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Sailing the Greek Isles aboard the Sea Cloud Fleet

<p>Explore the beautiful Cyclades as the ancients did, sailing from isle to isle under the power of the wind. The legendary tall ship Sea Cloud, and her modern counterpart Sea Cloud II, offer the chance to stand on deck and watch the orchestrated frenzy of crew members climbing aloft in the rigging to handset 30 sails. Our expedition visits iconic landmarks as well as hidden gems that are largely unknown to all but locals and discerning travelers. Visit small harbors and go on guided walks to learn firsthand about the history and contemporary life along these sun-drenched shores.</p>

Optional extras & upgrades

Optional tours and excursions available. Please contact us for more details.
06 September, 2025 to 13 September, 2025
More Cabin Categories & Prices Available
Please contact us for more information.
Category 01. From $19,120 AUD pp
Cabin features include a couch, television, small table, dressing table with mirror, a closet, two nightstands, minibar, safe, temperature controls, and telephone. The beautiful marble bathroom is equipped with a shower.
13 September, 2025 to 20 September, 2025
More Cabin Categories & Prices Available
Please contact us for more information.
Category 01. From $19,120 AUD pp
Cabin features include a couch, television, small table, dressing table with mirror, a closet, two nightstands, minibar, safe, temperature controls, and telephone. The beautiful marble bathroom is equipped with a shower.

Sailing the Greek Isles aboard the Sea Cloud Fleet itinerary:

show reverse itinerary
DAY 1 Athens, Greece / Piraeus / Embark Ship

 

Arrive in Athens and transfer to Piraeus, where you will embark the ship in the late afternoon. Settle into your cabin and take in our first Greek sunset at sea.

Arrival Time: Arrive before 4:00 p.m. local time.

Arrival City: Athens, Greece

Meals Included: Dinner

DAY 2 Sailing the Aegean

 

Our first morning on board is spent at sea, bound for the Cyclades and reveling in the blue magic of the Aegean horizon from our classic tall ship. Relax on deck with a book or journal. Watch the crew dance across the rigging to trim four masts’ worth of sails by hand. Attend interactive discussions led by our team of experts as they introduce the region’s history and ecology.

Meals Included: Breakfast, Lunch, Dinner

DAY 3 Tinos

 

Drop anchor at the island of Tinos, a sculptor’s haven dotted with villages full of terraced hillsides, Venetian-era dovecotes, and quarries renowned for their superb green marble. Explore the picturesque village of Pyrgos, generously adorned with carved marble facades. And visit the Church of Panagia Evangelistria. Built around a miraculous icon, it’s Greece’s holiest shrine–and thousands of pilgrims make their way here every year to pray.

Meals Included: Breakfast, Lunch, Dinner

DAY 4 Amorgós

 

The easternmost island of the Cyclades, Amorgós is a bit less frequented than many, but no less impressive. After dropping anchor, take in the beautiful domed churches and windmills of the main city, a scenic enclave perched in the mountains. Explore the Panagia Hozoviótissa monastery, clinging tenaciously to a cliff face above the sea. Like so many others in this region, it was built a millennium ago to protect a precious religious relic.

Meals Included: Breakfast, Lunch, Dinner

DAY 5 Santoríni

 

Venture into remarkable Santoríni—an island archipelago formed from a single volcanic cone that erupted 2,600 years ago to bury the resident Minoan culture in ash. Sail directly into the caldera and then drive through windswept vineyards to reach spectacular high views from the town of Oía. Tour the Archaeology Museum and excavations at Akrotiri, an important Minoan town preserved under volcanic ash like Pompeii, with well-built houses, streets, waterworks, pottery, and art.

Meals Included: Breakfast, Lunch, Dinner

DAY 6 Delos / At Sea

 

Designated a UNESCO site in its entirety, uninhabited Delos is an outstanding archaeological gem. In myth, it’s the birthplace of the twin Greek immortals Artemis (goddess of animals and the hunt) and Apollo (god of healing, music, and light). Spend a morning surveying the Terrace of the Lions and exquisite Temple of Apollo, among the many incredible ruins preserved here. This afternoon, the adventure continues aboard the ship.

Meals Included: Breakfast, Lunch, Dinner

DAY 7 Sífnos / At Sea

 

In the morning, set foot on a rugged island known for its flavors, its beaches, its 227 churches, and its poets. A quaint harbor and scenic upper chora (village) invite exploration, and tempting local comestibles can be found at a waterfront taverna. This is also a fine place for a brisk walk or a lazy stroll along the beach. As afternoon arrives, we prepare to hoist our sails once more and depart for Piraeus.

Meals Included: Breakfast, Lunch, Dinner

DAY 8 Piraeus / Disembark Ship / Athens

 

Enjoy a farewell breakfast on board before disembarking and transferring to the airport for your flight home—unless you’ve opted for our three-day post-voyage extension in Crete. A two-day pre-voyage extension in Athens is also available, should you want that upfront intro to the region.

Departure Time: Depart after 12:00 p.m. local time.

Departure City: Athens, Greece

Meals Included: Breakfast

Please Note:

Itineraries are subject to change.

Sailing the Greek Isles aboard the Sea Cloud Fleet reverse itinerary:

show main itinerary
Please Note: *

Itineraries are subject to change.

DAY 8 Piraeus / Disembark Ship / Athens *

 

Enjoy a farewell breakfast on board before disembarking and transferring to the airport for your flight home—unless you’ve opted for our three-day post-voyage extension in Crete. A two-day pre-voyage extension in Athens is also available, should you want that upfront intro to the region.

