All Itineraries

Cyclades & Dodecanese

Greek Islands Discovery

7 Days
300 nautical miles
7 destinations
May – October

Overview

Destination Overview: The Greek Cyclades

The Allure of the Cyclades: A Yachting Paradise

The Cyclades archipelago, a cluster of idyllic islands set in the heart of the Aegean Sea, represents the pinnacle of the superyacht experience. This is a realm where ancient myths and modern luxury converge, where whitewashed villages cascade down volcanic cliffs to meet crystalline turquoise waters. A yacht charter in the Cyclades is not merely a vacation; it is an immersion into a world of breathtaking beauty, cultural richness, and unparalleled freedom. The ability to navigate this stunning seascape at your own pace, to discover secluded coves and vibrant harbors, and to awaken each day to a new, breathtaking vista is a privilege that only a private yacht can afford. The close proximity of the islands allows for short cruising distances, maximizing your time for exploration and enjoyment. From the cosmopolitan glamour of Mykonos to the serene beauty of Sifnos and the dramatic landscapes of Santorini, the Cyclades offer a kaleidoscope of experiences, ensuring that every day of your charter is as unique and unforgettable as the last.

The Charter Season: When to Embark on Your Cycladic Odyssey

Ideal For

Island HoppersHistory BuffsCouplesFamilies

Yacht Recommendation

A 35–55m motor yacht handles the Meltemi winds well. Choose a vessel with a shallow draft for accessing the smaller island harbours and hidden coves.

Voyage Summary

Duration

7 Days

Total Distance

300 nautical miles

Best Season

May – October

Region

Cyclades & Dodecanese

Ports of Call

7 destinations

Ideal For

Island Hoppers, History Buffs, Couples, Families

Daily Sailing Distances

Day 1
Embark
Day 2
85 nm
Day 3
25 nm
Day 4
55 nm
Day 5
40 nm
Day 6
50 nm
Day 7
45 nm
Total300 nm
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YOUR JOURNEY

Day by Day

300 nautical miles across 7 extraordinary destinations. This is a sample itinerary — your captain will tailor every detail to your preferences.

Luxury yacht charter exploring the beautiful harbor of Kea island in the Cyclades, Greece.
1
EMBARKATION

Day 1

Athens to Kea - The Gateway to the Cyclades

Athens RivieraCape SounionTemple of Poseidon

Morning

Your journey begins in the historic heart of Athens. Step aboard your private yacht, a sanctuary of luxury and elegance, where the crew awaits to cater to your every whim. As you settle into your magnificent suite, a gourmet breakfast is served on the aft deck, offering panoramic views of the ancient city. The yacht then sets a course for the serene island of Kea, a hidden jewel in the Cyclades, leaving the bustling capital in its wake.

Afternoon

Arriving in Kea, the yacht anchors in a secluded bay, its turquoise waters beckoning you for a refreshing swim. The afternoon is yours to enjoy – indulge in the yacht's extensive collection of water toys, from jet skis to paddleboards, or simply bask in the Mediterranean sun. For those with a spirit of adventure, Kea’s rugged landscape offers a network of ancient trails, leading to breathtaking vistas of the Aegean Sea.

Evening

As twilight descends, the sundeck becomes the perfect setting for pre-dinner cocktails, with the setting sun painting the sky in hues of orange and pink. Ashore, the charming fishing village of Vourkari awaits, its waterfront tavernas serving the freshest seafood in a lively, yet relaxed, atmosphere. A memorable dinner at a celebrated local restaurant, such as the renowned Aristos, provides a perfect end to your first day. Returning to the yacht, a nightcap under a canopy of stars concludes a perfect introduction to the Cyclades.

Where to Dine
  • Island Club Restaurant at Athens Riviera — sophisticated seafood
  • Varoulko Seaside — Michelin-starred Greek seafood in Piraeus
Activities & Experiences
  • Visit the Temple of Poseidon at Cape Sounion at sunset
  • Explore the Stavros Niarchos Foundation Cultural Center
Insider Tip

Time your departure to pass Cape Sounion at sunset — the Temple of Poseidon glowing golden from the sea is unforgettable.

