📍 Greece

CYCLADES SAILING: CAPES, COVES AND HIDDEN VILLAGES

Q: What weather should you expect?

Spring (April-June): Perfect weather, blooming landscapes, ideal temperatures, fewer crowds, excellent value, Easter celebrations, optimal conditions. Summer (July-August): Warmest weather, peak tourist season, highest prices, crowded attractions, perfect for islands, vibrant nightlife, festival season. Fall (September-October): Warm seas, comfortable temperatures, fewer crowds, excellent weather, good value, harvest season, ideal photography. Winter (November-March): Mild weather, lowest prices, minimal crowds, rainy season, ski season mountains, cultural focus, cozy atmosphere.

Coves sheltering tavernas, centuries-old traditions, monasteries perched on cliffs, lively nightlife. Sailing the Cyclades in complete freedom.

≈ 21

Days

830

Stops

📖 11 min read 🔄 Last updated: 2026-01-17

Sail from Paros to Naxos and its marble traditions, then touch Iraklia and Schinoussa in pure island simplicity. Approach Amorgos and its cliff monasteries, taste Ios's contrast, then wind toward Milos and its volcanic landscapes before finding Santorini again, final majesty and unforgettable caldera.

Paros: marble fishing island hub
Naxos: marble traditions golden
Amorgos: cliff monastery dramatic
Santorini: volcanic caldera majesty
Milos: volcanic landscape unique
Folegandros: quiet village charm

Your day-by-day itinerary

Day

Parikia Paros

harbor capital where paros pulses

6 photos

Day 1

🔍

Discover

Parikia — old port, whitewashed alleys and windmills above the waterfront

Panagia Ekatontapiliani Church and waterfront promenade

🎯

Activities

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Swimming and beach — Livadia Beach (west of the port)

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Sheltered anchorage — Krios Beach depending on weather

🚗

Next stop

Distance: 12 km

Travel time: 14min

Day

Naousa Paros

fishing village windmills kiss water

8 photos

Day 2

🔍

Discover

Kolymbithres — granite formations and natural pools

Naoussa — port, alleys and maritime atmosphere

🎯

Activities

→

Choice of anchorage — Naoussa Marina or Ormos Plastira (depending on conditions)

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Snorkeling in the coves of Kolymbithres

🚗

Next stop

Distance: 16 km

Travel time: 19min

Day

Naxos Chora

marble town where traditions breathe

6 photos

Day 3

🔍

Discover

Naxos Chora — Portara (Apollo temple) and Venetian kastro

Old town — artisan workshops and shopping streets

🎯

Activities

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Sunset facing the Portara from the anchorage

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Quay walk and light provisioning

🚗

Next stop

Distance: 36 km

Travel time: 43min

Day

Iraklia Livadi

intimate island where time slows

4 photos

Day 4

🔍

Discover

Iraklia — Livadi bay and pristine natural atmosphere

🎯

Activities

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Snorkeling and swimming in Livadi bay

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Walk to the village (wild landscapes)

🚗

Next stop

Distance: 75 km

Travel time: 1h30

Day

Schinoussa Tsigouri

tiny island where locals gather

2 photos

Day 5

🔍

Discover

Schinoussa — Chora and viewpoints over the Small Cyclades

Tsigouri beach — turquoise waters

🎯

Activities

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Swimming and relaxation at Tsigouri

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Short hike to the village

🚗

Next stop

Distance: 34 km

Travel time: 41min

Day

Koufonisia Pori

secret coves where swimmers delight

4 photos

Day 6

🔍

Discover

Koufonissia — Pori beach and coves with translucent waters

Coastal walk from Pori to the sea caves

🎯

Activities

→

Sea kayaking / snorkeling in the coves

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Anchorage in Pori bay (anchorage holding to be checked)

🚗

Next stop

Distance: 18 km

Travel time: 22min

Day

Amorgos Katapola

monastery island cliffs pierce sky

6 photos

Day 7

🔍

Discover

Amorgos — arrival at Katapola, mountainous setting and preserved villages

Hozoviotissa Monastery — clinging to the cliff

Chora of Amorgos — windmills and narrow streets

Agia Anna — cove at the foot of the cliffs

🎯

Activities

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Quayside stroll in Katapola and organizing visits

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Light hike between viewpoints around Chora

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Swimming at Agia Anna (open sea, possible swell)

🚗

Next stop

Distance: 46 km

Travel time: 55min

Day

Ios Mylopotas

nightlife island golden beach shores

5 photos

Day 8

🔍

Discover

Ios — perched Chora and Cycladic alleyways

Mylopotas Beach — large sandy bay

🎯

Activities

→

Swimming / paddle in Mylopotas bay

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Anchorage in the bay (good holding, seasonal crowds)

🚗

Next stop

Distance: 70 km

Travel time: 1h24

Day

Santorini Black Beach

volcanic sand meets azure depths

6 photos

Day 9

🔍

Discover

Santorini — caldera and perched villages (views from the sea)

Black Beach (Perissa/Perivolos) — volcanic sand

Archaeological site of Akrotiri — Minoan city

Red Beach — red cliffs and pebbles

🎯

Activities

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Swimming on volcanic beach

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Wine tasting (island estates, land access from anchorage)

🚗

Next stop

Distance: 122 km

Travel time: 2h26

Day

Folegandros Agkali

quiet amphitheater cove perfectly serene

3 photos

Day 10

🔍

Discover

Folegandros — Chora perched, panoramic views

Agkali (Angali) — beach and neighboring coves

🎯

Activities

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Swimming and snorkeling at Agkali

