Milos stands out among the Cyclades for its stunning coastline, dramatic sea caves, and crystal-clear waters that beckon sailors and swimmers alike. Unlike many Greek islands, Milos offers a variety of sailing adventures that cater to different tastes—whether you’re after a full-day exploration or a romantic sunset cruise. We’re particularly fond of the Adamantas: Milos Sightseeing Sailboat Cruise, which features intimate group sizes, snorkeling in Kleftiko, and an onboard homemade Greek lunch. Its high ratings and personalized experience make it a standout for travelers wanting a balance of adventure and comfort.
For those with limited time, the Half-Day Morning Catamaran to Kleftiko offers a quick but memorable exploration of Milos’ most famous bay. Prefer a luxurious experience? The Full-Day Premium Catamaran Cruise combines style, space, and a focus on the island’s gems. Whether you prefer small-group outings or larger vessels, there’s a Milos sailing experience for you.
Below, we’ll walk through each of these top tours, highlighting what makes them unique, how they stack up in terms of value, and who they’re best suited for.
1. Adamantas: Milos Sightseeing Sailboat Cruise
This full-day sailing adventure covers the west side of Milos, including the famous Kleftiko and the Sykia Cave—both inaccessible by land. The cruise operates with a small group of up to 10 passengers, fostering a more personal experience. The itinerary includes stops for swimming and snorkeling in secluded bays, with the chance to explore Kleftiko’s caves in a dinghy.
What sets this tour apart is the detailed itinerary—every stop has a story, from the Catacombs of Milos to Klima and Akra Vani. The highlight is the Kleftiko stop, where you can enjoy a guided tour, swim, and sample homemade Greek tapas. The onboard lunch, served with an open bar of cold drinks, is often praised for its quality and authenticity. The guide’s willingness to share stories and take photos with GoPro cameras enhances the experience.
This tour is perfect for travelers who want an all-in-one day, with a focus on exploring caves and hidden beaches in a small group. The reviews highlight the personable crew and stunning scenery. At $181 per person, the value is high for an immersive day with plenty of swimming, eating, and photo opportunities.
Bottom Line: A well-rounded, intimate trip ideal for those seeking personalized service and access to inaccessible spots.
2. Milos: Half-Day Morning Catamaran Cruise to Kleftiko
For a shorter but equally memorable experience, this half-day cruise explores the wild western coast of Milos, focusing on the iconic Kleftiko bay and Kalogries beach. The trip lasts around six hours, making it a great option for travelers with tight schedules or those who prefer to spend the afternoon at the beach.
The tour’s standout feature is the chance to snorkel in the famous Kleftiko sea caves and see underwater life. The boat is a comfortable catamaran, which offers a smooth ride and plenty of space to relax. Tour guides focus on the natural beauty and history of the area, providing insights into the pirate stories and geology of the island.
Reviewers frequently mention the exceptional lunch—featuring fresh fruit and a buffet meal—that surpasses expectations. Many say this cruise was the highlight of their trip, appreciating the balance of sightseeing and swimming in a relaxed setting. At $175 per person, it offers good value given the quality of the experience and the convenient half-day format.
Bottom Line: Perfect for travelers wanting a taste of Milos’ scenic west coast, especially if time is limited but quality still matters.
3. Milos: Full-Day Catamaran Cruise to Poliegos and Kleftiko
This full-day catamaran tour takes you beyond Milos to explore the neighboring Poliegos Island, famous for its pristine beaches and hot springs. It’s a longer, more luxurious experience, emphasizing comfort and diverse scenery. Starting early, the boat visits several caves, including Kleftiko, with plenty of time for swimming, snorkeling, and relaxing.
What makes this trip stand out is the combination of stunning island views—traditional fishing villages, lava rocks, colorful houses—and the chance to explore lesser-visited beaches like Gerakas and its hot springs. The guide shares stories about pirate history and geology, enriching the experience. You also get to try paddleboarding and take photos with GoPro cameras.
Guests often comment on the personable crew and the quality of the onboard lunch, which is homemade and plentiful. The 10-hour duration is ideal for travelers seeking a comprehensive day of adventure and relaxation. Priced at $237, it offers excellent value for those wanting an in-depth exploration with added luxury.
Bottom Line: Best suited for travelers who want a full-day, rich experience with comfort, multiple stops, and water activities.
4. Milos: Kleftiko Sunset Catamaran Cruise with Meal & Drinks
Imagine watching the sunset from the deck of a luxurious catamaran while sipping wine and nibbling on Mediterranean dishes—this tour makes that possible. It departs from Adamantas and takes you to Kleftiko Bay, famous for its caves and pirate lore, with a relaxed atmosphere and plenty of water activities.