Stunning view of a classic whitewashed village on Sifnos island, a key destination for luxury yacht charters in the Greek Cyclades.
2
85 NM

Day 2

Kea to Sifnos - A Taste of Cycladic Charm

Hydra IslandCar-Free StreetsArt Galleries

Morning

Awaken to the gentle rhythm of the waves and enjoy a sumptuous breakfast as the yacht glides towards Sifnos, an island celebrated for its pristine beaches, picturesque villages, and exceptional cuisine. The morning’s cruise offers ample opportunity to relax and soak in the ever-changing coastal scenery.

Afternoon

Upon arrival, the yacht’s tender will take you to the enchanting medieval village of Kastro. Lose yourself in its labyrinthine streets, where whitewashed houses and ancient archways whisper tales of a bygone era. The panoramic views from the village’s edge are simply breathtaking. Later, the yacht will anchor in a tranquil cove, providing a private haven for an afternoon of swimming, sunbathing, and utter relaxation.

Evening

As evening approaches, the vibrant port of Kamares comes alive. Sifnos is a gastronomic paradise, and a visit to the acclaimed Omega3 restaurant is a must for any discerning foodie. Here, you can savor innovative dishes crafted from the finest local ingredients, accompanied by a selection of exquisite Greek wines. The lively yet sophisticated atmosphere of Kamares provides a perfect backdrop for an unforgettable evening.

Where to Dine
  • Omilos — elegant waterfront dining in a converted cannon factory
  • Sunset Restaurant — Mediterranean cuisine with harbor views
Activities & Experiences
  • Explore the car-free cobblestone streets and art galleries
  • Swim at Vlychos Beach, accessible only by water taxi
Insider Tip

Hydra has no cars or motorbikes — only donkeys and water taxis. It's the most authentic Greek island experience.

Exploring the moon-like landscape of Sarakiniko Beach in Milos on a luxury yacht charter in Greece.
3
25 NM

Day 3

Sifnos to Milos - Volcanic Wonders and Pirate Lairs

SpetsesPine ForestsOld Harbor

Morning

After a delightful breakfast, the yacht charts a course for Milos, a volcanic island of dramatic beauty. The coastline is a masterpiece of nature, with colorful rock formations and hidden sea caves. The legendary bay of Kleftiko, a former pirate hideout, is your destination. Its towering white cliffs and emerald waters create a scene of unparalleled beauty.

Afternoon

The afternoon is dedicated to exploring the wonders of Kleftiko. The yacht’s tender will navigate you through a network of sea caves and arches, revealing hidden beaches and secret passages. Kayaking and paddleboarding offer a more intimate way to experience this natural marvel. A refreshing swim in the crystal-clear waters is followed by a delectable lunch on board, prepared by your private chef.

Evening

As the day draws to a close, the yacht cruises to the charming fishing village of Pollonia. Here, you can enjoy a delightful dinner at one of the waterfront tavernas, such as the highly-regarded Gialos, which serves the freshest catch of the day in a picturesque setting. The relaxed ambiance of Pollonia provides a perfect contrast to the day’s adventures.

Where to Dine
  • On the Verandah at Poseidonion Grand Hotel — refined Greek cuisine
  • Tarsanas — fresh fish taverna on the old harbor
Activities & Experiences
  • Rent a horse-drawn carriage to explore the island
  • Visit the Bouboulina Museum
Insider Tip

The pine-fringed beach of Zogeria is only accessible by boat — your tender makes it an exclusive escape.

Enjoying a spectacular sunset cruise on a luxury catamaran near Santorini, a highlight of a Greek Islands yacht charter.
4
55 NM

Day 4

Milos to Santorini - The Jewel of the Aegean

MykonosLittle VeniceWindmills

Morning

Awaken to the captivating beauty of Milos and enjoy a final breakfast before the yacht sets sail for the legendary island of Santorini. The approach to Santorini is a spectacle in itself, as the sheer cliffs of the caldera rise dramatically from the deep blue sea. The whitewashed villages clinging to the clifftops create a scene that is both iconic and awe-inspiring.

Afternoon

The yacht anchors in the picturesque Amoudi Bay, nestled at the foot of the cliffs of Oia. A refreshing dip in the azure waters is followed by a sumptuous lunch on board. In the afternoon, the tender will take you ashore to explore the enchanting village of Oia. Wander through its narrow cobblestone streets, browse the chic boutiques, and admire the iconic blue-domed churches.

