Adamantas, the bustling port of Milos, is the perfect launchpad for exploring the island’s stunning coastline by boat. What makes Adamantas stand out isn’t just its lively fishing docks or charming cafes; it’s how accessible and diverse the sailing options are. Whether you’re after a relaxing day on a catamaran, a full-day adventure through sea caves, or a private yacht experience, the choices are plentiful. We especially love the Milkos: Full-Day Kleftiko Poliegos Sailboat Tour for its comprehensive itinerary and the Private Motor Yacht Cruise for its exclusivity and luxury. If you want to see the famous caves of Kleftiko or enjoy a sunset sail, Adamantas is your gateway to memorable seafaring moments.
If you’re considering a sailing trip, you’ll find options tailored to all tastes and budgets, from lively group tours to intimate private cruises. Some tours include lunch, drinks, and snorkeling gear, making them a great value for a full day on the water. For a more laid-back experience, a half-day cruise might be perfect, while those celebrating a special occasion might opt for a private charter. The variety ensures that everyone can find their ideal way to enjoy Milos’ beautiful sea.
Quick Overview
Our list features some of the best sailing experiences in Adamantas, blending shared group adventures with luxurious private cruises. You’ll find full-day tours like the Milkos: Full-Day Kleftiko Poliegos Sailboat Tour, which highlight Milos’ dramatic coastlines and caves, along with catamaran trips that offer unlimited drinks and a relaxed vibe. For those wanting exclusivity, there’s the Private Motor Yacht Cruise, perfect for families or small groups. Check below for detailed reviews and insights on each.
1. Milos: Full-Day Kleftiko Poliegos Sailboat Tour with Lunch
This full-day sailing tour offers a comprehensive look at Milos’ stunning coastline, starting from options at the Fish Market in Adamantas or Akra Vani. The journey takes you past fishing villages and iconic rock formations, with plenty of swimming, snorkeling, and photo stops, including the famous Kleftiko caves. You’ll explore these caves’ fascinating pirating history and enjoy a hearty homemade Greek lunch served onboard, paired with wine or beer.
What makes this tour stand out is its well-rounded itinerary—covering multiple beaches, sea caves, and several islands like Poliegos. The 9-hour duration is ideal for those who want a thorough experience, and reviews praise its value and the stunning scenery. It’s perfect for travelers who want a full day immersed in natural beauty with the convenience of an all-included trip. The guide’s commentary and the chance to paddleboard or relax in pristine bays add extra enjoyment.
Bottom Line: This tour offers a wide-ranging, all-day adventure with excellent value, especially for those who want to see the highlights with plenty of opportunities for swimming and local food.
2. Milos: Kleftiko & Poliegos Catamaran Trip with Meal & Drinks
For about $194, the Kleftiko & Poliegos Catamaran Trip provides a luxurious, relaxing way to see Milos and Poliegos. Departing from Adamantas, the tour takes you on a brand-new catamaran around the islands, with stops at Kleftiko, Gerakas, Sarakiniko, and the Blue Lagoon. The best part? Unlimited Greek food, beer, wine, and soft drinks, all served as you cruise.
The itinerary emphasizes swimming and snorkeling at four popular spots, including the famous Kleftiko caves. The friendly crew and new vessel create a comfortable, social atmosphere. Guests love the “delicious and plentiful” food and the relaxed vibe, which makes this tour stand out for its combination of scenic beauty and comfort. The expert skipper ensures a smooth trip, and the stops at beaches like Sarakiniko offer unforgettable photo opportunities.
Bottom Line: If you prefer a luxurious, all-inclusive day with the chance to swim in several iconic locations, this catamaran trip offers excellent value and a memorable experience.
3. Milos: Kleftiko Semi Private Sailing Cruise with Lunch
This semi-private 7-hour sailing cruise is ideal for those seeking a more intimate experience. It takes you along Milos’ west coast, visiting Kleftiko—famous for its sea caves and pirate lore—and Kalogries, where you can relax and swim. The tour includes lunch onboard, with options for swimming and snorkeling in inaccessible beaches.
The small-group setting allows for a personalized experience, and the experienced crew makes sure you get the most out of your time at each stop. With reviews giving it a 4.9/5, this trip is praised for its relaxed pace and the chance to explore hidden spots away from the crowds. It’s perfect if you’re after a more exclusive, less crowded sailing adventure.
