Half-Day Private Romantic Sailing Getaway to Kleftiko

Highlights

Inclusions

Itinerary

1. Gerakas is an impressive spot with rocky geological formation and can be reached only by boat. The water is crystal and if you agree for a stop you can jump from the boat for a swim while surrounded by a rocky and abrupt landscape.

   30 min

2. Tsigrado is a beach nestled between cliffs and known as the most secluded beach of Milos due to the difficulty it takes for visitors to reach coming from the land since the process of climbing down is not for the faint of heart. Keep in mind that during July & August the gulf of Tsigrado is getting really busy by sailing yachts and as a result we may have a stop for swim if you want in Firiplaka instead..

   Passes by

3. Right next to the lovely beach of Tsigrado lies the superb beach of Firiplaka. It is a long beach with silver sand and huge colored rocks forming its coastline. The waters in Firiplaka are really exotic: crystalline and shallow green-blue, they never fail to enchant anyone who had the chance to swim in them.

   Passes by

4. The beach of Gerontas is another beach in Milos located in the southern part of the island. When you arrive at the beach, the landscape will surely reward you for your effort. You will face a small bay with fine white rocks around it, a natural bridge between the sea and land on the right, which will impress you and definitely become part of your photo album.

   Passes by

5. Kleftiko is a series of white volcanic rocks, sea level caves and sea stacks used by “Captain Tromaras” [=meaning the Scary Captain in Greek] and his brothers as a shelter and a base for their pirate ship. Here the caves are offered for safe passage and exploration. The crystal clear water in combination with the underwater life and the volcanic rocks that have been carved through the years by the waves create one of the most beautiful wonders of nature worldwide

   1.5 h

Cancellation

Free cancellation up to 24 hours before the experience starts, for a full refund.

Reviews

Ratings come from 85 reviews collected by our booking partner. They are travellers' own words, in the order they were written — never reordered to flatter the experience.

Showing reviews written in English.

• 5transparent and proactive

  my review is going to be a little different. unfortunately we didnt go on our boat ride due to the potential for weather. dimitris was very transparent and honest when we showed up. he said we could go, but it was going to rain. he was kind and gave us space to discuss as obviously this was a big bummer. ultimately we decided not to go. dimitris was proactive in assuring us we’d get a full refund - which we did in under an hour. if hes this kind and thoughtful when he’s losing business, imagine how great he is when showing you milos by sea. i can’t recommend how he handled things enough

  ericmB4346RCSeptember 2026via Tripadvisor

• 5My boyfriend and I had an...

  My boyfriend and I had an amazing experience on this boat tour. It felt very laid back as it was just us and the hosts were very accommodating and ensured we had an amazing time. Just a heads up - because of the winds, your tour could be moved to an earlier or later date so make sure to not make this tour the last day of your trip. Overall, I give a 5/5 for experience.

  Natalie_ZSeptember 2026via Viator

• 5Amazing people who go above and beyond

  We had this booked, but sadly the boat that was going to take us took damage the day before that needed repairs, meaning that our trip had to be canceled. But Dimitris was so kind and helpful that he arranged to get a replacement trip with another company that was cheaper and reached more stops. So while I didn't actually go on the tour that I'm giving 5 stars, the people are so nice. If you book with them, they will treat you right.

  Dreamer19785277776August 2026via Tripadvisor

• 5Incredible 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.

  Bryan_ASeptember 2025via Viator

• 5BOOK 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 !!

  willfG1972DNSeptember 2025via Tripadvisor

• 5This 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!

  kelly_SAugust 2025via Viator

Know before you go

How it compares in Milos

• Its from-price is 186% above the median of the 61 day trips we list in Milos.
• It is shorter than most of them.
• By number of reviews it ranks 18 of 61.
• The operator lists free cancellation on it.

About Milos

Milos is a volcanic Cycladic island of white cliffs, sea caves and fishing hamlets, where the Venus de Milo was found in 1820.

Milos was shaped by volcanoes, and its coast is a patchwork of white, yellow and rust-coloured rock. Plaka, the hilltop capital, is a whitewashed village of winding lanes below a medieval kastro, and Adamas is the main port. A farmer found the Venus de Milo in 1820, and the statue now stands in the Louvre. Obsidian from the island was traded around the Aegean in prehistory.

Top-ranked sights in Milos: Kleftiko Beach, Sarakiniko Beach, Firopotamos Beach.

See all 154 experiences in Milos