Southern Cyclades Sailing Small Ship Cruise
Travel from Athens across the Southern Aegean aboard Running on Waves on an eight-day sailing journey combining celebrated Greek islands with quieter, less-visited destinations.
The route connects Milos, Folegandros, Santorini, Astypalea, Ios and Serifos, moving between volcanic coastlines, cliffside settlements, whitewashed villages and clear-water bays. It brings together internationally known landscapes with islands where life continues at a slower pace, creating space for both major sightseeing and time away from the busiest routes.
Each destination reveals a different side of the Aegean. Discover the colourful volcanic geology of Milos, the dramatic hilltop Chora of Folegandros, Santorini’s caldera and the butterfly-shaped landscapes of Astypalea. Ios combines lively island culture with quiet beaches, while Serifos completes the route with rugged terrain, traditional settlements and an extensive coastline.
Between island visits, guests can swim directly from the ship, snorkel, kayak, windsurf or relax in the Jacuzzi. The onboard programme may also include sail practices, entertainment and karaoke, adapted to the weather, sailing schedule and preferences of the guests. Optional diving and guided shore excursions can be arranged for an additional charge.
Full-board dining, spacious outdoor decks and a limited number of guests create a comfortable base throughout the journey. This cruise is designed for travellers who want to combine island-hopping, swimming, sailing and cultural exploration, with enough time to experience the distinctive atmosphere of every stop.
Afternoon
Arrive in Athens and make your way to Piraeus to board Running on Waves. After settling into your cabin, meet the crew and the other guests joining the voyage.
Take time to explore the ship’s open decks, lounge areas and onboard facilities. Guests arriving earlier can spend part of the day in Athens or walk around the marinas and waterfront of Piraeus before embarkation.
Evening
The journey begins with a welcome and safety briefing, followed by the first dinner on board.
The crew introduces the itinerary and explains how swimming stops, watersports and onboard activities will be organised during the week. Running on Waves is scheduled to leave Piraeus at approximately 22:00, beginning the overnight passage towards Milos.
Morning
Wake as Running on Waves approaches Milos, an island shaped by volcanic activity and known for its colourful cliffs, unusual rock formations and varied coastline.
After breakfast, go ashore to explore independently or join an optional excursion around the island.
Day
Possible highlights include Sarakiniko, where smooth white rock formations create an almost lunar landscape, and the fishing villages of Klima and Mandrakia, known for their colourful boat houses beside the water.
The island’s coastline also includes sea caves, sheltered coves and places such as Kleftiko that are best approached from the sea. Depending on the anchorage and weather, there may be time for swimming, snorkelling or exploring the surrounding water by kayak.
Evening
Return to Running on Waves for dinner and a relaxed evening on deck.
Watch the colours of the volcanic coastline change in the evening light as the ship leaves Milos and continues towards Folegandros.
Morning
Begin the day near Folegandros, a small mountainous island with a rugged coastline and a more restrained atmosphere than many of its Cycladic neighbours.
Breakfast is served on board before guests go ashore to explore the island.
Day
Visit Chora, built dramatically near the edge of a high cliff. Walk through cobbled lanes, whitewashed houses, small squares and the historic Kastro district.
Those looking for a more active route can follow the uphill path towards the Church of Panagia for panoramic views across the Aegean. Other possibilities include a visit to Agali or one of the island’s less-developed beaches, reached by road, walking path or local boat.
Evening
Return to Running on Waves for dinner or spend part of the evening in Chora, when the squares fill with tables and the island’s cafés and tavernas become the centre of local life.
The ship later continues towards Santorini.
Morning
Spend the first part of the day sailing through the Southern Aegean as Running on Waves approaches Santorini.
The island gradually appears above the water as a wall of dark volcanic rock crowned by white settlements.
Day
It's time to explore the island independently or join an optional excursion.
Walk through Fira or visit Oia for views across the caldera. Other possibilities include traditional inland villages, volcanic beaches, local vineyards or a viewpoint overlooking the islands created by Santorini’s ancient eruptions.
Evening
Return to Running on Waves for dinner as the ship leaves Santorini.
Spend the evening on deck watching the illuminated settlements above the caldera before the voyage continues east towards Astypalea.
Morning
Wake near Astypalea, a Dodecanese island whose two sections are joined by a narrow strip of land, creating its distinctive butterfly-like shape.
After breakfast, go ashore to discover an island that combines Cycladic-looking architecture with a quieter Dodecanese identity.
Day
Explore Chora, where white houses descend from the Venetian Querini Castle towards the sea. Traditional windmills mark the route through the upper town, while narrow lanes lead between small churches, cafés and viewpoints.
There may also be time to visit one of the island’s beaches or swim in a sheltered bay. Astypalea’s varied coastline and clear water make it well suited to snorkelling, kayaking and relaxed exploration from the ship whenever conditions allow.
Evening
Return to Running on Waves for dinner and a quiet evening on board.
As the ship leaves Astypalea, the route turns west again towards the Cyclades and the island of Ios.
