Semi-Private Sailing Cruises in Crete: Our Top 15

1.Small Group Sailing Trip to Dia Island with Lunch

★★★★★★★★★★5.0 · 162 reviews · 4 hours 30 minutes (approx.) · from $72Our pick

Review of Crete’s small-group sailing trip to Dia Island, with snorkeling, SUP, lunch, wildlife, hotel pickup, and practical booking advice.

“- Captain and staff including pick up driver were really nice - water is really clear - boat is clean - captain brought a sea urchin to show to everyone. That was cute. BUT - the Equipment is the worst snorkeling Equipment We ever had on such a trip - at first they just had 8 snorkels for 12 ppl. So the Captain handed me his private one. That one was good. Later he found some more and said i have to change. Then i had to Deal with the rubish everyone had. Water came with EVERY breath. I didnt make it 2 meters of the boat on second attempt.…”

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2.Dia Island Catamaran – Premium Lunch, Open Bar, Small Group

★★★★★★★★★★5.0 · 126 reviews · 6 hours 30 minutes (approx.) · from $181

Sail from Heraklion to Dia Island on a small catamaran with fresh lunch, open drinks, snorkeling, paddleboards, and a relaxed bay stop.

“The crew was really nice and did everything for its customers. It was a blast on the boat and very fun. Would go again.”

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3.Balos Shared Catamaran Cruise (small groups up to 10 or 22ppl)

★★★★★★★★★★5.0 · 53 reviews · 7 hours (approx.) · from $199

Review of Crete’s Balos catamaran cruise, with swimming, Gramvousa fortress, Cretan lunch, snorkeling, costs, and practical advice.

“Caring and friendly crew who were very focused on everyone having a great day. Transfer from our hotel to port was great and once on board we were provided with coffees, soft and alcoholic drinks, snacks, fresh fruit and a tasty lunch. At the swim stops there were floatation aids, snorkel masks, dry bags and tenders to shore provided. The waters were beautiful and clear. The aperol cocktail served on the sail back to port was a nice touch. Definitely recommend this tour over the public ferries which looked far too crowded! Thanks all for an amazing day!”

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4.Dia Island Catamaran – Premium Lunch, Open Bar, Small Group

★★★★★★★★★★4.9 · 42 reviews · 6.5 - 8.5 hours · from $176

Review the Dia Island catamaran from Crete, with a small group, open bar, gourmet lunch, swimming, snorkeling, and paddleboarding.

“It was the beast sailing cruise in my life. Everything was perfect! I enjoyed the food, the sea. Crew was really nice and welcoming! Highly recommend!”

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5.South Crete: Small group Full Day/ Sunset Sailing & Lunch

★★★★★★★★★★4.5 · 28 reviews · 5 to 7 hours (approx.) · from $108

Sail South Crete from Agia Galini to Paximadia and Agios Pavlos for swimming, snorkeling, lunch, wine, and sunset views.

“Thank you for a most wonderful way to see and experience Crete! We lloved our sail and snorkel at the Proxima Islands. We saw several squid and got to enjoy swimming in a cave there. On the way back we were treated to a delicious dinner and enjoyed the company of other passengers and crew. I highly recommend.”

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6.Small group 5,5h Sunset Sailing trip to Dia Island

★★★★★★★★★★4.5 · 26 reviews · 6 hours (approx.) · from $84

Review of a small-group sunset sail from Heraklion to Dia Island, with snorkeling, snacks, friendly skippers, and practical booking advice.

“Great time on the sea and snorkelling. The captain and skipper were very very friendly. Our teenagers loved it too.”

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7.Small Group Sailing Cruise from Agios Nikolaos in Mirabello Bay

★★★★★★★★★★5.0 · 21 reviews · 6 hours (approx.) · from $132

Review of Avanti Sailing’s six-hour Crete cruise from Agios Nikolaos, with Spinalonga views, Kolokitha swimming, lunch, and a small group.

“Christos and yannis were both great. Friendly and knowledgeable. Service was great on the boat. When we went around Spinalonga, we went a different way around from the masses so got clear pictures and views. Food on the trip was very good. Overall a great relaxing day.”

