When in Greece you can't go wrong with wandering around charming streets. For the past decade or so, this magical country has been chilling at the top of the adventure enthusiasts’ bucket list. If you have finally got a chance to go there, congratulations!! Save Athens for another time, and focus your time on some gorgeous Greek islands instead with island hopping with your yacht in various island destinations. And, here’s how you can make your Cyclade itinerary memorable.

• Soak up beautiful views
• Read lots of books
• Eat as much as authentic food as possible OR
• Do absolutely nothing - yes you read it right

Although 33 main habitated islands make up the Cyclades with much more small inhabitated isles, most of the visitors to Greece and the Cyclades flock to famous islands like Santorini and Mykonos. An incredible list of sights to explore, the archaeological ruins, rugged landscapes, and the Aegean Sea make the Cyclades the ideal sailing destination. Some tourist-trodden islands like Santorini and others far underrated and often completely unknown islands like Folegandros make an authentic taste of Greek island life.

Adventure, thrill and fun await you through the Cyclades Itinerary which is in fact the "milk-run" route for two weeks charter. On both the South and the North Cyclades group, you will be sailing through ports and anchorages. During the voyage you might stop for 2-3 hours in a bay or quiet beach or anchorage for light lunch or swim. Most of the evenings are spent at the islands' ports. If you like busy areas you might choose to rush ashore for sightseeing, dinner, or shopping, while others prefer to relax on board. Overnight is possible on quiet bays too - needless to say that destinations and exact routes are subject to weather conditions.
NOTE: It will have moderate difficulty level when it’s too windy.

1st Day - Alimos Marina Check-in at 17:00 ( or option for Lavrio port Departure in Cape Sounio )
Distance traveled: 00
GPS position: 37°54’51.81” N - 23°42’09.87” E

Our two-week adventure-filled itinerary begins at Alimos Marina - the starting point for most Athens yacht charters. With more than 1000 permanent berths, Alimos Marina is one of Greece's largest and busiest ports.

It is a perfect base for exploring the Greek coast and multiple island destinations in Aegean and Saronic Gulf. The infrastructure & ambiance of the Alimos Marina is incredible. It is located in the well known Southern suburbs of Athens so unlimited facilities are available with marine equipment provision stores, supermarkets etc so that you can stock up on necessities for your trip. There is an option also to arrange your departure to be from Lavrio port in company’s premises in Cape Sounio for saving few miles to your first destination with same well organized facilities and infrastructure to Alimos Marina.
Pro-tip: If you sail an extra mileage on the first days of such sailing holidays, it will help you be ahead of the wave of charter yachts flowing into the Athens

2nd Day - Alimos Marina ( Or Lavrio) → Vourkari (Kea)
Distance traveled: 37NM ( or 16 miles for Lavrio Option )
GPS position: 37.6657° N, 24.3239° E


On day two of our Cyclades Sailing Itinerary, we reach Vourkari. This small fishing village is a perfect spot for fishing enthusiasts. It has plenty of sailing boats & fishing boats so that you can pursue your adventures. It has just a few local residents. The inflow of tourists has increased due to recent developments by the tourists’ department. Some of the great restaurants will provide you food to tickle your taste buds, but remember food is not the only attraction in this place. Go visit cultural places, museums, and art galleries, if you are a history buff, this place is for you.

Vourkari’s prehistoric villa is also worth the visit. Want to have also some adventurous diving experience? It will absolutely be an unforgettable one as Kea is surrounded by a series of shipwrecks including well know Titanic´s twin sister vessel , floating hospital Britannic which sunk in Kea’s coastal water during WWI ! Other wrecks for diving are French ocean liner Burdigala to paddlewheel steamboat Patris and Germal Junkers 52 airplane from the WWII also. Seek for the professional diving excursions available in Kea as wreck diving is a demanding dive and requires professional support and include an unforgettable diving experience in your summer holidays !
 


3rd Day - Vourkari (Kea) → Ermoupolis (Syros)
Distance traveled: 34NM
GPS position: 37°26'30'' N 24°56'25'' E

Syros might not be as famous as Paros, Santorini, or Mykonos, but that’s where the island’s charm lies. The hilly island stands proudly in the sea half-way between Kythnos & Mykonos. Ermoupolis is the most picturesque capital, and the stately town exudes an old-world charm in keeping with its significance. This romantic and laid-back holiday destination brings in nostalgic & elegant vibes that enchant almost every visitor.

