Sailing the Greek Isles is a luxury cruise aboard the Sea Cloud II, an exclusive charter based on the historic windjammer Sea Cloud. Experience the Cyclades while under full sail aboard a romantic tall ship, relaxing on board while crew members climb the rigging and hoist the sails. Cruise alongside a team of expert guides who reveal the awesome history, culture and nature of the Greek Isles.

Cyclades are the Greek islands of the imagination, where colorful fishing boats are reflected in azure waters and whitewashed villages cascade down scrabbled slopes. They surround the sacred sanctuary of Delos, one of the most important archaeological sites in the western world. On the island of Tinos, explore the picturesque village of Pyrgos, adorned with carved marble facades, and visit the church of Panagia Evangelistria, Greece’s holiest shrine. Drop anchor at Amorgos and explore the city perched on a mountainside with beautiful domed churches and windmills. Sail inside the caldera archipelago of Santorini and walk the windswept vineyards of Oia before touring the excavations at Atrotiri, the ancient Minoan town perfectly preserved in ash after its desecration by volcanic eruption. Peruse famous pottery on the rugged island of Sifnos then stop into a waterfront tavern and walk along the welcoming shore.

Every moment of this organized mosaic of island jewels, historic substance, day-by-day living and Mediterranean flavor is as relaxing and magical as a Mediterranean cruise can be. Sailing the Greek Isles aboard the 94-guest Sea Cloud II perfects the atmosphere of elegance. Between bouts of history and mythology from expert guides, immerse in the contemporary culture and beauty of the Greek islands.

Read on for details about this trip, or learn more about AdventureSmith’s Greek Islands small ship cruises and Mediterranean cruises.

Sailing the Greek Isles Aboard the Sea Cloud Fleet Itinerary

Athens, Greece to Piraeus & EmbarkPiraeus to Athens, Greece

Sail through the Greek Isles in a historic fashion aboard a classic windjammer sailboat. This Greece cruise begins and ends in Athens, Greece, with transfers to embark and disembark the ship in Piraeus.

Route map of Sailing the Greek Isles aboard the Sea Cloud Fleet, round-trip from Piraeus with visits to Tinos, Delos, Amorgos, Santorini & Sifnos.

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

ACCOMMODATIONS Sea Cloud II: Lindblad
MEALS Dinner

Your first morning on board is spent at sea, bound for the Cyclades and reveling in the blue magic of the Aegean horizon from your 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.

ACCOMMODATIONS Sea Cloud II: Lindblad
MEALS Breakfast

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.

ACCOMMODATIONS Sea Cloud II: Lindblad
MEALS Breakfast

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.

ACCOMMODATIONS Sea Cloud II: Lindblad
MEALS Breakfast

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.

ACCOMMODATIONS Sea Cloud II: Lindblad
MEALS Breakfast

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.

ACCOMMODATIONS Sea Cloud II: Lindblad
MEALS Breakfast

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, prepare to hoist the sails once more and depart for Piraeus.

ACCOMMODATIONS Sea Cloud II: Lindblad
MEALS Breakfast

Enjoy a farewell breakfast on board before disembarking and transferring to the airport for your flight home—unless you’ve opted for a post-voyage extension.

ACCOMMODATIONS n/a
MEALS Breakfast

Included

Accommodations aboard ship; meals as indicated; beer, wine & full bar; excursions; services of expedition leader, historian, naturalist staff and expert guides; all port charges and service taxes; basic WiFi (enhanced and premium packages available for purchase). Gratuities for all departures of National Geographic Explorer, Orion, Endurance, Resolution, Sea Cloud, Jahan and Lord of the Glens.

Exclusions

Immigration fees; air transportation; extensions; meals not indicated; reserve wines & premium spirits; gratuities for all departures of Delfin II, Endeavour II, Islander II, Venture, Quest, Sea Bird and Sea Lion; personal items such as emails, laundry, voyage DVD, etc.; and insurance of any kind.

Payment & Cancellation 

In order to confirm this trip, a deposit of 15% of the total trip cost is required per person at time of booking. The balance of the trip price is due 120 days before the departure date. Guests who must cancel their trip for any reason must do so in writing. Standard cancellations are subject to the following per-person fees, based on number of days prior to departure:
120 or more days – 100% of deposit**
119 to 90 days – 50% of total trip cost
89 to 0 days – 100% of total trip cost
**Advance payments will be credited in the form of a Lindblad Expeditions Travel Certificate, valid for 12 months from the date of cancellation, and which may only be applied towards final payment on any future booking. 

Terms & Conditions

This trip is subject to AdventureSmith Explorations Terms and Conditions. Please read this information carefully and call us if you have any questions. A Traveler Information Form, which includes a release of liability, must be completed and signed by all travelers. Your Adventure Specialist will send you a unique link to complete this form along with a packing list and extensive pre-departure and travel insurance information upon booking confirmation.

Arrival & Departure

The Sailing the Greek Isles cruise begins and ends in Athens, Greece (ATH). We highly recommend arriving one day prior to your trip start date in case of any flight delay, cancellation or lost luggage issues. Plan flights to arrive to Athens before 4:00pm on Day 1 of the itinerary. Disembarkation is after breakfast on Day 8 of the outlined itinerary. Plan flights to depart Athens after 12:00pm Noon on Day 8. If you would like assistance with international flights, please visit our Booking Flights resource page. 

Activities

Whether you are looking for light activity options or more challenging outdoor pursuits, the ship’s crew can tailor most excursions to suit your skill level. Adventure activities may include hiking, village walks, historical site visits, swimming and guided walks.

Room Configuration

In addition to listed Solo cabin rates, select double-occupancy cabins may be available for single occupancy with a single supplement fee. If you would like to share accommodations with another guest of the same gender, we will be happy to try to accommodate you in select cabin categories. This program allows you to pay the per person double-occupancy rate whether or not a roommate is found. Contact AdventureSmith for further details and availability.

Families & Children

See the Deals section of this trip for any applicable child discounts. There is no special kids programming on this itinerary.

Travel Insurance

Protect your travel investment with insurance. Our partners at Travelex Insurance offer a variety of plans and policies to fit every trip and budget. For best value and coverage for pre-existing medical conditions, consider purchasing a policy at time of booking. Learn more about travel insurance or get a free quote.

Itinerary Notes

Use the itinerary as a guide only. Itineraries may be altered due to weather, wildlife, national park regulation or at the guides’ discretion. The ability to be flexible makes this type of adventure travel unique.

Cruise Rates & Dates

Departures of this itinerary are not currently available. Contact us for comparable Greek island small ship cruises.

Rates are variable per remaining availability and are subject to change.

Learn About the Small Ship on Your Itinerary

The Sea Cloud II: Lindblad is a romantic tall ship with classic charm and modern comforts, chartered by Lindblad Expeditions. This alluring three-masted barque captivates passengers and onlookers alike when her crew climbs the rigging and unfurls the sails.

Luxury 94 GUESTS 384 FEET

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