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8.Small Group Sailing Cruise from Heraklion to Dia Island

★★★★★★★★★★5.0 · 15 reviews · 6 hours (approx.) · from $102

Sail from Heraklion to uninhabited Dia Island for swimming, snorkeling, archaeology, sunset views, and a meal aboard a small boat.

“We had a wonderful time with the excellent team. All of us were excited to pass giant sea turtles as we were sailing and we saw a few different types of fish whilst snorkeling at Dia. We went on the sunset tour, which meant no early start and a fabulous end to the day watching the sunset on our way back to the harbour. Thank you for a fantastic trip. 100% recommended!”

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9.Small Group 5,5 hours Sailing Trip to Dia Island

★★★★★★★★★★5.0 · 11 reviews · 6 hours (approx.) · from $84

Review of a small-group sailing trip from Heraklion to Dia Island, with snorkeling, snacks, drinks, a 10-person limit, and practical booking tips.

“Très belle sortie en mer, le personnel est top.. A amezing boat... It's a very good trip with Dimitri et Alexandre”

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10.Balos Lagoon Kissamos Shared Sailboat Tour Experience

★★★★★★★★★★5.0 · 10 reviews · 8 hours (approx.) · from $156

Review of the Balos Lagoon and Gramvousa sailboat tour from Kissamos, with lunch, snorkeling, castle views, pricing, timing, and practical tips.

“It was a truly wonderful tour! The food was absolutely delicious, and the captain was very informative. We highly recommend this to anyone who wishes to experience the beauty of Crete.”

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11.Kolimvari Shared Sailing Cruise to Agioi Theodoroi Island

★★★★★★★★★★5.0 · 9 reviews · 5 hours (approx.) · from $132

Review of the five-hour Kolymvari sailing cruise to Agioi Theodoroi, with swimming, SUP, snorkeling, lunch, drinks, and hotel pickup.

“A relaxing afternoon on a yacht, being well looked after. The hospitality was excellent with great food and free flowing drinks.”

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12.Balos Beach and Gramvousa island shared group Sailing Cruise

★★★★★★★★★★5.0 · 7 reviews · 8 hours (approx.) · from $234

Sail from Kissamos to Gramvousa and Balos on a small-group yacht, with swimming, snorkeling, fortress views, and lunch on board.

“This was the best birthday vacation I have ever had with my two friends and thank you to Luis and Thennis not sure if that's how their name is spelled but they were amazing and their cooking was truly amazing they made everything so special we had such an amazing time!!”

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13.Semi-private Sailing trip with Lunch and Water Toys

★★★★★★★★★★5.0 · 7 reviews · 5 hours (approx.) · from $168

Review of Crete’s five-hour Lagoon 450F catamaran trip from Agios Nikolaos, with lunch, snorkeling, a slide, SUP, and sea scooter.

“This was really fantastic. It was a surprise trip for my wife and she absolutely loved it. So many water activities to choose from and there is even a slide which the other boats don’t have!! The food is really good too and drinks are included. Would totally recommend this trip and the blue lagoon is amazing! Thank you to the crew for accommodating us and making us feel welcome”

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14.Luxury escape Sailing, shared from Hersonissos or Heraklion port

★★★★★★★★★★5.0 · 6 reviews · 7 hours (approx.) · from $107

Review of LuxuryCrete’s shared sailing from Hersonissos or Heraklion to Dia Island, with swimming, lunch, snorkeling, drinks, and a small group.

“After a very warm welcome from Magda we set sail to the islland of Dia. On our way we enjoyed the historical stories of our skipper Drosos. At Dia island we did some snorkling and spotted a variety of fish. Meanwhile Droses and his girlfriend Dimitra prepared a very tasteful meal. The sunset on our way back to Crete was very beautiful. For us this sailing trip was certainly one of the highlights of our holiday at Crete.”

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15.Chania shared Sailing cruise in a small group

★★★★★★★★★★5.0 · 4 reviews · 4 hours (approx.) · from $118

Review of Chania’s four-hour small-group sailing cruise, with snorkeling, local snacks, island views, pricing, and practical booking advice.

“The boys running the boat were first class and the day was absolutely fantastic. Cruised to small island dropped anchor and snorkelled and swum in stunning surroundings then sailed all the way back to port , they could not do enough for is and we gladly recommend them to anyone”

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