Cycle & Cruise the Dodecanese : Kos to Rhodes by gulet

Cycle & Cruise the Dodecanese : Kos to Rhodes by gulet
ACTIVE PERIOD
Saturday to Saturday : May - June - September - October
DIFFICULTY LEVEL
3
DURATION
8 days
Cycle & Cruise the Dodecanese : Kos to Rhodes by gulet
Price from €3980
PRICE FROM € 3980 - DECLARE INTEREST

Overview

Cruise the Dodecanese aboard the elegant gulet Harmonia with a small group of fellow adventurers, exploring islands by bike under the guidance of expert Trekking Hellas cycling leaders. Each day blends gentle cycling, scenic cruising, and immersive cultural experiences — from ancient ruins and medieval villages to pristine beaches and volcanic landscapes. Discover the unique charm of each island, with opportunities to swim in hidden bays, savor local cuisine, and connect with Greece’s natural beauty and history. This journey offers a perfect mix of active adventure, relaxation, and authentic Greek island life.

Day 1
Arrival in Kos
Day 2
Kos Cycling & Cruise to Nisyros
Day 3
Cycling Nisyros Volcano & Cruise to Tilos
Day 4
Tilos Scenic Cycling
Day 5
Cruise to Symi & Island Ride
Day 6
Cruise to Rhodes & Free Exploration
Day 7
Rhodes Bike Adventure & Farewell Dinner
Day 8
Departure

Activities / Schedule

Arrival in Kos

Arrive at Kos Airport and meet your Trekking Hellas cycling leader for a smooth transfer to your hotel. Later, enjoy a welcome walk through Kos Town, where whitewashed streets meet lively squares, cafés, and ancient ruins. End the day with a traditional Greek taverna dinner, savoring fresh seafood, local wines, and the warm hospitality that defines the island.

Dinner included.

Kos Cycling & Cruise to Nisyros

Start with breakfast, then embark on your first bike adventure through Kos New & Old Town, with its Ottoman-era architecture, bustling markets, and leafy squares. Explore the Asklepion of Hippocrates, a stunning ancient healing temple surrounded by olive groves, where you can imagine life as it was 2,000 years ago.

After cycling, return to the gulet for lunch on board. In the early afternoon, set sail to Nisyros, a volcanic island famed for its active crater, hot springs, and charming villages. Feel the salty breeze as you glide across turquoise waters, and spend the evening wandering Mandraki’s narrow streets or sampling local cuisine at a harbor taverna.

Lunch included; dinner on your own.

Cycling Nisyros Volcano & Cruise to Tilos

After breakfast, cycle to the volcanic heart of Nisyros, where the crater’s lunar-like landscape, steaming vents, and rugged rock formations feel like another world. Capture photos from elevated viewpoints and take a moment to breathe in the warm, mineral-scented air.

Return to Mandraki for a coffee or stroll through its labyrinth of alleys, castles, and waterfront cafés before boarding the gulet for lunch. In the early afternoon, it’s time for a relaxing cruise to Tilos, an island of quiet coves, lush valleys, and Natura 2000-protected landscapes. Evenings here are slow-paced and serene, perfect for stargazing from the sundeck.

Lunch included; dinner on your own.

Tilos Scenic Cycling

Tilos is untouched and tranquil, with rolling hills, terraced olive groves, and sleepy villages. Begin cycling from Livadia and climb gently toward Megalo Chorio, Tilos’ traditional capital perched beneath a dramatic hilltop. Wander its stone streets, admire classic traditional houses, and enjoy panoramic views of the Aegean.

Continue to the monastery of Agios Panteleimonas, surrounded by fragrant herbs and sharp cliffsides. This bike ride is gentle yet rewarding, with plenty of photo stops, coffee breaks, and opportunities to appreciate Tilos’ authentic, slow-paced charm. Lunch will be served on board the gullet in the quiet bay of Livadia. Overnight in Tilos with dinner on your own.

Lunch included.

Cruise to Symi & Island Ride

After breakfast, cruise to Symi, one of the Mediterranean’s most photogenic islands, famous for its pastel-colored neoclassical houses cascading into a sparkling harbor. Lunch on board. Then, it’s time to disembark at Panormitis Monastery, a serene waterfront complex tucked into a sheltered bay, and start your bike journey across the island.

Ride through fragrant pine forests, past rugged coastline, and into Symi Town, with its lively squares, artisan shops, and charming cafés. Take time to wander narrow streets making the most of the perfect mix of activity and relaxation.

Lunch included; dinner on your own.

Cruise to Rhodes & Free Exploration

Cruise leisurely toward Rhodes, enjoying the sun on deck and stopping for a refreshing swim in St. George Bay or Seskli Island. Lunch is served aboard the gullet.

