Top Milos Sailing Tours

Enjoy two extended swimming stops in breathtaking turquoise waters. Swim, snorkel with the provided equipment, explore the coastline on a SUP, or simply relax aboard a comfortable sailing yacht while surrounded by the incredible scenery of Polyaigos. During your first swimming stop, enjoy a selection of traditional Greek meze, accompanied by water, soft drinks, local beer, house wine, and a small taste of traditional Greek ouzo—all included. At your second swimming stop, fresh seasonal fruit is served before sailing back to Kimolos. With a maximum of 12 guests onboard, this experience offers a relaxed, intimate, and personalized atmosphere, making it the perfect way to discover the hidden beauty of Polyaigos away from the crowds.

Experience one of the best Milos boat tours with a sailing cruise to Kleftiko along the island’s stunning west coast. Departing from Adamas, sail past volcanic landscapes, hidden coves and sea caves, with multiple stops for swimming and snorkeling in crystal-clear waters. Visit Kleftiko, swim at Kalogries Beach and explore Sykia Cave, some of Milos’ most iconic locations. Relax on deck and enjoy breakfast, lunch, drinks, seasonal fruits and traditional sweets served on board. With a small-group setting and experienced local crew, this sailing cruise offers a comfortable and unforgettable way to discover Milos. Highlights Full-day experience (10:00–17:00) Visit Kleftiko, Sykia Cave & Kalogries Beach Swimming, snorkeling and cave exploration Breakfast, lunch, drinks, fruits & sweets included Small-group experience with local crew Important Note: The itinerary is indicative and may be adjusted depending on weather, sea conditions, or for the safe operation of the cruise.

Explore the Aegean island of Milos on this sailing excursion. Enjoy a small group experience with up to 12 passengers that includes visits to Cape Vani, Kalogries Beach, and Agios Dimitrios bay. Check out the caves of Kleftiko and Sykia by dinghy, go swimming and snorkeling, and relax by the sea. Enjoy complimentary lunch, snacks, drinks, access to snorkeling equipment, and GoPro photos.

Enjoy a half-day cruise and discover the most beautiful places in Milos sailing on the West and South side of the island, exploring the caves of the famous old pirate bay of Kleftiko and discovering a part of the South side.

Experience Milos’ south coast and the white cliffs and coves of Kleftiko in style on this surprisingly affordable private sailboat charter. Enjoy unlimited bottled water, soft drinks including Coca-Cola and Fanta, a bottle of chilled white wine, and snacks, with a tender to get you right into the caves and shower and restroom on board. Good for up to eight travelers, with a high-quality Bluetooth sound system for your favorite tracks.

With its rugged arches and caves, Kleftiko Beach is one of Milos’ star attractions. Skip the long hike down and up and see it from the water on this intimate cruise with swim stops en route—and snorkeling gear included so you can make the most of the crystal waters. An open bar gets the party spirit flowing, while an authentic Greek lunch keeps you energized.

Milos is famed for its stunning, otherworldly coastal scenery, including the lunar-like Sarakiniko Beach—but the most impressive views aren’t reachable by land. On this small-group sailing tour, explore the island’s remoter west coast—a side of Milos most travelers miss—as you explore by boat. Along the way, listen to your skipper explain the island’s history and unique geology. Breakfast, lunch, and snacks are included.

With its caves and sea arches, Kleftiko Beach is one of Milos’ most spectacular locations. See it from the best vantage point—on the water—when you join this half-day catamaran cruise with a photo opp by Sikia Beach’s cave and a swim stop at Kalogries Beach. A fresh-cooked meal keeps the hunger pangs away, while water, soft drinks, beer, and wine keep you hydrated. Snorkeling gear lets you see the seascapes up close.

