Cyclades Islands Sailing Adventure
Cyclades Islands Sailing Adventure

Cyclades Islands Sailing Adventure

8 days

Sailing in CycladesSailing near the shores of one of the Cyclades IslandsGroup of travellers swimming in turquoise waters near KythnosDiving near Cyclades IslandsHiking in Kythnos Island (Greece)Small oldtown of one of the small towns in Cyclades IslandsKythnos shoreline as seen from the sailing boatSun tanning on the deck of the sailboatSailboat interiorSailboat in turquoise waters near the shores of GreeceMidday brunch time on a sailing boatGroup of walkers on Kythnos island while on a guided tourNaousa Port in ParosBoats at Port of Naousa in Paros island

Enjoy the Greek sun and sparkling waters of the Aegean as you sail the Cyclades Islands

The shining sapphire waters of the Aegean sea invite you to come and explore on the exciting Cyclades Islands Sailing Adventure. Board the sailing yacht that you’ll call home for the week and discover the freedom of boat life!

During this amazing tour, you’ll visit historic villages and ancient sites while you explore the islands. Sail to hidden coves and secluded beaches to swim, snorkel, and kayak in the turquoise waters. Experience the unique character of each island from lively Mykonos to laid-back Kythnos and Serifos. This island-hopping sailing adventure is the perfect way to experience the incredible Cyclades.

Highlights of the Cyclades Islands Sailing Adventure

Sail to secluded beaches and amazing islands including Kythnos and iconic Mykonos.
Hike to amazing ancient archaeological sites and on beautiful island trails as you explore the Cyclades.
Swim in the turquoise waters of the Aegean and sail to secluded beaches.
Enjoy delicious local cuisine as you explore authentic restaurants and tavernas at your island ports.


From $1,450USD
8 days
Partially Guided
Sailing Yacht
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Cyclades Islands Sailing Adventure

Cyclades Islands Sailing Adventure Itinerary

Day 1 Board Your Sailboat in Athens

Your tour begins at the dock in Athens where you’ll board the sailboat and get settled in your cabin. The crew will give you a tour of the boat and a safety briefing before you set sail. The destination for your first sail will be Kythnos Island.

When you arrive at the port in Loutra you can visit the natural hot springs and enjoy dinner on this lovely island.
Overnight Location: Sailing yacht at Kythnos Island
Meals: None

Day 2 Explore Kythnos and Syros Islands

This morning you’ll wake up to a beautiful day in Kythnos. Go on a hike from the port to visit the ancient Castle of Oria, explore the historic site, and take in the beautiful views of the Aegean. After your hike, you’ll return to the boat for an afternoon sail and a swim on your way to Syros island.

When you arrive you’ll have plenty of time to explore the beautiful churches and Cycladic architecture of the town of Ermoupoli.
Overnight Location: Sailing yacht at Syros Island
Meals: Breakfast, lunch

Day 3 Discover Amazing Mykonos

After an early morning sail, you’ll soon see the famous white buildings of Mykonos rising on the horizon. Spend the day exploring this amazing island and visiting its lively beaches on your own or book one of the many exciting tours. Some possibilities are a guided tour of the archeological sites on Delos, a walking tour of Mykonos, or even a cooking class to learn some secrets of Mediterranean cuisine.
Overnight Location: Sailing yacht at Mykonos
Meals: Breakfast

Day 4 Secluded Beaches and Fishing Villages

This morning you’ll enjoy the crystal waters and quiet beaches on the tiny island of Rinia. Swim, snorkel, or just relax in the sun and take in the views of this island paradise.

Next you’ll sail to Naousa on Paros island. Explore this small fishing village and visit the Venetian fortress or book a horseback riding or wine tour on the island. Paros is also the perfect spot for a hike or to rent a sea kayak to paddle the coast.
Overnight Location: Sailing yacht at Paros
Meals: Breakfast, lunch

Day 5 Island Hike to Chora

Today you have a day filled with incredible Greek scenery ahead of you! After a short sail to Antiparos, you’ll discover another secluded island paradise for you to enjoy.

Later you’ll hop over to the island of Serifos, where you can take a scenic hike to Chora. You’ll be awestruck by the amazing views on your way to the city, and then you’ll have dinner and soak in the atmosphere at a local taverna.
Overnight Location: Sailing yacht at Serifos Island
Meals: Breakfast

Day 6 Ancient Ruins and Beautiful Beaches

Sail back to Kythnos in the morning and dock in Merichas. From here you’ll take a hike to explore the historic sites of the island including Vryokastro, an archaeological site that unearthed important finds from the Mesolithic period. Then it’s on to the spectacular Kolona Beach where you’ll enjoy a swim and can have a picnic lunch.

Finally, you can decide if you want to spend more time exploring Merichas or Chora, which both offer great spots for you to have dinner.
Overnight Location: Sailing yacht at Merichas
Meals: Breakfast

Day 7 Sailing Day and Return to Athens

This morning you’ll start sailing back to Athens. Go for a final swim or snorkel during a stop on the way and enjoy a delicious lunch onboard.

