Sailing & Cycling the Cyclades Islands Tour (Private Tour)
€1.500,00
per personCyclades
8 days
2026, from March until October
Discover the beauty of the Cyclades in Greece on a unique 8 days private boat and cycling tour. Combine the freedom of island hopping by private vessel with the adventure of cycling through some of the most beautiful Greek islands. This customizable Cyclades tour is designed around your interests and preferences. With your own private vessel, bike, and experienced skipper, you can explore charming island villages, secluded beaches, hidden coves, and spectacular coastal landscapes at your own pace.
At a glance
- Difficulty: moderate
- Daily Distance: 22 – 51 km
- Daily Climb: From 353m
Customization of daily length and climb is possible.
Available bikes
- Trekking Bikes
- Road bikes
- E-bikes
- Tandem bike
Highlights
- Explore the Cyclades by private boat and enjoy a personalized island-hopping experience.
- Travel with an experienced skipper who can help you discover the best places to visit along the way.
- Create a flexible itinerary tailored to your interests, fitness level, and preferred pace.
- Visit hidden coves and secluded beaches that are difficult to reach by land.
- Cycle through the Cyclades and experience the islands from a different perspective.
- Experience complete privacy and comfort aboard your private vessel.
About this holiday
Imagine Island hopping onboard your own yacht, arriving at a new destination each day and discovering each island by bike. On this very special trip you will get to explore the islands in a completely unique way and create memories that will last a lifetime. You’ll discover the beauty of The Cyclades day by day, port by port, and even if you don’t want to cycle you are welcome to just enjoy the sights and sounds of the passing scenery.
We embark from Athens, to our adventure amongst the islands of the Aegean Sea: The Cyclades.
You will get to cycle amazing roads on the islands of Kythnos, Serifos, Sifnos, Paros, Syros and Kea. Sailing between these islands will even give you a chance to try your sailing skills if you wish, or just sunbath if you prefer.
We will have an average of 4 hours sailing time per day (depending on weather conditions), how you spend the rest of each day is entirely up to you. Whether you want to cycle one of our routes, visit a beach, shop, or simply relax, this trip is for you.
Custom programs can be created for you at an additional charge depending on the number of participants, duration and component parts of the tour.
Self-guided or Guided biking tour
Participating in a biking tour is one of the most pleasant ways to discover a destination in depth. Upon your arrival, we will supply you with access to GPS application with routes, digital tour info and of course your bike with all necessary equipment such as panniers, service kit, locks etc. During your stay in the islands, you will have the freedom to spend your time in any way you wish. Whether you decide to wake up early or start later, you cycle at your own pace and stop anywhere that catches your interest on the proposed route. In this way you are not obliged to follow a specific schedule but can just follow at your own tempo. Upon request we can arrange to have a cycling guide with you all along your tour.
And of course we provide 24h telephone support in case of emergency just to be sure everything rolls along smoothly.
A Sustainable Holiday
Arcas Travel Services believes in sustainable and responsible tourism, and is committed to having the lowest possible environmental impact. By employing only local guides and using only regional services we provide a form of tourism that benefits the community. The visitor also benefits by being able to come closer to authentic local cultures and traditions due to our unique local knowledge. We think tourism should be about respect and benefit to the local inhabitants and that responsible travelers will get more out of their holiday by giving a little bit back to the special places and people that they meet.
DAY BY DAY ITINERARY
Kindly note that this program is indicative . The final route will be decided on board in coordination with the Captain, taking into consideration your preferences and the weather conditions at that time.
DAY 1: Arrival-Lavrio
We arrive at the Port of Lavrio, whereupon, after collecting your bicycle, you can settle into your berth onboard our Catamaran. Later we gather for a welcome dinner to meet the Skipper.
DAY 2: Kea (25 km/ +571 m or 49 km /+1120 m)
In the morning we set sail for our first destination, the Island of Kea. Crossing the blue waters of the Aegean we arrive at the port of Korissia. Kea is different from the rest Cycladic islands and it has a unique charm. You can use the afternoon to discover the island for yourself on one of two routes 25 or 49 Km. You´ll pass beautiful beaches on your way to the capital of the island, Ioulida, that is well worth exploring. Wander through the small cobbled streets to the neoclassic city hall built by the architect Ernst Tsiller. Don’t forget to taste the jams and preserves that are a specialty of the island. Overnight on Kea.
