15 Milos Sailing Trips Worth Booking

1.Milos & Polyaigos Full-Day Sailboat Tour with Lunch

★★★★★★★★★★4.9 · 1,646 reviews · 10 hours · from $147Our pick

Spend 10 hours with Sailing Milos circling the island and visiting Polyaigos, Gerakas, and Kleftiko. Guides such as Dora, Niki, and Alexandra share local stories while the crew serves snacks, tuna pasta, salad, drinks, and wine. Expect three swim stops, caves, and a motor-powered boat rather than a quiet sailing trip.

“We can’t say enough wonderful things about Katherine and the rest of the crew. Everything was super well organized and the we learned so much about the history and geography of the island. They kept us well fed and the swimming stops were gorgeous. It is a long day though so just keep that in mind if you plan on bringing any kids/older guests as it is a full 10 hour sailing trip.”

Check availability →Read our full review

2.Kleftiko Sailing Day Trip with Snorkeling and Lunch

★★★★★★★★★★4.8 · 713 reviews · 8 hours · from $170

Spend eight hours sailing west from Adamas with an experienced crew, stopping at Kalogries, Kleftiko, and Agios Dimitrios. You will snorkel through sea caves, ride a small RIB into narrow rock passages, enjoy Greek food and drinks, and hear island stories from guides such as Giannis, Christos, and Dionysis.

“We took a yacht and sailed to multiple beaches areas around Milos that are only accessible by boat. We snorkeled and swam. Breakfast, lunch, and beverages were provided. Captain Giannis was so amazing. He was so passionate about sailing and sharing the beauty and soul of Greece through his stories and music. Christos and Dionysus were also so kind and shared their knowledge of sailing. An unforgettable, life changing way to experience Milos.”

Check availability →Read our full review

3.Best of Milos and Poliegos Catamaran snorkelling Cruise with BBQ

★★★★★★★★★★5.0 · 460 reviews · 9 hours (approx.) · from $241Top rated

Spend about nine hours aboard Polco Sailing’s Lagoon 440, cruising from Adamantas to Poliegos, Kleftiko, Gerakas, and other boat-access-only spots. Expect snorkelling gear, paddleboards, Greek meals, an open bar, Wi-Fi, and photos from the crew. Captains and crew may include Yannis, Dina, Flo, and Andreas.

“Tour was on Sept. 9, 2024. What an amazing tour! The staff members were fantastic, very friendly and chatty. The food was delicious and exceeded expectations. It really was freshly prepared on the catamaran. One of the best things was that this wasn't a "drink your face off" party boat. There was music playing but it wasn't loud at all. It really was a relaxed and enjoyable experience. Highly recommend.”

Check availability →Read our full review

4.Half-Day Morning Catamaran Cruise to Kleftiko

★★★★★★★★★★4.8 · 362 reviews · 6 hours · from $182

Join Milos Adventures for a six-hour catamaran cruise from Adamas to Kalogries and Kleftiko. You’ll pass colorful sirmata villages, swim in clear water, explore sea caves, and eat a fresh Greek lunch prepared onboard. Captain George and other rotating crew members keep the day relaxed and well organized.

“We had a lovely and relaxing day on the catamaran and swimming in amazing spots around Milos. The lunch was delicious and crew members very friendly and hospitable! A great way to see Milos”

Check availability →Read our full review

5.Catamaran Full-Day of Milos and Poliegos With Lunch & BBQ

★★★★★★★★★★5.0 · 262 reviews · 10 hours (approx.) · from $217

Spend about 10 hours sailing from Adamas around Milos and Poliegos, with swim stops at Kalogries, Kleftiko, Gerakas, and Galazia Nera. Breakfast, fresh BBQ lunch, drinks, snorkeling gear, towels, and an action camera are included. Crew members such as Clara, Elena, Christos, Anastasia, and Despina are praised for warm service.

“It was an unforgettable experience! Clara, Elena and Christos were so wonderful to have on board! The scenic views and swimming spots were amazing”

Check availability →Read our full review

6.Milos Sightseeing Sailboat Cruise

★★★★★★★★★★4.9 · 257 reviews · 8 hours · from $223

Spend eight hours sailing west from Adamantas with up to 10 people, stopping at Kalogries, Sykia Cave, Kleftiko, and Saint Dimitrios. Expect swimming, snorkeling, dinghy trips into caves, homemade Greek food, an open bar, and an adaptable route guided by crew such as George, Flora, Forrest, and Pascalis.

“A perfect day! Our hosts George and Flora were awesome and made the day. Highly recommended”

Check availability →Read our full review

7.CATAMARAN Kleftiko Poliegos & Round of Milos Lunch with Openbar

★★★★★★★★★★5.0 · 242 reviews · 9 hours (approx.) · from $289

Spend about nine hours aboard an Odysseus catamaran from Adamantas, circling Milos and Poliegos with swim stops at Kleftiko, Gerakas, Kalogries, and possibly Sarakiniko. The crew prepares breakfast, lunch, snacks, and drinks onboard, while guides such as Silvan, JP, Fay, Christos, and Facundo share stories along the way.

“Amazing way to see Milos! We only had 3 days in Milos and this was an incredible way to see the Island, especially parts of Milos we could only see via boat. The crew (especially Faye) were super friendly and made it so much more fun. The food was delicious, drinks were cold and plentiful, and the views were unreal. Highly recommend!!”

Check availability →Read our full review

8.Full-Day Sailboat Cruise with Food and Open Bar

★★★★★★★★★★4.8 · 233 reviews · 9 hours · from $212

Join Captain George, Minoas, and crew from Adamantas for a nine-hour sail around Milos. Swim at Kleftiko, Gerakas, and Blue Bay, see Klima and Skinopi from the water, and enjoy breakfast, lunch, fruit, beer, wine, and snorkel gear. The route changes with wind and sea conditions.

