Adamantas: Kleftiko Sailing Cruise with Meal and Swim Stops

Planning a trip to Milos? If so, a sailing cruise to Kleftiko might just be the highlight of your island adventure. While I haven’t personally done this specific tour, reviews and detailed descriptions paint a pretty enticing picture of what to expect. It’s the kind of day that combines stunning scenery, local flavor, and a good dose of relaxation—all aboard a comfortable vessel exploring Milos’s West Coast.

What makes this tour stand out? First, it offers multiple swim and snorkel stops in crystal-clear waters, giving you plenty of chances to cool off and soak in the scenery. Second, the authentic Greek food and homemade wine onboard turn the cruise into a delicious culinary experience. Third, the knowledgeable crew, especially the local skipper, share fascinating stories, adding a layer of cultural depth to the trip.

One possible consideration? The tour’s duration of 7 hours means you’ll want to be prepared for a full day on the water—though most find this time perfectly balanced between adventure and relaxation. It’s ideal for travelers who enjoy scenic boat rides, authentic local flavors, and a mix of guided storytelling.

This experience suits those wanting a combination of sightseeing, swimming, and tasting Greek culture, especially if you enjoy small group settings. It’s perfect for couples, families, or small groups of friends eager to explore Milos from a different angle.

Good To Know

• Authentic Greek Cuisine: Enjoy grilled octopus, fresh fruit, traditional snacks, and homemade wine onboard.
• Stunning Swim Stops: Visit caves, caves, and beaches, with plenty of chances to snorkel and explore underwater caves.
• Expert Local Guides: The crew offers detailed narration about Milos’s history and island life, enriching the experience.
• Beautiful Scenery: The boat passes traditional fishing villages, impressive rock formations, and iconic cave systems.
• All-Inclusive Value: Meals, drinks, snorkeling gear, towels, and Wi-Fi are included, making it a hassle-free day.
• Limited Group Size: Small groups up to 4 participants ensure personalized attention and a cozy atmosphere.

You can check if your dates are available here:

An In-Depth Look at the Kleftiko Sailing Experience

Starting Point and Departure

The adventure begins in Adamantas, with a straightforward meeting point right in front of the boat. The vessel, operated by Milosoneiro, boasts a friendly, welcoming crew ready to make your day memorable. The cruise typically lasts around 7 hours, with specific starting times depending on availability. Since there’s no hotel pickup included, you’ll need to arrive at the meeting point, but the location is easy to access from most accommodations in Adamantas.

The Itinerary and Scenic Route

The journey kicks off with a pass through traditional fishing villages like Skinopi, Klima, Areti, and Fourkovouni. These charming spots are famous for their colorful Syrmata houses—small, stilted fishing dwellings painted in bright colors, which create a picture-perfect backdrop. The crew offers insightful commentary about their significance, which adds a layer of appreciation for these small but vibrant communities.

Next, the boat approaches the Arkoudes (bears) rock formations, where nature has sculpted dramatic shapes resembling bears. Passing Cape Vani, the vessel then reaches the Sykia area. Here, you’ll get a chance to admire an open roof cave—a massive natural arch that offers a window into the sea beneath. The crew even allows time for swimming in the cave waters, an experience reviewers describe as “truly magical,” with crystal-clear water that’s perfect for snorkeling.

The Highlight: Kleftiko

The most anticipated part of the tour? Kleftiko, an area steeped in pirate legend and known for its towering white rocks and sea caves. The boat will give a guided tour of the area, with the skipper sharing captivating stories about the pirates who once used these caves as hideouts—a detail that adds a fun storytelling layer appreciated by guests.

Here, you’ll have plenty of time to swim in and around caves, exploring hidden nooks and crannies that only boats can reach. Reviewers mention how swimming through the caves feels like stepping into a secret world, with some describing the waters as “crystal-clear” and “breathtaking.” Post-swim, a delicious Greek lunch is served on deck, featuring grilled octopus, local snacks, and fresh fruit, all with an impressive view over the white rocks and turquoise waters.