Evening

The Santorini sunset is a spectacle not to be missed. Witness this magical moment from the privacy of your yacht’s sundeck, cocktail in hand, or from a cliffside bar in Oia. For dinner, a reservation at the world-renowned Lauda Restaurant is a must. Perched on the edge of the caldera, it offers a culinary experience that is as breathtaking as the views.

Where to Dine
  • is a must. Perched on the edge of the caldera, it offers a culinary experience that is as breathtaking as the views.

READY TO SET SAIL?

Let Us Plan Your Perfect Voyage

Every detail of this itinerary can be tailored to your preferences. Our charter specialists will craft a bespoke experience just for you.

Aerial view of a luxury tender anchored in the turquoise waters of Ios, perfect for swimming and exploring secluded coves.
5
40 NM

Day 5

Santorini to Ios - Sun-Drenched Beaches and Vibrant Nights

ParosNaoussa VillageGolden Beach

Morning

After a leisurely breakfast, the yacht cruises to the island of Ios, a haven of beautiful beaches and vibrant nightlife. The stunning Manganari Beach, with its golden sands and turquoise waters, is your destination. Here, you can spend the morning swimming, sunbathing, and enjoying the yacht’s water toys in a setting of idyllic beauty.

Afternoon

For a change of scenery, the tender can take you to the nearby Mylopotas Beach, one of the most popular in the Cyclades. Here, you can soak up the lively atmosphere and enjoy a refreshing drink at one of the beach bars. Alternatively, simply relax on the yacht and let the crew cater to your every need.

Evening

As the sun sets, the charming main town of Ios, Chora, comes alive. Its narrow streets are a maze of whitewashed houses, boutique shops, and lively bars. Enjoy a delicious dinner at a traditional Greek taverna, such as the acclaimed Lord Byron, before immersing yourself in the island’s legendary nightlife.

Where to Dine
  • Mario Restaurant in Naoussa — legendary fresh fish on the harbor
  • Siparos — farm-to-table dining in a garden setting
Activities & Experiences
  • Explore the fishing village of Naoussa with its Venetian fortress
  • Windsurfing at Golden Beach — one of Europe's best spots
Insider Tip

Paros' marble quarries produced the famous Parian marble used for the Venus de Milo. You can visit the ancient quarries.

Luxury catamarans and classic sailing yachts in the picturesque harbor of Naoussa, Paros, a gem of the Greek Islands.
6
50 NM

Day 6

Ios to Paros - Cosmopolitan Charm and Picturesque Harbors

SantoriniCaldera ViewsOia Sunset

Morning

After a final breakfast in Ios, the yacht sets a course for Paros, an island that perfectly blends cosmopolitan charm with traditional Greek beauty. The picturesque fishing village of Naoussa, with its charming harbor and Venetian fortress, is your destination. The morning is spent cruising and enjoying the amenities of the yacht.

Afternoon

Upon arrival in Naoussa, the tender will take you ashore to explore its enchanting streets. Discover hidden courtyards, browse the chic boutiques, and admire the local art galleries. A short cruise will then take you to the unique Kolymbithres Beach, where granite rock formations create a series of small, sandy coves – a perfect spot for a refreshing swim.

Evening

The waterfront of Naoussa is lined with an array of exceptional restaurants. A table at the celebrated Barbarossa is a must, offering exquisite seafood and unparalleled views of the harbor. After dinner, the village’s sophisticated cocktail bars, such as Agosta, provide a perfect setting for a nightcap.

Where to Dine
  • is a must, offering exquisite seafood and unparalleled views of the harbor. After dinner, the village’s sophisticated cocktail bars, such as **Agosta**, provide a perfect setting for a nightcap.
Iconic windmills of Mykonos overlooking the vibrant harbor, a must-see on a luxury yacht charter in the Greek Islands.
7
45 NM

Day 7

Paros to Mykonos - The Glamorous Finale

Caldera SwimHot SpringsFarewell

Morning

Enjoy a final, leisurely breakfast on board as the yacht cruises towards the glamorous island of Mykonos, the grand finale of your Cycladic adventure. The yacht will anchor in a secluded bay, offering one last opportunity for a refreshing dip in the Aegean’s turquoise waters.

