Greek Island Hopping: sailing the DODECANESE

Rhodes (or Rhodos) and Patmos are the most famous islands in this area. This archipelago is located in the south-eastern part of the Greek-Aegean Sea and consists of twelve bigger islands and one hundred and fifty smaller ones, with only twenty six of them remaining inhabited. The crystal clear waters, sandy beaches, archaeological remains, Byzantine art, Medieval monuments, and unique settlements are all waiting for you to discover them.

Smaller islands like Nisyros, Symi, Tilor or Halki are all charming and unique. The villages of Symi and Halki exhibit venetian style houses that overlook the small harbour, a highly recommended sight to be seen. Nisyros Island holds a sort of lunar type of atmosphere with its rather large, active volcano crater.

Day after day you will make new discoveries amidst the ocean, private beaches, and small towns where you can spend unforgettable evenings. Don’t miss out on the Greek food, quiet cafes, and live music. Let us help you with this exciting experience.

  • Relax 100% 100%
  • Nature 100% 100%
  • Nightlife 30% 30%
  • Adventure 30% 30%
  • History & Archeology 90% 90%
  • Shopping 80% 80%

Rhodes central

Symi town

Loryma Bay

Panormitis Monastery, Symi








7 Days Itinerary


Rhodes island

Rhodes has been an Italian colony for forty years and is the main island of the Dodecanese region. Majestically imposing fortified walls surround a labyrinth of stone paths that host an immensity of cafes, restaurants, shops and craftsman boutiques. Supermarkets here have an abundance of fresh, local, and seasonal produce along with a variety of international food. The harbour lies within the centre and is just a short walk to the medieval fortress dominated by St. John’s castle within the old town. Direct flights can be found in the main hub of the area.
Once finished here, we set sail, brushing past the medieval tower that guards Mandraki Harbour. Depending on your arrival time, you can choose to explore the old town or go for a wonderful dinner at a recommended restaurant, leaving harbour in the morning. You can also choose to leave harbour on the same day, in which case we will be sailing from the Europe region to Asia minor area.

Bozburun town

Sailing into the Yesilova Bay, we will anchor in the transparent waters, where you can swim around amphoras and clouds of tiny fish. Just before sunset, we will enter the quiet and welcoming village of Bozburun where you will delight in watching the elderly and younger men peacefully playing backgammon or dominos in the main square under the shade of a massive oak tree. The smell of Mediterranean spices will entice your senses. Also, gentleman can elect to experience the traditional barbers. Time-honored practices include not just shaving, but rather a spa treatment with massages. Ladies, feel free to watch in amusement and document the spectacle for the folks at home.

Symi island

After your relaxing breakfast and an enjoyable sailing experience along the northern coast of the bay, we will be stopping for a swim in a visibly stunning cove as we travel towards Symi Island. Upon arrival to Symi Island, we will drop the anchor in the strikingly beautiful Thessalona (or St John’s) Bay. While setting anchor, it’s tempting to jump in and walk ashore right away because of this world- famous Greek beach, as seen in various postcards. As lunch is being prepared onboard, you can encounter these crystal clear turquoise waters. Allowing time to relax or nap, we will then sail a short distance along the coast, entering the Venetian style village of Symi.

The most colourful pastel houses with red roofing create the village façade that frames the port, and is a spectacular view seen in typical pictures of Dodecanese architecture. The seaside holds various boutiques, cafes, and restaurants. This island is home to what we believe to be the best authentic Greek restaurant, located on the very edge of the bay with a terrace right on the beach. It comes very highly recommended for dinner. Before or after dinner, you can choose to indulge in a quiet drink at Michali’s Vapori lounge, located in the heart of the town. We encourage you to relax and enjoy the atmosphere because no driving is required to make it back to the yacht, which is docked only a few steps away. While the aroma of spices waft through the air, opt to enjoy the magical environment during this summer evening with the sounds Greek instrumental music found throughout the area.

Nisyros island

In the morning, after breakfast, we depart slowly, navigating through a terrifically prized narrow passage. The turquoise waters here are shallow and only a few feet deep. Afterwards, we arrive at Agios Emiliano (St. Emily) Beach for a swim, followed by a lunch onboard. While eating lunch you can see the tiny, white/blue house on the edge of the bay that enriches the entrance to this marvelous place. You can also opt to anchor a short distance away from the shore at the edge of the bay to enjoy a dip in the limpid waters. After lunch, you will have ample time to relax before a peaceful afternoon of sailing to reach your next destination.

