Sail and Hike the Dodecanese Islands

Your adventure begins on the legendary island of Kos, the second largest in the Dodecanese after Rhodes and a place where myth and history intertwine. According to legend, it was here that Heracles once came ashore after battling sea monsters sent by Hera. Later, it became the birthplace of Hippocrates, the father of modern medicine, whose influence still lingers in the island’s ancient healing sanctuaries.

Upon arrival, settle into your hotel and meet your Aegean Outdoors trip leader for an essential group briefing. Once the introductions are made, we’ll step out together for our first walking tour through Kos Town, a living museum of civilizations.

Strolling past the Castle of the Knights of St. John, we’ll follow paths where 17th-century Ottoman mosques, Italian WW2-era buildings, and Hellenistic ruins coexist in an architectural timeline. In the shade of palm-lined boulevards, you’ll see Roman villas with mosaic floors, Byzantine churches, and bustling local cafés that bring the ancient and modern together.

After the tour, we enjoy a welcome lunch before heading to the Kos marina, where our private sailing vessel awaits. As the sun begins to dip into the Aegean, we set sail for Nisyros island, crossing turquoise waters on a 3.5-hour passage toward one of Greece’s most extraordinary volcanic islands.

Tonight, we dock at the quiet port of Paloi and make our way to Mandraki, the island’s picturesque capital. There, we’ll dine at a traditional seaside taverna, enjoying fresh island cuisine under the stars—an idyllic start to a week of discovery.

Overnight in Nisyros (L,D)
Sailing Time: Kos to Nisyros – 3 hrs 30 min

Welcome to one of the most extraordinary natural wonders in the Aegean—the active volcanic island of Nisyros, a place where earth, fire, and myth still shape the land. Today’s experience is one-of-a-kind: an immersive hike into the island’s otherworldly caldera, surrounded by timeless villages and lunar landscapes.

Nisyros, shaped entirely by volcanic activity, is the youngest volcano in Greece. Despite its raw geology, the island is home to just four villages. Coastal Mandraki and Paloi hug the shoreline, while Emporeio and Nikia cling dramatically to the crater’s rim, offering breathtaking panoramic views of the vast caldera below.

Our day begins with a scenic drive to Nikia, a whitewashed village famous for its architecture and for Porta, its exquisite pebble-stone square—an emblem of traditional Dodecanese craftsmanship. From here, we lace up our boots and begin the descent into the 4-kilometer-wide caldera, a powerful geological formation born of eruptions that date back 160,000 years.

At the center lies the Stefanos Crater, one of the largest and best-preserved hydrothermal craters in Europe. Walking across its yellow-streaked floor, dotted with bubbling fumaroles and sulfur vents, is like stepping onto the moon. The landscape here hums with ancient energy, and in Greek mythology, it’s said that Hephaestus, the god of fire and blacksmithing, once worked deep beneath Nisyros, forging thunderbolts for Zeus himself.

After exploring the crater, we ascend on foot to the serene village of Emporeio, where the volcanic drama gives way to timeless village life. Perched high on the mountainside, we visit a family-run taverna and enjoy a well-earned lunch of traditional Nisyrian dishes—such as pythia, golden chickpea fritters served with almond-garlic dip—while gazing down over the very crater we just explored.

In the late afternoon, we return to Paloi port and rejoin our boat for a relaxing sail to the island of Tilos—a lesser-known paradise famous for its wild nature, fossil discoveries, and tranquil atmosphere. As we glide across the Aegean, the sun dips low behind Nisyros, and the scent of volcanic earth lingers as a vivid memory.

Overnight in Tilos (B,L,D)
Hiking Distance: 8.5 km | Duration: 4 hours
Elevation Gain/Loss: +260 m / -360 m
Sailing Distance: Nisyros to Tilos – approx. 2.5 hours

After having breakfast on board, we disembark on the serene island of Tilos, one of the most untouched gems in the Dodecanese. With only a handful of residents and vast areas of protected nature, Tilos offers raw beauty and ancient mystery in equal measure.

Our hike begins along the rugged coastline, offering sweeping views over the Aegean Sea. What appears at first to be a barren island slowly reveals its secrets as we follow centuries-old stone paths inland. Terraces once used for growing olives and carob now lie quiet, whispering stories of a once-thriving agrarian past.

