Top Milos Sailing Tours

The sea caves and swimming spots around Milos and Polyaigos are hard to reach without a boat and someone who knows the coastline. Cruise out for a full day of swimming, snorkeling, and exploring the old pirate coves, with the route and timing handled for you. Snacks, lunch, and drinks are all provided on board, so you can turn up and settle in while the crew runs the day.

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.

Set sail on an unforgettable luxury cruise aboard a Jeanneau 57 sailing yacht and discover legendary Kleftiko, one of Milos’ most iconic natural wonders. Departing from Adamas Port, this experience blends relaxation, adventure, and local storytelling in true Cycladic style. Sail along the stunning coastline, passing colorful Klima and the impressive Sykia Cave before reaching Kleftiko’s dramatic white rock formations, sea caves, and crystal-clear turquoise waters. Once a pirate hideout, the area is rich in history and volcanic beauty, with fascinating stories shared by your skipper along the way. Anchor in secluded coves for swimming, snorkeling, and stand-up paddleboarding, with time to explore caves and arches from the water. Back on board, enjoy a freshly prepared Mediterranean meal with unlimited drinks as you relax in comfort. Designed for small groups and authentic island vibes, this cruise is perfect for couples, friends, and travelers seeking a refined yet fun sea adventure.

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.

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.

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.

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.

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 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.

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.

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).

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.

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.

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.

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.

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!

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.

Explore the stunning volcanic coastline of Milos—and enjoy three swim stops plus a stop in Kleftiko—during this full-day sailing excursion. Enjoy close-up views of Milos' attractions, from the colorful fishing village of Klima to the rock formations of Cape Vani. Other highlights include a swim and snorkel stop at the ancient pirate hideout of Kleftiko, and swimming at Kalogries Beach and Agios Dimitrios.

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.

Milos is famed for its stunning volcanic coastlines, but the best views—and swimming spots—typically aren’t reachable by land. Spend the day out on the open water during this full-day private sailing cruise. Deluxe packages include lunch and drinks, plus get-down swimming or paddle-board stops at Kleftiko and Kalogries beaches.

Sailing around the Aegean Sea doesn’t have to break the bank. Instead of arranging a costly private charter, explore both the coastlines of Milos and the uninhabited island of Poliegos during this cost-effective, small-group excursion. Spend the day swimming, snorkeling, or paddle-boarding in secluded bays and caves—or simply relax on the crew-staffed boat with a drink in hand.

With its volcanic origins, dramatic scenery, and turquoise waters, Milos is one of Greece’s most spectacular islands—and this full-day yacht tour offers the perfect way to discover its highlights. Hop aboard your vessel at Adamas, and set sail. Admire colorful rock formations, visit numerous beaches (including Kleftiko Beach), enjoy meals and beverages, have free time to swim and snorkel, explore Poliegos Island, and more.