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

Experience the Stunning Greek Islands on a Private 2-Day Sailing Tour Around Milos, Kimolos, and Polyaigos

When it comes to exploring Greece’s islands, few ways offer a blend of adventure, authenticity, and relaxed luxury quite like a private sailing trip. This 2-day tour around Milos, Kimolos, and Polyaigos promises an intimate look at some of the Aegean’s most captivating spots, all from the deck of a comfortable sailing boat. While we haven’t personally taken this exact trip, the glowing reviews and detailed itinerary make it clear that it’s a fantastic way to see these islands away from crowds and typical tourist traps.

What really appeals are the spectacular views, well-curated stops, and the opportunity to enjoy Greek flavours onboard. Plus, the chance to sleep overnight in a charming Cycladic village adds a special touch to the experience. The potential downside? Given the weather-dependent nature of sailing, some itinerary adjustments might occur, so flexibility is key. This trip is perfect for travelers craving authentic island moments, private experiences, and a taste of the sea—especially if you’re up for a mix of sightseeing, swimming, and relaxing on the water.

Key Points

• Private and intimate experience, suited for groups up to 4 people
• All-inclusive meals including breakfast, lunch, and drinks onboard
• Access to secluded spots only reachable by boat, like Pelagios and Kleftiko
• Flexible itinerary that adapts to weather conditions for a smooth trip
• Excellent value considering the personalized experience and all inclusions
• Most booking 70 days in advance, so plan ahead to secure your spot

An Authentic Greek Sailing Adventure: What to Expect

This tour combines the charm of Greek islands with the comfort of a private vessel, making it ideal for travelers who want more than just a crowded boat tour. The entire experience is designed to give you a personalized journey, where you’ll enjoy the freedom to choose stops, swim in crystal-clear waters, and savor local flavors. Plus, with only your group on board, it’s a terrific way to celebrate a special occasion or simply escape the crowds.

A Day-by-Day Breakdown of the Itinerary

Day 1: Milos and Kimolos

The journey begins promptly at 10:00 am from Adamantas, a convenient pickup point if you’re staying nearby. The first stop is the picturesque village of Klima, famous for its colorful, traditional houses and small church. The crew will take you there for around 10 minutes — enough to snap photos and soak in the views. It’s a lovely introduction to Milos, with its crystal waters inviting for a quick swim.

Next, you’ll sail to Sarakiniko Beach, often called the “moon landscape” due to its surreal, white, volcanic formations. The landscape is otherworldly, making it an easy highlight. As some reviews note, cliff-jumping here is popular with those seeking a bit of adrenaline, and the scenery is truly unlike any other in Greece. You’ll spend about 45 minutes here, allowing enough time to explore and splash around.

From there, the boat heads to Goupa Beach in Kimolos, affectionately known as “the elephant beach” thanks to its shape. This is your lunch stop, with fresh Mediterranean fare served onboard—think simple yet delicious seafood, salads, and local specialties. Swimming here is perfect after a hearty meal, with transparent waters and soft sands.

The day wraps up at Kimolos’ port of Psathi, a charming spot where you’ll stay overnight. The village is small but full of authentic character, with local restaurants and cafes just a short walk from the boat. Reviewers mention that walking into Kimolos village is like stepping back in time, with its narrow alleys and friendly atmosphere. Many guests enjoy unwinding here with a cocktail after dinner, soaking in the sunset views.

Day 2: Polyaigos and Kleftiko

The second day kicks off with a swim at Myrsini Bay, a beautifully unspoiled spot accessible only by boat. The waters are inviting, and the island’s uninhabited nature makes it feel like discovering a secret hideaway. Guests typically spend about an hour and a half here, floating and sunbathing in peace.

Next, you’ll head to a secluded, sandy beach on Milos—a perfect spot for more swimming and relaxing. This area is known for its warm baths and stunning waters, ideal for unwinding before lunch. Matched with authentic Greek mezze onboard, it’s a sweet break that combines good food with a stunning setting.

