Individual arrival at the Athens marina. Boarding from 2 pm. You discover your cabin, your schooner and the crew. First dinner on board, in the quiet of the harbour. Night lulled by the sea.
Cycling and sailing in the Cyclades: 8 days from saddle to deck, island to island
Each morning, you open your eyes in your cabin and discover a new Greek island through the porthole. Breakfast is served on deck, facing a sea of deep blue. Your bike (electric if you wish) awaits for a panoramic ride between white villages, turquoise coves and fragrant olive groves. In the evening, the schooner takes you back on board for a dinner of local flavours, lulled by the lapping of the water. With Kelifos, this 8-day trip combines the best of cycling and sailing in the Cyclades and the Saronic Islands, without ever unpacking your bags.
The e-bike option, available at booking, transforms every climb into simple pleasure and lets you enjoy the panoramas fully without rushing. It is the ideal way to discover the winding roads and gentle passes of these sun-drenched islands, keeping all your energy for swims, visits and terraces.
From gourmet Kythnos to pistachio-rich Aegina, via secretive Serifos, pastel-fronted Syros the capital, and verdant Poros, you ride six islands in six cycling days, each with its own character and flavours. The stages take you along quiet roads, between hilltop villages, Byzantine monasteries, golden-sand beaches and ancient sites like the Temple of Aphaia. And each afternoon, the sail between islands offers a moment of pure relaxation on deck, watching the coastlines glide by.
Program
The schooner casts off at dawn. First island: Kythnos, renowned since antiquity for its honey and cheeses. Your ride takes you from the port of Merichas to Chora, perched on a plateau, with spectacular views over the coves below. Flower-filled lanes, whitewashed houses, shaded terraces: the charm works immediately. You continue to Driopida, tucked inland, before descending to Merichas for a swim and a drink on a terrace facing the sea.
In the morning, a ride on Serifos, a small island far from the tourist trail. From the port of Livadi, you pedal along a winding road to the upper town, whose cubic white houses stretch along a ridge above the sea, a striking panorama. A stop at the Byzantine monastery of the Archangel Michael, then back via the east coast. In the afternoon, sail to Syros, administrative capital of the Cyclades. A free stroll through Ermoupolis, its neoclassical facades, its lively squares and its wide harbour promenade where the cafes vie for charm.
A morning ride along the south coast of Syros, punctuated by bays and coves. You pedal to the fine beach of Galissas, pass the convent of Saint Barbara, then return to Ermoupolis along the hills. The town, built on two hills, offers a unique atmosphere in the Cyclades: pastel houses, classical facades, a bustling market. In the afternoon, sail to Kea.
From the natural harbour of Korissia, you climb to Loulis, the island's capital, before descending to the white-sand beach of Otzias for a well-earned swimming break. Return to Korissia, then sail to Poros in the Saronic Gulf. Arriving at Poros harbour is a spectacle in itself: white and ochre houses reflected in the calm waters of the channel. A typical Greek evening on the harbour.
After breakfast on board, a ride to the 18th-century monastery of Zoodochos Pigis, then a tour of the island along roads bordered by pines and orange trees. Just before the end of the stage, the Russian Bay welcomes you with its sandy beach and turquoise waters, an irresistible invitation to swim. Back to the port, then sail to Aegina in the golden afternoon light.
A final cycling day on Aegina, famous throughout Greece for its pistachios. A fine climb to the sanctuary of Aphaia, a remarkably preserved Doric temple overlooking the Aegean Sea on both sides, a breathtaking panorama. Return via the Nektarios monastery and a ride across the island to Aegina town. Final sail to Athens harbour. Farewell dinner on board.
Final breakfast on board, disembarkation before 9 am. You leave with salt on your skin, the taste of Aegina pistachios and landscapes filling your eyes. An extension in Athens is possible.
Dates, prices and booking
Below you will find detailed dates and prices: comfort types, departure dates, options, supplements and reductions. Please note, this trip is popular and places are quickly limited, we advise you to plan ahead. Send us an availability request, we will get back to you as soon as we receive your request.
Contact
Price does not include
- travel to/from the boat in Athens
- meals not included
- drinks (payable on board to the captain)
- beach towels
- individual site visits
- bicycle rental
- possible port taxes payable locally
- tips
- booking fees
- insurance
- anything not listed under "Price includes"
- accommodation for 7 nights in double cabin on the lower deck
- 2 days full board and 5 days half board on board
- bottled mineral water on board
- guiding on each stage by an English-speaking guide
- visits as scheduled in the itinerary
- group entrance fees to museums and archaeological sites
- bed linen and towels
- single cabin supplement on the lower deck: 50% of the trip price
- upper deck cabin supplement: on request
- e-bike hire: 252 EUR / person
- bike insurance against theft and damage: 28 EUR
- special dietary requirements (payable on site): 70 EUR
- transfer between Athens airport and the port: on request
- child discount up to 16 years in a double cabin: 200 EUR
Your advisor

Giovanna Crippa
Product Manager Europe
Practical information
You stay in a double cabin on the lower deck, with private bathroom. Depending on the date, you board the schooner Thalassa (Marina Zeas) or the motor yacht Erato (Marina Alimos). Bed linen and bathroom towels are provided. The boat is your floating hotel: no packing and unpacking, your belongings stay in your cabin throughout the trip. Wi-Fi available on board (reception varies at sea). Single cabin available on request.
The e-bike is highly recommended to make the most of this trip. Equipped with a Bosch Active+ motor and Shimano hydraulic brakes, it transforms the climbs into pleasant rides and leaves you all your energy for discoveries and swims. Book at registration. Minimum height: 1.50 m. Wearing a helmet is compulsory (we recommend bringing your own).
Two days full board and five days half board on board. Meals feature local flavours. For free lunches, your guide points you to each island's best tavernas. Bottled mineral water available on board.
Cycling stages range from 23 to 35 km per day, on panoramic, quiet roads. The terrain is hilly (that is the nature of Greek hills), but the e-bike makes every climb perfectly accessible. You ride at your own pace: after the morning briefing with the guide, you are free to stop for a photo, a swim or a coffee on a terrace.
Registration from one person. The group is international; the main language on board is English.
8 days / 7 nights / 6 cycling days.
Boarding on Day 1 from 2 pm at the Athens marina (Alimos). Disembarkation on Day 8 before 9 am at the same marina.
From May to October. Spring (May to June) and autumn (September to October) offer the most pleasant temperatures for cycling and the most inviting seas for swimming.
Looking to continue your discovery of Greece? Explore our trips to the Cyclades, our holidays in Crete or our escapes to the Ionian Islands. Discover Greece on foot or on a guided holiday with an English-speaking leader.
Reviews
This trip doesn't have reviews yet. Discover what travelers say about similar trips.
Claude 7/31/26 • Naxos and Amorgos self-guided walking holiday: 10 days - Kelifos
— A sporty, sociable epicurean
Jean-Bernard 7/31/26 • Serifos, Sifnos and Milos self-guided walking holiday: 10 days - Kelifos
— Interesting but monotonous in terms of terrain and scenery
— A haven of peace, a return to nature, human connection
Etienne 7/31/26 • Serifos, Sifnos and Milos self-guided walking holiday: 10 days - Kelifos
— An excellent trip—I highly recommend it. In the future, it might be helpful to make the travel documents less complicated and repetitive.
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