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Sunset from the anchorage

🚗

Next stop

Distance: 76 km

Travel time: 1h32

Day

Sikinos Alopronia

remote island where silence reigns

6 photos

Day 11

🔍

Discover

Sikinos — high perched village and panorama over the archipelago

🎯

Activities

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Wild anchorage (few infrastructures)

🚗

Next stop

Distance: 42 km

Travel time: 51min

Day

Milos Adamas

volcanic harbor where rocks glow

6 photos

Day 12

🔍

Discover

Milos — Kleftiko: white cliffs and marine caves (exploration by dinghy)

Adamas — port and promenade

🎯

Activities

→

Snorkeling at Kleftiko (open sea, day anchorage)

🚗

Next stop

Distance: 19 km

Travel time: 23min

Day

Kimolos Rema

colorful island chalk cliff wonder

2 photos

Day 13

🔍

Discover

Kimolos — Prassa beach (white sand) and Chorio village

Rema Bay — sheltered coves

🎯

Activities

→

Swimming at Prassa, cove breaks

🚗

Next stop

Distance: 60 km

Travel time: 1h12

Day

Sifnos Platys Gialos

pottery village where tradition lives

6 photos

Day 14

🔍

Discover

Sifnos — Platys Gialos and large sandy beach

Discovery of pottery crafts (subject to access)

🎯

Activities

→

Swimming and paddleboarding at Platys Gialos

🚗

Next stop

Distance: 4 km

Travel time: 4min

Day

Sifnos Vathy

fishing harbor blessed mountain shade

6 photos

Day 15

🔍

Discover

Ormos Vathy — peaceful anchorage and sheltered cove

Apollonia — capital of Sifnos (white alleyways)

🎯

Activities

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Walk in the south of the island and neighboring beaches

🚗

Next stop

Distance: 79 km

Travel time: 1h34

Day

Serifos Megalo Livadi

mining island history terraced slopes

4 photos

Day 16

🔍

Discover

Serifos — Megalo Livadi and steep cliffs

🎯

Activities

→

Sunset from the anchorage or the hills

🚗

Next stop

Distance: 60 km

Travel time: 1h12

Day

Kythnos Kolona

thermal island ancient healing springs

6 photos

Day 17

🔍

Discover

Kythnos — Kolona, sandbar connecting the islet to the main island

🎯

Activities

→

Swimming between two seas (depending on weather, exposure)

🚗

Next stop

Distance: 41 km

Travel time: 49min

Day

Despotiko Antiparos

island caverns where light transforms

4 photos

Day 18

🔍

Discover

Despotiko (south of Antiparos) — wild anchorages facing crystal-clear waters

🎯

Activities

→

Swimming and snorkeling around Despotiko

🚗

Next stop

Distance: 20 km

Travel time: 24min

Day

Parikia Paros

harbor capital where paros pulses

6 photos

Day 19

🔍

Discover

Coastal return via the west of Paros — end-of-cruise panoramas

🎯

Activities

→

Last quick swim depending on time slot and weather

🗺️ Itinerary map

🗺️ Nearby itineraries

🛡️ Travel advice - Greece

Check official recommendations

UK Foreign Travel Advice →

❓ Frequently asked questions

What weather should you expect?

Spring (April-June): Perfect weather, blooming landscapes, ideal temperatures, fewer crowds, excellent value, Easter celebrations, optimal conditions.

Summer (July-August): Warmest weather, peak tourist season, highest prices, crowded attractions, perfect for islands, vibrant nightlife, festival season.

Fall (September-October): Warm seas, comfortable temperatures, fewer crowds, excellent weather, good value, harvest season, ideal photography.

Winter (November-March): Mild weather, lowest prices, minimal crowds, rainy season, ski season mountains, cultural focus, cozy atmosphere.

How many days should I plan?

We believe you will enjoy this itinerary best by dedicating between 17 and 25 days. The next step will allow you to adjust the duration of your stay.

What to discover in Greece?

Ancient civilization birthplace with stunning islands, incredible history, and Mediterranean lifestyle. Experience mythology sites, beautiful beaches, and authentic Greek culture. The country offers cultural depth with natural beauty and culinary excellence. Greece provides historical significance with island paradise and cultural authenticity in Mediterranean setting.

CYCLADES SAILING: CAPES, COVES AND HIDDEN VILLAGES

Your day-by-day itinerary

Parikia Paros

Discover

Activities

Next stop

Naousa Paros

Discover

Activities

Next stop

Naxos Chora

Discover

Activities

Next stop

Iraklia Livadi

Discover

Activities

Next stop

Schinoussa Tsigouri

Discover

Activities

Next stop

Koufonisia Pori

Discover

Activities

Next stop

Amorgos Katapola

Discover

Activities

Next stop

Ios Mylopotas

Discover

Activities

Next stop

Santorini Black Beach

Discover

Activities

Next stop

Folegandros Agkali

Discover

Activities

Next stop

Sikinos Alopronia

Discover

Activities

Next stop

Milos Adamas

Discover

Activities

Next stop

Kimolos Rema

Discover

Activities

Next stop

Sifnos Platys Gialos

Discover

Activities

Next stop

Sifnos Vathy

Discover

Activities

Next stop

Serifos Megalo Livadi

Discover

Activities

Next stop

Kythnos Kolona

Discover

Activities

Next stop

Despotiko Antiparos

Discover

Activities

Next stop

Parikia Paros

Discover

Activities

🗺️ Itinerary map

🗺️ Nearby itineraries

MYTHS, BLUE DOMES AND BEACHES OF THE CYCLADES