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

A Practical Look at the 2-Day Private Sailing Tour around Milos, Kimolos, and Polyaigos

Imagine slipping away from the busy crowds of Greece’s popular islands for a more intimate, sea-scented escape. This 2-day private sailing tour, costing around $2,810 for up to 4 people, offers just that. Led by an experienced crew, this adventure takes you on a cruise around Milos, Kimolos, and Polyaigos, with overnight stays aboard a sailing boat. You’ll visit hidden beaches, explore caves, and enjoy delicious Greek food—all while soaking in some of the most spectacular views the Cyclades have to offer.

What we love about this experience is how it combines authentic island charm with the convenience of a private tour. The chance to wake up anchored in quiet bays, with the sea as your front yard, makes it a perfect getaway for couples or small groups craving a more personal connection to the islands. Plus, the included complimentary breakfast, lunch, and drinks mean you can focus on relaxing and enjoying the scenery without the hassle of planning meals.

One thing to consider is the weather dependency—since it’s a sailing trip, rough seas or bad weather might cause itinerary adjustments or cancellations. Also, it’s a somewhat premium experience, so it’s best suited for travelers seeking a special, private escape rather than budget-conscious backpackers.

This tour suits those who value quiet, scenic escapes, are comfortable on a boat, and want to see parts of the islands that are only accessible by sea. If you’re looking for a luxurious, personalized adventure that blends sailing with authentic island visits, this is a perfect choice.

Key Points

• Private, intimate experience designed for groups up to 4 travelers.
• Includes all boat expenses, fuel, taxes, and meals, providing transparent pricing.
• Highlights uninhabited Pelagios Island and iconic beaches like Sarakiniko and Kleftiko.
• Offers the chance to swim, sunbathe, and explore caves in secluded bays.
• Has a flexible itinerary that may adjust with weather conditions.
• Excellent reviews praise the stunning scenery and the crew’s hospitality.

Exploring the Itinerary in Detail

Day 1: Milos & Kimolos Highlights

The journey begins at 10:00 am in Adamantas, Milos—an ideal starting point close to the ferry terminal and the main town. From here, the first stop is Klima, a charming fishing village famous for its colorful, traditional houses and clear waters. Imagine wandering through narrow streets or taking a quick swim in the crystal-clear water—a perfect way to start your adventure. Reviewers like Willem mention that sailing is a great way to see the islands and that the crew was friendly, making this first stop feel welcoming and authentic.

Next on the itinerary is Sarakiniko Beach, often called the “moon landscape” because of its unusual, white volcanic rock formations. It’s a must-see for anyone visiting Milos—an otherworldly place that’s fun to explore on foot or by boat. The option of cliff-jumping adds an adventurous touch, especially when approached from a boat. The 45-minute stop allows plenty of time for photos and a quick dip, perfect for those who love dramatic scenery.

Afterward, you’ll head to Kimolos, specifically to Goupa Beach, also known as “the elephant beach”. Here, you’ll enjoy a lunch break with excellent Mediterranean-style food and fresh seafood. The water is ideal for swimming, and the relaxed pace allows you to really soak in the authentic Cycladic atmosphere.

The day concludes at Psathi Port, a quaint harbor town with friendly restaurants and patisseries. The small village of Kimolos is about 15 minutes’ walk from the port, giving you a chance to explore its narrow streets, whitewashed buildings, and local charm. Many travelers, including Willem, appreciate this authentic village experience after a day on the water.

Day 2: Exploring the Hidden Gems of Polyaigos & Kleftiko

The second day kicks off with a swim in Myrsini Bay, an uninhabited island with pristine waters. This stop on Polyaigos is praised for its seclusion and beauty, giving you a true escape from the crowds. The 1.5-hour break is ample for swimming and relaxing. Reviewers like Willem highlight the stunning views and peaceful setting, describing it as a favorite part of the trip.

Next, you’ll visit a boat-access-only beach on Milos, with its golden sands and warm waters, perfect for a lazy afternoon. The inclusion of an aperitif “mezze” onboard makes this stop special—a chance to enjoy local flavors in a spectacular setting.

The highlight of the trip is Kleftiko Beach, known for its fantastic caves and pirate history. Here, you can explore caves in a dinghy or paddleboard, adding an active element that many reviews praise. The lunch served at Kleftiko offers a relaxed, scenic meal—another highlight that reviewers consistently mention as delicious and authentic.

What to Expect from This Sailing Experience

This tour is about enjoying the freedom of the sea while discovering lesser-known parts of the Cyclades. Besides the stunning vistas, you’ll get the chance to swim in secluded bays and explore caves, which are impossible from land-based tours. The crew’s hospitality is often praised—many reviewers mention the friendly, attentive service that makes the experience feel truly personalized.

Meals are included—breakfast and two lunches—so you won’t need to worry about finding food during the day, freeing you to focus on the scenery and relaxation. Drinks are also included, making it easy to toast to your adventure without fuss.

You should be comfortable with a small boat environment and prepared for weather changes. The tour is flexible, and the crew may adjust stops based on conditions—so flexibility is key. The private nature of the tour means you can customize your experience somewhat, which many travelers find adds to the value.

The Experience’s Value

While the cost (~$2,810) might seem high, the all-inclusive nature—meals, fuel, taxes, and a private boat—means you’re paying for a luxurious, hassle-free experience. Many review comments focus on the value for money, especially considering the personalized service and access to exclusive spots like Pelagios Island.

Who Will Love This Tour?

This experience is best suited for couples or small groups looking for a luxury, private escape. If you value secluded beaches, scenic caves, and authentic village visits, this tour will meet your expectations. It also suits travelers wanting a flexible, personalized experience without the crowds typical of land-based tours.

Final Thoughts

This 2-day private sailing trip offers an excellent way to see parts of Milos, Kimolos, and Polyaigos that are inaccessible by land. The combination of stunning scenery, authentic villages, and secluded beaches creates a memorable experience. While it’s a bit pricey, the all-inclusive setup and the chance to sleep overnight on a sailing boat elevate it to a special level of adventure and comfort.

If you’re after a personalized, scenic escape with plenty of swimming and exploring, this tour will delight you. It’s especially ideal if you prefer small-group or private experiences that emphasize authentic island life over tourist crowds.

FAQs

Is this a private tour? Yes, only your group will participate, making it a personalized experience.

What’s included in the price? All boat expenses, fuel, taxes, berth fees, plus breakfast and two lunches.

Can I cancel if the weather is bad? Yes, cancellations are possible up to 3 days in advance for a full refund, and the tour may be canceled due to poor weather.

Are drinks included? Yes, drinks are provided throughout the trip.

What’s the maximum group size? Up to four people, making it intimate and personalized.

Is the tour suitable for children? The data doesn’t specify, but most travelers who can enjoy boat trips and water activities would be comfortable.

How long are the stops? Stops vary from 45 minutes at Sarakiniko to 2 hours at Kimolos, with some longer periods for swimming and exploring caves.

What should I bring? Swimwear, sun protection, a hat, and a camera are essentials—remember, you’ll be on the water most of the day.

This sailing adventure offers a blend of natural beauty, authentic village life, and the thrill of exploring Greece’s lesser-known islands by sea. For those craving a private, scenic, and relaxing escape, it’s an experience that promises lasting memories.