Sailing Boat Small Group Kleftiko and Sikia Cave West of Milos

If you’re visiting Milos and looking for a way to truly appreciate its rugged beauty and intriguing coastline, a sailing tour like this one offers a fantastic perspective. This full-day experience takes you around the island’s most photogenic spots, with stops for swimming, snorkeling, and exploring hidden caves—all while enjoying the comfort of a small-group boat. It’s a balanced mix of adventure, relaxation, and authentic Greek charm.

What we love about this tour is how it combines the unforgettable scenery of Milos with the intimacy of a small group, making it easier to connect with your hosts and fellow travelers. Plus, the included meals and drinks mean you won’t have to worry about packing a thing. However, one thing to keep in mind is that this is a weather-dependent activity—sailing just isn’t the same without a good breeze.

This tour is perfect for travelers who want a relaxed, scenic day on the water, especially those who appreciate local stories and stunning views. It’s suitable for most fitness levels and ages, making it an excellent choice whether you’re a seasoned sailor or just in need of a peaceful boat day. But if you’re craving high-speed thrill rides or want to explore every cove in depth, you might find this experience a little laid-back for your taste.

Key Points

Beautiful scenery from the water: This tour offers unique perspectives on Milos’ volcanic coastline and colorful fishing villages, often inaccessible by land.
All-inclusive food and drinks: Breakfast, lunch, snacks, and local beverages keep you refreshed without the hassle of organizing food.
Snorkeling gear included: Easy access to snorkeling equipment makes swimming in crystal-clear waters a breeze.
Small-group intimacy: With a maximum of 18 travelers, the tour creates a relaxed atmosphere perfect for chatting with guides and fellow explorers.
Flexible stops: The itinerary features several swim and sightseeing stops, including the famed Kleftiko and Kalogries Beach, with stories that bring the sites to life.
Weather-dependent sailing: The experience relies on good weather and wind; some reviews mention that sails may stay furled if conditions aren’t ideal.

An In-Depth Look at the Milos Sailing Experience

The Meeting Point and Departure

Your day begins early at the Odysseus A. Yacht Cruises office in Adamas port, with departure scheduled for 8:45 am. The meeting is straightforward, near public transportation, and the check-in process is smooth. Expect a small, intimate group—generally around 18 guests—that makes the entire experience feel personal and relaxed.

The First Stop: A Fishing Village with Prehistoric Roots

As the boat sets off, the first stop takes you to one of Milos’ charming fishing villages. These villages have been inhabited since prehistoric times, with soft limestone used to build quaint cave houses. Reviewers appreciated this stop for its authenticity and the chance to see the colorful houses up close, which they say look like they’re straight out of a postcard.

Klima and the Syrmatas

Next, you’ll pass by Klima, a long stretch of traditional fishermen’s houses painted in shades designed for easy recognition—originally painted different colors for their owners’ convenience. The views here are particularly vibrant, with the colorful homes against the backdrop of the sea, offering fantastic photo opportunities.

Fourkovouni and Pirate Stories

The boat then heads toward Fourkovouni, a small hill at the entrance of Adamas Bay. It’s steeped in local legend—this is where pirates once hung out and, according to stories, where pirates were caught and hanged. Guides often share these tales, adding a fun layer of history to the scenery.

Cape Vani: A Manganese Marvel

One of the standout landmarks is Cape Vani, renowned for its multicolored rock formations—reds, yellows, oranges, greens, and grays—created by centuries of manganese mining. Reviewers mention how mesmerizing these cliffs are, especially when viewed from the water, with the colors shifting in the sunlight.

The Swim Stops: Kalogries Beach, Kleftiko, and Agios Dimitrios

The tour’s highlight is undoubtedly Kleftiko, a former pirate hideout that’s now a legendary swimming spot. Here, you’ll anchor for around two hours, giving you plenty of time to snorkel in the clear waters, explore sea caves, and soak in the dramatic surroundings. Reviewers describe Kleftiko as a “shelter of pirates,” with some noting the stories they learned from the guides made the experience even more memorable.

Before Kleftiko, you’ll stop at Kalogries Beach, a remote spot renowned for its calm, crystal-clear waters—perfect for a peaceful swim. Many guests mention how relaxing this stop is and how it sets the tone for the day.

The last swimming stop is at Agios Dimitrios Beach, where you can swim to the charming chapel and ring the bell. Reviewers found this spot to be a delightful way to wind down the day, with some describing it as “the perfect way to end a relaxing trip.”

