Cyclist riding road bike along dry coastal path with sea and cliffs in background
village lefkes in Paros island
Panoramic aerial view of the popular beach of Moni island, next to the village Perdika on Aegina island with turquoise sea, Saronic Gulf, Greece
Cycling on beach in Naxos
Greek ruins at the Temple of Aphaia on the island of Egina (Saronic Islands Aegean Sea) ancient roman columns, blue sky golden hour soft light (goddess monument) historic remains, Greece Mediterranean
Old white windmillls by the sea in Mykonos
Aerial view of sea Marina in Poros island, Aegean sea, Greece.
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Cyclades Bike & Boat Tour

7 days / 6 nights

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Discover the magic of Greece by bike and boat – explore the best of the Cyclades Islands, where history, culture, and stunning landscapes converge.

Starting point

Athens

Finish point

Athens

Fitness level

2/5

Tour type

Gravel / E-bike

Season

From April to October

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Highlights

  • Island-hop through the Aegean by bike
  • Cycle Sifnos’s quiet trails and whitewashed chapels
  • Explore Paros’s breezy coastal loops and fishing harbors
  • Ascend through Naxos’s mythic heartland
  • Experience the lesser-seen side of Mykonos
  • Wind through narrow streets, uncover timeless tavernas, and savor regional specialties

What’s included in the price?

Self-guided

6 nights in 3-star hotels with breakfast
Digital guidebook with itinerary, route instructions, and practical information
GPS navigation with an easy-to-use app
Tour design and organization
Service and support during your tour
Luggage transfer

NOT INCLUDED

Ferry tickets
Tourist tax

OPTIONAL EXTRAS

Accomodation upgrade
Airport transfer
E-bike
Gravel bike
MTB
Regular bike
Single supplement

Pedal your way through paradise on this unforgettable island-hopping cycling adventure across the Cyclades!

This 7-day self-guided cycling holiday takes you on a sun-soaked journey through Greece’s most captivating islands: Sifnos, Paros, Naxos, and Mykonos.

Each day offers a new island to explore by bike, with thoughtfully crafted loop routes that reveal local culture, hidden beaches, ancient ruins, and mouthwatering cuisine.

On Sifnos, you will ride through peaceful landscapes of terraced hills and hidden chapels. In Paros, you’ll follow coastal roads and discover charming harbors and hillside villages. Naxos will reward your efforts with sweeping mountain views and routes lined with olive groves and ancient ruins.

Even glamorous Mykonos will reveal its quiet, rustic side as you cycle past traditional farms and seaside chapels.

With booked accommodations, GPS routes at your fingertips and a comprehensive digital guidebook to lead the way, this tour will ensure you’ll experience Greece as few ever do – up close, at your own pace, and always with the Aegean by your side.

Top Places You'll See

From natural wonders to authentic local culture, the route is packed with memorable sights—these are our absolute favorites.

Athens, Greece -  Monastiraki Square and Acropolis

Athens

With over 3,000 years of recorded history, Athens remains one of the world’s oldest continuously inhabited cities. The Acropolis, crowned by the Parthenon (built in 438 BC), dominates the skyline and offers sweeping views over the Attica plain. Stroll through Plaka and Monastiraki, where neoclassical houses stand above layers of Roman and Byzantine ruins. The city’s lively rhythm blends archaeology, street life, and Mediterranean flair in a way few capitals can match.

The Church of Seven Martyrs in Kastro, Sifnos, Cyclades Islands, Greece

Sifnos Island

Sifnos is known for its pottery tradition dating back to the 6th century BC and for its network of over 100 kilometers of marked trails connecting hilltop monasteries and fishing villages. Its capital, Apollonia, showcases classic Cycladic architecture with narrow lanes and whitewashed houses. The island’s calm roads, terraced hills, and small coves invite unhurried exploration. It remains one of the lesser-crowded islands, favored for its authenticity and culinary heritage.

old port in Paros at sunset. Greece

Paros Island

Located in the heart of the Aegean, Paros has been inhabited since the Neolithic era and is famous for its ancient Parian marble, once used to sculpt Venus de Milo. Cyclists and visitors alike pass Naoussa’s Venetian harbor, coastal windmills, and Byzantine churches such as Panagia Ekatontapiliani, built around 326 AD. Inland, olive groves and vineyards spread across gentle hillsides. The blend of ancient artistry and modern island charm defines Paros’ enduring appeal.

