Greece · MILOS SAILING TRIPS
Milos is a ring of mined white rock and the best of it is unreachable by car. These 15 trips cover Kleftiko, Sykia and the crossing to Polyaigos, compared on boat size, how many coves they reach and what the day costs.
Spend 10 hours circling Milos aboard a small motor-powered sailboat, with swim stops at Polyaigos, Gerakas, and Kleftiko. Guides such as Dora, Niki, and Alexandra share island stories, while the crew serves snacks, tuna pasta, salad, drinks, and wine. Bring sun protection, a towel, and a jacket.
“Amazing day, Dora was an excellent host who worked very hard”
Spend eight hours sailing from Adamas along Milos’ west coast with an experienced crew, stopping at Kalogries, Kleftiko, and Agios Dimitrios. You’ll snorkel through white-rock caves by yacht and RIB, enjoy breakfast snacks, a Greek lunch, drinks, and underwater photos. Crew names have included Captain Giannis, Juliano, Christos, Dionysis, and the two Georges.
“We really loved the whole day, there was plenty of adventure, swimming, great food and drinks, new information about Milos and perfect entrance into Pirate Bay. We had amazing time sailing around Milos. It was definitely the best tour from our trip.”
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.”
Sail from Adamas along Milos’ volcanic coast, passing colorful sirmata houses, Arkoudes, Cape Vani, Kalogries Bay, Sikia Cave, and Kleftiko. You get swim and snorkel time, a traditional onboard lunch, snacks, wine, and soft drinks. The crew may include captains George, Spiros, or Nikos, with Greek and English guiding.
“Loved it although I would have preferred if the group size was a bit smaller so you could lounge on the boat easier. Food was excellent and the guides were awesome. Recommend this activity!”
Spend about eight hours sailing around Milos from Pollonia or Adamas, with stops at Kleftiko, Sykia, Fyrligos, or Gerakas. You’ll snorkel with crew guidance, explore caves by small boat, eat Greek food, and enjoy drinks throughout the day. The crew may include Juliano, Vitaly, RJ, Effi, Christo, or Vasili.
“Vitaly, and the rest of the crew were amazing to ride with! The scenery was spectacular. The accommodations (food, drink, additional small boat explorations) were great. Would HIGHLY recommend joining this excursion. Thanks all!”
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.”
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.”
Spend eight hours sailing from Adamantas around west Milos with a crew of up to 10 people. Swim at Kalogries and Agios Dimitrios, explore Sykia Cave and Kleftiko by dinghy, and enjoy homemade Greek food, drinks, and GoPro photos. Crews vary, with George, Flora, Forrest, and Pascalis among the guides praised for warm, lively service.
“We had the best day! George and Carlotta were phenomenal, and the places were saw were breathtaking!”
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.”
Set sail from Adamas for nine hours around Milos, stopping at Kleftiko, Gerakas, Poliegos, Blue Bay, and more. Captain George and crew members such as Minoas often handle the sailing, cooking, drinks, and island stories. You get breakfast, lunch, fruit, beer, wine, snorkel gear, and several chances to swim.
“Great tour of all the beaches of Milos! So much swimming in various places. Great day in Milos would definitely recommend. Our crew was also so nice and friendly !”
Spend about nine hours aboard a small-group boat from Adamas, exploring Milos’ western coast with stops for swimming and snorkeling. You’ll see syrmatas, Cape Vani, Kalogries Beach, Kleftiko, and Agios Dimitrios. Meals, snacks, drinks, and snorkel gear are included. Crew names vary, with Fay, Facundo, Christos, Alex, and others featured on recent trips.
“This tour is a MUST! The captain was amazing! She got so close to all the major sites and was very informative. This was a very laid back and relaxing experience!”
Spend 8 to 9 hours sailing around Milos aboard a shaded catamaran limited to 12 people. Swim at Kalogries, Sykia, Kleftiko, and Agios Dimitrios, enter caves by dinghy, and enjoy homemade Greek food, drinks, snorkel gear, Wi-Fi, and GoPro photos.
“Great trip, Georgina and Marcus were the best. Food, swimming and cave venturing was was the highlight . Highly recommend”
Sail from Adamas along Milos’ volcanic coast to Kalogries, Sikia Cave, and Kleftiko. Expect swimming, snorkeling, a Greek buffet, drinks, and a small catamaran group of up to 22. Captains such as George, Elias, Nikolas, and Dimitris have drawn strong praise for their care and cooking.
“Great half day out. We saw so many great sights and beautiful island scenery. The swims were wonderful and the lunch was outstanding.”
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!”
Spend 9 to 10 hours sailing around Milos with a small group of up to 20 people. Julio and the two Georges may guide you through Kleftiko’s caves, sea tunnels, swimming spots, and local stories, with snorkeling gear, meals, drinks, and onboard facilities included. Choose a departure from Adamas or Pollonia.
“STOP LOOKING FOR OTHER MILOS SAILING TOURS. Book this one now. The captain and crew were terrific. Knowledgeable, friendly and caring guys. Amazing sights, history, food and swimming. Swim in caves, cliff jumping spot too! THE BEST.”
Every island we sail from, and every kind of day that leaves it.
