Full day private sailing cruise around Milos island

If you’re dreaming of a day spent exploring Milos from the water—without the crowds or tourist traps—a private sailing cruise might be just what you need. This experience offers a tailored way to see some of the island’s most beautiful and inaccessible spots while enjoying the comfort of a well-maintained sailboat.

What we love about this tour? First, the flexibility and personalized attention make it feel like a bespoke adventure. Second, the stops at stunning beaches and caves promise a mix of relaxing swims, snorkelling, and exploration. Lastly, the onboard food and drinks elevate the experience, turning it into a true feast for the senses.

A possible consideration? The tour’s price point (around $1,636 for up to 8 guests) might seem high for some, but the level of intimacy and exclusive access often justifies it. This trip best suits those seeking an authentic, relaxing, and visually spectacular day on the water—perfect for couples, friends, or small families wanting a special Milos memory.

Key Points

• Private & personalized: The boat is exclusive to your group, ensuring a tailored experience.
• Stunning stops: From Kleftiko’s caves to Agathia Beach, each location offers unique photo opportunities and swims.
• Expert crew: Guides like Nico and Marion are praised for their hospitality, knowledge, and attention to detail.
• All-inclusive food & drinks: Enjoy local specialties, Greek wine, and fresh fruit, making the day truly indulgent.
• Flexible itinerary: The route can change depending on weather and your preferences, ensuring comfort and safety.
• Value for money: Although costly, the private nature, comfort, and curated stops make this a memorable splurge.

Introduction

Imagine cruising along Milos’s coast on a classic 43ft Oceanis sailboat, feeling the sun on your face and the wind in your hair. That’s what this full-day private sailing cruise promises—a chance to see the island from a whole new perspective without the hassle of crowded tours or shared boats.

What really sets this experience apart are three things: the personal attention from the crew, the chance to explore hidden beaches and caves inaccessible by land, and the delicious onboard meals that make it feel like a floating Greek feast. Add to that the stunning scenery and the friendly, professional guides—like Nico and Marion—and you’ve got a recipe for a memorable day.

The only thing to bear in mind is that this is a premium experience with a price tag around $1,636 for up to 8 guests. If budget isn’t your primary concern and you’re craving a private, flexible, and picturesque adventure, this tour will suit you perfectly. It’s especially ideal for couples, families, or small groups looking to celebrate or simply indulge in an authentic Milos experience.

The Itinerary: A Day of Exploring Milos from the Water

Starting Point and Early Highlights

The cruise kicks off from Adamas at 9:00 am, a convenient meeting point for most travelers. From there, the sailboat gently glides past Milos’s traditional fishing villages such as Klima and Skinopi. These colorful settlements are picture-perfect, with their quaint houses called Sirma used as boat garages—an intriguing slice of local life that many travelers miss when sticking to land-based tours.

As the boat continues, it passes the famous Arkoudes rocks—shaped like a bear—a natural marvel and a favorite photo spot. The voyage then takes you around Cape Vani, showcasing the island’s striking volcanic landscape and the vivid blue waters that surround it. This area reveals Milos’s rugged, unspoiled charm and sets the tone for an adventurous day ahead.

Stop 1: Agathia Beach (45 minutes)

The first stop at Agathia Bay offers a tranquil, secluded spot for swimming and relaxing. The waters here are famously clear, and it’s common to see fish darting beneath the surface—a real treat for snorkellers. Reviewers mention walking along the quiet beach or just soaking up the sun on the deck before enjoying a local breakfast onboard, a delightful start to your day.

Expect about 45 minutes here, which is enough for a dip, some exploration, and a bite of traditional Greek snacks. It’s a peaceful introduction that sets a relaxed tone for the rest of the trip.

Stop 2: Agios Ioannis (1 hour)

Next, the boat pulls into one of the three coves at Agios Ioannis—another stunning spot with vibrant cliffs and whitewashed structures. If weather permits, the crew may ferry you into the Sykia cave using a dinghy, giving you a chance to explore Milos’s secret caves and swim in their pristine waters—a highlight noted by many reviewers.

The cave visits add a splash of adventure and give you a chance to marvel at Milos’s volcanic geology. The time here allows for swimming, photo ops, and possibly discovering some marine life.

Stop 3: Kleftiko Bay (2 hours)

The day’s most famous and spectacular stop is Kleftiko, often called Pirate’s Bay for its dramatic volcanic cliffs and sea caves. This is the flagship destination, and reviewers repeatedly mention it as the most memorable part of the trip.

You’ll join the captain in a dinghy tour to explore caves and hidden corners, with some reviews mentioning optional adrenaline activities like cliff jumping. During this leg, the crew’s attention to safety and fun shines through—many reviewers say they appreciated the guides’ genuine enthusiasm and local knowledge.