Panorama of Naxos Chora town, Naxos island, Greece Cyclades

Naxos Island

Naxos is the largest and most fertile of the Cyclades, rising to Mount Zas at 1,003 meters, the highest peak in the island group. Ancient myths name it as the childhood home of Zeus, while archaeological remains date back to the Bronze Age. The Portara, a marble gateway from a 6th-century BC temple, welcomes visitors to the harbor. Mountain villages, lush valleys, and seaside ruins make Naxos a richly layered stop for both history and landscape lovers.

Traditional greek windmills on Mykonos island, Cyclades, Greece

Mykonos Island

Mykonos became a major Aegean trading hub as early as the 11th century BC, later flourishing under Venetian rule in the 15th century. The island is instantly recognizable for its 16th-century windmills, white cube houses, and Little Venice waterfront. Beyond its famous nightlife, Mykonos holds a preserved Cycladic core with stone lanes and hidden chapels. Its balance of cosmopolitan energy and island heritage keeps it among Greece’s most photographed destinations.

Our Bikes

To ensure the best possible experience on your cycling adventure, we offer top-quality bikes for rent. Our fleet features the latest models, meticulously maintained for both performance and comfort.

To match each rider with the right equipment, our team will also assist you in selecting the most suitable bike based on your physical profile, personal preferences, and the technical requirements of the tour.

Black road bike with drop handlebars isolated on a white background

Road Bikes

Best for: Paved routes, longer distances, and climbs


Our road bikes are lightweight, fast, and built for endurance. They typically feature carbon or high-quality aluminium frames, smooth gearing, and reliable components—often Shimano 105 or similar. Well-suited for long days in the saddle, they’re perfect for climbs, steady cruising, and covering serious distance on tarmac.


Black and red hybrid trekking bicycle isolated on white background

Trekking Bikes

Best for: Multi-day touring, relaxed pace, and varied surfaces


These high-quality trekking bikes are built for comfort over multiple days. They feature a relaxed riding position, smooth-rolling wheels, and often come with practical additions like an adjustable stem, rear rack, or mudguards. They're not necessarily built for speed, but more for enjoying the ride.

Blue trekking e-bike with rear rack and fenders isolated on white background

Touring E-Bikes

Best for: Comfortable trekking, touring, longer distances, and hilly routes


These pedal-assist electric bikes are designed to make riding easier and more enjoyable—especially on longer or hillier routes. They come with powerful mid-drive motors, long-lasting batteries, and comfortable riding geometry for smooth support across varied terrain. With intuitive controls and quality components, they’re a great choice for riders who want extra assistance without giving up the feel of a real ride.


Frequently Asked Questions

Self-guided cycling tours are crafted for a personalized and flexible experience on two wheels. Discover wonders at your leisure, with the liberty to modify your route or itinerary as you wish. Our committed team meticulously takes care of all aspects, including accommodation arrangements, comprehensive planning, GPS navigation assistance, and ongoing support, to ensure a peaceful and captivating trip. This journey celebrates independence, personal discovery, and authentic cultural encounters.

Our tours are divided into three levels of difficulty: Leisurely, Moderate, and Challenging, defined by the typical daily itinerary, though there can be variations in challenge during the trip.


Leisurely tours are perfect for those looking for a relaxed journey amidst beautiful landscapes, without the need for long-distance cycling or navigating difficult terrains. Typically, these tours cover 30-50 km per day, with an elevation gain of up to 500m. This allows for numerous opportunities to enjoy the scenery, sample local cuisine, and visit quaint villages and towns along the route.


Moderate bike tours cater to those who desire a combination of picturesque routes and a bit of a challenge. Covering 50-80 km per day with an elevation gain of up to 1000m, these tours take you through beautiful landscapes and charming villages, featuring both flat and hilly terrains. They provide plenty of chances for exploration and also offer a rewarding cycling experience.


Challenging bike tours are designed for seasoned cyclists looking to challenge themselves. These tours cover 80-120 km daily with an elevation gain of up to 2000m and involve steep climbs and challenging routes. Suitable for those with a high level of fitness and stamina, they offer a sense of achievement and stunning views, making the effort worthwhile.

We are dedicated to finding the ideal match for your cycling journey. We work closely with a range of accommodation providers, all of whom adhere to our quality criteria, though their availability might change, particularly during high-demand seasons. Moreover, we offer the flexibility to customize your trip according to your personal tastes and budget, guaranteeing that we find the accommodation that best suits your needs.

