2-Day Private Sailing Tour around Milos, Kimolos and Polyaigos

Introduction

A 2-day private sailing adventure around Milos, Kimolos, and Pelagiaigos offers a wonderful escape from the busy crowds, immersing you in the natural beauty and charm of the Greek islands from the comfort of a sailing boat. This exclusive journey, priced at just over $2,800 for a group of up to four, provides a tailored experience that’s highly rated — with a perfect 5 out of 5 from nine reviews. It’s a thoughtfully curated trip that combines scenic cruising, swimming stops, and visits to some of the most photogenic spots in the Aegean.

What I find particularly appealing about this tour is how it balances active exploration with relaxation. You’re not just a spectator but a participant — sunbathing on deck, hopping into crystal-clear waters, or wandering through authentic Cycladic villages. The crew, led by Oscar Private Sailing, receives high praise for their attentiveness, making this a seamless, stress-free experience. On the flip side, it’s important to consider that itinerary adjustments are weather-dependent, which could mean some changes to what’s originally planned.

Two standout features make this tour shine: first, the chance to sleep aboard a sailing boat overnight, giving you a taste of island life that many simply cannot access on a day trip. Second, the authentic stops like Klima and Kimolos deliver a more genuine feel of Greece than mainstream tours. However, a possible consideration is that the overall cost might seem steep if you’re traveling solo or on a tighter budget, but for a small group seeking a premium experience, it offers remarkable value.

Key Points

• Unique Overnight Experience: Staying aboard the boat offers a memorable perspective of island life.
• Authentic Stops: Visits to Klima, Kimolos, and Pelagiaigos offer genuine, less commercialized Greek island charm.
• Scenic & Active: Swimming, cave exploration, and beach hopping keep the trip lively and engaging.
• All-Inclusive Meals: Complimentary breakfast, lunch, and drinks make this a convenient, all-in-one escape.
• Weather Flexibility: It’s weather-dependent, so plans may shift for safety.
• Small Group & Personal Service: Private tour offers intimacy and tailored attention.

Discovering Milos from the Deck

The journey begins in the picturesque village of Adamantas on Milos. The boat departs around 10:00 am, which gives you the whole day to soak in the sights. The first stop at Klima is a visual delight, with its iconic colorful Sirmata houses and a charming church. You’ll have about 10 minutes here — enough time for a quick photo and perhaps a dip into the crystal waters.

Next, you’ll cruise over to Sarakiniko Beach, often called the “moon landscape” by visitors. This volcanic, lunar-like terrain, with its stark white rocks and turquoise water, is entirely unlike any other beach. The 45-minute stop here is perfect for an easy walk, photo opportunities, or cliff-jumping if you’re feeling adventurous — as many previous travelers have enjoyed.

Why This Matters for You

Seeing Sarakiniko by boat means fewer crowds and a more relaxed experience. Plus, the crew’s tip to jump from the cliffs adds a fun, adrenaline-filled highlight. The scenery is breathtaking and totally Instagram-worthy, making it a must-see, especially if you’re a fan of unusual landscapes.

Kimolos: The Authentic Greek Village

After a day of sightseeing, the boat heads to Goupa Beach on Kimolos, also called “Elephant Beach” because of its shape. Here, you’ll enjoy a Mediterranean-style lunch with fresh seafood and local flavors. The water is clear and inviting, perfect for a swim before or after eating.

In the late afternoon, you’ll arrive at the small, charming port of Psathi where you’ll spend the night. With its simple, authentic vibe, Psathi offers a true taste of Cycladic island life, with nearby restaurants and pastry shops to indulge in. The village of Kimolos is a short walk, and many guests find wandering its narrow streets delightful — a perfect intro to what makes Greek island villages so uniquely inviting.

Benefit for Travelers

The overnight stay at Kimolos gives you a relaxed, unhurried experience. Instead of the usual day-trip hustle, you can enjoy a leisurely dinner and unwind with views of the sea under the stars — an unexpectedly peaceful way to end your first day.

Exploring Pelagiaigos and Beyond

On the second day, the adventure continues with stops at Myrsini Bay on Pelagiaigos, an uninhabited island famous for its otherworldly beauty. You’ll have about an hour and a half here to swim, sunbathe, and explore the untouched landscape. This part of the trip is highly praised for its tranquility and raw, natural vibe.