Back on the boat, a full Greek-style lunch is served—freshly cooked onboard with local ingredients. The food is a highlight, with guests praising the delicious flavors and the effort put into making it a true Greek feast. After lunch, there’s ample time to snorkel around the bay or simply relax on the deck, soaking up the scenery.

Stop 4: Agios Dimitrios (45 minutes)

As you head back toward Adamas, the final stop is at Agios Dimitrios Bay, where one of the island’s oldest churches sits. It’s a quiet, less-visited spot, perfect for a final swim, shell collecting, or ringing the tiny church bell. Many reviewers mention how peaceful and authentic the setting feels, offering a gentle end to a busy day.

Here, you can enjoy another dip, some fruit salad, and reflect on the day’s adventures before heading back to the meeting point.

What Makes This Tour Special?

The personalized, private nature of the tour ensures you’re not part of a large crowd. As multiple reviews highlight, Nico and Marion are passionate, attentive guides who tailor the experience based on weather, your interests, and swimming confidence. They’re praised for their professionalism, friendliness, and local knowledge, which elevate the journey from a simple boat ride to a curated adventure.

The stops for swimming and snorkelling are carefully selected. Visitors rave about the transparency of the waters, especially at Agathia Beach and Kleftiko, where marine life and volcanic formations create a surreal backdrop. The optional cave exploration in Agios Ioannis adds a layer of discovery that many find enchanting.

The onboard meals and drinks also stand out. Guests often mention the delicious local breakfast, Greek lunch, and generous supply of wine and beer. These details turn a boat trip into a true Mediterranean feast, making the experience feel indulgent and authentic.

The flexible itinerary is a major plus. The captain can adjust stops or route based on weather conditions or group preferences, ensuring everyone’s comfort and safety. This adaptability is crucial in Greece, where wind and sea conditions can change unexpectedly.

The Price and Value

While $1,636 for a private, nine-hour cruise might seem steep, consider what you’re getting: a completely tailored experience, exclusive access to prime spots, a crew dedicated to your comfort, and a feast of local food and drink. For groups of up to 8, this cost splits into a reasonable per-person expense, especially compared to multiple land-based tours or large boat trips lacking personalization.

Guests consistently express high satisfaction, citing the intimacy, the knowledgeable guides, and the stunning scenery as worth the price. Many reviewers highlight the professionalism and warmth of Nico and Marion, which adds a personal touch that big tour operators often lack.

Who Should Consider This Tour?

This cruise is ideal for small groups, couples, or families seeking an exclusive, relaxed day on the water. If you prioritize comfort, personalized service, and authentic experiences, this trip offers excellent value. It’s perfect for those wanting to see hidden coves, explore caves, and enjoy local food in a setting that feels special and private.

However, if you’re on a tight budget or prefer a more scheduled, less flexible tour, you might find other options more suitable. But for a memorable, picture-perfect day with a touch of luxury, this cruise hits the mark.

The Sum Up

This private sailing cruise around Milos blends scenic beauty, adventure, and authentic local flavors into a single, well-crafted experience. The attention from Nico and Marion, along with the carefully chosen stops, ensures you’ll see some of the island’s most captivating spots—like Kleftiko’s caves and Agathia Beach—while enjoying the comfort of a private sailboat.

The inclusion of delicious meals and drinks, flexible itinerary, and small group setting make it a standout choice for travelers looking to indulge in Greece’s natural beauty without the crowds. It’s a fantastic way to make the most of your time on Milos, especially if you value personalized service and stunning scenery.

Whether celebrating a special occasion or simply craving a peaceful day on the sea, this tour offers a genuine taste of the island’s charm, wrapped in comfort and adventure.

FAQs

How long is the cruise?
The tour lasts approximately 9 hours, giving you ample time to enjoy each stop and relax onboard.

What is included in the price?
The price covers breakfast, a full onboard Greek lunch, coffee, tea, soda, and alcoholic beverages including beer and local wine. It also includes snorkeling equipment.

Is the tour suitable for children?
Most travelers can participate, and the guides are attentive to safety, making it suitable for families with children who are comfortable around water.

Can the route be changed due to weather?
Yes, the itinerary may be amended or canceled depending on weather conditions or other safety considerations. The guides will adjust accordingly, with options for different routes.

What should I bring?
Though towels and sunscreen aren’t included, it’s wise to bring your own, along with any personal items you might need for swimming or sun protection.

How private is the tour?
Since it’s a private experience, only your group will participate, ensuring privacy and a tailored experience.

This comprehensive review should help you decide if a private sailing adventure around Milos fits your travel style. With its mix of stunning scenery, personalized attention, and genuine hospitality, it promises a memorable slice of Greek island life from the comfort of a well-equipped sailboat.