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Milos Sailing Tour: Custom Yacht Experience
4.9
82 Ratings
Milos VIP Services - Private Sailing cruises to Kleftiko, Kimolos and Polyaigos
Embark on a half-day private romantic sailing getaway to Kleftiko with Milos VIP Services. Explore caves, swim in crystal-clear waters, and enjoy the stunning scenery of Milos island.
Embark on a half-day private romantic sailing getaway to Kleftiko with Milos VIP Services. Explore caves, swim in crystal-clear waters, and enjoy the stunning scenery of Milos island.
Duration:
5 hours
Cancellation:
24 hours
Highlights
- Gerakas Beach - Gerakas is a stunning location featuring a rocky geological formation, accessible only by boat. The water is crystal clear, and if a stop is agreed upon, visitors can enjoy a swim surrounded by a dramatic rocky landscape.
- Tsigrado Beach - Tsigrado is a beach nestled between cliffs, renowned as the most secluded beach on Milos…
- Gerakas Beach - Gerakas is a stunning location featuring a rocky geological formation, accessible only by boat. The water is crystal clear, and if a stop is agreed upon, visitors can enjoy a swim surrounded by a dramatic rocky landscape.
- Tsigrado Beach - Tsigrado is a beach nestled between cliffs, renowned as the most secluded beach on Milos due to the challenging access from land, which requires a daring descent. During July and August, the Tsigrado gulf becomes quite busy with sailing yachts, so a swim stop might be made at Firiplaka instead.
- Firiplaka Beach - Adjacent to the charming Tsigrado Beach is the magnificent Firiplaka Beach. This long beach features silver sand and large, colorful rocks along its coastline. The waters at Firiplaka are truly exotic, with crystalline, shallow green-blue hues that captivate all who swim there.
- Gerontas Beach - Located in the southern part of Milos, Gerontas Beach offers a rewarding landscape upon arrival. Visitors will find a small bay surrounded by fine white rocks and a natural bridge connecting the sea and land on the right, making it a perfect addition to any photo album.
- Kleftiko Beach - Kleftiko is a collection of white volcanic rocks, sea-level caves, and sea stacks once used by “Captain Tromaras” [meaning the Scary Captain in Greek] and his brothers as a hideout for their pirate ship. The caves here provide safe passage and opportunities for exploration.
The combination of crystal-clear water, vibrant underwater life, and volcanic rocks sculpted by waves over the years creates one of the world’s most breathtaking natural wonders.
What's Included
- Cave exploration with our tender
- High Quality sound system with Bluetooth connection for iOS or Android
- WC & Shower On Board
- Snacks
- Alcoholic beverages
- Carbonated beverages
- Bottled water
- Cave exploration with our tender
- High Quality sound system with Bluetooth connection for iOS or Android
- WC & Shower On Board
- Snacks
- Alcoholic beverages
- Carbonated beverages
- Bottled water
What's Not Included
- Towels
- WiFi
- Towels
- WiFi
Additional Information
Get the top-rated bespoke sailing adventure in Milos at unbeatable rates! Step aboard Veronica, our classic yacht, and meander along the island’s southern coastline with our skilled team for an unbeatable picturesque voyage!
Expect a continuously shifting panorama of vivid beaches, land rocks, and sea stacks, all encapsulated by every imaginable shade…
Get the top-rated bespoke sailing adventure in Milos at unbeatable rates! Step aboard Veronica, our classic yacht, and meander along the island’s southern coastline with our skilled team for an unbeatable picturesque voyage!
Expect a continuously shifting panorama of vivid beaches, land rocks, and sea stacks, all encapsulated by every imaginable shade of blue. This makes sailing with Milos VIP Services an indelible experience!
We anchor at Kleftiko for an all-inclusive 90-minute swim and cave exploration. Should you prefer, we can abbreviate this stop and navigate to a previous landmark for another swim on our way to Kleftiko!
Location
Milos VIP Services - Private Sailing cruises to Kleftiko, Kimolos and Polyaigos
A member of our team will be waiting for you close to the entrance of Thalassopetra tavern in Agia Kyriaki beach. After welcoming you and introducing each other we walk towards the beach where our tender is ready to bring you on board and start the experience!
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.
