The 12 Best Island Hopping Sailing Trips in Milos

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

★★★★★★★★★★5.0 · 460 reviews · 9 hours (approx.) · from $241Number one

Spend about nine hours aboard POLCO Sailing’s Lagoon 440, cruising from Adamantas to Poliegos, Kleftiko, Gerakas, Kalogries, and more. Expect swimming, snorkeling, paddleboarding, Greek tapas, a BBQ lunch, drinks, Wi-Fi, and underwater GoPro photos. The crew may include Yannis, Dina, Flo, Elena, or other POLCO team members.

“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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2.Round of Milos and Poliegos Sailing boat snorkelling cruise

★★★★★★★★★★5.0 · 262 reviews · 9 hours (approx.) · from $193

Spend about nine hours aboard a small sailing boat with a crew such as Andreas, Spyros, Dina, or Nick, visiting Kleftiko, Gerakas, Poliegos, Kalogries, and more. Snorkeling gear, homemade lunch, drinks, WiFi, and emailed GoPro photos are included. Expect a relaxed day on the water, with limited shade and no hotel pickup.

“Amazing boat day! Dina, Spiros, and Andreas were great - we had plenty of time to jump in the water and relax on the boat. The food that Dina made was INCREDIBLE!!! There was no snorkeling or paddle boarding, but the overall experience was terrific.”

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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 aboard a catamaran limited to 22 people. Swim at Kalogries, Kleftiko, Gerakas, and Galazia Nera, pass Sykia Cave and old mining sites, and enjoy breakfast, fresh BBQ lunch, snacks, drinks, snorkeling gear, and an action camera. Crew names vary, with Clara, Elena, Christos, Anastasia, and Despina among the guides.

“We recently enjoyed a full-day cruise around the island, and it was an unforgettable experience thanks to Clara, Christos, and Elena. Clara's boundless energy and leadership kept our team engaged and enthusiastic throughout the day. Christos, with his exceptional boat skills and excellent driving, ensured we navigated the waters safely and smoothly. Elena prepared the most beautiful lunch, easily the best meal we've had in Greece so far. Her culinary talents added a delicious and memorable touch to our trip. This cruise was a highlight of our visit, and we highly recommend it to anyone looking for an exceptional experience.”

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

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

Spend about nine hours aboard a shared catamaran from Adamantas, visiting Kleftiko, Kalogries, Gerakas, Poliegos, and possibly Sarakiniko. Swim, snorkel, photograph sea caves, and enjoy breakfast, a cooked Greek lunch, snacks, and beer and wine. The crew may include Silvan, JP, Christos, Fay, Facundo, or Nikos, depending on the sailing.

“Lovely boat and crew. Well worth taking a day to go around the island and get to see great stops and some of the most incredible water colors.”

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5.Full-Day Catamaran Cruise to Poliegos and Kleftiko

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

Spend about 10 hours aboard a spacious catamaran from Milos, with stops at Kleftiko, Gerakas, and Poliegos. Swim in clear coves, see sirmata fishing houses and volcanic cliffs, and enjoy a cooked lunch with wine, beer, soft drinks, and fruit. Crews led by captains such as Nick and George speak Greek and English.

“I love our captain and the food Setved by Maria was fantastic!”

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6.Full day sailing cruise on the West side of Milos island

★★★★★★★★★★5.0 · 136 reviews · 9 hours (approx.) · from $175

Spend about nine hours sailing west of Milos with Nikos and Marion, stopping at Agathia, Agios Ioannis, Sykia, Kleftiko, and Agios Dimitrios. Swim, snorkel, explore caves by dinghy, and enjoy breakfast, a cooked Greek lunch, drinks, and fruit salad. The route changes with the wind.

“Nikos and Marion were an awesome team. 10/10 experience, great fun!! Ask Nikos about cliff jumping ☺️”

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7.Full-Day Kleftiko Poliegos Sailboat Tour with Lunch

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

Spend nine hours sailing from Adamas along Milos’s volcanic coast, with swims at Agathia, Kleftiko, Gerakas and Poliegos. Expect breakfast, Greek lunch, fruit, drinks and snorkeling gear. Crews often include Christos and George, though names can vary. Weather determines the final route.

“Amazing day on the water with the crew, who were so friendly and kind to everyone. We had really strong wind that day, so the crew were really skilled at putting everyone at their ease and working out an alternate route so that we made the most of several sheltered spots and overall had a wonderful day. Tasty food, and beautiful scenery.”

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8.Catamaran Full Day Cruise: Poliegos – Kleftiko

★★★★★★★★★★5.0 · 90 reviews · 9 hours 30 minutes (approx.) · from $253

Spend about nine and a half hours sailing from Adamas along Milos to Kleftiko, Sikia, Gerakas, and Poliegos. Swim from the catamaran, explore sea caves, and enjoy snacks, drinks, wine, and a home-cooked Greek lunch. Captains George and Nick and crew members such as Elya and Elias have been praised for warm, attentive service. The boat holds no more than 22 people.

“The trip itself was wonderful ! The crew was very helpful and the lunch was excellent! My only complaint was that I booked this tour in particular because it said it started in Adamantas and ended in Pollonia which was where we were staying. It ended in Adamantas which meant we had to pay another 35 euros for a taxi ride home instead of walking back to our hotel.”

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9.Full day Milos and Poliegos Catamaran Cruise

★★★★★★★★★★4.8 · 63 reviews · 10 hours · from $218

Meet the Tassis Trinity Yachting crew at Adamas at 8:30 AM for a full-day catamaran trip around Milos and Poliegos. You will swim at Agathia, Kleftiko, Gerakas, and other clear-water bays, explore pirate caves, pass Klima and the sulphur mines, and eat homemade Greek food with beer, wine, water, and soft drinks included.

“Best experience I had in Greece! Staff was super chill, the catamaran was just great and the places we have visited were amazing”

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10.❖ Milos: Small Group Yacht Tour—Kleftiko Sarakiniko Poliegos

★★★★★★★★★★4.8 · 53 reviews · 5 hours · from $200

Spend five hours aboard the Raptor, a stylish speedboat sailing from Agia Kiriaki to Kleftiko, Sarakiniko, Polyaigos, Kimolos, and more. Swim, snorkel, use the paddleboard, and enjoy Greek food, fruit, sweets, wine, beer, and soft drinks. The English and Greek crew adjusts the route for wind and sea conditions.

“We had an amazing time on our cruise, everyone on board was professional and knowledgeable and the places we visited were amazing, highly recommended!”

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11.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 from Adamas, visiting Poliegos, Kleftiko, Sykia, Gerakas, and more. You will swim, snorkel, paddleboard, eat a BBQ lunch, and enjoy drinks and snacks. The crew may include Dina, Forrest, and Yannis, with shaded seating and GoPro photos included.

“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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12.Milos & Poliegos Catamaran Cruise Homemade Full menu BBQ & Drinks

★★★★★★★★★★5.0 · 34 reviews · 9 to 10 hours (approx.) · from $252

Spend 9 to 10 hours aboard a Naya Yachting catamaran from Adamas, visiting Kalogries, Sykia, Kleftiko, Gerakas, and Poliegos. You get homemade breakfast, a Greek BBQ lunch, drinks, swimming gear, and a vegan option. The cruise is offered in English and returns to the port.

“10 out of 10!! Must do it! Honestly it was the highlight of our trip. Family owned businesses so their attention to detail was phenomenal! Definitely would recommend this !! Again it’s a must do!!!!”

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