Our Top 15 Sea Cave Sailing Trips in Milos

1.Kleftiko Sailing Day Trip with Snorkeling and Lunch

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

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.”

Check dates →Read our review →

2.Half-Day Morning Catamaran Cruise to Kleftiko

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

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!”

Check dates →Read our review →

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

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

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.”

Check dates →Read our review →

4.Sailing Boat Small Group Kleftiko and Sikia Cave West of Milos

★★★★★★★★★★5.0 · 200 reviews · 9 hours (approx.) · from $169

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!”

Check dates →Read our review →

5.Milos caves snorkelling Catamaran Cruise in a small group

★★★★★★★★★★5.0 · 199 reviews · 8 to 9 hours (approx.) · from $241

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”

Check dates →Read our review →

6.Catamaran Half Day Morning Cruise: Kleftiko

★★★★★★★★★★5.0 · 196 reviews · 6 hours (approx.) · from $187

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.”

Check dates →Read our review →

7.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!”

Check dates →Read our review →

8.Kleftiko Full Day Sailing Cruise with Snorkeling & Lunch

★★★★★★★★★★5.0 · 157 reviews · 9 to 10 hours (approx.) · from $169

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.”

Check dates →Read our review →

9.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 pass Klima, Cave Vani, Bear Rocks, and Sykia Cave, with swimming, snorkeling, breakfast, lunch, fruit, and drinks included. Weather can change the route, but the crew adjusts the day to keep you on the water safely.

“10/10!! We loved our guides, Giannis, Angel and Emilois, they were accomodating and just all round good vibes! The food was yummy and they always made sure our drinks were full! Kleftiko was magical and so was Kipos with the hot water cave. I would highly recommend this trip!”

Check dates →Read our review →

10.Kleftiko Sunset Catamaran Cruise with Meal & Drinks

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

Spend 5.5 to 7 hours aboard a modern DanEri Yachts catamaran from Adamantas. You’ll see Klima, Cape Vani, Sykia Cave, and Kleftiko, with a Mediterranean meal, open-bar drinks, SUP boards, snorkeling gear, and a sunset finish. Groups are limited to 20, and private options are available.

“This was an excellent time. The food, the music, the views, the crew were all amazing. Highly recommend this experience.”

Check dates →Read our review →

11.Full-Day Kleftiko Poliegos Sailboat Tour with Lunch

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

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.”

Check dates →Read our review →

12.Half-Day Sunset Cruise Catamaran to Kleftiko with Lunch

★★★★★★★★★★5.0 · 105 reviews · 6 hours (approx.) · from $187

Join Trinity Yachting for a six-hour sunset catamaran from Milos. You’ll swim at Kleftiko and Kalogries, view Sykia Cave and Klima, eat a Greek lunch, and enjoy beer, wine, snacks, and a sunset mojito. The boat carries up to 22 people, with free transport from Adamas to Agia Kiriaki.

“We were hesitant to book a sunset tour rather than a morning session but it was the best decision. It was so beautiful, food was insanely good, and staff were amazing (Clara, Christos and Elena). We were very lucky and had an amazing group and met so many new people! Highly recommend over a morning session”

Check dates →Read our review →

13.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.”

Check dates →Read our review →

14.Half-Day Private Romantic Sailing Getaway to Kleftiko

★★★★★★★★★★5.0 · 81 reviews · 5 hours (approx.) · from $784 per boat

Set out from Agia Kyriaki with a private crew, often including Dimitris, Jim, James, Nicko, or other Milos VIP Services captains. Cruise to Kleftiko, swim at quiet southern beaches, and use the small tender to pass through sea caves. Wine, fruit, cheese, water, music, a shower, and a WC are included.

“My group of 4 friends chose to do this private tour instead of one of the larger group tour options on the island and it was so worth it! We are not experienced enough to rent/drive a boat on our own, and so this was a perfect choice for us. The tour starts at Agia Kiriaki Beach, there is plenty of parking on site, and then you'll meet your tour guides in front of the tavern. Our captains were so friendly, helpful, and ensured we were comfortable the entire time. We loved the snacks and wine provided. They also took pictures of us! The tour itself is great, you get…”

Check dates →Read our review →

15.Kleftiko Morning Catamaran Cruise with Lunch & Drinks

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

Spend 5.5 to 7 hours aboard a modern DanEri Yachts catamaran from Adamantas. Sail past Klima and Cape Vani, pause at Sykia Cave, then swim, snorkel, paddleboard, and eat a fresh Greek lunch at Kleftiko. The English-speaking crew, including Andreas, Ilias, and Captain Joseph, provides drinks, gear, shade, and plenty of practical help.

“This was genuinely one of the best boat tours I’ve ever been on. The crew were all super attentive, kind and funny. They gave anyone that was cold blankets and were constantly making sure everyone had refreshments. The food was also so tasty and made with love. They take you to all the most beautiful and picturesque sights in Milos. Highly recommend!!!”

Check dates →Read our review →