Sailing Cruise Itinerary in the Dodecanese up to Samos
A sailing cruise from Kos to Samos offers a unique experience across the stunning waters of the eastern Aegean, exploring the charming islands of the Dodecanese, steeped in authenticity and far from the hustle of mass tourism.
Our adventure begins in Kos, from where we set sail to Kalymnos, renowned for its sponge fishing traditions and spectacular cliffs, a haven for climbing enthusiasts.
From there, we navigate north to Lipsi, a small island with a laid-back atmosphere, secluded beaches, and crystal-clear waters—perfect for those seeking tranquility and breathtaking views. Our journey continues to Arki, a wild and sparsely inhabited island, ideal for lovers of remote coves and the natural allure of isolated locales.
Next, we stop at Agathonissi, a small gem featuring a welcoming village and an authentic ambiance, where the local hospitality will make you feel instantly at home. This island offers a glimpse into genuine Greek island life, far from the beaten track.
The cruise concludes in Pythagoreio, on the island of Samos, where history and nature harmoniously blend. In Samos, you can extend your holiday by exploring ancient ruins, strolling through the historic streets of Pythagoreio, or relaxing on pristine sandy beaches.
Throughout the cruise, we will primarily sail in the mornings, leaving the afternoons free for leisure. You can stroll along hidden beaches, take refreshing swims in transparent waters, or explore underwater wonders through snorkeling.
Evenings will offer a mix of adventure and serenity. Some nights, we will explore the charming villages and harbors, where you can savor traditional Greek cuisine, immerse yourself in local culture, and meet the friendly residents known for their hospitality. Other nights, we will anchor in remote coves, under a starry sky, enjoying gourmet dinners prepared by your skippers. These joyful and magical moments will make every day an unforgettable experience.
Start Your Unique Sailing Experience from Kos on Walkabout
First Day of Your Sailing Vacation
The adventure begins at 6 PM with boarding in Kos, easily accessible from Italy via direct flights. We meet in Kefalos, a peaceful spot near the airport, perfect for kicking off the journey. After settling into your cabins and unpacking, a delightful dinner awaits you aboard, freshly prepared by your skippers. The evening concludes with a leisurely stroll along Kefalos’ serene waterfront, soaking in the relaxing atmosphere and enjoying the shimmering lights reflecting off the nearby Nisyros waters.
Second Day of Your Sailing Vacation
At dawn, after a hearty breakfast, we hoist the sails and head north. The steady northern breeze invites us to fully embrace sailing, allowing everyone on board to take part in maneuvers and try their hand at tacking. The exhilarating upwind journey challenges the bow against the waves, giving everyone the thrill of this immersive sea adventure.
By midday, we drop anchor in a secluded cove with crystal-clear waters. A refreshing swim immerses us in the heart of Mediterranean beauty, followed by a relaxing lunch aboard: a moment of comfort and camaraderie, surrounded by the sea breeze and the peaceful bay.
In the afternoon, a short sail brings us to the lively town of Pothia, the capital and main port of Kalymnos. The evening promises a delightful dinner in a traditional taverna nestled among the town’s charming alleys. With tables set outdoors, you’ll have the chance to savor authentic Greek dishes and immerse yourself in the local atmosphere—a perfect ending to a day filled with excitement and discoveries.
A beautiful upwind sail to the northern bay of Kalymnos
Third Day of Sailing Vacation
We depart from the lively atmosphere of Pothia, the capital of Kalymnos, to immerse ourselves in the serenity of one of the island's most scenic bays. Here, we anchor to relax and soak in the stunning surrounding landscape.
After a fresh and delicious lunch prepared onboard, we continue exploring the coastline using the tender, seeking out even more secluded beaches. In these small coves, where we will likely be the only visitors, we have the chance to experience a moment of absolute tranquility, surrounded only by the sound of the waves and the unspoiled beauty of nature.
The evening culminates with a gourmet dinner prepared by your skippers, who bring refined flavors to the table, turning the onboard meal into a special moment of joy and camaraderie. This day offers a perfect combination of the vitality of sailing, moments of relaxation, and culinary delights.
Leros: Windmills, Castles, and Stunning Sunsets in the Heart of the Aegean Sea!
Fourth Day of Your Sailing Vacation
Our sailing adventure continues northward, with Leros as our next destination. After an exciting morning of navigation, we drop anchor in a picturesque bay, perfect for a refreshing swim and a few dives into crystal-clear waters. Surrounded by natural beauty, the setting invites you to relax and unwind.
In the afternoon, we arrive at the charming bay of Pandeli, a living postcard. Before us stands the iconic windmills, and just above, the majestic castle looms, exuding ancient charm and commanding views of the landscape.
Pandeli is a traditional Greek fishing village where heritage slowly blends with elegant restaurants and refined shops. The golden sandy and pebble beach adds a rustic touch of beauty to this tranquil spot. From the bay, a trail winds up toward the castle, passing by the timeless windmills—one of the island's most recognizable landmarks.
For those seeking adventure, a sunset hike to the castle is highly recommended. The journey offers breathtaking views at every step.
Alternatively, immerse yourself in the local culture by visiting the nearby town of Lakki, a unique destination with deep historical ties to Italy. Known as Porto Lago, Lakki was developed during the 1930s Italian occupation and retains its architectural influence to this day.
