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

Exploring the Greek Islands by Sail: A Deep Dive into the 2-Day Private Sailing Tour around Milos, Kimolos, and Polyaigos

When it comes to experiencing the Greek islands, sometimes the best moments come from stepping away from the crowds and seeing these beautiful spots from the water. This private 2-day sailing tour around Milos, Kimolos, and Polyaigos promises just that—an intimate, scenic voyage with plenty of opportunities to swim, explore, and enjoy authentic local flavors.

What we love about this experience is the personalized nature of a private tour, allowing you to set your own pace and focus on the sights that interest you most. Plus, the chance to stay overnight on a boat adds a layer of adventure that many day trips just can’t match.

A potential consideration is the weather—since this is a sailing tour, conditions can influence the itinerary. While the trip is well-planned, flexible adjustments might be necessary if the weather turns less cooperative.

This tour suits travelers who love the idea of cruising, appreciate a more exclusive experience, and want to see some of the most stunning sights accessible only from the sea. It’s especially ideal if you’re after a mix of relaxation, adventure, and authentic local scenery.

<h3 id="section-0">Key Points

• Private and exclusive, perfect for personalized experiences
• Includes overnight stay aboard the boat for an added sense of adventure
• Multiple stops for swimming, exploring caves, and sightseeing along beautiful coastlines
• Delicious Mediterranean-style meals included, adding to the relaxed vibe
• Flexible itinerary that can adapt for weather conditions
• Ideal for those seeking a scenic, immersive escape from crowded tourist spots

What’s on Offer: A Genuine Look at the 2-Day Sailing Adventure

The charm of this tour is that it’s a private experience for up to four people. That means it’s more tailored than a large group cruise, giving you the flexibility to linger at favorite spots or skip something if you prefer. The entire journey is designed to maximize your time on the water, soaking up the views, tasting local food, and exploring hidden corners accessible only by boat.

At a glance, the cost of approximately $2,810.69 per group might seem high, but considering it covers all boat expenses, fuel, taxes, and two meals per day, the value becomes clearer. You’re paying for exclusivity, comfort, and a curated experience that you won’t find in standard tours.

Starting Point & Duration

The tour kicks off at 10:00 am in Adamantas—a central hub on Milos—and wraps up back there at the end. The two-day duration means you get plenty of time to relax and enjoy without feeling rushed, with most travelers booking this roughly 70 days in advance, which speaks to its popularity.

The Itinerary: From Towns to Caves and Hidden Beaches

Day 1: Milos Highlights

The first day is a delightful mix of sightseeing, swimming, and local flavor. Your crew will first take you to Klima, a picture-perfect village renowned for its colorful, traditional houses and quaint charm. Here, you can enjoy a quick swim in the crystal-clear waters and soak in the laid-back village atmosphere.

Next up is Sarakiniko Beach, often dubbed the Moon landscape, thanks to its otherworldly rock formations. This spot is a must-see and offers fantastic photo opportunities. Many visitors love cliff-jumping here, so if you’re feeling adventurous, this is your chance.

The lunch stop is at Goupa Beach in Kimolos, affectionately called “the elephant beach” because of its shape. The clear waters and relaxed vibe make it an ideal spot for a leisurely swim and enjoying a fresh Mediterranean lunch onboard. It’s a relaxed, scenic setting that perfectly blends food, fun, and scenery.

In the late afternoon, you’ll arrive at Kimolos’s port of Psathi, where you’ll stay overnight. This small, charming village offers cozy restaurants and patisseries, perfect for unwinding after a day on the water. The nearby village of Kimolos is also worth a stroll—authentic, unpretentious, and full of character.

Day 2: Polyaigos and Beyond

Day two kicks off with a visit to Myrsini Bay on Polyaigos, an uninhabited island famous for its untouched beauty. Here, you can swim and sunbathe in a peaceful setting—an ideal way to start your day.