Departure Time: Depart after 12:00 p.m. local time.

Departure City: Athens, Greece

Meals Included: Breakfast

DAY 7 Sífnos / At Sea *

 

In the morning, set foot on a rugged island known for its flavors, its beaches, its 227 churches, and its poets. A quaint harbor and scenic upper chora (village) invite exploration, and tempting local comestibles can be found at a waterfront taverna. This is also a fine place for a brisk walk or a lazy stroll along the beach. As afternoon arrives, we prepare to hoist our sails once more and depart for Piraeus.

Meals Included: Breakfast, Lunch, Dinner

DAY 6 Delos / At Sea *

 

Designated a UNESCO site in its entirety, uninhabited Delos is an outstanding archaeological gem. In myth, it’s the birthplace of the twin Greek immortals Artemis (goddess of animals and the hunt) and Apollo (god of healing, music, and light). Spend a morning surveying the Terrace of the Lions and exquisite Temple of Apollo, among the many incredible ruins preserved here. This afternoon, the adventure continues aboard the ship.

Meals Included: Breakfast, Lunch, Dinner

DAY 5 Santoríni *

 

Venture into remarkable Santoríni—an island archipelago formed from a single volcanic cone that erupted 2,600 years ago to bury the resident Minoan culture in ash. Sail directly into the caldera and then drive through windswept vineyards to reach spectacular high views from the town of Oía. Tour the Archaeology Museum and excavations at Akrotiri, an important Minoan town preserved under volcanic ash like Pompeii, with well-built houses, streets, waterworks, pottery, and art.

Meals Included: Breakfast, Lunch, Dinner

DAY 4 Amorgós *

 

The easternmost island of the Cyclades, Amorgós is a bit less frequented than many, but no less impressive. After dropping anchor, take in the beautiful domed churches and windmills of the main city, a scenic enclave perched in the mountains. Explore the Panagia Hozoviótissa monastery, clinging tenaciously to a cliff face above the sea. Like so many others in this region, it was built a millennium ago to protect a precious religious relic.

Meals Included: Breakfast, Lunch, Dinner

DAY 3 Tinos *

 

Drop anchor at the island of Tinos, a sculptor’s haven dotted with villages full of terraced hillsides, Venetian-era dovecotes, and quarries renowned for their superb green marble. Explore the picturesque village of Pyrgos, generously adorned with carved marble facades. And visit the Church of Panagia Evangelistria. Built around a miraculous icon, it’s Greece’s holiest shrine–and thousands of pilgrims make their way here every year to pray.

Meals Included: Breakfast, Lunch, Dinner

DAY 2 Sailing the Aegean *

 

Our first morning on board is spent at sea, bound for the Cyclades and reveling in the blue magic of the Aegean horizon from our classic tall ship. Relax on deck with a book or journal. Watch the crew dance across the rigging to trim four masts’ worth of sails by hand. Attend interactive discussions led by our team of experts as they introduce the region’s history and ecology.

Meals Included: Breakfast, Lunch, Dinner

DAY 1 Athens, Greece / Piraeus / Embark Ship *

 

Arrive in Athens and transfer to Piraeus, where you will embark the ship in the late afternoon. Settle into your cabin and take in our first Greek sunset at sea.

Arrival Time: Arrive before 4:00 p.m. local time.

Arrival City: Athens, Greece

Meals Included: Dinner

* = Indicative
Map for Sailing the Greek Isles aboard the Sea Cloud Fleet
Sea Cloud II, the ship servicing Sailing the Greek Isles aboard the Sea Cloud Fleet

Sea Cloud II

Vessel Type: Tall Ship (Sailing)

Length: 105 metres

Passenger Capacity: 88

Built: 2001

Sea Cloud II is a romantic tall ship that masterfully blends the elegance of classic sailing with the comfort and convenience of modern luxury. Inspired by her legendary predecessor from the 1930s, this three-masted barque is fitted with 23 sails and is hand-sailed whenever possible, adding a sense of theatre and tradition to every voyage. With 44 cabins accommodating just 88 guests, the atmosphere aboard remains intimate and relaxed, while the interiors evoke the charm of a bygone era—polished wood, sweeping staircases, and vintage nautical style—all paired with the contemporary standards of a premium expedition ship.

Guests aboard Sea Cloud II enjoy spacious decks for sun-soaked sailing days, al fresco dining on the Lido Deck, and a wellness area featuring a sauna, massage therapy, and fitness facilities. The ship’s welcoming indoor spaces include an elegant dining room and a comfortable lounge for evening Recaps hosted by expert field staff such as historians and photo instructors. Meals focus on locally sourced ingredients and regional cuisine, served in an informal yet refined setting. With an open Bridge policy and wide, accessible passageways, Sea Cloud II invites guests not just to relax, but to immerse themselves fully in the experience of life under sail.

Cabin layout for Sea Cloud II
• Experience the Cyclades while under full sail aboard a romantic tall ship

• On UNESCO World Heritage-listed Delos, the mythological birthplace of twin gods Artemis and Apollo, visit the Temple of Apollo, an important archaeological site

• At Tinos, see the active pilgrimage site of Panagia Evangelistria and terraced hillsides

• Explore the cliffside Panagia Hozoviótissa monastery in Amorgós and ride a cable car down from a clifftop in beautiful Santorini

• Explore Athens on a two-day pre-voyage extension or Crete on a three-day post-voyage extension