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
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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 Cape Sounio/ Kythnos island - Serifos island
What better than a morning dive from the boat, under the imposing temple of Poseidon, before even taking breakfast?! After breakfast on board, you will set our compasses with direction the island of Serifos, where you can find the Cycladic simplicity you might be looking for.
In case you are in Kythnos, you can go on a morning hike, before setting sails to the unspoiled and charming island of Serifos (≈ 44nm, ≈ 6 hrs sailing).
Once we reach the port, we welcome you to walk with us uphill all the way to Chora, the main town of the island. It is a steep, yet short walk up and the views, especially from the Venetian fortress will captivate your senses! Stroll through the narrow streets and get lost in Chora! Enjoy your dinner in one of the traditional tavernas and why not, some drinks afterwards in one of the fancy bars.
Overnight Location: Sailing yacht at Serifos Island
Meals: Breakfast, lunch
Day 3 Serifos - Kimolos island
Today you will sail towards one of the least touristic and most authentic Cycladic islands, Kimolos (≈ 21nm, ≈ 3 hrs sailing). Kimolos is another volcanic island, whose name derives from the Greek word “kimolia”, which is translated into chank. The island is the perfect getaway for those looking to escape the crowds and enjoy peacefulness and tranquility, among some spectacular white sandy beaches and tiny villages.
You will spend the day anchored at one of its pristine beaches (depending on the weather), before reaching the port, from where you can walk to Chora, the main town, explore its narrow, cobbled streets and locally run restaurants and bars.
Overnight Location: Sailing yacht at Kimolos
Meals: Breakfast
Day 4 Kimolos – Polyegos island – Milos island
Right opposite Kimolos lies the small uninhabited island of Polyegos, a secluded paradise with turquoise crystal clear waters that will definitely captivate your senses. This will be your first swimming stop for today. You will have time to enjoy swimming, snorkeling, dives from the boat or simply relax on the deck and sip the sun.
You will then sail along the south coastline of Milos to reach the spectacular coves of Kleftiko, probably the most photographed beach of Milos and for a reason! Kleftiko is a former pirates’ hideout with imposing volcanic rock formations, countless caves and turquoise crystal clear waters, accessible only by boat or on foot via a hiking trail.
There will be time for swimming, exploring the numerous caves and enjoying lunch on board, before sailing towards the port of Milos, where we will spend the night.
Overnight Location: Sailing yacht at Milos
Meals: Breakfast, lunch
Day 5 Milos - Sifnos island
After breakfast on board, you can go on a morning tour around the island to see some more of Milos’ highlights, such as the moonscape-like Sarakiniko beach, the 2nd most well-known landmark after Kleftiko, the catacombs, the place where Venus de Milo was discovered, the ancient theatre and the picturesque fishing village of Klima with its colorful postcard – like houses (tour duration approx. 3hrs, at an extra cost).
You can then say goodbye to Milos and set sails to your next destination, the charming and aristocratic island of Sifnos (≈ 20 – 24 nm, ≈ 3 – 4 hrs sailing). The exact spot/marina where you will spend this evening depends on the weather conditions.
Once in Sifnos, do not miss the chance to visit the traditional and historic settlement of Kastro, a lovely cliff-top village, which literally means Castle. Kastro is built on top of the ruins of the ancient capital of the island, it has a strong medieval character and it offers spectacular panoramic views over the Aegean sea!
Overnight Location: Sailing yacht at Sifnos Island
Meals: Breakfast
Day 6 Sifnos - Kythnos island
After breakfast, you’ll set sails to Kythnos island, another hidden gem of the Cyclades that has managed to maintain its authentic character (≈ 38nm, ≈ 5 – 5.5 hrs sailing).
You cannot visit Kythnos, without going to the unique beach of Kolona, one of the island’s landmarks! Kolona is actually a strip of sand joining Kythnos with the islet of Agios Loukas, creating a landscape of unparallel beauty! Once there, you can enjoy swimming and snorkelling, as well as lunch at the only tavern on the beach. You can also walk all the way up on top of Agios Loukas islet and enjoy the panoramic views it offers.
Later you will head to Merichas, the main port of Kythnos, where you will spend the evening (unless you prefer to spend your last night before returning to Athens anchored at a secluded beach, gazing at the stars and enjoying all the tranquillity our sailing yacht can offer.
Overnight Location: Sailing yacht at Kythnos
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
This guided tour is run as a mixed group on a scheduled departure. Private departures are available on request.
Prices below are per person:
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 $650 USD-$675 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
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
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
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
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?
Meals
6 breakfasts and 3 lunches are included. Dinners, drinks, and alcoholic beverages are not included.
Accommodations
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
- Security deposit of 200 EUR in cash (fully refunded during the disembarking)
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.
Learn MoreCyclades Islands Sailing Adventure Map
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