Morning
Begin the day as Running on Waves approaches Ios, an island in the heart of the Cyclades.
Although Ios is widely known for its nightlife, it also has a quieter side shaped by traditional villages, hilltop churches and beaches away from the busiest parts of the island.
Day
Go ashore to explore Chora, where white houses, small squares and churches rise above the harbour. Walk through its narrow lanes or continue uphill towards Panagia Gremiotissa for views across the surrounding islands.
Guests looking for time beside the sea can visit Mylopotas or one of the more secluded beaches around the coastline. Depending on the ship’s anchorage, swimming, snorkelling and watersports may also be available directly from Running on Waves.
Evening
Return to the ship for dinner or spend part of the evening ashore.
As Running on Waves leaves Ios, relax on deck while the ship begins its north-western passage towards Serifos.
Morning
Wake near Serifos, one of the less-developed islands of the western Cyclades.
After breakfast, go ashore to explore its rugged landscape, traditional settlements and extensive coastline.
Day
Visit Chora, built across a steep hillside above the port. Its whitewashed lanes climb towards the remains of the Venetian castle, with wide views over the island and the Aegean.
Serifos is also known for its beaches and mining heritage. Possible stops include Psili Ammos, Ganema or Vagia, while the former mining area around Mega Livadi reveals a different part of the island’s history.
There may be time for a final swim, snorkelling session or kayak trip before returning to the ship.
Evening
Return to Running on Waves for the farewell dinner.
Spend the final evening on deck as the ship leaves Serifos and begins its overnight passage back towards Athens.
Morning
Running on Waves arrives in Piraeus.
Enjoy a final breakfast on board before saying goodbye to the crew and the guests who have shared the journey.
Disembarkation marks the end of the cruise. Guests remaining in Athens can continue towards the historic centre, visit the Acropolis or extend their journey through mainland Greece.
Itineraries are subject to change.
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Additional charges:
Port Taxes: €395 EUR
Vessel Type: Three-Mast Sailing Vessel, Barquentine
Length: 64 metres
Passenger Capacity: 42
Running on Waves is a majestic three-mast barquentine and one of the world’s largest sailing yachts, offering a rare blend of authentic sailing adventure and five-star luxury. At 64 metres in length and carrying just 42 guests, she delivers a truly exclusive yachting experience. With her sleek silhouette and full sail performance reaching up to 17 knots, she brings the romance of the sea to life while maintaining ultra-low emissions. Guests are treated to personalised service from a dedicated crew of 21, ensuring every detail is handled with care and elegance. Her small size allows access to hidden harbours and intimate marinas that larger vessels simply cannot reach.
Life on board is designed for indulgence and discovery. From sunbathing on the spacious Sun Deck to sipping cocktails at the Ocean Bar or relaxing in the Jacuzzi Pool at the bow, every space invites relaxation. Cabins feature refined nautical interiors, marble-finished bathrooms, and modern comforts such as air conditioning, satellite TV, and underwater camera feeds. Whether you’re dining on Mediterranean cuisine, unwinding in the massage lounge, or watching the horizon from the observation point above the bowsprit, Running on Waves is more than a voyage—it’s a celebration of freedom, beauty, and the art of slow travel.
Special Offers on Southern Cyclades Cruise
30% off the cabin fare if booked more than 9 months prior to departure date of your chosen cruise;
20% off the cabin fare if booked 9 to 6 months prior to departure date of your chosen cruise;
10% off the cabin fare if booked 6 to 3 months prior to departure date of your chosen cruise.
Prices online do not show the discounted rates. Terms and conditions apply. This special offer is subject to availability. Please contact us for more details.
Inclusions
• Full board
• Complimentary coffee, tea, still water and crackers available at the bar counter throughout the day
• Kayaks, windsurf boards, fins and masks for snorkeling
• Entertainment on board: sailing practices, yoga classes, karaoke
• SAT TV in the cabins
• Jacuzzi, Internet
Exclusions
• Cocktails, alcohol and soft drinks in the bar
• Diving equipment rental, diving instructor services, and underwater group tours
• Water skis, wakeboards etc.
• Instructors for windsurfing and diving
• Bus excursions with invited guide
• Laundry services
• Air tickets, transfer and visa cost
• Service charge (tips) is € 14 per guest per day (on guests’ decision)
• Port fees
Small Ship Cruise
Highlights
• Discover the Southern Cyclades’ volcanic landscapes – Explore Milos’ colourful rock formations and hidden bays, admire Santorini’s spectacular caldera, and experience the distinctive volcanic scenery that shapes these remarkable Greek islands.• Visit picturesque villages and quieter Aegean islands – Discover Folegandros’ dramatic cliffside Chora, Astypalea’s butterfly-shaped landscapes, Ios’ whitewashed streets and Serifos’ rugged coastlines and traditional settlements.
• Enjoy an active sailing holiday in Greece – Travel aboard Running on Waves with opportunities for swimming, snorkelling, kayaking and windsurfing between island visits, alongside optional diving and guided shore excursions.
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