Nisyros Island
The massive smokey crater in the centre of the island is an active volcano, making this one of the most impressive places in Greece. We will dock in the relaxing environment of an adorable, small marina that is newly refurbished. The marina is also excellently serviced with various restaurants and cafes. The kindness of the island locals is notably remarkable everywhere you go. An hour before sunset, we recommend some exploration with an excursion to the volcano crater. On the way back, we will stop at the main village Nikkia, which is situated uphill and built on the peak of the crater. The unique, circular stone-paved main square here has become a trademark of the Greek isles. Before returning to the marina for another culinary experience, you can choose to enjoy some local ouzo spirit here. Just a few feet from our boat, a typical Greek-family-owned-and-operated restaurant serves local specialties prepared with traditional family recipes.
In the morning, after your breakfast and our grocery supply run, we will navigate south towards Tilos Island while being encouraged forward by a pleasant breeze.

Tilos island

As we approach the north side of Tilos Island, you can see the Ormos Playiou Bay adjacent a magnificent cliff that is dominated by the Saint Pandeleimon, a Greek orthodox monastery. This is our perfect spot recommendation for an enjoyable swim. Enroute to Livadia Village, we will stop for lunch at Ammochostos Bay, surrounded by an interesting red sand beach.
Tilos Island is among one of our favorites for being authentic and off the regular tourist-beaten path. We recommend a visit to Magali Chorio, the main village uphill. A trip from the port is the most pleasant while on scooters or AVS, so you can enjoy the breeze on a hot summer evening. You can also opt for a taxi ride instead. Once you reach the top, you will be amazed by the sights around you. The center of this village is ornamented with a church yard whose mosaic floor, made up of different types and colours of pebbles, represents its superior craftsmanship. Mrs. Sophia’s Kafenion is a perfect spot for a refreshing drink at sunset. This traditional Greek café lets you sip your drink and other nibbles on the rooftop terrace that overlooks the ocean. Local food specialties include cheese, olives, the daily catch of anchovies, fish, and fresh grilled octopus. With the bright evening ahead, you can explore the island.
A little further up the mountain, you will find the Saint Pandeleimon. This monastery is home to a few monks and has a beautifully charming atmosphere. For a romantic night, the Micro Chorio village is recommended. The unique café there is built right into the ancient Greek civilization remains, adorned by lamps and candles all the way to their magnificent terrace under the stars, a truly magical setting.

Halki island

Our morning starts with a relaxing view of the village while you have coffee and breakfast. Afterwards, we set sail towards the south side of the island. Along the way, you can enjoy the steep red cliffs that form all types of animal and face shapes. A deep and particularly jagged cove ending with a white pebble beach inside the Saint Constantinos bay will be our exotic location for lunch. The amusing cormorants and the most colourful baby fish will be our company as we swim here. In the early afternoon, after your rest and lunch, we will set sail again for the southbound trip to Halki Island.

Halki Island
As we sail towards austere mountain rocks that sink into the sea, a narrow strait discloses the most exquisite, unknown island village. The venetian style architecture on this small island is quaint because that is about all there is. The few shops, cafes, small restaurants, and the clear water in the port all make this adventure unique. A campaign promoted by the Greek government back in the 80’s was Filoxenia, which literally means ‘the love of foreigners’. We think that it must have originated on this island. Named “The Island of Peace and Friendship” by the authorities, it gives you an idea of the friendliness, generosity, and the welcoming spirit of the people here.

Alimia island

Situated just in front of Halki island, uninhabited Alimia island is home to the ancient Hellenistic site. In the Middle Ages, this island was a refuge for the Rhodes maritime fleet and it has been a protected National Trust reserve ever since. At the farther end of the bay, a trademark Greek white and blue chapel sits for all to see, plus you can hike to the ancient fortress located on the rocky hill above the bay. After our breakfast stop, swim, and possible hike on the island, we will set sail to the east. The sight that will open up before you of Mediterranean bush, vegetation, and incredibly deep green/blue coloured water is enticing. You can jump in and have a swim in this wild place where nature remains untouched.

Loryma Cove
Crossing back over to the Rhodes side, you will be experiencing sailing under wind at its best. It will take a couple of hours as we sail to Loryma for our last night out aboard. Loryma (or Bozukkale) Bay is accessible only by the sea and the closest port is a half hour away. There are no roads to get there, just bare mountains, a few bushes, an organic farm, and a solitary homemade wooden pier that leads to a small family run restaurant. You will experience the most amazing fresh fish dishes here, and if they are lucky with their daily catch, they know how to create perfection in their grilled octopus. There are also many other Oriental specialties based on their daily catch and the local seasonal ingredients from the organic farm in the backyard. In any case, the Sailor’s House Restaurant will leave a unique memory of this trip.

Rhodes Island

A breakfast of scrambled eggs, fresh cheese, home-made yogurt, wild honey, and local olives will be served, either onboard or ashore. We then head back to Rhodes with a pleasant couple of hours sailing.

Prior to disembarking, we will have a briefing and a summarizing impression of your sailing cruise over a drink in the harbour, say our goodbyes and see you soon!

Your private taxi will take you right to the airport for your safe return home.

Explore more Greek Island Hopping Tours:

Cyclades Islands 

Ionian Islands

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