Next, the boat visits a secluded sandy beach accessible only by boat in Milos, perfect for a dip, relaxation, or a Greek “mezze” onboard — small bites and drinks capturing the essence of local flavors. The highlight is Kleftiko Beach, a former pirate hideout surrounded by towering cliffs and caves. A dinghy or paddleboard allows you to explore the caves up close and discover secluded swimming spots, making this one of the most photogenic and adventurous parts of the tour.

Authenticity & Unique Experiences

Many past travelers mention the cave exploration and lunch at Kleftiko as highlights. The captain’s knowledge and friendliness turn these stops into genuine, fun experiences rather than just sightseeing. The opportunity to paddle around caves or relax in hidden bays makes this sailing trip feel like discovering secret corners of Greece.

Practical Details & What You Should Know

The tour includes breakfast, two lunches, and all boat expenses, including fuel and berthing fees. It starts at 10:00 am from Adamantas and ends back in the same place, with pickup offered for added convenience. Keep in mind, dinner isn’t included, so you’ll want to plan for a local meal on your final night. The entire experience lasts about two days, with most travelers booking 70 days in advance – a sign of its popularity and desirability.

The small group size (up to four people) is ideal if you prefer a more personalized and private experience. It’s a good fit for those who want the flexibility to explore at their own pace and enjoy intimate moments on the water.

Cost & Value

At around $2,810 for a group of four, this tour isn’t cheap — but it’s a comprehensive, all-inclusive experience that combines comfort, exclusivity, and access to sights few others get to see. For travelers craving a deep dive into Milos and nearby islands with personalized service, it offers excellent value.

Who Will Love This Tour?

This experience is best suited for travelers looking for an authentic, relaxed, and exclusive way to experience the Greek islands. It’s perfect for small groups, couples, or friends who want the privacy and flexibility that come with a private boat. If you’re interested in swimming, cave exploration, and discovering unspoiled beaches, this tour checks all those boxes. It also appeals to those who appreciate good food and a touch of adventure.

The Sum Up

Taking a private sailing tour around Milos, Kimolos, and Pelagiaigos offers a rare chance to enjoy Greece’s stunning coastline away from crowded beaches. The mix of scenic cruising, authentic village visits, and adventurous stops like cave exploration guarantees a memorable trip. The “overnight aboard” element makes it uniquely special — offering a genuine taste of island life that many day-trippers miss.

While the price may seem steep to some, the high praise from past travelers for the stunning views, delicious food, and attentive crew suggest it’s money well spent. It’s an ideal experience for those who value personalized service, authentic encounters, and a slower, more immersive way to see these beautiful islands.

If you’re looking for a blend of relaxation, adventure, and authentic Greek charm, this sailing tour might be the highlight of your trip to Milos. Just remember to book early — it’s popular for a reason.

FAQ

Is this a private tour?
Yes, it’s a private experience only for your group, up to four people, which means personalized attention and a tailor-made itinerary.

What’s included in the price?
All boat expenses, fuel taxes, berth fees, breakfast, and two lunches with drinks are included. Dinner is not included.

Can I cancel if the weather is bad?
Yes, cancellations are possible up to three days in advance for a full refund, and the tour will be canceled or rescheduled if weather conditions are unsafe.

Is pickup offered?
Yes, pickup is available from your accommodation or a convenient meeting point in Adamantas.

How physically active is the tour?
Most stops involve swimming or exploring caves, so some comfort with water and walking on uneven surfaces can enhance your experience.

Is it suitable for children?
While most travelers can participate, consider the nature of water activities and boat time; it’s best suited for older children and teens.

What should I bring?
Swimwear, sunscreen, hat, sunglasses, and a towel are recommended. A camera for photos is a must.

How long does each stop last?
Stops vary from 10 minutes at Klima to several hours at Kimolos and for cave explorations, usually around 1 to 2 hours each.

Are the meals plentiful?
Yes, the included lunches are Mediterranean-style with fresh seafood, and drinks are available throughout the day.

Who would enjoy this tour most?
Travelers looking for a relaxed, personalized experience who love swimming, caves, authentic villages, and beautiful scenery.

This private sailing tour offers a balanced mix of natural beauty, authentic experiences, and relaxed luxury — perfect for anyone eager to see Milos and nearby islands from a unique vantage point.