Half-Day Sailing Trips in Greece: 15 to Book

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

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

Review of Santorini Star Sailing’s 5-hour catamaran cruise, with swimming stops, seafood BBQ, open bar, hotel transfers, and sunset options.

“Mika, Kostas, and Bill were phemoniminal! We had such a blast! The food was tasty, the stories and history were memorable, the sense of humor brought everyone on the catamaran together. I have never experienced something like this and 10/10 I reccomend ^_^”

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2.Private Half-Day Sailing Trip to Dia Island

★★★★★★★★★★4.9 · 466 reviews · 4.5 hours

Sail privately from Heraklion to Dia Island for swimming, snorkeling, fishing, fresh fruit, drinks, and optional lunch in a beautiful Cretan bay.

“very friendly guide, bad luck with the weather, but nevertheless definitely recommended”

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3.Half-Day Morning Catamaran Cruise to Kleftiko

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

Review of Milos’ six-hour catamaran cruise to Kleftiko, with swim stops, Greek lunch, drinks, sea caves, and practical booking advice.

“This boat trip was a highlight of our trip to Milos! The food was amazing and so was the turquoise water. However I would've been interested to hear about the history of the Kleftiko.”

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4.Half-Day Sailing Cruise to Shipwreck Bay

★★★★★★★★★★4.9 · 260 reviews · 6 hours · from $112Best value

Sail from Thessaloniki to Epanomi’s shipwreck beach for clear-water swimming, Greek lunch, wine, dolphins, and a relaxed small-group cruise.

“We had a great day at sea with Makis! the trip went very smooth. he has floats and snorkel masks for you to use. the food he provided was top notch and plentiful, make sure to come with an appetite! I can't recommend this enough.”

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

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

Review of Athens’ 5-hour catamaran cruise, with swimming, snorkeling, Greek lunch, drinks, crew details, value, and practical tips.

“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

Review of Athens’ four-hour sunset catamaran cruise, with Greek food, swimming stops, drinks, crew tips, value advice, and practical details.

“It was a great cruise. The captain and crew were very friendly and helpful. We were served an excellent evening meal with drinks.”

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7.Half-day Kleftiko, Catamaran Trip | Lunch & OpenBar

★★★★★★★★★★4.9 · 152 reviews · 5 hours · from $188

Sail from Adamas to Kleftiko on a five-hour Milos catamaran cruise with swimming, snorkeling, fresh meals, drinks, and island views.

“We had an amazing day on the sea with even better crew on board! The food was delicious and the tour was the best we have done in Milos! 😊”

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

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

Review of Milos’ sunset catamaran to Kleftiko, with snorkeling, Greek lunch, drinks, swimming stops, and free shuttle transport.

“What a perfect day in Milos. We have been on several catamaran rides in the Aegean and this was one of the best. Alex at Trinity Yachting was helpful in coordinating our transportation from our hotel in Pollonia to the boat and back to our hotel. His responses were immediate and very pleasant. It was such a pleasure to meet him. The crew are all very pleasant and doing everything to make your trip memorable. We had a few stops for swimming. They had a nice amount of time at each location. They were offering beverages continuously on our trip. The meal they prepared was delicious and authentic Greek food.…”

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

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

Review of Skiathos Katerina Traditional Sailing, with swim stops, Greek lunch, snacks, wine, practical tips, costs, and who should book.

“Best activity in Skiathos! Captain, mate and chef went all out. Food was delicious and plenty of it. Dimitri was able to tell us about every stop and was very hospitable. Captain made every effort to keep us away from crowds including adjusting the itinerary to get ahead of the crowds”

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10.Half-Day Private Romantic Sailing Getaway to Kleftiko

★★★★★★★★★★5.0 · 81 reviews · 5 hours (approx.)

Review of Milos’ private sailing trip to Kleftiko, with cave access, swimming stops, wine, snacks, pricing, tips, and practical advice.

“Great experience. Both crew members were super nice and knowledgable about what we were seeing across the south coast of Milos. You stop at Kleftiko and go around the caves on the sailship's dingy boat. Then you take some time to swim (they have snorkel goggles) and eat some snacks. After that you go back and stop again on another beach. All the time white wine is available and you can either out your own music. Perfect tour, super recommended.”

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11.Sailing Nafplio | All Inclusive Half-Day Cruise

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

Review of Nafplio’s 4.5-hour all-inclusive sailing cruise, with Bourtzi views, Romvi swimming, snorkeling, food, drinks, and practical tips.

“It was an amazing experience. Beautiful boat, nice people and very informative. Had an amazing time. They took us to 3 different spots and prepared lunch and snacks for us. There was also beer, wine and cold water available for us. The water was beautiful, the weather was beautiful and the experience was well worth it. 5 stars! Highly recommend.”

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12.Half-Day Sailing Cruise to Shipwreck Bay !

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

Review of Thessaloniki’s half-day sailing cruise to Epanomi Shipwreck Bay, with swimming, snorkeling, homemade Greek lunch, wine, and practical tips.

“Slow, relaxing yacht with a small group of people. You get to swim and snorkel...and we saw dophins. Food is delicious cooked on board, fresh and delightful. The white wine was lovely too. We would highly recommend the trip.”

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

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

Review of Santorini Star Sailing’s private five-hour catamaran cruise, with Red Beach, the volcano, Thirassia, swimming stops, food, pricing, and tips.

“It was amazing! The best catamaran ever. We had the best time and the best views. The food was amazing as well as the crew. I would recommend again and again! We also had the best the weather. We took the best photos and smam in October!.”

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

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

Review of Agios Nikolaos luxury sailing cruises to Spinalonga and Kolokytha Bay, with swimming, snorkeling, drinks, snacks, and sunset options.

“We had an amazing sailing trip around the islands! The water was crystal clear, and we even got to go snorkeling. Our hosts were fantastic — friendly, knowledgeable, and spoke excellent English. They shared lots of interesting cultural facts and made the whole experience unforgettable. Highly recommend this company!”

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15.Half-day Private Cruise with Sailing Yacht

★★★★★★★★★★5.0 · 5 reviews

Review of Corfu’s private half-day sailing cruise, with Old Town views, swimming stops, snacks, drinks, snorkeling, and practical booking advice.

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