The 15 Best Half-Day Sailing Trips in Greece

1.Half-Day Exclusive Catamaran Cruise in Santorini with Meal and Open Bar

★★★★★★★★★★5.0 · 2,975 reviews · 5 hours (approx.) · from $133Number one

Spend about five hours aboard a catamaran from Vlychada Marina, stopping at Red Beach, the Santorini hot springs, and Thirassia. You’ll get hotel pickup, an open bar, swimming and snorkeling, and a fresh onboard meal with shrimp, mussels, Greek salad, pasta, and barbecue. Crew members may include Giannis, Natalie, Alex, Mika, Kostas, or Bill.

“What a fun day on the water! The staff Bill, Mika and Kostas were very welcoming and knowledgeable! The food was the best that we have ever had on a boat excursion. We had plenty of room to move around and it was not crowded. We had 4 different stops to swim and snorkel. It was a wonderful day on the water in Santorini!”

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2.Private Half-Day Sailing Trip to Dia Island

★★★★★★★★★★4.9 · 466 reviews · 4.5 hours · from $459 per boat

Sail privately from Heraklion to Dia Island with a two-person crew, then spend 2.5 hours at Saint George Bay swimming, snorkeling, fishing, and using a paddleboard. Water, soft drinks, wine, fruit, and equipment are included. Add hotel transfers or an onboard meal for extra convenience.

“Sailing trip was great, guides gave a lot of explanation concerning the boat, island and history.”

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3.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!”

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4.Half-Day Sailing Cruise to Shipwreck Bay

★★★★★★★★★★4.9 · 260 reviews · 6 hours · from $112Cheapest deck

Join captain Makis and his crew aboard the Blue Foam for a six-hour sailing trip from Nea Michaniona. Swim or snorkel near the Epanomi shipwreck, relax on deck, watch for dolphins, and eat a fresh Greek lunch with wine. Groups are limited to eight, keeping the boat friendly and personal.

“we had a lovely day even in October the ocean was beautiful and the hospitality excellent, would recommend for anyone interested in getting away and enjoying a quiet time at sea!”

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5.Half-Day Morning Catamaran Cruise with Meal & Drinks

★★★★★★★★★★4.9 · 233 reviews · 5 hours · from $159

Sail from Alimos Marina along southeast Athens toward the Athenian Riviera and Vouliagmeni Bay. Your skipper and host handle the boat, swimming stops, snorkeling gear, and a generous lunch of seafood pasta, salads, and Greek appetizers. Expect a small-group setting, wine and beer, and roughly five hours on the water.

“Fabulous!! Our host cooked the most amazing food while also being an exceptional host! And our captain of the boat was wonderful in driving, showing us our surroundings, being friendly and accommodating! This was an AMAZING value!”

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6.Half-Day Sunset Catamaran Cruise with Meal & Drinks

★★★★★★★★★★5.0 · 167 reviews · 4 hours · from $159

Spend four hours aboard a modern catamaran sailing from Alimos Marina along the Athenian Riviera. Your English-speaking crew prepares seafood pasta, salads, and Greek appetizers, with wine, beer, and water included. Expect a quiet small-group cruise, swimming stops, snorkel gear, and sunset views, though departure times can affect how much sunset you see.

“I really enjoyed the hospitality by niki our guide she was amazing and very helpful I was very at ease and comfortable definitely recommended sailing with her!”

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7.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!”

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8.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”

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9.Wooden Sailboat Full- or Half-Day Trip with Meal

★★★★★★★★★★5.0 · 88 reviews · 8 hours · from $159

Spend the day aboard Katerina, a 62-foot wooden sailboat built in 1958, with captain Dimi and a friendly crew. Swim and snorkel at beaches such as Lalaria, Kastani, Panormos, Tsougria, and Arkos, then enjoy snacks, a fresh Greek meal, wine, fruit, and dessert. Choose a full-day cruise or half-day sunset sailing.

“Fantastic experience! We were well looked after throughout the day with cold drinks, snacks and bbq lunch. Beautiful swim stops.”

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10.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…”

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11.Sailing Nafplio | All Inclusive Half-Day Cruise

★★★★★★★★★★5.0 · 67 reviews · 4 hours 30 minutes (approx.) · from $144

Join Sailing Nafplio for a four-and-a-half-hour cruise with no more than nine people. You will pass close to Bourtzi Castle, swim and snorkel near Romvi Island, and enjoy provided gear, snacks, lunch-style food, water, beer, and wine. The crew shares local history and returns you to Nafplio.

“Absolutely worth the money. The crew was very friendly and knowledgeable about the local area. They served great snacks, food and drinks. It was one of the passangers birthday and they whipped out a cake with a candle. The snorkling spots were great as well. Super chill and great vibes.”

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12.Half-Day Sailing Cruise to Shipwreck Bay !

★★★★★★★★★★5.0 · 60 reviews · 6 hours (approx.) · from $114

Join captain Makis and his crew for a six-hour sailing cruise from Nea Michaniona, about 40 kilometers from central Thessaloniki. Sail to Shipwreck Epanomi, swim or snorkel near Navagio beach, explore the wreck from the water, and enjoy homemade Greek food, wine, and coastal views aboard a 46-foot Hunter sailboat.

“Wonderful, relaxing and a little surreal experience. Homemade meal and nice conversation. Swimming in blue sea.”

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13.Half-Day Tailor-made Private Catamaran Cruise in Santorini

★★★★★★★★★★5.0 · 39 reviews · 5 hours (approx.) · from $958

Set out from Fira at 10:00 am on a private Santorini Star Sailing catamaran, with hotel pickup and a five-hour route to Red Beach, the volcanic caldera, Thirassia, and views of Oia. Expect swimming stops, a meal prepared onboard, and a crew that may include Mika, Tzannis, Fotis, Natalia, or Tomi.

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14.Luxury Sailing Cruise in Agios Nikolaos: Half-Day & Full-Day

★★★★★★★★★★4.9 · 25 reviews · 4 - 6 hours · from $117

Sail from Agios Nikolaos across Mirabello Bay on a new yacht with an English-speaking skipper and crew. You will circle Spinalonga for photos, swim and snorkel at Kolokytha Bay, and enjoy Cretan snacks, drinks, towels, SUP equipment, and music. Choose a 4-hour half-day trip, a 6-hour full-day outing, or a private sunset celebration.

“This was one of the highlights of our trip! The team were so friendly and made sure we had everything we needed. They tailored the trip to the pace we wanted so we ended up going to a few nice swimming spots. Would 100% recommend!”

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15.Half-day Private Cruise with Sailing Yacht

★★★★★★★★★★5.0 · 5 reviews · from $440 per boat

Spend four private hours aboard a sailing yacht from Marina Gouvia, with views of Corfu Old Town, the Old Fortress, Garitsa Bay, Mouse Island, and Lazareto Island. Swim at the Royal Baths and Vido Island, watch planes pass over Mouse Island, and enjoy sandwiches, snacks, drinks, towels, snorkel gear, and a skipper.

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