The Included Meals and Beverages

Food is a big part of this tour’s appeal. After the first swim, a local snack is served—simple but tasty, giving everyone a boost. Lunch, prepared on board, is a Greek-style meal at Kleftiko, cooked fresh and served with plenty of wine and beer. Reviewers raved about how delicious and satisfying the meal was, often noting it as a highlight of the trip.

Snacks and seasonal fruit are offered in the afternoon, keeping energy levels high while you’re still exploring or lounging. The drinks flow freely, with wine, beer, soda, and bottled water included, making for a convivial, relaxed atmosphere onboard.

The Guides and Crew

Multiple reviews mention how friendly and knowledgeable the crew is—especially the captain and guide, Christos. They’re often praised for storytelling, sharing local history, and making sure everyone feels safe and comfortable. Guests appreciate the personal touch, with some describing the guides as “top-notch” and “informative,” which elevates the experience beyond just sightseeing.

What You Can Expect in Terms of Value

At $150 per person, this tour offers a well-rounded experience considering the duration (around 9 hours), the quality of the stops, and the meals provided. The small-group format ensures that you’re not just another face in a crowd, and the inclusion of snorkeling gear and meals adds to the overall value.

In comparison to other tours, especially those that involve transportation or separate meals, this package stands out as a good deal—particularly because the food is homemade and of high quality, and the scenery is unmatched from the water.

The Weather Factor

A couple of reviews highlight the weather dependency of sailing tours. Some mention that sails might stay furled if conditions aren’t windy enough, which means the boat will mostly motor along—still enjoyable but less traditional. If you’re hoping for a classic sailing experience with sails billowing, check the weather forecast beforehand; otherwise, enjoy a peaceful cruise with stunning views.

Who Should Consider This Tour?

If you’re looking for a relaxed, scenic day on the water with plenty of swimming and stunning photo ops, this tour hits the mark. It’s especially suited for those who want to learn some local stories and enjoy authentic Greek food without the hassle of organizing a meal themselves. Given the small group size, it’s perfect for travelers who prefer an intimate, personalized experience.

This trip also caters well to families, couples, or solo travelers who appreciate a balance of adventure and leisure. If you’re a snorkeler or a lover of coastlines, you’ll particularly enjoy the stops, especially at Kleftiko. However, if you’re after high-energy activities, high-speed sailing, or want to explore every cove in detail, you might find this tour a touch laid-back.

Frequently Asked Questions

Is the tour suitable for all ages?
Yes, most travelers can participate; it’s suitable for a wide age range, thanks to the gentle pace and inclusive activities.

What should I bring?
While towels, sunscreen, and hats aren’t included, it’s a good idea to bring these along. Comfortable swimwear, a waterproof case for electronics, and a sense of adventure will serve you well.

Does the tour include boat sailing?
While the description suggests a sailing experience, some reviews note that the sails may stay furled if the weather isn’t windy. The focus remains on sightseeing, swimming, and relaxing.

How long is the tour?
The experience lasts approximately 9 hours, starting at 8:45 am and returning to the meeting point in Adamas port.

Are meals included?
Yes, breakfast, lunch (cooked onboard at Kleftiko), snacks, and drinks (including wine and beer) are all provided.

What are the main stops?
Stops include Kalogries Beach for swimming, Kleftiko for exploring pirate caves, and Agios Dimitrios Beach for a final swim.

Is snorkeling equipment provided?
Yes, snorkeling gear is included, making it easy to explore the underwater sights.

Can I cancel if my plans change?
Yes, cancellations are free if made more than 24 hours in advance. Less notice may result in no refund.

What makes this tour stand out?
The combination of stunning scenery, small-group intimacy, delicious onboard meals, and the stories shared by guides creates an engaging and memorable experience.

Final Thoughts

This small-group sailing tour around Milos offers a balanced mix of scenic beauty, cultural stories, and relaxing swims—all within a comfortable and well-organized package. You’ll get close-up views of iconic sites like Kleftiko and Cape Vani, swim at pristine beaches, and enjoy homemade Greek cuisine. The atmosphere is friendly and informal, making it ideal for those wanting a laid-back day on the water.

For travelers who prioritize stunning vistas, tasty local food, and a personal touch, this tour hits all the right notes. It’s especially suited for those who enjoy snorkeling, storytelling, or simply unwinding in a beautiful setting. While weather can influence sailing conditions, the overall experience remains impressive and worth the price.

If you’re after a day of memorable sights, good company, and delicious food, this Milos sailing trip could be the highlight of your Greek island adventure.