The next stop is a secluded sandy beach only accessible by boat. Expect warm waters, golden sands, and a relaxed ambiance, perfect for a few more hours of swimming or simply soaking up the sun with a Greek “mezze” onboard, which adds a delightful local flavor to the experience.

Finally, you’ll explore Kleftiko Beach, the iconic pirate hideout turned popular sailing destination. The impressive caves and rock formations, along with the chance to explore via dinghy or paddleboard, make this a highlight. This bay’s history and natural beauty make it a must-visit on your Greek island adventure.

What’s Included & What’s Not

The tour includes breakfast, two lunches, all boat expenses—fuel, taxes, berth fees—and drinks throughout the day. You’ll be well-fed and comfortable, with the crew taking care of most details, so you can truly relax and enjoy the surroundings.

Dinners aren’t included, so you might want to explore the local eateries in Kimolos or plan for a special night out after your boat stays docked.

Our Take on the Experience

From what we’ve seen and read, travelers consistently praise this sailing adventure for its stunning scenery and authentic vibe. One reviewer called it their favorite part of visiting Greece and highlighted the “great crew and destinations.” The fact that it’s a private tour adds a special touch—you’re not just another face in a crowd but truly able to tailor your experience.

The stops at unique beaches like Sarakiniko and Kleftiko, combined with the opportunity to explore caves and enjoy fresh food, make it feel like a well-rounded, immersive escape. Plus, staying overnight on the boat lends the trip an extra layer of adventure, making it more memorable than a typical day cruise.

A few travelers mentioned that the value for money is quite good considering everything included, especially for such an exclusive experience. The only caveat might be weather-dependent adjustments—if storms roll in, your itinerary might shift, but the crew’s flexibility should help keep the experience enjoyable.

Who Should Consider This Tour?

This sailing tour is best suited for those who value privacy, comfort, and a personalized experience over a large group tour. It’s ideal if you want a relaxed pace, stunning views, and the chance to explore some of Greece’s lesser-known spots.

Travelers with an adventurous streak will love the cave explorations and swimming stops, while those seeking a peaceful, scenic getaway will appreciate the calm waters and authentic villages. It’s not necessarily geared toward families with young children, but older kids and teenagers who enjoy boats and outdoor adventures could find it an exciting trip.

Final Thoughts

This 2-day private sailing tour offers an intimate, scenic way to see parts of Milos, Kimolos, and Polyaigos that are often missed by regular travelers. With well-planned stops, gorgeous landscapes, delicious food, and overnight accommodation aboard, it’s a memorable option for travelers looking for a mix of relaxation and discovery.

If you’re craving a unique, personalized sea adventure that balances sightseeing with leisure, this trip could be just the ticket. Keep in mind the weather, book in advance, and prepare for a journey full of stunning views, quiet beaches, and authentic Greek island charm.

FAQ

Is this tour suitable for families or children?
While the tour is private and flexible, it’s best suited for those comfortable on boats and with some outdoor activity. It’s not specifically marketed as family-friendly, but older children who enjoy boating and swimming may find it enjoyable.

What’s the best time to book?
Most travelers book about 70 days in advance, which indicates this experience is popular and in demand, especially during peak season.

Are meals included?
Yes, breakfast and two lunches are included, with drinks served throughout the day. Dinner is not covered, so you might want to dine out in Kimolos after the boat docks.

Can I adjust the itinerary for weather?
Yes, the itinerary can be flexible based on weather conditions. The crew will do their best to ensure a smooth experience, rescheduling stops if needed.

How long is each day’s sailing?
The full experience spans approximately two days, with specific stops lasting from 45 minutes to a couple of hours. The schedule provides a good balance between sightseeing and relaxation.

What’s the group size?
This is a private tour for up to four people, which helps keep the experience intimate and personalized.

If you’re after a scenic, relaxing way to explore some of Greece’s most beautiful islands by sea, this sailing adventure looks like a fantastic choice. Just come prepared for some sunshine, splashes, and a touch of Greek sea magic.