In the afternoon, explore Rhodes’ UNESCO-listed Old Town, a living museum of cobblestone streets, medieval fortifications, and lively squares. Take a gentle stroll through knightly inns, quaint boutiques, and historic streets, experiencing centuries of history without rushing.

Lunch included; dinner on your own.

Rhodes Bike Tour & Farewell Dinner

After breakfast, transfer to the west side of Rhodes for today’s ride. Begin in Kalavarda, cycling through rolling countryside and coastal roads, with easy climbs made effortless by your e-bike. Visit Ancient Kameiros, where ruins tell stories of classical Greece, and continue to Kritinia Castle, perched above the Aegean with panoramic views of neighboring islands. Lunch will be organized at one of Rhodes countryside villages.

Return to Kalavarda and board the gulet for a farewell dinner on deck, sharing highlights, laughter, and memories from your week of active exploration, island culture, and maritime serenity.

Lunch and dinner included.

Departure

After breakfast, bid farewell to the crew and fellow travelers. Your Trekking Hellas cycling leader will escort you to Rhodes Airport, ensuring a smooth departure. Leave with lasting memories of crystal-clear waters, sun-drenched villages, and the gentle rhythm of the Dodecanese by gulet.

Important Info

In a glance

SURFACE AREA
Dodecanese Islands
CURRENCY
euro (€)
TIMEZONE
UTC+02:00 (EET)

Highlights

  • Cycle through the historic streets of Kos, explore the Asklepion, and sail to the volcanic island of Nisyros for a crater hike unlike any other.
  • Experience the serene charm of Tilos, cycling past terraced olive groves, tranquil villages, and Natura 2000-protected landscapes, all while embracing the island’s sustainable, eco-friendly ethos.
  • Cruise to Symi, explore pastel-colored neoclassical towns, ride through fragrant pine forests, and visit the iconic Panormitis Monastery.
  • Discover Rhodes off the beaten track and ride through rolling countryside to ancient ruins and hilltop castles, combining history, scenery, and active exploration.
  • Enjoy small-group cruising aboard the gulet, with opportunities to swim in secluded bays, savor fresh local meals, and connect with Greece’s islands from the unique perspective of the Aegean Sea.

Prices

Tour's price from 3980 euro per person. 

Single supplement from 1640 per person

For more information, including pricing, please get in touch. Rates per person vary by travel month (May–October or June–September) and group size (8–12 guests).

 

General Information

Pre- and Post-Tour Stays
To make your journey even more relaxed, we are happy to arrange additional nights in Kos or Athens before the tour begins, allowing you to arrive at an easy pace and start your adventure well rested. Likewise, we can organize extended stays in Rhodes after the tour, with a choice of carefully selected locations and accommodations. Whether you wish to explore more of Greece, enjoy extra time by the sea, or simply unwind, just contact us and we’ll take care of the details.

Touring Bikes & E- Bikes - Models

For Touring Bikes : Ideal EZIGO

For E-Bikes :  Ideal Prisma E610 WAVE SUV

 

Bike Routes

Bike Routes — Distance

Please note: While we have planned scenic routes for each day, distances and elevation may be adjusted to match the group’s pace, weather, or local conditions. Our experienced Trekking Hellas cycling leaders ensure that every ride is safe, enjoyable, and tailored so everyone can experience the islands at a comfortable and rewarding pace.

 

Day

Route

Distance

Day 1

Kos – New & Old Town – Asklipeion Ippocrates

26 miles

Day 2

Nisyros – Volcano Mandraki

24 miles

Day 3

Tilos – Livadia - Megalo Chorio Loop

14 miles

Day 4

Panormitis - Symi Town

18 miles

Day 6

Kalavarda - Kameiros - Kritinia Castle 

23 miles

Equipment

Please consider taking along the following items on your trip. This is not a fixed list, but more of a guideline, so feel free to add and remove items as you see fit.
Greece has a temperate climate. Base your clothing on the “layering system”, if it is hot you can “peel off” layers quickly, if it is cooler and windy you can quickly “dress up”.

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

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

Clothing Accessories

  • Sun hat or baseball cap

Footwear

  • Cycling footwear
  • Lightweight and supportive walking shoes
  • 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
  • Travel pillow
  • Motion sickness remedies
  • Personal first-aid kit
  • Insect repellent (lowrisk)
  • Electrical adapter plug/converter

The lighter you travel, the easier you travel. Use your best judgment and pack as lightly as possible. You will appreciate light luggage towards the end of your trip.

Cycle & Cruise the Dodecanese : Kos to Rhodes by gulet

Price from €3980

DECLARE INTEREST

FAQs

What should I bring with me?

  • What is listed above in Equipment section

What's the meeting point & time?

Meeting Point: Kos Port

Time: 10.00 am

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