Experience a full-day Milos sailing cruise around Milos and Polyaigos aboard a comfortable sailing yacht. Departing from Adamas, sail along Milos’ coastline with stops at hidden bays, sea caves and crystal-clear waters. Swim and snorkel in stunning locations including Kleftiko, Gerakas and the turquoise waters of Galazia Nera. Relax on deck, enjoy the scenery and make the most of multiple swimming stops. Breakfast, lunch, snacks, drinks and local treats are served on board. With a semi-private group and experienced local crew, this cruise is the perfect way to discover the best of Milos and Polyaigos in one unforgettable day. Highlights Full-day Milos & Polyaigos sailing cruise Visit Kleftiko, Gerakas & Galazia Nera Breakfast, lunch, snacks & drinks included Semi-private experience (up to 22 guests) Professional local skipper and crew Important Note: The itinerary is indicative and may be adjusted depending on weather, sea conditions, or for the safe operation of the cruise.

If you love the sea, if you seek to escape from the everyday routine, if you long for the intense emotions of nature, if you seek to broaden your horizons, then a catamaran sailing boat adventure is precisely what you want. Milos beauties are mostly hidden and unreachable by land. The catamaran will lead you to beautiful, pristine and isolated beaches, far from the hassle of the crowds. With this cruise, you will have the chance to discover most of the island coastlines and see the huge diversity of colours, caves and beaches Milos has to offer.

Our luxury catamaran combines space and style, crafted to offer you complete comfort. Whether you stretch out on a sunbed, unwind in a shaded lounge, or dance under the open sky, you'll always find your perfect spot. Soft, uplifting music sets a warm and joyful tone throughout the day. Between smiles and melodies, you'll enjoy Greek snacks, a light brunch, and a delicious lunch — all included. Espresso, tea, water, soft drinks, local Greek white wine and beer are available whenever you wish. For those seeking adventure, the sea becomes your playground. Try stand-up paddleboarding, explore underwater life with snorkeling gear, or simply drift on an inflatable noodle. And of course, our iconic pink flamingo float is always ready for your next unforgettable photo. Whether you're after excitement or gentle relaxation, there's something for everyone.

With its caves and sea arches, Kleftiko Beach is one of Milos’ most in-demand locations. See it in style when you book this catamaran cruise, with meals, snacks, and drinks included plus snorkeling gear, fishing kit, pool noodles, and stand-up paddleboards (SUP) to entertain you. Choose between morning and sunset cruises, and upgrade to include transfers: You can also make lifetime memories with a private cruise just for your group.

See the coast of Milos minus the beachside crowds in one relaxing half-day boat trip from Agia Kiriaki. Ideal if you’re short on time, this half-day cruise includes time to swim in the calm waters of Gerontas Bay and Kleftiko, plus a scenic route past the blonde sands of Gerakas, Tsigrado, Firiplaka and Katergo beaches. Iced coffee, raki, and local treats are among the perks.

Some of Milos’ most beautiful spots can only be reached from the sea. Soak up the views in style on this small-group cruise by charming sailboat. Discover Kleftiko Beach’s sculptural formations, drop anchor at cliff-framed Gerakas beach, and swim in the turquoise waters of Poliegos, an uninhabited island. Your day includes breakfast, lunch, and drinks, including alcoholic beverages, for maximum comfort.

The coastline of the island of Milos is home to many beaches and coves you can’t reach by land. Explore the natural seascapes and dive into deep blue waters on this full-day sailing cruise as you swim and snorkel at various spots around the island, and explore the bright limestone rocks of Kleftiko, an old pirate cave.

Sailing across the coastline, we will pass by the traditional fishing villages of Skinopi, Klima with the colorful little houses – called “Sirmata”- built by the seaside, Areti and Fourkovouni.

Then, we will visit Arkoudes, a complex of lava rocks, which takes its name from its characteristic shape, of a bear. 

Opening the sails, we are heading to the impressive Cape Vani and our first stop for a swim, the natural bay of Kalogries. Follows the stunning cave of Sikia, where we will be able to see the characteristic hole in its roof as well as the entrance of the cave. 
 The famous old pirate bay of Kleftiko is the next stop, where our crew will guide you to explore it ! 

Next will visit beach of Gerakas and its hot springs. 
 Then we will head to the largest uninhabited island of the Cyclades, Polyaigos. There we will swim in the "Blue Waters", an area with amazing turquoise waters. 
Last stop for photography is Glaronisia (three volcanic islands).