The trail leads us uphill to the “ghost village” of Mikro Chorio, a hauntingly beautiful medieval settlement abandoned in the mid-20th century. Out of its 220 homes, only the stone shells remain, alongside round threshing floors, cisterns, and ancient olive presses—silent witnesses to Tilos’ rural heritage.

After a loop hike back to the port town, we enjoy a swim in the island’s clear blue waters, and in the afternoon, we set sail for the colorful island of Chalki.

Overnight in Chalki (B,L,D)
Hiking: 8 km / 3 hrs | Elevation Gain & Loss: 350 m
Sailing: Tilos to Chalki – 2 hrs

Today we explore Chalki, a tiny island with a grand personality. Unlike the cubic whitewashed houses of many Cycladic islands, Chalki’s harbor is framed by 19th-century neoclassical mansions painted in warm tones of ochre, rose, and blue. Locals here still dive into the port from their front steps—a rare kind of Mediterranean life still intact.

We walk through the cobbled streets of the town and hike uphill to the Castle of the Knights of St. John, built on a strategic high point during the Crusades. From its crumbling battlements, we take in stunning views across the sea to Rhodes, and perhaps even spot our sailboat waiting in a cove below.

After descending, a refreshing swim awaits before we enjoy lunch aboard. In the late afternoon, we sail toward Symi, where we’ll drop anchor in a remote bay and sleep beneath a starlit sky.

Overnight in Symi (B,L,D)
Hiking: 8 km / 3 hrs | Elevation Gain & Loss: 320 m
Sailing: Chalki to Symi – 3 hrs

Today’s hike offers a dramatic change of scenery as we explore Symi, the first forested island on our journey. After a morning swim, a dinghy brings us to the trailhead, where we begin our climb along steep cliffs with jaw-dropping sea views.

We ascend into lush cypress forests, a striking contrast to the stark limestone peaks above and the deep blue waters below. As we traverse the spine of the island, the trail begins to descend toward Symi Town, one of the most beautiful harbors in the Aegean. The sight of pastel-colored neoclassical homes cascading down the hillsides is nothing short of cinematic.

In the afternoon, enjoy free time to explore the boutiques, galleries, and harbor cafés of this cosmopolitan island, once made wealthy by sponge diving and shipbuilding.

Overnight in Symi (B,L,D)
Hiking: 6 km / 3 hrs | Elevation Gain: 290 m / Loss: 300 m

Today we slow down and savor the flavors and traditions of Greek island life. In the peaceful bay of Emporios, we’re welcomed by Irene and her mother Katina, descendants of a long-standing Symiot family who once thrived in the sponge-diving trade.

At their seaside home, you’ll learn how to prepare classic dishes like tzatziki, stuffed tomatoes, and spanakopita, all baked in a traditional wood-fired oven. But more than a cooking class, this is a window into the soul of Symi—where food, family, and sea are forever intertwined.

Overnight in Symi (B,L,D)
Hiking: 3 km / 1 hr

We say farewell to Symi and board a morning ferry to the island of Rhodes, the historical heart of the Dodecanese and a place where Byzantines, Crusaders, Ottomans, and Italians all left their mark.

Upon arrival, we enter the UNESCO-listed Medieval Town of Rhodes, one of the best-preserved in Europe. Behind its formidable stone walls lie Gothic towers, Ottoman fountains, and labyrinthine streets lined with artisan shops and lively tavernas.

In the evening, we gather for a farewell dinner in a traditional taverna, toasting to the islands, the friendships formed, and the unforgettable journey we’ve shared.

Overnight in Rhodes (5-star hotel) (B,L,D)
Ferry: Symi to Rhodes – 2 hrs

After one last leisurely breakfast, your Sail & Hike the Dodecanese journey officially concludes. Whether you’re heading home or extending your time in Greece, you’ll carry the stories, flavors, and breathtaking landscapes of the Aegean with you.

But the adventure doesn’t have to end here..

You can choose to explore more of Rhodes, with its sun-drenched beaches, ancient ruins, and atmospheric villages—or continue your travels to other iconic Greek destinations. Aegean Outdoors offers a variety of tailor-made extensions throughout Greece, including Crete, the Cyclades, Meteora, Northern Greece, and Peloponnese adventures. Whether you seek more hiking, cultural immersion, or coastal relaxation, we’re here to plan your next chapter. (B)

Until then—”kalo taxidi” (safe travels)!