Customer Ratings
4.9
(82 Ratings)
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Bryan_a
Sep 29, 2025
Incredible Private Sailing Experience - We had an incredible day sailing with Dimitris on his yacht Veronica. Dimitris was an excellent host and guide; he proactively communicated with me that he recommended starting our tour one hour later than scheduled because it would allow slight winds to settle down for ideal sailing conditions. He promptly met us at the designated time, took us to his yacht via a tender, and took us to many places on the island only accessible via boat. He took pride in ensuring we had a magical time, and he delivered on that. When we reached Kleftiko, one area was quite crowded with other boats, so Dimitris went to another area to anchor his yacht and took us via tender through the caves and cliffs to have an even better experience than we would have otherwise had. He provided white wine, an assortment of fresh fruit, and delicious cheeses and rusks for a snack. We swam, sunned on secluded beaches, explored caves, and enjoyed the sun and turquoise waters. I highly recommend sailing with Dimitris. He couldn’t have been nicer, more professional, more informative, or more fun. A private excursion with him is far superior to the other tour boats on the island that were crowded with dozens of people.
Review provided by Viator
Willfg1972dn
Sep 1, 2025
BOOK THIS!! - Dimitrios is incredibly knowledgeable about all the spots. Highly recommend - my fiancé and I had an incredible time on the sunset cruise with him. 10/10 !!
Review provided by Tripadvisor
Kelly_s
Aug 20, 2025
This is a MUST - This is going to be one of the most memorable parts of our trip to Milos. Dimitris knew all the best spots and took amazing care of us the whole time. Make sure you book with him you will not regret it!
Review provided by Viator
Olivia_m
Jul 29, 2025
Amazing time! - We had an awesome time on this boat ride! Jim and James were great captains, we had so much fun and the views were amazing. They took us to the caves on the little boat, which was an unreal experience. There were a few stops to other beaches where we got to swim and hangout. Trip was well worth it! Two of us were seasick and they were very nice and tried to help us as much as possible :) the wine and snacks were a great touch and we overall had the best time! Would definitely recommend.
Review provided by Viator
Baileysj8125xi
Jul 12, 2025
We had an amazing time!! - We had such an amazing time on this boat tour! The views were amazing and our captains were great. Would 100% recommend it to anyone visiting Milos
Review provided by Tripadvisor
Judith_l
Jul 6, 2025
Perfect day! - Met Dimitris and Dimitris at the Thalassopetra Taverna and that was just the beginning! A zodiac ride out to our boat for a half day tour. Perfect guides that are friendly, funny and knowledgeable. They were accommodating asking if we wanted to make additional stops. The zodiac was tuned behind to get us into the caves! Very cool…in more way than one! We stopped fur a dip and some wine and cheese and fruit. A truly perfect day. Give these two captains a shout and let them take you for a sail!
Review provided by Viator
Amanda
Jul 3, 2025
Amazing time! - We had a group of 6 of us, we had an amazing time! Our guides were friendly and accommodating. They let us bring our two pups on board and they treated them like royalty. Would highly recommend booking!
Review provided by Tripadvisor
Cynthia_n
Jun 25, 2025
Beautiful Views and Great People! - Amazing!!!! From start to finish this was a great experience. I received a message days before our reservation informing me of a high winds forecast from a gentleman named Dimitris. I really appreciated how communicative he was and his dedication to safety. He kindly asked around to move other people’s bookings and did everything in his power to make sure we got to cruise for our honeymoon in Milos and we are so appreciative! When we got on the boat we met Jim and James who were so helpful, kind, and funny. I also really appreciated their dedication to safety and making sure we had the best time ever. It was so fun chatting with them, and they are such professionals; we knew we were in great hands with their sailing, etc. as they absolutely knew what they were doing. The views were breathtaking and the boat is beautiful and spacious! We loved swimming to the coves and little private beaches. This activity was without a doubt the highlight of our honeymoon. Don’t hesitate to book this if you want to have a great time!
Review provided by Viator
D000448
Jun 19, 2025
Great crew. Beautiful scenery. - Really excellent time. Even though it was extremely windy, we had a great trip, beautiful scenery lots of enjoyment. The two-man crew was super accommodating and friendly. Had a couple of great swim stops.
Review provided by Tripadvisor
Nadean_l
Jul 7, 2025
Dissapointing and nothing like advertised. RIP OFF! - Nothing like advertised, Never once used the tender even though in the description of the tour it says “cave exploration with tender”. We asked for it a few times only to be told they couldn’t use it due to council laws. Didn’t even offer to take us in closed a little closer to shore. Hot wine! No ice in esky. Was told not to expect comforts of ice or cold wine due to it being a boat. We are boat people so we know how easy it is to get an esky of ice for drinks. Disgusting nibbles. A handful of bread sticks with tinned strawberry jam. Hot stinky cheese that wasn’t refrigerated and smelt off and hot watermelon. The whole thing was a rip off. Only good thing was the swimming, we should of paid for a cheap boat to get us out there to swim.
Review provided by Viator
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