Sailing the Greek Isles Aboard the Sea Cloud Fleet
Explore the beautiful Cyclades as the ancients did, sailing from isle to isle under the power of the wind. The three-masted barque Sea Cloud II offers the chance to stand on deck and watch the orchestrated frenzy of crew members climbing aloft in the rigging to handset 23 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.
Highlights
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
View our brochure for more details
Mediterranean: Food & Wine
View our brochure for more details
Mediterranean: Food & Wine
View our brochure for more details
Mediterranean: Food & Wine
Itinerary
Expedition
Starts atPiraeus (Athens), GreeceEnds atPiraeus (Athens), Greece
Day 1
Athens, Greece / Piraeus / Embark Ship
Arrive in Athens, the capital city of Greece, and transfer to Piraeus where you'll embark the ship in the late afternoon. Settle into your cabin and go above deck for a glass of champagne as you set sail this evening.
Arrival Time: Arrive before 4:00 p.m. local time.
Arrival City: Athens, Greece
Meals Included: Dinner
Day 1
Athens, Greece / Piraeus / Embark ShipArrive in Athens, the capital city of Greece, and transfer to Piraeus where you'll embark the ship in the late afternoon. Settle into your cabin and go above deck for a glass of champagne as you set sail this evening.
Arrival Time: Arrive before 4:00 p.m. local time.
Arrival City: Athens, Greece
Meals Included: Dinner
Day 2
Sailing the Aegean
Your first morning on board is spent at sea, bound for the Cyclades and reveling in the blue magic of the Aegean horizon from this 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 your team of experts as they introduce the region’s history and ecology.
Meals Included: Breakfast, Lunch, Dinner
Day 2
Sailing the AegeanYour first morning on board is spent at sea, bound for the Cyclades and reveling in the blue magic of the Aegean horizon from this 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 your 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 3
TinosDrop 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 4
AmorgósThe 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 3,600 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 5
SantoríniVenture into remarkable Santoríni—an island archipelago formed from a single volcanic cone that erupted 3,600 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 World Heritage 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 6
Delos / At SeaDesignated a UNESCO World Heritage 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, the crew prepares to hoist the sails once more and depart for Piraeus.
Meals Included: Breakfast, Lunch, Dinner
Day 7
Sífnos / At SeaIn 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, the crew prepares to hoist the sails once more and depart for Piraeus.
Meals Included: Breakfast, Lunch, Dinner
Day 8
Piraeus / Disembark Ship / Athens
Disembark in Piraeus and transfer to the airport for flights home or explore more on a three-day post-voyage extension in Crete.
Departure Time: Depart after 12:00 p.m. local time.
Departure City: Athens, Greece
Meals Included: Breakfast
Day 8
Piraeus / Disembark Ship / AthensDisembark in Piraeus and transfer to the airport for flights home or explore more on a three-day post-voyage extension in Crete.
Departure Time: Depart after 12:00 p.m. local time.
Departure City: Athens, Greece
Meals Included: Breakfast
Expedition Team
Our captains, crew, staff and guides make up the most experienced team in the industry—committed to making every voyage unforgettable. Veteran captains, with decades at sea, are experts at navigating in all conditions, while seasoned naturalists bring advanced knowledge in fields such as geology, wildlife biology and climate science. Many of these professionals have been with us for decades, and their insights bring each destination to life in ways that profoundly enrich your journey. Their expertise is the foundation for the meaningful and transformative experiences we offer in the world’s most extraordinary places.
Special Offers
CELEBRATE LIFE'S MILESTONES
10% OFF BACK-TO-BACK VOYAGES
SAVE 5% TRAVELING AS A GROUP
COMBINING OFFERS
View our brochure for more details
Mediterranean: Food & Wine