“We had an amazing boat day yesterday! The whole team was truly special, especially Sam from Australia, who made the experience even more fun. The food was excellent, and we always felt safe and well taken care of. The boat took us straight to the best spots around the island, and seeing them directly from the water was unforgettable. I can only recommend this trip – I would choose this boat again any time!”

Check availability →Read our full review

9.Full-Day Catamaran Cruise to Poliegos and Kleftiko

★★★★★★★★★★4.9 · 159 reviews · 10 hours · from $247

Sail around Milos for 10 hours with a Greek and English-speaking crew, stopping at Kleftiko, Sikia Cave, Gerakas, and Poliegos. Captain Nick, Captain George, and chef Elias are among the crew members guests may meet. Lunch, drinks, snacks, and swimming gear are included.

“It was a great trip with lovley guides and delicious lunch and snacks - thank's so much for this day!!”

Check availability →Read our full review

10.Half-day Kleftiko, Catamaran Trip | Lunch & OpenBar

★★★★★★★★★★4.9 · 152 reviews · 5 hours · from $188

Join Giannis, Emilios, and Angelos for a five-hour catamaran from Adamas to Kleftiko. You will swim beneath sea arches, snorkel with provided gear, enjoy breakfast, lunch, seasonal fruit, and free drinks, while the crew shares Milos stories and adjusts the route when winds require it.

“The tour was amazing. The entire crew was super nice and helpful. The catamaran was very new and the crew was very helpful at communicating and making it to be the best experience after we saw rain in the morning. When we got to the lunch spot, it was gorgeous weather and water. Would definitely recommend. The boat was spacious and the view was amazing. Food was quite good, and lots of services and drinks. Overall would definitely recommend this experience and the crew”

Check availability →Read our full review

11.Kleftiko Sunset Catamaran Cruise with Meal & Drinks

★★★★★★★★★★4.9 · 121 reviews · 5.5 - 7 hours · from $182

Sail from Adamantas on a modern catamaran to Klima, Cape Vani, Sykia Cave, and Kleftiko. You get swimming, snorkeling, SUP, Mediterranean food, an open bar, shaded lounges, and a sunset return. The group is capped at 20, with optional pickup and private bookings available.

“This was a fun afternoon however the sea did not completely play ball with strong winds and a good wind chop. Kleftiko bay was beautiful and we enjoyed a swim here followed by a fabulous dinner. A very enjoyable trip and would highly recommend.”

Check availability →Read our full review

12.Full-Day Kleftiko Poliegos Sailboat Tour with Lunch

★★★★★★★★★★4.8 · 111 reviews · 9 hours · from $159

Join a nine-hour Milos sailing trip with Christos, George, or another friendly crew team. Swim at Kleftiko, Gerakas, Agathia, and Poliegos, see Sykia Cave and fishing villages, and enjoy breakfast, Greek lunch, fruit, beer, wine, and soft drinks aboard.

“Big thank you to the whole team at Trinity Yachting who made our sailing trip a fantastic and fun experience from start to finish. All very well organised. Matis the captain navigated his way around the coastline while providing a commentary of the island history and choosing the best spots to stop for swimming in crystal blue waters with scenic surroundings. His crew member Niko was an excellent host to all of us on board catering to everyone's needs, always smiling while he worked helping the captain, serving the drinks and preparing delicious food. During our final stop we all enjoyed listening to the captain playing on his guitar while…”

Check availability →Read our full review

13.Full-Day Catamaran Cruise with Food and Open Bar

★★★★★★★★★★4.8 · 102 reviews · 10 hours · from $281

Spend 10 hours aboard the catamaran Together with Odysseus A. Cruises, sailing from Adamantas around Milos and Poliegos. Swim at Kleftiko, Gerakas, Kalogries, and the Blue Lagoon, with fresh meals, an open bar, snorkeling gear, and commentary from the crew.

“The weather was perfect The food was amazing It was worth the extra money for the top of the range experience Our gorgeous three crew members were dedicated to their jobs and good boaties Would definitely recommend to anyone 😀”

Check availability →Read our full review

14.Full Day Luxury Catamaran with Full Meal & Open Bar

★★★★★★★★★★5.0 · 91 reviews · 9 - 10.5 hours · from $253

Sail from Adamantas aboard a spacious catamaran for 9 to 10.5 hours. You’ll visit Kleftiko, Polyegos, Triades Beach, Sykia Cave, and Klima, with Greek meals, drinks, SUPs, snorkeling gear, and attentive English-speaking crew. Some departures feature Zacharias and Jozef.

“It was a perfect and truly satisfying experience! Thanks to all the spots and preparations chosen by our guide, I was able to create so many wonderful memories. Highly recommended! The guide and captain were incredibly kind, and most of the guests were from America and Canada. I was able to build such meaningful connections with everyone. It honestly felt like a dream come true. Thank you so much!”

Check availability →Read our full review

15.Kleftiko Morning Catamaran Cruise with Lunch & Drinks

★★★★★★★★★★4.9 · 72 reviews · 5.5 - 7 hours · from $182

Sail from Adamantas with DanEri Yachts on a 5.5 to 7-hour catamaran cruise to Klima, Cape Vani, Sykia Cave, and Kleftiko. Ilias, Andreas, and Captain Joseph are among the crew members named for this outing. Expect swimming, snorkeling, paddleboarding, a Mediterranean lunch, and an open bar.

“What a beautiful day with the most sensational crew. The catamaran is immaculate, so much pride taken with this vessel, it made cruising a pleasure. Ilias you are fabulous - a definite 5/5!”

Check availability →Read our full review