Milos isn’t just about breathtaking beaches or the colorful houses; it’s also a sailor’s paradise. With its crystal-clear waters, hidden caves, and inaccessible bays only reachable by boat, Milos is one of Greece’s top destinations for sailing adventures. Whether you prefer a full-day exploration or a romantic sunset cruise, there’s a sailing experience tailored for you. We’re particularly fond of the Adamantas Sightseeing Sailboat Cruise because it combines personalized service with a comprehensive itinerary, including stops at Kleftiko and Sykia Cave, all while enjoying Greek tapas and homemade lunch. For a shorter yet equally memorable trip, the Half-Day Catamaran to Kleftiko offers a great taste of Milos’ most famous bay.
If you’re eyeing a luxurious, all-day private-style experience, the Full-Day Premium Catamaran Cruise provides stunning scenery around Poliegos and Milos with multiple swimming stops and gourmet food. For sunset lovers, the Kleftiko Sunset Catamaran Cruise combines the magic of a Milos sunset with water activities and a delicious dinner onboard. Whichever you choose, sailing in Milos offers unforgettable views, lively marine life, and the chance to see some of Greece’s most dramatic coastlines from the water.
1. Adamantas: Milos Sightseeing Sailboat Cruise
At number 1 on our list, the Adamantas Sightseeing Sailboat Cruise stands out for its intimate small-group experience, with up to 10 passengers, ensuring personalized attention. This full-day tour covers the west side of Milos, including Kleftiko and the Sykia Cave, both inaccessible by land, making this trip a true highlight for explorers. The boat trip includes stops for swimming and snorkeling in crystal-clear bays, with options for dinghy rides inside the caves.
What makes this tour special is the variety of stops—officially nine—culminating in Kleftiko with a guided tour and homemade Greek lunch. The onboard open bar, Greek tapas, and GoPro photo opportunities make it a well-rounded package. Reviewers love the personable guides and the stunning scenery, with many calling it “a trip to heaven”—an experience that balances adventure with comfort. The price of around $181 is competitive given the length, diversity of stops, and included food and drinks.
Bottom line: This tour suits travelers looking for an intimate, well-organized day with plenty of swimming, cave exploring, and good food. The small group size enhances the experience, making it feel more like a day with friends than a large tour.
2. Milos: Half-Day Morning Catamaran Cruise to Kleftiko
Next, for those short on time but eager for a taste of Milos’ most famous bay, the Half-Day Morning Catamaran Cruise hits the spot. Priced at $175, this 6-hour trip explores the west side of Milos with stops at the secluded Kalogries beach and Kleftiko. It’s ideal for travelers who want a quick, yet immersive experience.
This tour shines for its peaceful setting and immaculate boat. Guests enjoy swimming and snorkeling in Kleftiko’s caves and the transparent waters of Kalogries. The guide’s commentary and the delicious buffet lunch make it stand out, with reviewers calling the food “phenomenal.” The half-day format makes it perfect for travelers who want to combine a boat trip with other activities or those with limited time.
Bottom line: This tour offers excellent value, especially if you prefer a half-day experience with plenty of swimming and cave exploration. It’s suitable for families and travelers who want a manageable, high-quality boat trip.
3. Milos: Full-Day Catamaran Cruise to Poliegos and Kleftiko
For those wanting a full-day adventure, the Full-Day Catamaran Cruise to Poliegos and Kleftiko is a top choice. Priced at $237, it offers around 10 hours of sailing, swimming, and sightseeing. The trip includes swimming at Poliegos’ majestic waters, exploring the famous caves of Kleftiko, and discovering lighthouse views over the Aegean.
What makes this trip stand out is the balance of relaxation and exploration. Guests rave about the fun and informative guides who share stories about the pirate history of Milos and its caves. The delicious lunch and drinks onboard add to the experience, with many reviewers mentioning they’ll never forget the scenic coastline and clear waters. The flexibility of stops and the chance to discover both Milos and Poliegos makes it a favorite for serious boat lovers.
Bottom line: This tour is great for active travelers who want to maximize their day at sea, with plenty of swimming, sightseeing, and a relaxed pace. It’s perfect for those interested in both natural beauty and local stories.
4. Milos: Kleftiko Sunset Catamaran Cruise with Meal & Drinks
Number 4 is the Kleftiko Sunset Catamaran Cruise, a perfect choice to experience Milos’ most iconic scenery during sunset. Costing $181, this 5.5-hour tour combines water activities, like swimming and snorkeling, with a romantic sunset over Kleftiko. The boat is a luxurious catamaran, offering plenty of space for relaxation.