Afternoon

The afternoon is dedicated to exploring the iconic landmarks of Mykonos Town. Wander through the charming streets of Little Venice, with its colorful houses perched on the water’s edge, and admire the famous windmills that stand as silent sentinels above the town. A farewell lunch at a seaside restaurant, such as the legendary Nammos on Psarou Beach, provides a fitting end to your culinary journey through the Cyclades.

Evening

As the sun sets on your unforgettable voyage, the crew will host a farewell cocktail party on the yacht’s sundeck. Raise a glass to the memories made and the beauty of the Greek islands. You will then be chauffeured to Mykonos International Airport for your departure, your heart filled with the magic of the Cyclades.

Where to Dine
  • on Psarou Beach, provides a fitting end to your culinary journey through the Cyclades.

COMPLETE ROUTE

Your Sailing Route

300 nautical miles across 7 destinations. Click any marker to explore that day's details.

85nm
25nm
55nm
40nm
50nm
45nm

Destination Gallery

Real photos from the stunning locations on this itinerary.

PERFECT YACHTS FOR THIS ROUTE

Yachts Available in Cyclades & Dodecanese

These superyachts operate in the region and are ideal for this itinerary. Your charter specialist will match the perfect vessel to your requirements.

Charter Yachts in Cyclades & Dodecanese

68 yachts

Crewed superyachts available for charter — prices are weekly starting rates

BUNKER — 131' CRN luxury charter yacht in Cyclades & Dodecanese

BUNKER

131' (40m)·CRN
from €157,320/6 days
FEATURED
12 Guests·5 Cabins
FREEDOM — 158' Radez luxury charter yacht in Cyclades & Dodecanese

FREEDOM

158' (48m)·Radez
from €110,000/6 days
22 Guests·11 Cabins·12 Crew
WIND OF FORTUNE — 170' CRN luxury charter yacht in Cyclades & Dodecanese

WIND OF FORTUNE

170' (52m)·CRN
from €105,000/5 days
16 Guests·7 Cabins·11 Crew
CRISTAL — 160' Custom luxury charter yacht in Cyclades & Dodecanese

CRISTAL

160' (49m)·Custom
from €90,000/6 days
30 Guests·15 Cabins·11 Crew
BELLA — 157' Custom luxury charter yacht in Cyclades & Dodecanese

BELLA

157' (48m)·Custom
from €90,000/6 days
21 Guests·10 Cabins·12 Crew
AQUARELLA — 137' Devonport luxury charter yacht in Cyclades & Dodecanese

AQUARELLA

137' (42m)·Devonport
from €85,000/6 days
12 Guests·5 Cabins·7 Crew
OHANA — 160' Custom luxury charter yacht in Cyclades & Dodecanese

OHANA

160' (49m)·Custom
from €75,000/5 days
30 Guests·14 Cabins·12 Crew
WHITE PEARL I — 111' SunSeeker luxury charter yacht in Cyclades & Dodecanese

WHITE PEARL I

111' (34m)·SunSeeker
from €75,000/6 days
8 Guests·4 Cabins·6 Crew
AQUILA — 121' FA luxury charter yacht in Cyclades & Dodecanese

AQUILA

121' (37m)·FA
from €69,000/6 days
12 Guests·5 Cabins·7 Crew
BLACK SWAN — 164' Custom luxury charter yacht in Cyclades & Dodecanese

BLACK SWAN

164' (50m)·Custom
from €67,500/3 days
20 Guests·10 Cabins·13 Crew
ANTHEA — 170' Custom luxury charter yacht in Cyclades & Dodecanese

ANTHEA

170' (52m)·Custom
from €65,000/3 days
20 Guests·10 Cabins·12 Crew
MOBIUS — 124' Cantieri luxury charter yacht in Cyclades & Dodecanese

MOBIUS

124' (38m)·Cantieri
from €65,000/6 days
12 Guests·5 Cabins·6 Crew

Showing 12 of 68 yachts in Cyclades & Dodecanese

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YOUR VOYAGE AWAITS

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This itinerary is a starting point. Your dedicated charter specialist will refine every anchorage, restaurant reservation, and shore excursion to create a voyage uniquely yours.

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Greek Islands Discovery

Cyclades & Dodecanese · 7 Days

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