It’s home to the rich culture depicted in its wonderful architecture today- from its neoclassical buildings to the elegant mansions. It is an incredible place for a cultural buff.
 




4th Day - Ermoupolis (Syros) → Tinos

Distance traveled: 11NM
GPS position: 37.5773° N, 25.1652° E

Ravel the beauty of Tinos with its six villages and one monastery. Caution - you might get some of the fairy tale vibes as you go through this place. The exceptional traditional architecture, extended use of marble in the houses, and the small paths running between the houses will give you a unique feeling. The views are perfect, particularly during the sunset. Feel the place's calmness and learn its history as you explore this lively & authentic place. The shrine of the Holy Church of Panagia Evaggelistria of Tinos is the most important orthodox shrines of pilgrimage in Greece and one of the most famous throughout the world. For the inhabitants of the island is their most sacred place.
 


5th Day - Tinos → Mykonos

Distance traveled: 10NM
GPS position: 37.4467° N, 25.3289° E

Just 10 NM from the Tinos is the beautiful island of Mykonos. It is known for its vibrant life and white architecture. If you love partying, trust me, you will end up having so much fun. The place is known for the glow & glitter and that’s the authentic charm of the island. Make sure you spend some time exploring the magic of the Old Town and around too.

You can anchor at Mykonos Old Port harbor, which is home to everything. Or you can choose to anchor in the beautiful beaches at Aghai Anna bay.
 


6th Day - Mykonos → Naoussa (Paros)

Distance traveled: 20NM
GPS position: 37.1236° N, 25.2387° E

Just 20 NM away from Mykonos is the beautiful picturesque fishing village of Naoussa. It is known as the prettiest village for a reason, it has whitewashed, flowered little chapels, churches, and houses. Despite the influx of tourists throughout the year, the lovely village has been able to keep its traditional charm and authenticity.

Naoussa is located in a huge bay in the northern part of Paros.
 


7th Day - Naoussa (Paros) → Ios

Distance traveled: 32NM
GPS position: 36° 42' 59.99" N 25° 19' 60.00" E

Honestly, Ios has two faces, the nightlife, and its magnificent days - but both are enchanting. Boasting one of the typical seductive Cycladic landscapes, Ios is an absolute Cycladic paradise and is home to the picturesque clifftops, narrow cobbled alleys, whitewashed houses, and of course mesmerizing Ios beaches.

Chora, the delightful capital of Ios has everything you would look for in a sailing trip. The Cycladic island that sits in the heart of Aegean is popular among youth for its nightlife. But that’s just one of the aspects the Ios has. You can go to the golden beaches & mesmerize the crystal clear Aegean waters. If you got lucky to spend the night, you will be amazed to see the nightlife as bars & restaurants come alive while the sun takes a dip into the golden beaches.
 


8th Day - Ios → Santorini

Distance traveled: 21NM
GPS position: 36.3932° N, 25.4615° E

Day 8 of the Cyclades sailing itinerary stops at Santorini - the sailing heaven. Santorini has something for everyone, there are a lot of inlets to explore & cliff faces to marvel at. You will fall in love with the charming little villas sprinkled all over the hill that offers breathtaking views of the bay. Grab a glass of white wine or cup of coffee and spend some time on the patio - it’s dreamy!

Santorini is just 21NM away from the gorgeous Ios. This mountainous island has a thriving nightlife, white sandy beaches, and an active volcano. Moor overnight at the Skala to avoid powerful winds.
 


9th Day - Santorini → Folegandros

Distance traveled: 25NM
GPS position: 36.6171° N, 24.9161° E

A less known island, but the most loved one. Folegandros’ tourism season doesn’t kick off until June, which means even if you go there in May, the island will still be very quite. Kick back, relax and make some unforgettable memories together before the peak season at this off-the-beaten island that is just accessible by boat.

Interestingly, it has a total population of just 650 people , making this island  so authentic ! And, it’s no wonder most people have never even heard of Folegandros - the loved island.



10th Day - Folegandros → Adamas (Milos)

Distance traveled: 34NM
GPS position: 36.7253° N, 24.4448° E

On the 10th day of the Cyclades, we reach the port of Adamas - the principal harbor on Milos island. It is the vibrant cultural center from where you can easily access Plaka, Trypiti, and Klima's foremost villages.

