Milos is a standout among the Cyclades islands for its variety of sailing experiences. Unlike some Greek islands that are primarily land-based attractions, Milos offers a stunning coastline of sea caves, dramatic rock formations, and secluded beaches only accessible by boat. The best part? You get to see it all from the water, with options that suit both casual visitors and serious sailors. We particularly love the Milos caves snorkelling Catamaran Cruise for its small group intimacy and the chance to snorkel in hidden coves or explore the Cave of Sykia — a true highlight for those eager to combine sightseeing with swimming. For a shorter but equally memorable trip, the Catamaran Half Day Morning Cruise to Kleftiko is perfect for fitting into a busy schedule. And if you’re seeking the ultimate in exclusivity, the Full Day Private Sailing Cruise offers a personalized day tailored just for you.
Quick Overview
Our list covers seven of the best sailing experiences in Milos, from small group day tours to private multi-day cruises. Whether you want an 8-hour snorkelling adventure, a half-day exploration of Kleftiko, or an entire two-day private voyage, there’s a tour here to match your style and pace. Each tour is distinguished by its itinerary, group size, and what’s included — from included food and drinks to access to the most iconic sea caves. Now, let’s take a closer look at each option.
1. Milos caves snorkelling Catamaran Cruise in a small group
Starting with a bang, this small-group catamaran cruise offers a personalized experience for up to 12 passengers. It’s a standout because of its intimate setting and the focus on snorkeling in pristine coves. Onboard, you’ll find ample space and shade, making the day comfortable even on sunny days. The crew handles all the logistics, so you just relax, enjoy included food and drinks, and use provided snorkel gear to explore the undersea world.
The tour’s itinerary is packed with highlights: you’ll visit Klima, the first capital of Milos, where you can snap photos of the colorful fishing village and learn some local history. Next, you’ll pass the 19th-century iron and manganese mine along the bay of Adamas, stopping for a swim and photo opportunity. The first swim at Kalogries Beach lasts around 30 minutes, perfect for a snorkel and a light brunch. The next major stop is Sykia Cave, where you’ll get to explore the cave’s interior by dinghy — an unforgettable experience. With rave reviews praising the crew’s attentiveness and the quality of the food, this tour offers excellent value for a full day of adventure.
Bottom Line: Ideal for those who want a relaxed, small-group day with plenty of swimming, snorkeling, and cave exploring.
2. Catamaran Half Day Morning Cruise: Kleftiko
For those short on time but eager to see Milos’ most famous sea caves, the half-day cruise to Kleftiko hits the mark. This 6-hour adventure takes you along the island’s west and south sides, exploring sea caves, lava formations, and crystalline waters. The itinerary is designed for maximum sightseeing with a relaxing pace.
The tour begins with a cruise past traditional fishing villages like Skinopi and Klima, with colorful houses called “Sirmata.” The highlight is the Pirate Bay of Kleftiko, where you’ll spend about 2 hours swimming, snorkeling, and exploring the caves. The crew guides you to the best spots, and you can enjoy a buffet lunch onboard with drinks, making it a delicious break amid the stunning scenery. Reviewers mention that the food is excellent, and the stops are truly beautiful — perfect for quick but memorable adventures.
This trip is best suited for travelers who want a taste of Milos’ iconic coastal scenery without committing an entire day. It’s a good choice for families or people who want to squeeze a boat trip into a busy itinerary.
Bottom Line: Perfect for a half-day escape to Milos’ most picturesque caves and beaches with good food and friendly crew.
3. Catamaran Full Day Cruise: Poliegos – Kleftiko
If you’re after a truly comprehensive sailing experience, the full-day cruise around Poliegos and Kleftiko offers a fantastic way to explore Milos’ lesser-known treasures. With around 9.5 hours on the water, this tour is ideal for those who want to see a wide variety of coastlines and hidden beaches inaccessible by land.
Beginning early, the cruise covers Kalogries Beach, Sikia Cave, and the Pirate Bay of Kleftiko with plenty of time to swim, snorkel, and take photos. It also includes stops at Poliegos, an uninhabited island known for its pristine beaches and dramatic landscapes, as well as scenic stops at Kimolos and other points along the coast. The crew provides onboard snacks, drinks, and a delicious lunch, making this a real feast for the senses.
Guests rave about the diversity of scenery and the chance to access isolated beaches and caves. Because the tour covers more ground, it’s well-suited for adventurous travelers keen to see as much as possible in one day.
Bottom Line: An immersive, full-day exploration perfect for active travelers who don’t want to miss the island’s most spectacular coastlines.
