Greece · FULL-DAY SAILING TRIPS
Every trip has one spare day in it. These 15 full-day sailing trips are the ones that justify handing it to a boat, priced and timed so you can decide over breakfast.
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”
Join Lambros, Anastasia and George aboard the Aeolus for a seven-hour sailing day from Skiathos. Swim at Tsougria, Kastani and quiet coves, snorkel with provided gear, paddleboard, and eat a fresh Greek lunch cooked on board. Choose a shared small-group cruise or private outing, with route changes possible in poor weather.
“This was our 2nd time on this beautiful yacht. The whole experience is amazing. The time spent sailing and the quiet coves we visited were wonderful. Our hosts were incredible, the food is fabulous . This trip is not to be missed 😍”
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.”
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 !”
Meet your skipper and hostess at Naxos marina for a full-day sailing trip toward the Small Cyclades. Panagiotis, Olga, Alex, and other crew members may guide the boat, choosing calm bays based on wind. Expect three swim and snorkel stops, lunch, snacks, drinks, and a return around 6:00 to 6:30 PM.
“Amazing day! Highly recommended ! Great guides and good food! Lovely places!”
Sail from Kos Harbor on a comfortable 20-meter Greek sailing boat with an English-speaking crew, including Nikki and the captain. You’ll stop at two quiet swim and snorkel spots, visit Pserimos, and eat a fresh Greek-style lunch on board. Recent departures have often carried only 10 to 12 people, though the boat may vary by date.
“We had the most amazing time on the boat, we were so well looked after, the food was amazing, the views incredible, the sea was crystal clear and everything about the trip was five star”
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.”
Sail privately from Heraklion to Dia Island with a two-person crew, stopping at Saint George Bay and another swimming spot. You can snorkel, fish, use a paddleboard, and relax with fruit, soft drinks, water, and local white wine. Boats range by group size and budget, with optional hotel transfers and onboard meals.
“We told the guides we were more interested in sailing than the excursions and they accommodated our request. The Elan 37 is a fun boat and she sailed well even in light winds. The lunch was delicious and we enjoyed it in an idyllic bay on Dia island. The captain and first mate were vey kind and helpful with our two kids. I highly recommend this excursion and will book again if we return to Crete.”
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 ☺️”
Set sail from Skopelos with Alexandra and Antonis of Kardous Sailing aboard the well-kept Clipper 41 Thassos. This eight-hour trip visits three quiet spots in the Alonissos Marine Park for swimming, snorkeling, and stand-up paddling. Breakfast, lunch, drinks, and safety gear are included, with space for no more than eight people.
“Everything was absolutely fantastic! The boat, the places we stopped at for swimming and relaxing, the breakfast of yogurt with honey and fruit, the lunch of an amazing Greek salad and cheese pie and onion pie, all wonderful! Most of all our hosts were generous, kind, and great to talk with. By all means….DO THIS!!!”
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.”
Join Odysseus A. Cruises aboard the catamaran Together for a 10-hour Milos and Poliegos sailing day. Swim at Kalogries, Kleftiko, Gerakas, and the Blue Lagoon, with stops shaped by weather. JP, Nikos, Syvan, and the skipper serve fresh onboard meals, drinks, snorkeling gear, and island stories.
“The team was amazing! From the capital to the skipper to the chef - Truly so accommodating and kind. We loved it and would 100% recommend!!”
Spend 9 to 10.5 hours aboard a spacious DanEri Yachts catamaran from Adamantas. Swim at Polyegos, Triades, and Kleftiko, use SUPs and snorkeling gear, and enjoy brunch, Greek lunch, cheese, fruit, wine, beer, and soft drinks. Crew members such as Zacharias and Jozef add warm, attentive service to a polished day at sea.
“The cruise was amazing, saw amazing sites, crew was fantastic, knowledgeable, and ran everything seamlessly. Lunch was delicious and all the water accessories (paddle boards, floaties, googles) were fun.”
Join Captain Dimitris and crew members such as George or Evgenia for a 6 to 6.5-hour yacht trip from Mykonos to Delos and Rhenia. Explore Delos independently, swim and snorkel from the boat, try paddleboarding, and eat a Greek buffet with wine, beer, and soft drinks. Check your booking carefully because departure times and meeting points can vary.
“We had a lovely day sailing from Mykonos to Delos and then Rhenia. Highlights were Delos, the beautiful water at Rhenia and the lunch, which was great. We felt that we would have benefitted from slightly more time in Delos but enjoyed the day regardless.”
Every island we sail from, and every kind of day that leaves it.