DAY 3: Syros (29 km /+387 m)
Today we set sail to Syros, an island at the centre of the Cyclades. We will arrive at the small port of Finikas and will dock there till next morning. Our ride today is a tour around the island passing beaches and hamlets set in the rolling countryside. We stop at Ermoupoli, the capital of the Cyclades, which is set upon two hills, and where you will get to spend some time exploring the city. Neoclassical buildings, the historic theatre and the old medieval city all make the capital unique. Don’t forget to taste the traditional “Loukoumi” of Syros, or to try the cafes and the local tavernas. Overnight in the Port of Syros.
DAY 4: Paros (27 km /+353 m or 51 km /+517 m)
Our next destination is the iconic Island of Paros with its world-famous windmills. You will cycle through picturesque villages, with their white houses, and passing idyllic rural settings will enjoy an unforgettable day. Again, we suggest two routes, one short, which is easy for everyone and a longer one for those who want a challenge. Overnight on Paros.
DAY 5: Sifnos (28 km/ +568 m or 51 km / +1127 m)
Today our destination is Sifnos, an island that some consider to be the most beautiful of all. Sifnos has more than 350 churches and monasteries many of which are considered historical monuments. Once again, the local architecture is imposing, and the small white buildings create a landscape all their own. Culture, gastronomy, and art are all combined on this island which will make a visit here one of the highlights of your trip. Again, there are 2 options for the cyclist, one easier and the other more challenging. We recommend visiting the northern shore of the island to reach the picturesque small church situated there. Then ride south to Apollonia, the capital of the island, or continue to the villages and down to the beach. Overnight is on Sifnos.
DAY 6: Sérifos (26 km /+677 m or 37 km / +946 m)
Today we will first set sail for Serifos, upon arrival we will take a cycle ride around the island and then we will sail north to the island of Kythnos for the night. According to the Greek mythology Serifos Island is the birthplace of Perseus and home to the Cyclops who were the children of Poseidon. The Ancient Greeks believed that the Cyclops lived in a cave, above Megalo Livadi Bay, and that they had built the walls, remnants of which are seen throughout the island. Serifos is a small, but very picturesque, island and Chora, the capital is built on the slope of a very steep hill!! Our route will take you around the island and then onto Chora. The island has some fairly steep hills, and the highest summit is at 585m, however it is not big, and cyclists really enjoy their time here.
DAY 7: Kythnos (22Km /+435m or 43Km /+809m)
We wake in the Port of Merichas, on the Island of Kythnos. With only 1310 local habitants, it is quiet here in winter, but comes alive in the summer. On our cycle ride we will pass through the capital, on through beautiful hill country and finally arriving at the village of Dryopida. Here there is a cave full of stalactites and stalagmites which has been a hiding place for the villagers from pirates and Ottomans alike. Tavernas and cafes welcome you in for a drink, on this, your final day in the saddle. In the afternoon we sail back to Lavrio, stopping off on the way for swimming at Kolona, perhaps the most beautiful beach in the Cyclades! Overnight on board.
DAY 8: Lavrio – Departure
We Greeks don’t like to say goodbye. Instead we prefer to say «Εις το επανιδείν» which means that we hope to see you again some time!
PRICING
Tour price: from €1500 per person*
includes:
- Sail boat with skipper for 7 nights/8 days
- Sheets and towels
- Access to GPS application
- Mobile phone mount for the handlebar
- Complete information about the area
- 24h telephone support
excluding fuel, meals for the skipper, flight tickets, excursions on your free time, entrance tickets for archaeological sites & museums etc.
*The price may vary depending on the type of vessel, any extra services etc.
Bike rental
- Trekking bike 100€/week
- Road bike 140€/week
- E- bike 260€/week
- Τandem 270€/week
- Helmet 10€
- GPS device upon request 80€/week
Accommodation
During this Cyclades private boat tour, you will stay on board your sailing vessel throughout the journey. Depending on the vessel selected, you will stay in comfortable cabins designed to provide a relaxing and private space after a day of exploring the Greek islands.
