15 Semi-Private Sailing Cruises in Crete Worth a Whole Day

1.Dia island : Small Group Sailing Trip to Dia Island with Lunch

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

Set sail from Heraklion’s Old Venetian port with a certified crew, such as Costas, Mario, George, or Harry, for Dia Island’s quiet coves. You’ll have about 90 minutes for swimming, SUP, snorkeling, and sunbathing, followed by an organic lunch, fruit, soft drinks, and wine. Pickup is included within 10 kilometers.

“Friendly skipper and crew, great first time sailing experience for my friend and excellent anchorage choice as well. Would return to them again!”

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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

From Heraklion, sail with an English-speaking crew to Dia Island aboard a catamaran limited to 14 people. Expect a light brunch, fresh Mediterranean lunch, local beer and wine, swimming, snorkeling, paddleboarding, fishing, Wi-Fi, and time to relax in a sheltered bay.

“This is the company to use for a snorkel sailing adventure. Thomas, Anise, and Alexander took great care of us. Water was crystal clear. Plenty of time at Dia in a secluded cove. A wonderful day, high recommend! Dolphins were an added bonus.”

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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

Sail from Chania toward Balos Lagoon and Gramvousa Island on a catamaran with a small group. Expect swimming, snorkeling gear, Cretan snacks, drinks, a homemade Greek lunch, and time to visit Gramvousa’s hilltop fortress. Guides including Yannis and Georgio provide local background, while pickup from a Chania meeting point may be added during booking.

“Great time exploring and seeing different beaches. We loved Balos, absolutely stunning and worth the trip. The boat ride was a lot of fun, plenty of space with good food and drink. The staff was wonderful and we really enjoyed the 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

Spend 6.5 to 8.5 hours sailing from Crete to Dia Island aboard a new catamaran for up to 15 people. You’ll get espresso, brunch, an organic Mediterranean lunch, unlimited local wine and beer, and time to swim, snorkel, fish, or paddleboard. The crew speaks English and Greek, with hotel pickup available from selected areas.

“The Sunset Cruise was very enjoyable with plenty of space on board the catamaran, excellent service, a great crew and delicious food, highly recommended!!!”

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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

Join captain Lukas and a certified crew for a small-group sail from Agia Galini to Paximadia or Agios Pavlos. Swim, snorkel, use the SUP boards, enjoy a Cretan meal with wine, and return around sunset. The route depends on wind and sea conditions, with free pickup within 5 km.

“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

Set sail from Heraklion at 3:15 pm for a roughly six-hour trip toward Dia Island. You’ll pass the Venetian harbor and Koules Fortress, swim and snorkel near Agios Georgios, and watch the coast change in the evening light. George and other English-speaking skippers are praised for warm, attentive service. Fuel, drinks, snacks, and gear are included.

“Simply exceptional! We booked our boat trip 27/07 for the end of our stay in Crete and we were not disappointed. George, our skipper, was wonderful, kind and attentive. He simply made our day! Many thanks to him! Last but not least, the whole experience was very well organized and lived up to the description! Thank you for this extraordinary memory!”

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

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

Join Avanti Sailing for a six-hour cruise from Agios Nikolaos with a maximum of 10 people. Captain Christos, Yannis, Georgios, or Ioannis may lead the day, guiding you past Spinalonga to Kolokitha for swimming, snorkeling, paddleboarding, fishing, and lunch. Local wine, soft drinks, fruit, and water are included.

“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

Set sail from central Heraklion to uninhabited Dia Island aboard a luxury sailing boat. You get about six hours on the water, with time for swimming, snorkeling, a meal, island walks, and a look at an ancient Minoan port. Groups are capped at 10 people, and sunset departures are available.

“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

Set out from Heraklion’s Old Venetian Harbor for about six hours on a small-group sailing trip to Dia Island. Dimitri and Alexandros guide the boat, explain the yacht and equipment, and help shape the day. Snorkel, watch fish, collect shells, and enjoy snacks, soda, and bottled water. The boat holds no more than 10 people.

“Nous avons beaucoup aimé l'excursion en voilier dirigé par Dimitri et alexandros. C'était très sympa le snorkelling⛵🤿☺️.”

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10.Balos Lagoon Kissamos Shared Sailboat Tour Experience

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

Sail from Kissamos Port with George, Christopher, or captain Cristos on an eight-hour shared trip limited to 10 people. Swim at Balos Lagoon, snorkel near Gramvousa’s shipwreck, climb toward its Venetian castle, and enjoy local food, wine, beer, water, and soft drinks aboard.

“Great tour! Highlight of the trip! the boat was great and we loved Balos Lagoon. Lunch was great too!”

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11.Kolimvari Shared Sailing Cruise to Agioi Theodoroi Island

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

Sail from Kolymvari to protected Agioi Theodoroi Island on a small shared yacht with up to 14 people. Lucas and Jason may host your cruise, with time for swimming, snorkeling, SUP, fishing, and a fresh three-course meal. Hotel pickup is offered from Chania and nearby resorts.

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12.Balos Beach and Gramvousa island shared group Sailing Cruise

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

Spend about eight hours sailing from Kissamos to Gramvousa and Balos Lagoon in a small group of up to eight. Swim, snorkel, climb the Venetian fortress, and eat a fresh meal cooked aboard. Crew names associated with departures include Vasilis, Themos, Jo, Luis, and Thennis. The yacht Izabela has also been used.

“Do not pass on this experience if in Crete. This was the best vacation day I have ever had. The boat was beautiful. The crew Themos and Jo were great hosts, very skilled and friendly. The meal served for lunch was delicious and better than most restaurant food I’ve had in Greece.. The two beach destinations were absolutely beautiful.. We had a blast, hiking, snorkeling and exploring.. 10/10!”

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

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

Board a Lagoon 450F catamaran in Agios Nikolaos for about five hours on Crete’s coast. Your captain takes care of the sailing while you enjoy a Mediterranean lunch, snacks, soft drinks, snorkeling, a transparent canoe, SUP, sea scooter, fishing gear, and an inflatable slide. The trip returns to the marina.

“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

Sail from Hersonissos or Heraklion toward Dia Island, Crete’s protected Zeus Island. Swim at Virgin Mary’s Bay and Agrielia Bay, use snorkeling and fishing gear, paddleboard, and enjoy a freshly prepared Mediterranean lunch with soft drinks, water, fruit, and local wine. The crew may include Magda, Drosos, Dimitra, or other LuxuryCrete staff.

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15.Chania shared Sailing cruise in a small group

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

Spend about four hours sailing from Chania with no more than eight people aboard. The crew takes you along the Cretan coast to a small island, where you can swim and snorkel before sailing back to port. Local snacks, seasonal fruit, drinks, and snorkeling gear are included. Bring your own sea towel.

“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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