The highlight of the trip is Kleftiko Beach, famous for its pirate hideouts and dramatic cliffs. The sea caves and rock formations provide the perfect backdrop for exploration. Guests can hop into a dinghy or paddleboard to explore the caves, as some reviews mention. It’s a chance to get up close with Milos’ rugged beauty, with about 1.5 hours allocated for exploring and lunch onboard.

What Makes This Tour Stand Out?

Personalized Experience in a Stunning Setting

Unlike crowded group tours, this private sailing trip ensures you’re not just another face in the crowd. The all-day boat access to hidden beaches and caves means you’ll see places most travelers only dream of. The reviews highlight how much guests appreciated the authenticity and intimacy of this tour, with many saying it was their favorite part of visiting Greece.

Comfort and Convenience with All-Inclusive Meals

For around $2,810 for a group of four, this experience offers remarkable value. The price covers all boat expenses, fuel, taxes, and berths, along with breakfast and two lunches. The onboard meals, especially the seafood and tapas, are frequently praised as delicious and plentiful, ensuring you’re well-fed without extra hassle.

Expert Crew and Flexibility

The crew is known for their professionalism and friendliness, which makes a big difference when navigating the unpredictable Aegean weather. The itinerary is subject to change based on conditions, but this flexibility guarantees a safe and enjoyable trip. Reviewers have mentioned that the crew makes the experience smooth and fun, often sharing local insights and tips.

Practical Details and How to Make the Most of It

Timing and Duration

Starting at 10:00 am allows for a full day of exploration, with the trip wrapping up back at the meeting point after about two days. The overnight stop at Kimolos gives travelers a chance to experience local life firsthand, away from tourist-heavy spots.

Group Size and Privacy

Limited to four people per group, this tour is perfect for small parties, romantic getaways, or a private family adventure. The small group size ensures personalized attention and a relaxed atmosphere.

Booking and Planning

Given that most guests book around 70 days in advance, it’s wise to plan ahead, especially during peak season. Cancellation policies are flexible if weather turns unfavorable, providing peace of mind.

Final Thoughts: Is This Tour Right for You?

This private sailing experience around Milos, Kimolos, and Polyaigos offers a rare opportunity to see some of Greece’s most beautiful, lesser-known spots without the crowds. It’s especially well-suited for travelers who love the sea, enjoy authentic local atmospheres, and want a bespoke adventure. The combination of scenic stops, delicious onboard meals, and the comfort of privacy makes it a memorable choice.

However, keep in mind that sailing trips are weather-dependent, so a flexible mindset helps. If you’re after a laid-back, intimate voyage with plenty of swimming, sightseeing, and local flavor, this tour hits the mark.

In short, it’s a fantastic option for those seeking a blend of adventure and relaxation in the Greek islands, at a price that reflects a thoughtfully curated, exclusive experience.

FAQ

How many people are in each group?
The tour is private for up to 4 people, making it intimate and perfect for small groups or couples.

What meals are included?
You’ll enjoy breakfast and two lunches onboard, featuring Mediterranean dishes and seafood. Drinks and additional dinners are not included.

Is there a specific starting time?
Yes, the tour departs at 10:00 am from Adamantas, Greece.

Can I cancel if the weather looks bad?
Yes, cancellations are allowed up to 3 days in advance for a full refund, and the trip can be rescheduled if the weather isn’t suitable.

What are the main highlights of the itinerary?
Top stops include Klima village, Sarakiniko Beach, Goupa Beach in Kimolos, Myrsini Bay in Polyaigos, and the famous Kleftiko Bay with its caves and rock formations.

Is this experience suitable for children or non-swimmers?
Most travelers can participate, and the trip involves swimming stops, so you might want to consider comfort with water activities.

What’s the best time to book?
Most guests book about 2-3 months in advance, especially if traveling in peak season.

How do I get to the meeting point?
The trip begins at a designated pickup point in Adamantas, which is easily accessible from many accommodations on Milos.

This private sailing adventure promises a perfect blend of scenic beauty, authentic local charm, and personalized service—ideal for those looking to experience Greece’s islands in a relaxed, meaningful way.