Greek Island Hopping: sailing the CYCLADES

To accomplish a real authentic Greek experience, going beyond the crowded tourist routes is very highly recommended. The archipelago of the Cyclades islands is in the heart of the Greek Aegean Sea. The islands forming it encircle the rocky islet of Delos (‘cyclade’ meaning circle in Greek),which in ancient times was considered to be the political and religious centre of the known world. Twenty-one bigger islands and twenty smaller ones make up this archipelago. Many places are still uninhabited and wild. All of these islands are a delightful experience and each one expresses its own genuine flow of nature. As a top World destination for yacht island cruises and private sailing boats, these isles are ideal to hop around with your family or friends. White-washed stony houses adorned with deep blue domes, ancient windmills, beaches of golden sand, ancient ruins, and tavernas (little restaurants) that serve delightful Mediterranean cuisine with locally produced wine are all unique features of these isles. Perfect for your unforgettable Greek island cruise.
Exploring all of these beautiful islands from sea to land during your Greek sailing vacation is a great option for you to choose. This brief itinerary offers an overview of your experience while on vacation here – from bays only accessible by sea, to the unique history and architecture of these villages. Nightlife is included on island hopping tours also, if you’re interested.

  • Relax 100% 100%
  • Nature 100% 100%
  • Nightlife 80% 80%
  • Adventure 90% 90%
  • Shopping 90% 90%
  • History & Archeology 70% 70%
Exploring all of these beautiful islands from sea to land during your Greek sailing vacation is a great option for you to choose. This brief itinerary offers an overview of your experience while on vacation here – from bays only accessible by sea, to the unique history and architecture of these villages. Nightlife is included on island hopping tours also, if you’re interested.

Get Started

We are excited you are gaining an interest in trying out our sailing vacation tours. Let’s start working towards it together and have fun arranging it to the very last detail. 

Call on (+1) 201-253-1848 or email us here.

Sandra, London Boat Show 2013 portrait

Kea Island

Makronisos Island

Kythnos Island

Serifos Island

Sifnos Island






Antiparos & Despotico


Naxos South








7 Days Greece sailing trip Example Itinerary East side of Cyclades

These tour itineraries are merely examples and sample of what you could enjoy. these are not cookie cutter tours, all Armstrong tours are entirely customizable to satisfy your desires.

Paros Island

This central hub is the perfect starting point for your vacation. The main town, Parikia, is also a ferry port, but in our experience the marina is tiny and usually very busy. The Prevalent wind during the summer season in this area is harsh, so we suggest embarking to the other side of the island via taxi or public transport. The narrow streets are adorned with bougainvillea flowers, boutiques, countless cafes, lounges, and restaurants. Interested in archeology? The museum here holds ceramic artwork and sculptures from archaic and classical periods. The Katapoliani Church, literally the 100 doors church, holds significant monumental importance to the town. Being the third biggest isle, located in the centre of the Cyclades, it is a modern holiday resort spot and will be one of our bases for boarding and landing. The whitest marble in the world comes from the gentle mountains that dot the landscape, while the rest of the island is flat and covered with endless vineyards. There are picturesque little towns with dazzling white houses, paved alleys, arched churches, and wonderful beaches. We also include this island in our Small Cyclades Archipelago Route, which is considered to be an ideal getaway for those in need of peace and rest. With the constant pounding of the sea on the rocks that line the shores of indented beaches and the wild beauty of the scenery around you, combined with a desire to escape from the ambitious summer crowds,you will appreciate all the reasons that these islands attract the more connoisseurtype of visitors.

Naoussa Town
This is the second largest town on the island. The marina here is modern and offers comfort. Restaurants are located directly on the docks with fishing boats just a few inches from the tables. The little castle on the sea, the narrow streets filled with houses and a myriad of boutiques make this an extremely stylish night-out spot. The town comes alive in the evening with a cheerful atmosphere and a loving nature. We will welcome you onboard with a drink while we get to know each other. We will review what your itinerary will look like and where it will take us. Dinner is in a superb inner village taverna that you will absolutely fall in love with and you can choose to bring the evening to a close with a cocktail on the port while relaxing in one of the comfy beach lounges.

Naxos Island

This is another one of the larger islands in this archipelago. For thousands of years it has been an important place of Greek polytheism worship and culture as many vestiges are still present on these shores. Famous among them is the Apollon Gate which is visible from just a few hundred feet off port. This solid boarding location has its own airport. It is very well connected with the islands Mykonos and Paros, both popular international airport destinations. The Town of Naxos lies close to port, in a maze of colorful streets filled with all sorts of boutiques, tavernas, and cafes. We will take you for a walk in the labyrinth-style streets in the heart of the old town. Feeling up for some night-life in the evening? Just outside the centre is a massive beach filled with lounge bars and all-night music bars.

