Southern Cyclades Sailing Small Ship Cruise

date_range
8 days from

£2415 GBP pp

* Current p/p indicative rate.

Overview
Highlights
Dates & Prices
Itinerary
Map
Ships

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.

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.
Capacity: 42
Feture image for 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.

  • 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.

Availability is always subject to confirmation. Please check with us before booking flights

19 June, 2027 to 26 June, 2027 on Running On Waves
Prices

Prices quoted here are often dependent on currency fluctuations. Please check with (01432 507450 or info@small-cruise-ships.com) for the very latest price, which may well be cheaper than the one advertised here.

Tween Deck Cabin. From
£2599 GBP pp (+ Port Taxes £336 GBP pp)
Tween Deck Cabin. From
11–12m² King or triple beds available Nautical decor, Gobelin tapestry Ideal for couples, solo travelers, or families
28 August, 2027 to 04 September, 2027 on Running On Waves
Prices

Prices quoted here are often dependent on currency fluctuations. Please check with (01432 507450 or info@small-cruise-ships.com) for the very latest price, which may well be cheaper than the one advertised here.

Tween Deck Cabin. From
£2415 GBP pp (+ Port Taxes £336 GBP pp)
Tween Deck Cabin. From
11–12m² King or triple beds available Nautical decor, Gobelin tapestry Ideal for couples, solo travelers, or families
Main Deck Suite. From
£5125 GBP pp (+ Port Taxes £336 GBP pp)
Main Deck Suite. From
14–20m² King beds, Mediterranean interiors Direct access to open decks Mosaic entry, teak flooring, redwood furniture
25 September, 2027 to 02 October, 2027 on Running On Waves
Prices

Prices quoted here are often dependent on currency fluctuations. Please check with (01432 507450 or info@small-cruise-ships.com) for the very latest price, which may well be cheaper than the one advertised here.

Tween Deck Cabin. From
£2415 GBP pp (+ Port Taxes £336 GBP pp)
Tween Deck Cabin. From
11–12m² King or triple beds available Nautical decor, Gobelin tapestry Ideal for couples, solo travelers, or families
Main Deck Suite. From
£5125 GBP pp (+ Port Taxes £336 GBP pp)
Main Deck Suite. From
14–20m² King beds, Mediterranean interiors Direct access to open decks Mosaic entry, teak flooring, redwood furniture
show reverse itinerary
Day 1 Piraeus/Athens

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.

Day 2 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.

Day 3 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.

Day 4 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.

Day 5 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.

Day 6 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.

Day 7 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.

Day 8 Piraeus/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.

Please note:

Itineraries are subject to change. 

Day 1 Piraeus/Athens

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.

Day 2 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.

Day 3 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.

Day 4 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.

Day 5 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.

Day 6 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.

Day 7 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.

Day 8 Piraeus/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.

Please note:

Itineraries are subject to change. 

Itinerary also available in reverse
Running On Waves
Vessel Type: Three-Mast Sailing Vessel, Barquentine Length: 64 metres Passenger Capacity: 42 Running On Waves is one of the biggest sailing yachts in the world. According to SOLAS convention,…

Running On Waves

Vessel Type: Three-Mast Sailing Vessel, Barquentine

Length: 64 metres

Passenger Capacity: 42

Running On Waves is one of the biggest sailing yachts in the world. According to SOLAS convention, the highest safety standards are maintained on board a vessel of this class, the same as would apply to a cruise liner carrying thousands of passengers. “Running on Waves” operates under the flag of Malta.

The ship was conceived to combine maneuverability of a sport yacht, the highest standards of comfort and decor, and a shallow draft that allows calling at small marinas inaccessible even to many a big yacht, let alone cruise liners. The unmatched draft of 3.2 metres was made possible owing to a brilliant idea to use lead ballast. The uniqueness of a number of technological solutions confirmed by the US Patent Department.

Every guest of ours enjoys 15,5 square metres of available open teakwood deck space, that is three times more than aboard most expensive cruise ships and would befit a most prestigious private mega-yacht.

The policy of the Company is to always keep the boat in a mint condition. That is why, despite her tender age, we do profound refitting every winter, so that in Spring she welcomes you in full glamour of perfection.

Sails are our main driving power, thus we boast unbeatably low level of fuel consumption, on average 75 l per hour only, which is about 10 times lower than on a motor boat of a comparable size.

Premium comfort notwithstanding, RUNNING ON WAVES is nothing close to a floating hotel or a museum on water, she is a supercharged windship, and with favourable wind can run at 16 – 17 knots under sail. The ship’s superbly efficient ratio of sailing surface to displacement 2 sw.m/t makes her one of the fastest sailboats of old and new times.

To make sailing comfortable at any sea conditions, cutting-edge technologies were used, such as pitch-killing stabilizers, while sophisticatedly calculated mass distribution prevents the hull oscillation frequency from resonating with the frequency, which affects human vestibular system. There are desalinators on board which account for the unlimited supply of fresh water. Air–conditioning throughout the vessel makes you feel a sheikh even in hottest days of Mediterranean summer. Our state-of-the-art hydraulic ramp at the stern of the vessel allows for a direct access to water for swimming and water sports.

Sun Deck

Primary feature — a spacious deck for sunbathing with 16 chaise lounge chairs, which are accessible at any time absolutely free of charge. Additionally, the ship has a large area of covered surfaces, creating vast shaded zones on open decks, which allow for an enjoyable cruise while being protected from the sun. A fresh water Jacuzzi-swimming pool, accommodating six people, is located in the fore of the ship. In the aft of the ship, navigation equipment is behind the command bridge, followed by the massage center and the lounge area. A tour of the command bridge can be arranged at passenger’s request. One may enjoy professional massage services in the massage parlor, followed by some downtime on a small sofa in the lounge area.

Main Deck

The restaurant located on the Main deck is ready to please the ship’s guests with delicacies of Mediterranean cuisine. A fantastic Ocean Bar, located in front of the restaurant in the central part of the deck, offers refreshing drinks and exotic cocktails. You can enjoy your breakfast seated on comfortable sofas located in the cockpit, aft of the ship. Smoking is not prohibited in this zone. An observation deck in the fore of the ship is above the bowsprit, creating the feeling of flying over the water! Mini-suites and Premium cabins are located on the main deck. Size of the cabins vary from 16m2 to 20m2 (172ft2 – 215ft2).

Tween Deck

Passenger cabins occupy most of the tween deck. Crew cabins, companion cabins for the crew and the galley are also located on the tween deck. Fully equipped Water sports center with access to a hydraulic ramp is located in the stern. The stern can be opened up and lowered onto the water, transforming into a diving deck for water sports and recreation. Standard cabins and economy class cabins are located on the tween deck. Cabin sizes vary from 11m2 to 12m2 (118ft2 – 129ft2).

Deck plans are for illustrative purposes only – The actual ship and cabin layout may differ.

Cabin layout for Running On Waves
Overview
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Dates & Prices
Itinerary
Map
Ship

8 days from £2415 GBP pp

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