We recommend booking your tour as soon as possible, particularly for sought-after tourist destinations where accommodation options are limited. Top choices tend to be reserved quickly, often getting fully booked for the summer season well before the arrival of spring.

Addressing specific dietary needs can depend on their complexity. In Greece, vegetarian dishes are commonly available, but sourcing vegan meals may be more challenging in rural regions or smaller towns. It’s important to note that lunch stops typically occur at traditional restaurants, where the ability to accommodate special dietary requirements beyond their regular menu might be limited. Please consider this when planning your cycling tour.

The optimal cycling season in Greece extends from mid-April to mid-October. In higher elevation areas, such as the mountainous regions, it’s best to plan your cycling trips from mid-May to September.

Tours in Greece are feasible in light rain, provided you have suitable attire. Summer often brings afternoon thunderstorms, so starting your tours early in the day is advisable. Should challenging weather conditions be anticipated, we will endeavour to adapt the tour schedule accordingly.

On cycling trips, luggage transfer allows you to ride without carrying heavy bags. Each morning, you leave your luggage at the designated spot—often the hotel reception—and it’s transported to your next overnight stop. Your bags are usually waiting for you when you arrive. Weight limits and pickup times can vary slightly depending on the service provider.

Ratings & Reviews

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World discovery Top Rated Brand

drewbob

Verified customer

We had a wonderful tour of Greece on bikes. All of the hotels and towns were unique and wonderful, the rides were a reasonable length for my wife and we had a great time on our own without guides. Thank you very much and I would do the exact trip again.

Winding mountain road traversing steep, rocky slopes covered in green vegetation under a blue sky.
Sandy beach with lounge chairs under umbrellas and people wading in calm coastal water
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Peter Georgiadis

Verified customer · 8 months ago

The Sparta self guided tour was the best cycle tour I’ve ever done. Everything from the apps and their ease of use, routes, sights, places of interest, places to eat and accommodation selection was absolutely sensational. A credit to Timotej, Janez and Klemen for their skill in preparing such a journey and incredible experience for us. Already thinking about the next one!!

Cyclist standing by Spartan statue with Greek flag under blue sky

Steve G

Verified customer · 8 months ago

I completed the self guided Cycladic and Sparta tours. The itinerary put together included breathtaking bike routes, excellent hotel stops, top recommendations for places to visit and eat. Using the Trip app to manage the entire tour by phone was seamless and effortless. Logistics in Greece, like transporting luggage, can be difficult and the team worked well with the local providers to overcome all of these challengers.

Mystie Pineda

Verified customer · 2 months ago

I found this place with a simple Google search, and I never could’ve expected the custom experience I received. They provided options to help my husband and I hone in on exactly what we wanted to do for our honeymoon. We had perfectly curated GPS-lead rides all across the country, they booked all of our hotels, and planned all of our transportation. Every place that we went was so beautiful. I’m so grateful that we found this company to help us plan our honeymoon, couldn’t have asked for a better experience!

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Bill Wright

Verified customer · 3 months ago

I was able to tailor a bike tour itinerary along the Adriatic coast that suited our group during the shoulder season. We added individual pre and post-trip activities which went smoothly. Our trip included stops in Italy, Slovenia and Croatia. The trip planner, guide and support team were great.

barney barnhart

Verified customer · 3 months ago

Brilliant planning, great communication, terrific hotels and accommodations, interesting cities and beautiful scenery plus amazing routes.

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All available guidance options

Self-guided

Those who like good adventure and limitless flexibility should go on a self-guided cycling holiday. It offers complete freedom, multiple detour opportunities, and exploration at your own pace without having to adapt to a group.

Hassle-Free

We handle itineraries, accommodations, and anything else you prefer not to deal with, so you can enjoy a carefree holiday.

Completely Customizable

Flexibility is our middle name — whether you want more or less, or just beyond ordinary, we’ll make it happen.

Book with confidence

We are a financially protected company, fully bonded and insured, keeping your money safe and allowing you to travel with confidence.

Unbeatable support

Our 24/7 customer support is where we show our passion, bringing you a better experience by making your well-being our number one priority.

from 2.250 € /person
Discover unforgettable cycling holidays in Greece with our self-guided Bike Tours. Explore scenic landscapes and rich culture on our bespoke Greece bicycle tours.

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Lan Lajovic
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