Panoramas Bay
Far south of the island of Naxos, after an exciting sailing experience, you will arrive in Panoramas Bay. We call it the Jingle-bell Bay because of the sound that the sheep bells make when they move within their pastures around sunrise. This special place is a deep bay sheltered from the wind where you can immerse yourself in nature.

Koufonisi Island

A few miles south of Naxos there is a tiny little sun-kissed island, a unique place amid all Greek isles. The surrounding waters are a deep shade of turquoise. The marina is friendly and quiet, along with the village which is perfect for a fish-based dinner and good drink. We recommend the loukoumades, a common Greek mini doughnut in one of the many bars here with choice views. The atmosphere is just right for a swim and lunch onboard, while in the bays of Kato Koufonisi or at Pori beach. This beach holds a beachfront restaurant that serves a particular Mediterranean delicacy comprised of tiny, fresh fried fish (finger food). Feel free to enjoy the white wine or the ouzo spirit as well.

Donoussa Island
Located a short distance north of Koufonisi, this beautiful island bay holds clear, blue water and an impressive, explorable, large sea cave. Not very crowded and untouched by mass tourism, this island has remained the same over time with untamed, steep coasts.

Amorgos Island

The easternmost isle of the Cyclades is mountainous, with deep creeks and quaint villages, far from common route of tourism. Ancient ruins and important archaeological finds testify to the prehistoric inhabitants of this place. This Island has many diversities. It is a mixture of steep coastlines and precarious jagged areas, rich with caves and beautiful beaches. In the bay of Nikouria you’ll find an ideal place to spend the night at anchor, underneath the starlit sky, and wake up in the morning with a dip in the crystal-clear waters. The main port here is Katapola and the small fisherman village of Egiali, off-port, is very welcoming. The Chora, with its plastered houses is built around the Venetian castle and is situated on the top of the mountain. The view from the top of the castle that overlooks the village encompasses many of the surrounding islands. We can help you find the key to experiencing this stunning spectacle at sunset. The famous monastery of Chozoviotissa is not far from here. This white fortress seems glued to the surrounding black cliffs that overlook the sea, and is the islands most renowned site. In the evening, for dinner, we suggest the island specialty called Patatato in one of our recommended taverna.

Irakleia and Skinoussa Islands

These small islands, which also belong to the Small Cyclades Archipelago, have yet to be spoiled by mass tourism and remain quiet, with exploratory features. The small port offers only a few berths for yachts and often the boats are tied to each other or to the fishing boats. It retains a genuine charm that compliments the simplicity of the village’s inhabitants,with only a few cafes and three taverna, all serving local fish-based specialties and tasty original Greek dishes. Sometimes instead of the little port, we spend the night at anchor just south of the island next to an impressive white sand beach. From there, we either take a 10-seater local bus or travel by foot because of the panoramic views.

Sikinos Island

Secluded at the southern tip of the archipelago, Sikinos Island is another place for those in need of peace. Although probably the smallest port in Greece, it is still home to many fishing boats. The main village is located in the mountains on top of the island and stretches along a ravine. Stone houses are also found here, along with the Pantanassa church. Plenty of olive groves, with a variety of olives, are found scattered around the island. A hike to the Zoodochos Pigi monastery on the pinnacle of the island is recommended- this is an austere fortress with a magnificent view. It is easy to find an exquisite dinner along the streets of this isle inside one of the local taverna or café where locals gather throughout the buzzing squares.

Ios Island

Little creeks make this isle’s coasts very attractive to those travelling by sea, but the island is mostly mountainous with countless little churches, olive trees, and vineyards. There are beautiful sandy beaches with crystal clear waters. The main town here is built up the hill, all in white with narrow alleys, little shops, cafes, and tavernas. Everything, view-wise, seems tiny as if built for a dollhouse. The natural beauty, nightlife, and history of this Island release a rare energy leaving you in awe, wanting more. We will then reach the most renowned beach Manganari,with its emerald waters, located in Mylopotamou bay. Recommended travel to the main village is via bus or motorbike/AVS. The highest point of the village is the church of Panagia Gremiotissa where you can enjoy a breathtaking view that reaches all the way to Santorini Island. On the southern shore of the isle, we will stop for lunch at the Tris Klissies Bay or the three churches bay. This is a place of hidden coves split into three branches where the shades of the waters are a mesmerizing mixture of blue and green. Lucky for us, not many sailors know about it which makes it an unforgettable memory for you and your loved ones.

This is our last stop on this well-connected itinerary for those only with us for the one week. For those traveling to Santorini or back to Athens you can easily find transportation.