The highlight is the sunset itself—views of the sky changing colors over the sea are genuinely spectacular. During the cruise, you’re encouraged to swim, snorkel, or even stand-up paddleboard in clear waters. The dinner, served onboard, includes fresh, homemade Mediterranean dishes, which many reviewers praise for their quality. The open bar keeps drinks flowing, making this an ideal romantic or special occasion trip.
At 5.5 hours, it’s a shorter, more intimate experience focused on enjoying nature’s beauty at dusk. Reviewers mention the crew’s friendliness and the peaceful setting as top reasons to book. The $181 price includes dinner, drinks, and an unforgettable sunset experience.
Bottom Line: A perfect choice for couples or anyone wanting a relaxing, scenic evening on the water.
5. Milos: Full-Day Premium Catamaran Cruise Kleftiko & Polyegos
As the name suggests, this premium experience offers a luxurious full-day exploring Milos and Polyegos from a spacious 44’ catamaran. The day includes swimming in Kleftiko, paddleboarding, and snorkeling in some of the clearest waters in the region.
What makes this tour special is the all-inclusive approach—homemade Greek lunch, unlimited drinks, and plenty of water activities—delivered with attentive service. The boat’s size and layout allow for comfort, even on busy days. The guide’s storytelling and the variety of stops, including the hot springs at Gerakas, make it a comprehensive adventure.
Rated 5/5 with glowing reviews, guests love the personal touch of the crew and the quality of food and drinks. At $215, it offers a luxurious, all-in-one day that balances exploration, relaxation, and gourmet dining. It’s best suited for travelers ready to indulge and who value comfort and service.
Bottom Line: Ideal for travelers seeking a high-end, all-inclusive day on the water with a mix of adventure and relaxation.
6. Milos: Full-Day Catamaran Cruise with Paddle Board
This daylong cruise combines the fun of paddleboarding with the comfort of a spacious 41’ catamaran. It includes swimming, snorkeling, and exploring remote beaches and caves, like Sykia and Kleftiko. It’s a relaxed, all-inclusive trip where you can try stand-up paddleboarding or just soak up the sun.
Highlights include a visit to the Sykia Cave, where you can explore the impressive underground chambers, and a stop at Kleftiko for snorkeling and swimming. The onboard lunch, with Greek tapas and drinks, gets rave reviews for authenticity and quality. The boat’s size means you’ll have plenty of space to move around and find your favorite spot.
With a 4.9 rating and a price of $226, this tour offers excellent value for those wanting a balanced mix of water activities, sightseeing, and comfort. It’s especially good for groups or families looking for a flexible, fun day.
Bottom Line: Best suited for active travelers who want a full day of swimming, paddling, and exploring in comfort.
7. From Adamas: Milos and Poliegos Catamaran Cruise with Lunch
This extensive cruise departs from Adamas and takes you around both Milos and nearby Poliegos. It’s a full-day, all-inclusive trip aboard a spacious 44’ catamaran with a focus on comfort and variety. You’ll swim in gorgeous waters, explore caves, and enjoy a BBQ lunch with vegan options.
A unique aspect is how the boat circumnavigates Milos, passing by its most significant sites while providing insights into their history. The stops include Kleftiko, Poliegos, and other beaches like Tsigrado. The onboard food, praised for its homemade quality, pairs well with the unlimited drinks.
Rated 4.9/5, travelers recommend it for its comprehensive itinerary and friendly crew. At $226, it’s a good choice for travelers wanting a complete day with multiple swimming stops and a focus on comfort and good food.
Bottom Line: Well-suited for those wanting a full exploration of both Milos and Poliegos with gourmet meals and water sports.
How to Choose Your Perfect Milos Sailing Tour
When selecting a sailing experience in Milos, consider your budget, available time, and activity preferences. If you want an intimate, personalized day with cave exploration, the Adamantas cruise is ideal. For a shorter, relaxed outing, the Half-Day Catamaran hits the spot.
Travelers seeking luxury and full access to multiple islands should look at the Premium Catamaran, while those interested in a sunset experience will love the Sunset Catamaran Cruise.
If your goal is a comprehensive exploration, including the chance to paddleboard and snorkel, then the Full-Day with Paddle Board or the From Adamas Cruise are excellent options.
Tip: Book early, especially in peak summer months, as these tours are popular and fill quickly. Always check availability and choose based on your preferred pace and activities.
Milos offers an impressive range of sailing options—from quick half-day trips to full-day luxury adventures. Whether you want to explore secluded caves, enjoy a sunset with wine, or paddleboard in crystal waters, there’s a tour tailored for you. For a well-rounded, personal experience, the Adamantas cruise is hard to beat, but don’t overlook the luxurious Premium Catamaran or the scenic Full-Day Poliegos trip. Research your priorities, book early, and prepare for a memorable day on the water.