Katerina Sailing Boat Milos is a family-run sailing experience offering authentic and intimate trips around the island of Milos. With Captain Katerina at the helm, we welcome guests aboard to explore the hidden side of Milos — from sea caves and secret beaches to unforgettable sunsets and sunrises. mission is to share the beauty of the Aegean with a warm smile, homemade food, and a touch of Cycladic magic. We begin day just before sunrise, sailing from Adamas into the calm morning sea to witness the first light over the Aegean. Guests are invited to swim in peaceful bays during the golden hour, enjoy a homemade breakfast, and capture the serenity of Milos in the early morning glow. As the journey continues, we visit remote spots perfect for snorkeling, exploring, and relaxing. Later in the trip, we serve a full lunch on board, featuring homemade dishes, local wine, and fresh fruit. We return to Adamas, leaving you refreshed, fulfilled, and filled with unforgettable memories

Sail along the Milos coastline and take in views of Klima’s colorful ‘Sirmata’ houses as well as the villages of Skinopi, Areti, and Fourkovouni on this full-day catamaran cruise setting out from Adamantas. Explore geological marvels, such as the Arkoudes lava rocks, and jump into the warm ocean waters for a swim in secluded island bays.

This private sailing cruise offers a premium, all-inclusive experience on a modern sailing yacht exclusively for you. With a dedicated captain and hostess on board, you enjoy personalized service, tailored itineraries, and complete privacy. Unlike group tours, this experience includes freshly prepared food, unlimited drinks, and access to secluded coves and hidden spots only a true sailing yacht can reach. A fully customized, luxurious day on the sea of Milos.

Experience the magic of Milos on a luxury catamaran cruise designed for total comfort and adventure. Your journey begins at Adamantas, sailing first to the otherworldly lunar landscape of Sarakiniko for breathtaking photos of its famous white rocks. Next, dive into the electric blue waters of Galazia Nera on Polyegos Island, a hidden paradise known for its striking turquoise color. We continue to the tranquil Spathi Beach for a relaxing swim and a freshly prepared Greek lunch featuring organic, local ingredients. Afterwards, we reach the legendary Kleftiko, a former pirate hideout with towering cliffs and sea caves. Here, the sea becomes your playground – enjoy snorkeling, stand-up paddleboarding, or relaxing on our iconic pink flamingo. The return journey is equally spectacular. Capture photos of the majestic Sykia Cave and dramatic Cape Vani before sailing past the colorful "syrmata" boat garages of Klima village. With an open bar, professional crew, and elegant atmosphere.

Join this group catamaran cruise that goes to both Milos and Poliegos, plus serves up a homemade menu with barbeque and drinks. You don’t need to organize anything. Just show up ready to swim in turquoise water, snorkel, hang out on the beaches, and maybe swim in natural hot springs. You can also check out a traditional fishing village, Kilma.

Enjoy amazing moments in Milos island! An ideal cruise for you in order to see the most famous spots here in Milos such as Kleftiko the old famous pirate bay with the transparent waters! A short cruise that includes everything that you wish for your dreamy vacations. Swimming, snorkelling and for the end an amazing sunset!  You are free to explore the paradise!

[Up to 7 Guests] Private Cruise in Milos and across the Cyclades • Morning, Sunset, or Full Day options • Explore Kleftiko, Sarakiniko & more on a luxury open-yacht • Open bar and meals included Charter the entire yacht on a Private Cruise in Milos and the Cyclades, with three curated route options across Milos, Kimolos, and Poliegos. Our cruises cover more coastline than you'll find on a typical private charter. Your captain shapes the day around your preferences and confirms your meeting point 48 hours before departure. Hotel and villa pick-up available upon request. – Every route is tailor-made. Discuss your preferred stops and durations directly with your captain. Half-Day cruises include 5 to 6 stops over 5 hours, Full-Day cruises include 7 to 8 stops over 8 hours. Stops may be adjusted on the day based on conditions. Book your Private Cruise!