The 10 Sailing Trips with Lunch in Milos That Earn Their Price

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.”

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2.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.”

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3.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”

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4.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.”

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5.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…”

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6.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!”

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7.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!”

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8.Milos and Poliegos Catamaran Cruise with Lunch

★★★★★★★★★★5.0 · 49 reviews · 9.5 hours · from $235

Spend 9.5 hours aboard a spacious 44-foot catamaran with guides Dina, Forrest, and Yiannis. Swim at Poliegos, explore Kleftiko’s sea caves by snorkel and paddleboard, enjoy a BBQ lunch and open bar, and circle Milos with stops at its most striking coastal sites.

“FOREST, DINA, & YANNIS (John) are the BEST! If you’re looking to do a tour in Milos THIS IS IT. We were well taken care of with multiple meals/snacks/drinks and various other items. We visited the most beautiful locations while the staff made the trip fun, inviting, and comfortable. Even if you get sea sick… the staff are amazing and there to help you have the best time. After much research… this trip exceeded expectation. BOOK it now. Don’t miss this.”

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9.Kleftiko Semi Private Sailing Cruise with Lunch

★★★★★★★★★★4.9 · 21 reviews · 7 hours · from $141Best value

Spend seven hours sailing west from Adamas with Lena, Nikolas, or another experienced crew team. Swim at Kalogries and Kleftiko, look into Sykia cave, see Milos fishing villages, and enjoy lunch, fruit, sweets, drinks, and snorkeling gear aboard.

“Dimitri and Nikos were absolutely amazing. The destinations were incredible. The food was plentiful and delicious. The two men were attentive and very informative. I would highly recommend this tour. We had an absolutely fantastic experience.”

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10.Kleftiko Sailing Cruise with Meal and Swim Stops

★★★★★★★★★★5.0 · 11 reviews · 7 hours · from $212

Join skipper Ilias and the Oneiro crew for a seven-hour sail from Adamantas along Milos’s west coast. You’ll see colorful syrmata houses, swim at Sykia, Kleftiko, and Kalogries, and enjoy Greek food, homemade wine, ouzo, octopus, fruit, and folklore music.

“They were very informative about Milos. They made us feel like we were family. We went on another boat tour two days before this one. All tho it was almost the same tour and we loved that one as well. Adamantas was made it even more special. We plan to come back to Milo’s in a year or two and will be booking with them again.”

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