More Great Thing To Do Nearby

Kalogries Beach and Afternoon Swims

After exploring Kleftiko, the boat heads to Kalogries Beach, a shallow spot with warm, gentle waters perfect for relaxing swims. Most guests find this a welcome rest spot, especially after the more adventurous cave swims. During this time, onboard drinks—like ouzo—and sun-dried octopus grilled to perfection keep spirits high, complemented by traditional Greek music. These moments turn into a laid-back, Mediterranean celebration, often highlighted by reviews praising the authenticity of the food and the friendliness of the crew.

Return Journey and Scenic Wrap-Up

On the way back, the vessel sails past Vani and through Klima, with the captain opening the sails for a scenic cruise to end the day. The changing afternoon light casts stunning colors on the rocks, giving the entire trip a peaceful, almost cinematic feel. The cruise concludes back at the starting point in Adamantas, leaving you with a sense of having seen some of Milos’s most beautiful nooks while enjoying a day of good company and good food.

Why the Experience Is Worth It

The value of this tour isn’t just in the sights; it’s in the carefully curated experience. The inclusion of meals and drinks turns a boat trip into a full-day cultural feast, especially with options for vegetarians, vegans, and those with gluten or lactose sensitivities. Many guests mention the generous portions and the high quality of food, including grilled sun-dried octopus and homemade wine—rare treats that make the day feel truly special.

The small group size (up to 4 participants) ensures personal attention from the crew, particularly the skipper, Ilias, who is praised for his passion and storytelling skills. As one reviewer notes, Ilias’s tales about the island’s folklore and pirate legends make the experience both fun and educational.

What we love about this tour

• The guided narration adds depth and context, making the scenery more meaningful.
• The swimming in caves provides that perfect mix of adventure and tranquility.
• The authentic Greek cuisine onboard elevates the day beyond just sightseeing.
• The small group setting fosters intimacy and personalized service.

Potential considerations

• The cruise’s 7-hour duration might be long for some, especially if you prefer shorter excursions.
• Weather conditions can affect the route, with strong north winds possibly rerouting the tour to southern beaches like Tsigrado and Kabanes.
• The tour is not suitable for very young children or those with mobility impairments, so check personal needs beforehand.

Final Thoughts

This Kleftiko sailing cruise offers a full-day exploration of Milos’s scenic and cultural treasures. It combines the thrill of swimming in caves, the pleasure of authentic Greek cuisine, and the charm of learning local stories—wrapped up in a small, friendly group setting. The experienced crew ensures safety and comfort, while the breathtaking landscapes make it all worthwhile.

For those who love water-based adventures, appreciate good food, and enjoy storytelling, this tour hits all the right notes. It’s especially valuable for travelers seeking a personalized experience away from crowded group tours, and for anyone wanting to see Milos’s rugged coast from a different perspective.

Is the tour suitable for vegetarians or those with dietary restrictions?
Yes. Meals and drinks are included and options are available for vegetarians, vegans, gluten-free, and lactose-free diets.

What should I bring?
Sunglasses, sun hat, swimwear, camera, sunscreen, and a passport or ID. Towels are provided onboard.

Can I swim in caves or around Kleftiko?
Absolutely. Many guests mention swimming through caves as a highlight, with plenty of time for snorkeling and exploring.

What’s the meeting point?
You meet directly in front of the boat in Adamantas. No hotel pickup is included.

How long is the tour?
Approximately 7 hours, with specific start times depending on availability.

Is the group size small?
Yes, limited to 4 participants, ensuring a more intimate experience.

What if the weather is windy or rough?
The tour may reroute to the southern part of Milos, such as Tsigrado or Kabanes, for a smooth, wave-free experience.

Are children under 3 years old allowed?
No, this tour isn’t suitable for children under 3.

Is there wifi onboard?
Yes, wifi is available, so you can share your adventure or check in with loved ones.

What makes this tour stand out from others?
The combination of expert narration, authentic Greek cuisine, and the small-group feel creates a memorable, personalized adventure on the water.

This sailing trip from Adamantas to Kleftiko promises a delightful blend of adventure, culture, and relaxation. Perfect for those who want to see Milos in style and comfort while enjoying authentic flavors and breathtaking views.

You can check if your dates are available here: