentally Greenest Island in the Mediterranean as its energy derives entirely from solar and wind power.

After some swimming stops in the middle of the Aegean Sea and a wonderful refreshing lunch on board, we reach the main port of Tilos, picturesque Livadia.

Today’s hike combines all you have ever thought of Greece. Starting from Livadia, the trail leads us along the coastline to lovely beaches, including a red beach – due to the colour of its sand. Thereafter, having reached Lethra Beach, a green tree-lined paradise, we begin the ascent towards Mikro Chorio (meaning small village in Greek).

Once a densely populated village, it is now deserted. Houses have been abandoned and they remain along with the narrow alleys, green courtyards and its few present inhabitants – goats. During the summer months a bar operates here from which customers can stroll around this unique “ghost” village. Picturesque as it may be, we are forced to leave it behind, in order to start our descent back towards our starting point, Livadia.

In the evening, free time for dinner or easy wander at Livadia bay!

Sailing: 20 N. Miles (approximately 3 hours)

Hiking: 7.5 Km (Actual Hiking time 3 hours)

Meals: Breakfast and Lunch on board

Tilos to Symi & Hike

After breakfast, set sail toward Symi, stopping at the secluded Agios Emilianos Bay for a refreshing swim in crystal-clear waters and a light lunch on board. From here, your hiking adventure begins. Follow scenic trails through a fragrant pine forest, alive with aromatic herbs and dotted with small chapels, as you make your way toward the historic Agios Roukouniotis Monastery, a fortified complex dating back to the 15th century.

Along the route, pass St. John Church, perched above the turquoise waters and offering stunning views of the distant mountains — a perfect spot to pause, reflect, and capture unforgettable photos. Continue to the monastery of Agios Roukouniotis and the Old Windmill viewpoint, where the sun casts its golden glow over the Turkish Coastline.

After soaking in the breathtaking views, a short transfer brings you to Gyalos Town, where you rejoin your gulet. Dinner is on your own, allowing time to stroll the charming harbour streets or unwind on deck under the Aegean sky.

Cruising: 30 N. Miles (approximately 5 hours – stops included)

Hiking: 5.8 Km (Actual hiking time 3 hours)

Meals: Breakfast and Lunch on board

 

Symi walk & Cooking Class

After a leisurely breakfast on board at Gyalos, your guide will walk with you through the beautiful alleys of Symi town including “Kali Strata” & the Upper Village neighbourhood for great views. Then, you will step into the flavours of Symi with a hands-on cooking class. Using fresh, local ingredients sourced from the island, you’ll learn to prepare traditional Greek dishes — from vibrant salads and meze to classic mains — guided by experienced local chefs. It’s a chance to discover the secrets of Greek cuisine, taste your creations, and connect with the island’s culinary culture.

The afternoon is free to explore Symi at your own pace. Wander through the colourful streets, discover hidden corners and charming shops, or simply relax by the picturesque harbour, soaking in the island’s unique atmosphere. Dinner on board.

Walking: In Symi town & Chorio (approximately 1,5 hours)

Meals: Breakfast & Dinner on board and Lunch in a taverna

Symi to Rhodes - Farewell

On the last day of our Sailing and Hiking Tour, we sail to Rhodes.

Rhodes is the largest island of the Dodecanese and boasts the richest history. On our way we will have the opportunity to swim in some more bays, like St George Disalonas (on Symi Island) and enjoy a delicious lunch on board, before reaching Mandraki harbour. Entering the harbour is a truly unique experience due to views of the walls that surround the Old Medieval Town.

We say our goodbyes in the early afternoon upon check-out from Armida, leaving you free to explore the Old Town at your own pace and enjoy dinner independently, as our services come to a close here—bringing a memorable journey to a heartfelt end.

Sailing: 24 N. Miles (approx. 3.5 hours)

Meals: Breakfast and Lunch on board

What's included

Included

  • 4 nights on a sailing boat (double cabins)
  • Professional Skippers and crew
  • Daily Breakfast and lunch
  • Hikes (Days 2, 3)
  • Walks (Days 1, 4)
  • Cooking class (Day 4)
  • Local transfers in Nisyros & Symi
  • Professional English speaking Guide
  • All necessary port fees and fuel

Accommodation

Armida Sailboat (or similar)

Armida is a Hanse 370 yacht.

Specially equipped for your sailing & hiking holiday in the Dodecanese Islands.

Armida has, three double bed cabins, a sitting area, a bathroom with a shower cabin and a kitchen equipped with a cooker, oven and a refrigerator.

Above deck, a shaded area provides welcome relief from the Aegean sun without sacrificing the sailing ability this vessel is renowned for.

Its friendly crew will enhance your experience with their sailing experience and knowledge of the secret gems they will take you through your voyage.

Your local host

The Hellas Team

We organize outdoor activities in classic Greek destinations (eg. Santorini, Athens, Crete, Rhodes ) as well as in less known regions of Greece (Tzoumerka, Karpenisi ), but they are all off the beaten path, and we aim to support local communities and contribute to their more sustainable development. The concept of meaningful and respectful travel lies in the heart of our endeavors. We strongly embrace and implement a socially and environmentally responsible policy by promoting the protection of nature and environmental awareness. We strive to educate and make a positive impact in this corner of the world, whilst ensuring that you experience the real Greece and make life long memories and friends on the way!

We organize outdoor activities in classic Greek destinations (eg. Santorini, Athens, Crete, Rhodes ) as well as in less known regions of Greece (Tzoumerka, Karpenisi ), but they are all off the beaten path, and we aim to support local communities and contribute to their more sustainable development. The concept of meaningful and respectful travel lies in the heart of our endeavors. We strongly embrace and implement a socially and environmentally responsible policy by promoting the protection of nature and environmental awareness. We strive to educate and make a positive impact in this corner of the world, whilst ensuring that you experience the real Greece and make life long memories and friends on the way!

The Hellas Team image

Location

Your sailing and hiking adventure begins in Kos, a Greek island near to the coast of Turkey. From there, you’ll visit islands such as , Tilos, Symi and Nisyros, before finishing in Rhodes.

Meeting Point : Kos Port – 10am

FAQs

What should I bring?

Luggage

Duffel bag or rolling luggage
Day pack to carry camera, water bottle and snacks etc.
Luggage locks and tags

Outerwear

Mid-weight polar fleece sweater
Rain jacket and rain pants, or poncho

Clothing

Hiking shorts
Casual clothing made of light-weight fabrics
T-shirts
Long-sleeve shirt
Hiking pants, loose and easy to move in
Underwear
Swimsuit

Clothing Accessories

Sun hat or baseball cap

Footwear

Lightweight and supportive hiking boots, broken-in with good ankle support
Beach sandals
Casual, comfortable shoes for evening

Accessories

Sunscreen and lip protection
Sunglasses and retainer strap
Beach towel

Optional Accessories

Security pouch or money belt
Trekking poles or walking staff
Camera, memory and batteries
Reading and writing materials
Watch with alarm or travel alarm
Travel pillow
Motion sickness remedies
Personal first-aid kit
Insect repellent (lowrisk)
Electrical adapter plug/converter

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