Top 11 Sailing Trips in Heraklion

1.Dia Island Sailboat Cruise with Swimming and Meal

★★★★★★★★★★4.8 · 2,579 reviews · 5.5 hours · from $95Our pick

Sail from Heraklion’s Old Venetian Harbour to protected Dia Island aboard a small yacht for up to 14 people. Captain Petros and crew members such as Sofia, Giannis, Mariana, and Manos may host your trip, with swimming, snorkeling, paddleboarding, a Mediterranean meal, unlimited drinks, and sunset options.

“Fantastic few hours in the Greek sea, lovely crew DELICIOUS food and gorgeous sunset! Love love love”

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2.Sailboat Cruise to Dia Island with Drinks & Lunch

★★★★★★★★★★4.9 · 1,287 reviews · from $90

Join a small shared cruise or private sailing trip from Heraklion to Dia Island. Swim and snorkel in Saint George Bay, try fishing, enjoy lunch and unlimited drinks, and sail back with an attentive crew such as Marcos, Vasilis, Dimitris, or Alexandra.

“A beautiful and relaxed boat trip including a lovely little meal. I enjoyed it a lot. Thanks to captain and skipper and also the other travelers.”

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3.Sailing Cruise to Dia Island with Drinks and Meal

★★★★★★★★★★4.9 · 778 reviews · 6 hours · from $106

You’ll sail from Heraklion’s Old Venetian Harbor to Dia Island with a certified crew, often including Stelios, Celia, Captain Nick, Kristina, or Iorgu. Swim, snorkel, paddleboard, fish, hike, and enjoy shrimp spaghetti, salad, fruit, wine, soft drinks, and raki aboard a small-group yacht.

“Lovely chilled boat cruise with two swimming stops… the island is uninhabited just some goats but it’s all about boat life!! Lush food, beer and wine and soft drinks flowing all day and raki shots for the hard-core”

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4.Dia Island Sailing Cruise with Snorkeling

★★★★★★★★★★4.7 · 742 reviews · 4.5 - 7 hours · from $82

Sail from Heraklion with a professional crew, often including Ernesto and George, to uninhabited Dia Island. Swim in clear bays, snorkel, paddleboard, and enjoy Greek salad, tzatziki, seafood pasta, fruit, wine, and soft drinks. Choose a half-day or full-day trip, with small groups of up to 18.

“A really enjoyable and relaxing day. The group was small and everyone chatted with eachother and also with the two crew who were great. It was my first time on a sailing boat which I really enjoyed as well. Would highly recommend!”

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5.Sailing Cruise to Dia Island with Meal and Water Activities

★★★★★★★★★★4.5 · 526 reviews · 5 hours 30 minutes (approx.) · from $96

Sail from Heraklion to uninhabited Dia Island aboard a yacht or catamaran, with swimming, snorkeling, SUP, fishing, lunch, wine, beer, and soft drinks included. Expect about an hour at sea each way and three hours in a sheltered bay. Boats and crew may vary.

“We were collected from our hotel and taken to the port. Our first experience in a sail boat and really enjoyed it. Food and drinks were included. The water at Dia island was gorgeous to swim in. Then a journey back watching the sunset was the perfect ending.”

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6.Private Half-Day Sailing Trip to Dia Island

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

Spend 4.5 hours on a private sailing boat from Heraklion to Dia Island, with a two-person crew, drinks, fruit, snorkeling gear, fishing equipment, and paddleboards. Anchor in Saint George Bay, the setting once explored by Jacques Yves Cousteau, and add a fresh onboard meal if you wish.

“Communication with the provider was excellent from point of booking to the day of the event. They answered my many questions and was helpful with facilitating a cake delivery for my daughters birthday. The round trip taxi service was fairly priced, the driver arrived in time & was very friendly and accommodating. The boat was lovely & the crew Ilias & Nikiforas were fantastic. Really friendly& welcoming guys. Dia Island was beautiful & the journey to and from the island was equally as enjoyable. All round a perfect excursion and well worth the money. Thank you”

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7.Sailing Trip to Dia Island with Lunch & Swimming

★★★★★★★★★★4.8 · 414 reviews · from $67

Set Sails takes you from Heraklion to Dia Island on a small-group yacht cruise with swimming, snorkeling, fishing, SUP, and lunch. The crew may include George, Vaso, Spiros, or Marina. Choose port departure or selected transfers, then spend about three hours anchored at Saint George Bay.

“My partner and I loved this trip! Vaso & Spiros were fantastic guides. Snorkeling at Dia Island was super fun and the water was nice and warm. We enjoyed chatting with the others guests on the boat - had some wine together which was fun. Highly recommend this experience!”

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8.Sunset Sailing Cruise Dia Island with Snorkeling

★★★★★★★★★★4.6 · 242 reviews · from $63Best value

Sail from Heraklion to uninhabited Dia Island with a small crew, swimming, snorkeling, paddleboarding, food, wine, and raki. Depending on the boat and departure, you may meet crew members such as Alex, Kostas, Emanuel, Constantine, Thanos, or Eleanor. Choose a shared or private catamaran and a half-day or full-day outing.

“This experience was the cherry on the cake for our trip here. For a cheap price a 4 hour boat-trip with food, amazing view on the sea and sunset, snorkling and swimming. The guides/captains were all very kind. 10/10 would recommend.”

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9.Private Full-Day Sailing Trip to Dia Island

★★★★★★★★★★4.9 · 140 reviews · 6.5 hours

Take a private sailing boat from Heraklion to Dia Island with a two-person crew, swimming stops, snorkeling gear, fishing equipment, paddleboards, fruit, drinks, and local white wine. Add hotel transfers or an onboard meal for a more polished day.

“We told the guides we were more interested in sailing than the excursions and they accommodated our request. The Elan 37 is a fun boat and she sailed well even in light winds. The lunch was delicious and we enjoyed it in an idyllic bay on Dia island. The captain and first mate were vey kind and helpful with our two kids. I highly recommend this excursion and will book again if we return to Crete.”

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10.Dia Island Morning Sailing Trip with Snorkeling

★★★★★★★★★★4.9 · 100 reviews · 6 hours · from $82

Meet Cretan Yachts at Heraklion’s Old Port and sail with a local captain toward Dia Island. You’ll have about three and a half hours for swimming, snorkeling, snacks, fruit, music, and photos, with names such as Nickolas, Dimitris, and Alexandros appearing among the friendly crew.

“An absolutely fantastic trip, it was so intimate and exclusive only 2 families on the boat 8 of us and two crew. The crew were amazing nothing was too much trouble for them, we set sail for Dia Island on the yacht, there was only us and another sml boat snorkeling equipment was provided, saw lots of fish , an eal type of fish, caterpillar type of creatures and an octopus which was the highlight of the day. drinks and lunch were perfect. Would definitely recommend this trip.”

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11.Catamaran Sailing to Dia with Lunch in Heraklion, Crete(EST 2024)

★★★★★★★★★★5.0 · 64 reviews · from $142Top rated

Set sail from Cafe Marina in Heraklion for a five-and-a-half-hour trip to Dia Island aboard a new Lagoon 46 catamaran. Swim in a quiet cove, snorkel, use the SUP boards, enjoy traditional Cretan pasta, and return with drinks included. The group is limited to 17 people.

“Captain and crew were awesome. It was an incredible day on and in the water. Our lunch was delicious. Highly recommend this excursion.”

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