The highlight is the dinner onboard, featuring a Mediterranean-style menu, and unlimited drinks—beer, soft drinks, and wine. The itinerary includes a stop at Kleftiko, where you can photoshoot and explore caves before settling in for a stunning sunset. Reviewers say the crew is friendly and the views are spectacular, making it ideal for couples or anyone seeking a romantic evening.
Bottom line: Best suited for romantic travelers or those wanting a luxury experience with incredible sunset views, water activities, and good food. It’s a memorable way to end a day in Milos.
5. Milos: Full-Day Premium Catamaran Cruise Kleftiko & Polyegos
This luxury full-day cruise for around $215 offers an all-inclusive experience aboard a premium catamaran. Covering Kleftiko and Polyegos, it invites you to swim, snorkel, and paddleboard in crystal-clear waters. The boat’s spacious design allows for plenty of comfortable spots to relax while soaking in the scenery.
What sets this trip apart is the attention to detail—with local, homemade Greek food, a variety of water activities, and stunning photo opportunities of the white rocks and light-blue seas. The reviews highlight the well-paced itinerary, friendly crew, and delicious food. It’s the most comprehensive, luxurious option for those wanting to indulge in Milos’ beauty.
Bottom line: Suitable for luxury travelers and water sport enthusiasts, this cruise combines comfort, adventure, and fantastic scenery for a full-day of sailing pleasure.
6. Milos: Full-Day Catamaran Cruise with Paddle Board
Number 6 offers a full-day experience on a spacious 41′ catamaran for $226. The tour emphasizes swimming, snorkeling, and paddleboarding at remote beaches and Kleftiko caves. The itinerary features dinghy rides inside caves and GoPro photo opportunities.
Guests rave about the comfortable boat, delicious Greek tapas, and the flexibility of stops for water activities. The tour’s highlight is the chance to stand-up paddleboard in some of the most pristine waters. The reviews mention the friendly crew and the scenic beauty of the stops, making it ideal for active travelers who want a full day of exploration.
Bottom line: Perfect for active families or adventurous couples, this trip combines comfort, water fun, and scenic exploration.
7. From Adamas: Milos and Poliegos Catamaran Cruise with Lunch
This extended 9.5-hour cruise costs about $226 and offers a comprehensive circumnavigation of Milos and its nearby island Poliegos. The boat boasts a spacious 44′ and features paddleboarding, snorkeling, and pools of water to relax in. The included BBQ lunch with vegan options is a highlight, along with passing fishing villages and the impressive Kleftiko caves.
Guests consistently praise the friendly guides, good food, and the diverse stops. Many mention the relaxed pace and the scenic coastline as unforgettable. This tour provides a full immersion into Milos’ coastal beauty.
Bottom line: Ideal for travelers wanting a comprehensive day, with plenty of time for swimming, snorkeling, and sightseeing in style and comfort.
8. Milos: Full Day Milos and Poliegos Catamaran Cruise
Number 8 offers a 10-hour day on a smaller boat for $182. It features several stops at beaches like Glaronesia and Thiorichia, with opportunities for snorkeling and swimming. The tour includes breakfast and lunch, with plenty of drinks to keep you refreshed.
Guests highlight the beautiful beaches, friendly crew, and the informative commentary about pirating history. The flexible itinerary and small group size allow for a more intimate experience.
Bottom line: Great for history-minded travelers and those who prefer a more relaxed pace with lots of swimming and scenic stops.
9. Catamaran Full Day Cruise
Our final choice is a straightforward full-day catamaran cruise with a perfect 5-star rating. For $260, you enjoy swimming at Kleftiko, visiting fishing villages, and sailing past Cape Vani. The small number of reviews points to a personalized, high-quality experience with attentive service.
Bottom line: Best for luxury seekers and those wanting a seamless, intimate day at sea with classic Milos sights.
How to Choose
When deciding between these sailing options, consider your budget, time available, and interest in activities. For a shorter, scenic half-day, the Half-Day Catamaran to Kleftiko provides a quick yet satisfying taste. If you want immersion and luxury, the Full-Day Premium Catamaran or the Full Day Milos and Poliegos Cruise are top choices. For romantic sunsets, the Sunset Catamaran is unbeatable.
Think about your activity level—if swimming and paddleboarding are priorities, tours like the Full-Day Catamaran with Paddle Board fit well. For history and scenery, tours passing by fishing villages and lava rocks offer extra flavor. Booking early is advisable, especially in peak season, to secure your preferred date and boat.
Milos offers a diverse range of sailing experiences that suit every traveler, from quick snapshots to luxurious full-day adventures. Whether you’re after a romantic sunset, a family outing, or an active exploration, Milos’ waters won’t disappoint. Remember, these trips fill up fast—so plan ahead and set sail for unforgettable memories on this stunning Greek island.