Bottom Line: This tour’s intimate setting and flexible itinerary make it ideal for travelers who prefer a quiet, more personal day on the water with excellent food and swimming.
4. Kleftiko Trip Catamaran: Half day | Lunch & Open Bar
At just 5 hours, the Half-day Kleftiko Catamaran Trip is a great option for those short on time but wanting a taste of Milos’ best sights. Departing from Odyssey A Cruises, it includes visits to Skinopi Beach, Klima, and the Kleftiko caves. The highlight, of course, is swimming in the crystal-clear waters of Kleftiko, with snorkel gear provided.
The lunch onboard features seasonal fruits and delicious local dishes, and the open bar ensures you can sip wine or soft drinks throughout. You’ll enjoy a smooth sailing experience with a friendly crew, and the shorter duration makes it more accessible for travelers with tight schedules or who prefer a lighter experience. The reviews are glowing, especially noting the delicious food and beautiful scenery.
Bottom Line: Perfect for a quick but immersive journey to Kleftiko, with the added bonus of an open bar and a relaxing half-day on the water.
5. Adamantas: Kleftiko Sailing Cruise with Meal and Swim Stops
This 7-hour sailing tour from Adamantas has a solid reputation for its beautiful sail along the West Coast of Milos, stopping at Kleftiko and other scenic bays. It includes stops for swimming, snorkeling, and a delicious Greek meal onboard, featuring grilled octopus and homemade wine.
Rated 5/5, this tour is highly praised for its friendly crew and authentic Greek atmosphere. The highlight is swimming through the caves of Kleftiko, which creates unforgettable memories. The tour balances relaxation with exploration, making it ideal for travelers wanting a true taste of island life at a reasonable price.
Bottom Line: This tour hits the sweet spot for those seeking an authentic, full-day experience with great food, swimming, and spectacular views.
6. Milos: Private Half-Day Catamaran Cruise to Kleftiko Bay
Looking for exclusivity? The Private Half-Day Catamaran Cruise offers a luxurious, personalized experience for up to 10 people. Departing from Adamantas, it takes you to Kleftiko, Sykia Cave, and along the white cliffs of Kleftiko Bay, with options to swim, snorkel, or relax on deck.
This private cruise is perfect for families, couples, or groups celebrating special occasions. The chef-prepared Mediterranean lunch and drinks onboard allow for a leisurely, tailored day. The reviews highlight how the private nature makes it a memorable, stress-free experience, ideal for those who value comfort and exclusivity.
Bottom Line: If you want privacy, flexibility, and luxury, this is your best choice for a tailored day on the water.
7. Milos: Private Motor Yacht Cruise to Kleftiko – Sykia
Finally, the Private Motor Yacht Cruise provides the ultimate in exclusivity, available for up to 4 people at around $2,417. This customizable cruise takes you to Kleftiko, Sarakiniko, or Polyaigos, depending on your preference, with a professional crew guiding the way.
It lasts between 5 and 8 hours, giving you flexibility. The yacht offers luxurious comfort, with water activities like swimming and snorkeling, plus the chance to enjoy spectacular scenery—perfect for celebrating a special event or simply indulging in a private, stress-free day.
Bottom Line: For travelers who want the best in comfort and customization, this private yacht is a perfect splurge.
How to Choose
When selecting your ideal sailing experience, consider your budget, schedule, and interests. For a comprehensive day with many stops and included meals, the Full-Day Kleftiko Poliegos Sailboat Tour offers the best bang for your buck. If you prefer luxury and privacy, the Private Yacht or Private Half-Day Catamaran are hard to beat.
For travelers short on time but eager for a taste of Milos’ caves, the half-day options are perfect. Those who want a more personalized experience might lean toward semi-private cruises, while families or groups celebrating special moments will find the private options ideal.
Booking early is advisable, especially in peak summer months, as these tours tend to fill quickly. Check availability and start times when planning around your Milos itinerary.
Final thoughts
From lively group adventures to intimate private charters, Adamantas offers something for every sailor. If you’re looking for a full day of exploration, the full-day sailboat is unbeatable. For a relaxed, luxurious experience, the catamaran trips shine. And for a truly exclusive journey, the private yacht provides ultimate comfort and flexibility.
No matter which you choose, a day on the water in Milos promises unforgettable views, great food, and the chance to see some of Greece’s most iconic sea caves. Be sure to book early, especially in high season, to secure your spot on the perfect sailing adventure.