6 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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