4. Milos: Small Group Yacht Tour—Kleftiko Sarakiniko Poliegos
For a more exclusive, semi-private experience, this small-group yacht tour takes you to iconic spots like Kleftiko, Sarakiniko, and Poliegos. With a focus on personalized service and access to hidden spots, this tour is perfect for travelers who prefer a luxury feel without going full private.
The 6-hour itinerary includes stops at Kleftiko, where you can snorkel and explore caves, and Sarakiniko, the famous moon-like landscape of white volcanic rock. The tour also visits Poliegos, with time for swimming and sightseeing, plus scenic photo stops along the way. The crew shares local insights and provides onboard Greek flavors and drinks, adding a cultural flavor to the adventure.
Rated highly for its friendly, attentive crew and the authentic hospitality, this tour is ideal for small groups or couples seeking privacy and a tailored experience. Reviewers mention how the route is weather-adapted, ensuring comfort and safety.
Bottom Line: Best suited for those seeking a more intimate, luxurious day on the water with access to Milos’ top sights.
5. Full Day Sailboat Private Kleftiko & Blue Lagoon with Lunch
Looking for a completely private experience? This full-day private sailboat allows up to 8 people to explore Milos at their own pace. For about 9 hours, you’ll visit Kleftiko, the Blue Lagoon, and other hidden beaches, all with a dedicated captain and crew.
The tour includes snacks, drinks, and a full onboard lunch, plus the flexibility to customize stops based on your preferences. The itinerary features crystal-clear waters at Kalogries, sea caves at Sykia, and pirate caves at Kleftiko. You’ll also have the chance to relax in secluded beaches and enjoy photos of the rugged coastlines.
Reviews highlight how staff are attentive and friendly, making this an ideal choice for families, couples, or small groups wanting total privacy. The luxury setting and tailored itinerary make it worth the higher price point.
Bottom Line: A fantastic option for private groups wanting a customizable, all-day sailing adventure with full onboard service.
6. Full day private sailing cruise around Milos island
For travelers seeking ultimate exclusivity, this full-day private sailing cruise aboard the Oceanis sailboat “La Pomme Bleue” offers a personalized way to see Milos. With up to 8 guests, it’s perfect for families or friends who want to craft their own itinerary.
Starting from Adamas, the cruise passes Klima and Skinopi, then sails past Arkoudes and the Cape Vani. The crew takes you to the most scenic spots for swimming, snorkeling, and photo opportunities. The boat allows for freedom to explore, with stops at secluded beaches, and you can enjoy sunbathing on the deck while soaking in the views.
Guests describe this experience as a memorable, relaxed day with excellent service and beautiful scenery. It’s a good fit for those wanting to avoid crowds and have a tailor-made day on the water.
Bottom Line: Excellent for private groups who want maximum flexibility and a high-end, peaceful experience.
7. 2-Day Private Sailing Tour around Milos, Kimolos and Polyaigos
Finally, the 2-day private tour is the ultimate way to truly learn about Milos and nearby islands. Up to 4 people can join this overnight cruise aboard a sailboat, exploring Kimolos, Polyaigos, and other uninhabited islands.
The first day includes stops at Klima, Sarakiniko, and Elephant Beach with time for swimming and lunch onboard. The second day takes you to Kimolos and Polyaigos, with scenic photo stops and plenty of time to relax and explore. The itinerary is flexible, and the crew will adapt based on weather and your interests.
Reviews mention that this tour is the most exclusive and memorable way to see the islands, encouraging early booking due to limited availability. It’s best suited for small groups wanting a luxury experience with a personal touch.
Bottom Line: Perfect for those who want a multi-day, private sailing adventure with full customization.
How to Choose Your Perfect Milos Sailing Experience
When deciding between these options, consider your budget, how much time you have, and whether you want a private or group experience. For a short, fun-filled adventure, the Half Day Kleftiko Cruise offers great value. If you prefer a more personal, luxurious day, the Small Group Yacht Tour or the Full Day Private Cruise might be better suited.
For travelers with more time and a sense of adventure, the 2-day private tour promises a deep dive into Milos and neighboring islands. All tours are best booked early, especially in peak summer months, to secure your spot.
Final Thoughts
Milos offers a wide array of sailing experiences, from intimate day trips to multi-day private cruises. Whether you’re after snorkeling in caves, exploring iconic spots like Kleftiko, or enjoying a private charter, there’s something for every kind of sailor. For those who want a balanced combination of sightseeing, swimming, and good food, the Milos caves snorkelling Catamaran Cruise proves hard to beat.
If you’re after a luxurious, bespoke experience, the private or semi-private options will deliver. Either way, Milos’ spectacular coastline and secluded beaches await your arrival — just remember to book early to make sure you don’t miss out on the best days in the sun on this remarkable island.