Lakki stands as an extraordinary example of modernist urban planning. Wide avenues, Art Deco-style buildings, and rationalist architectural details reflect the Italian governance of the Dodecanese. The town’s buildings, with their clean lines and elegant simplicity, narrate a fascinating story of this historical era.
As the day winds down, the magic of Leros truly comes alive at sunset. The windmills and castle glow in warm golden hues, transforming the landscape into a living masterpiece. It’s an unforgettable moment, solidifying Leros as one of the most enchanting stops on our journey through the wonders of the Dodecanese.
The Charm of Lipsi by Sailboat: Pristine Beaches and Encounters with Marine Wildlife!
Fifth Day of Your Sailing Vacation
After breakfast—and for the sporty ones, a refreshing morning dive—we set the bow of our sailing boat northward, heading to the heart of the Dodecanese archipelago: the enchanting island of Lipsi.
Our sailing adventure brings us to this corner of paradise, where crystal-clear waters embrace golden sandy beaches and secluded coves.
Lipsi offers a variety of breathtaking bays and beaches, perfect for relaxation and disconnecting from the world. We anchor in the turquoise waters of Platis Gialos and Katsadia, indulging in rejuvenating swims and soaking up the sun on pristine beaches.
We’ll guide you to hidden coves and secluded inlets, where the only sounds are the gentle waves and the melodies of birds. In one such spot, we’ve previously sighted a monk seal and her pup. Keep your eyes on the horizon—you might just spot this delightful marine mammal.
In the afternoon, we take a scenic walk into the heart of the island to explore its picturesque village. With cobblestone streets, seaside cafés, and welcoming tavernas, we immerse ourselves in Lipsi's authentic atmosphere. The warm hospitality of the locals turns every stroll into an opportunity to uncover the island’s true essence.
At the traditional harbor tavernas, we savor local delicacies such as fresh fish, olives, and feta cheese. To end the meal on a sweet note, we indulge in Loukoumades drizzled with honey. All of this is perfectly paired with a glass of Greek wine as the sun slowly sets on the horizon, painting the sky in hues of gold and pink.
Remote Beaches and the Authentic Charm of the Arkoi Archipelago!
Sixth Day of Sailing Vacation
A delightful navigation takes us to Arki, a small island in the Dodecanese, located northeast of Lipsi. Part of the Archipelago of Arkoi, this is one of the tiniest and most serene islands in the Dodecanese.
Arki is known for its peaceful, laid-back atmosphere and its pristine, remote beaches. There are no shops, cars, or roads here, making it an untouched haven. The sea around Arki is of a Caribbean-like quality, especially at Tiganakia Bay, an indescribably magnificent lagoon where we’ll drop anchor aboard our Walkabout sailboat.
The island features unspoiled, hilly landscapes. Its scenic trails offer opportunities for hikes amidst nature, perfect for exploring on foot.
The port of Arki, often referred to as Arki Town, is a charming collection of whitewashed houses and a few traditional tavernas, where time seems to stand still.
In the late afternoon, we hoist the sails again for a pleasant sail toward Agathonissi. This remote, untouched gem of the Dodecanese is a sanctuary of tranquility and natural beauty. Largely ignored by mainstream tourist routes, Agathonissi offers an authentic connection with rural and genuine Greek island life. Surrounded by crystal-clear waters and peaceful beaches, the island welcomes visitors with its slow pace and the warm hospitality of its small community.
The main village, Megalo Chorio, is a picturesque cluster of white houses with colorful shutters and narrow alleys where time feels frozen. Known for its traditions proudly preserved by the local community, Agathonissi showcases a simple yet meaningful way of life. Strolling through the village offers a glimpse into the history and daily lives of its inhabitants, who rely on fishing, farming, and livestock for their livelihoods. These activities produce fresh, authentic products you can savor in the local tavernas.
We spend the night in a secluded cove with incredibly clear waters.
By night, the island unveils an exceptionally vivid starry sky, free from artificial lights, creating a magical and intimate atmosphere that makes staying here a truly memorable experience.
Green Coastlines, Unique Wines, and Archaeological Treasures in Samos
Seventh Day of Sailing Vacation
We wake up surrounded by the crystal-clear waters of Agathonissi, an irresistible invitation to start the day with a refreshing swim. After a hearty breakfast on board, we hop on the tender to explore the small secluded beaches of the bay. These hidden gems, accessible only by sea, offer a close encounter with untouched nature and the rejuvenating silence of the island.
In the afternoon, we hoist the sails for the final leg of our adventure, heading towards Samos. The final sail takes us to Pythagoreio, where our journey concludes. The evening welcomes us in the lively port of Pythagoreio, with its twinkling lights and joyful atmosphere. We enjoy dinner at a traditional taverna, immersed in the authentic charm of the village, savoring local flavors and ending our experience in a festive and convivial atmosphere.
Farewell Samos: End of the Cruise and New Discoveries Ashore
Last Day of the Sailing Vacation
After breakfast, we reach the least pleasant moment of the cruise: saying goodbye and promising to meet again soon.
We bid you farewell at the Pythagorion marina in Samos. The island has so much to offer, even from the land. What better opportunity to spend some time exploring it and visiting its fascinating archaeological sites?
The itinerary stops are subject to changes due to weather conditions or other unforeseen circumstances that may prevent or hinder navigation to reach them or anchoring. Any changes to the itinerary are made exclusively to ensure better vacation organization and to guarantee the safety and comfort of our guests.