Milos is the most westerly of the larger Cyclades. It is home to monumental natural harbors in the Mediterranean. Travel around to find the incredible monuments, art galleries and admire the architectures, and you can't go wrong with wandering around charming streets.
One of the best places to sail with your yacht, as they are only accessible by yacht are the astonishing spot of Kleftiko in South part of Milos which was an old pirates' hideout and now one of the most popular tourist attractions in Milos island. It is a unforgettable experience of navigating until there for a swim or staying overnight at anchor. Kleftiko is famous for its crystal-clear water, elaborate caves and imposing rock formations.
Another worth visiting beach is Sarakiniko situated on the north shore of the island with its distinctive greyish-white volcanic rock shaped by waves over the years into amazing shapes often compared to a moonscape.



11th Day - Adamas (Milos) → Kamares (Sifnos)

Distance traveled: 24NM
GPS position: 36.9890° N, 24.6748° E

On day 11 you will reach Kamares, where the sky is a brilliant blue, the days are bright, and the sun is hot. The dreamy Kamares has everything you’d expect from a Greek seaside village. It has vibrant whitewashed homes that tumble down the hills to the main street where daily life takes place. Mesmerize the lively scenes as you see the kids ride bikes in the road, scooters whizz by, waiters rush across delivering orders to the tables overlooking the bay, stray cats meander about looking for a snack. At the same time, the fishermen ply their daily catch at the harbor.

Immerse among the locals, and you will love catching a glimpse of the real Greece. Of all the villages you will visit, Kamares will make you feel at home.
 


12th Day - Kamares (Sifnos) → Livadi (Serifos)

Distance traveled: 12NM
GPS position: 37.1427° N, 24.5138° E

We will be at Livadi on the 12th day of our two weeks charter. Being the main port of Serifos, Livadi has the best tourist infrastructure. Take some time to explore the villages that offer various options for restaurants, taverns, bars, and clubs. Watch the magical sunrise views, spend some time at the beach or mesmerize its nightlife, a mix of quiet spots with a great atmosphere!

In case you plan to spend your whole day, head to a close beach of Livadakia, which is a well-sheltered location from the winds offering many facilities as well. In the case of Livadi beach, it is a little less quiet since many ferries arrive and dock.
 


13th Day - Livadi(Serifos) → Merichas(Kythnos)

Distance traveled: 21NM
GPS position: 37.3887° N, 24.3978° E

Your final stop before returning to Alimos Maria will be picturesque Merichas, which has kept its traditional appearance throughout the years. It is the main port on the island of Kythnos. The bay is divided by a sandy spit, making this an excellent spot for protected swimming in the shallow water and taking the dinghy for some sundowners on the beach.
Another excellent beach for staying overnight at anchor or even for a quick swim is the marvelous double sided beach of Kolones ,on of the most well known sightseeing spots of Kythnos. Exploit the most of your privilege as Kolones is only accessible by sea and the restaurant which is built uphill with the astonishing view of the double side beach will leave you with an unforgettable experience. Alternatively , cook dinner on board, enjoy the fresh meal, as you witness the golden sunset in this stunning bay.
 
 
 

14th Day - Merichas (Kythnos) → Alimos Marina

Distance traveled: 45NM
GPS position: 37°54’51.81” N - 23°42’09.87” E

It's time to return your yacht to the base and sail to Alimos Marina from Merichas around 45NM. (or 25 NM in case you select Lavrion return) Take this opportunity to visit remarkable Poseidon Temple in Cape Sounio overlooking Aegean Sea  before you could head to the your final destination,  enriching your experiences even the last day of your sailing vacation.

On your arrival in final destination, explore some Greek and Italian restaurants nearby and some will deliver straight to your boat. You will also find a snack bar inside the marina that doubles as a coffee shop but has rather steep prices. If you are looking for a budget-friendly option, you will find fast-food chains within 5-10 minutes of walking. Within the Alimos marina ground is a nightclub for fun purposes, catering to the sailors' after-dark party needs. 

 


15th Day - Check out at 9:00

The next morning at 9:00 is the checkout after two weeks of adventures, fun, and thrill. Say farewell to your fellow sailors, as you begin your next adventure and head to Athens International Airport.