When you arrive at the Lavrio marina you can visit some of the sights in Athens, and then return for your last night on the sailing yacht.
Overnight Location: Sailing yacht at Athens
Meals: Breakfast, lunch, dinner

Day 8 Disembark in Athens

You’ll have to check out of your cabin this morning and begin your journey home or continue on your Greek adventure. Book ahead to spend some extra time in Athens!
Overnight Location: None
Meals: None

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Cyclades Islands Sailing Adventure Price and Dates

Pricing for this sailing tour of the Cyclades depends on whether you choose to join an existing group on a specific date or if you prefer a custom tour for your group only, as well as the kind of cabin and dates of travel you choose. Note that for fixed-departure dates, a minimum of 4 travellers is required to run the tour.

The best time to travel to Greece for sailing is the warm late spring-early fall, from early June through mid-September.

Private Guided Cyclades Islands Sailing Adventure

Have your own private tour with just your group! There are various boat rentals available for groups from 4 to 8 (with some catamaran models that can fit up to 12). The price depends on the group size, chosen yacht category and your travelling dates. Please contact us with your preferred dates and group size to learn about all the options available. Please note that the departures are on every Saturday.

  • Economy monohull yacht: starting from $1,895 USD per person
  • Prestige monohull yacht: starting from $2,050 USD per person
  • Economy catamaran: starting from $2,250 USD per person
  • Prestige catamaran: starting from $2,295 USD per person

Join a Group Tour on the Cyclades Islands Sailing Adventure

Make new friends and join a group sailing in Greece. Prices below are per person:

Sep 03, 2022
Sep 10, 2022
From Athens, Greece
To Athens, Greece
8 days / 5+ Spaces Left
Oct 08, 2022
Oct 15, 2022
From Athens, Greece
To Athens, Greece
8 days / 5+ Spaces Left

Accommodation on the Cyclades Islands Sailing Adventure

Your accommodations on this tour will be on a crewed sailing yacht. The boat can accommodate 8 to 10 guests. You’ll be able to swim and relax on the boat, or lend the skipper a hand and help with the sailing.

In some cases, the accommodation listed below may need to be substituted for other comparable accommodations.

Single Rooms and Solo Travellers
Rooms are double occupancy. You can pay a supplement of $625 USD-$650 USD (depending on the departure date) to have a private cabin on scheduled departure tours. Solo travellers may be required to pay a supplement.

Economy monohull yacht

Night 1-7

Cabin Onboard Crewed Economy Monohull Yacht

The size of the boat depends on the numbers of guests, but you can expect to sail in a yacht from 43 to 51ft long that has 3-6 cabins with 2-5 wc’s. The examples of yacht model are Bavaria 49 and Oceanis 43.

Prestige monohull yacht

Night 1-7

Cabin Onboard Crewed Prestige Monohull Yacht

This type of yacht offers 4-6 cabins with 2-5 WC’s (depending on your group size) and ranges from 38 to 52ft. The examples of models are Bavaria Cruiser 48, Bavaria Cruiser 51 and Bavaria Cruiser 46.

Economy catamaran

Night 1-7

Cabin Onboard Crewed Economy Catamaran

The size of the boat depends on the numbers of guests, but you can expect to sail in a catamaran yacht from 28 to 52ft long that has 3-6 cabins with 2-5 wc’s. The examples of yacht model are Lagoon 39 and Lagoon 380.

Prestige catamaran

Night 1-7

Cabin Onboard Crewed Prestige Catamaran

The size of boat starts from 42ft and some models meant for bigger groups offer en suite facilities. Also, these yachts are newer (build between 2015 and 2021). Some examples are Lagoon 42 and Lagoon 50.

What’s Included in the Cyclades Islands Sailing Adventure?


6 breakfasts and 3 lunches are included. Dinners, drinks, and alcoholic beverages are not included.


Accommodations for 7 nights are included. Accommodations before and after the tour in Athens are not included but can be added as a supplement.

Transportation during the Tour

Transportation for you and your luggage are included throughout the tour on the sailing yacht. Transfers from the airport or central Athens to the marina are not included.

Also Included

  • Sailboat with skipper and group leader
  • Hiking tour on Kythnos on Day 1 and 6 and optional Serifos hike
  • Use of onboard snorkelling equipment
  • Port taxes, gas, electricity, water, and port charges
  • Bed linens and towels
  • Cleaning fee
  • VAT, Yacht and liability insurance

Not included

  • Flights
  • Visas if required
  • Meals, drinks, or snacks not previously mentioned
  • Anything not mentioned as included
  • Gratuities for tour guides or other staff if desired
  • Travel insurance

Optional Extras

  • Additional nights before or after the tour
  • Single occupancy upgrades
  • Optional activities or excursions (guided tour to Delos, cooking class in Mykonos, and optional activities in Paros)

Frequently Asked Questions about Cyclades Islands Sailing Adventure

Trails Beyond has been leading adventures in Greece since 2013. Bringing local expertise combined with global experience, Trails Beyond is a boutique tour operator with itineraries that go beyond the conventional. Trails Beyond has a special expertise in sailing, and offer a unique vantage point to those who want to soak up all that Greece has to offer.

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Cyclades Islands Sailing Adventure Map

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Is this tour for me?

We rate this tour as a 1/5. This tour has a flexible itinerary that allows you to choose how much you want to hike, swim, and explore. Accommodations are on a sailboat, so it is most suitable for people who are comfortable on a small boat and confident in their swimming abilities.

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