15 Heraklion Sailing Tours Worth Casting Off For

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 Dia Island aboard a small yacht with up to 14 people. You’ll swim, snorkel, paddleboard, and eat shrimp linguini, Greek salad, and Cretan appetizers. English-speaking crew members such as Mariana, Manos, Sofia, Giannis, and Captain Petros have earned warm praise for friendly service, with afternoon trips offering sunset views.

“The perfect day! Our guided were all so kind and accommodating. The boat was beautiful, spacious, and had plenty of fun equipment. The lunch was delicious and abundant, as well and the drinks! Overall, a fantastic experience. Would absolutely do it again!”

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2.Sailing Cruise to Dia Island with Drinks and Meal

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

Sail from Heraklion’s Old Venetian Harbor to Dia Island with a certified crew, often including Captain Nick, Stelios, Celia, Kristina, or Iorgu. Swim, snorkel, fish, paddleboard, hike, and eat a fresh lunch onboard. Choose hotel pickup or meet beside Marina Café, and consider an afternoon departure for sunset.

“We had an amazing trip to Dia island with Stelios and Celia! We decided to try the full day trip over the half day and are so glad we did. Definitely pay the bit more if you can! The pickup from our hotel was right from the door and on time, we were welcomed on board at the harbour and at the island had a chance to try snorkelling and SUP for the first time. Lunch was prepared while we swam and we had plenty of chance to sunbathe without feeling under pressure to do anything to a schedule. The whole experience was so relaxing, we felt like welcomed guests…”

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3.Dia Island Sailing Cruise with Snorkeling

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

Sail from Heraklion with a professional crew to Dia Island, about an hour offshore. Swim in clear bays, use the included snorkeling and paddleboard gear, and enjoy drinks with either seafood pasta and Greek salad or a lighter half-day meal. Ernesto and George are among the crew members praised for their care and stories.

“Thank you for the nice sailing trip to Dia Island. We had a really great time, the staff has been super nice and caring! We had some nice food and our glutenfree and vegan wishes were considered. We would really recommend this trip and would love to come again one day.”

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4.Sunset Sailing Cruise Dia Island with Snorkeling

★★★★★★★★★★4.7 · 529 reviews · 4.5 - 7 hours · from $82

Sail from Heraklion to uninhabited Dia Island with a small crew of up to 18 people. Swim, snorkel near an old Minoan port, use the paddleboard, and enjoy Greek food onboard. Full-day trips include salad, tzatziki, and seafood pasta, while half-day trips include tomato pasta. Crew members such as Andreas and George add local stories and friendly help.

“We had a wonderful time! There were a lot of people on the boat but it didn’t feel crowded. The cove where we anchored was lovely — our only complaint was that a party boat anchored nearby and played loud (bad) house music the whole time. It made the experience slightly less idyllic, but we tuned it out eventually, food was delicious, guides were friendly and cooked a delicious dinner, and the sunset was dreamy. A perfect way to spend our afternoon/evening in Heraklion!”

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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 about three hours in a sheltered bay for swimming, snorkeling, paddleboarding, fishing, and sunbathing. Lunch, fruit, Greek appetizers, beer, wine, soft drinks, and equipment are included. The boat carries up to 14 people, though some departures may use a larger catamaran.

“Great day out ,everything was perfect from start to finish.If your coming to Crete on holiday don’t miss out on this trip”

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6.Sailing Trip to Dia Island with Lunch & Swimming

★★★★★★★★★★4.8 · 517 reviews · 6 hours · from $100

Sail six nautical miles from Heraklion to Dia Island with a maximum of 10 people. Captains George, Panos, and Vaso provide local stories, swimming time, SUP boards, snorkeling gear, fishing equipment, lunch, and unlimited drinks. Optional minivan pickup makes this a practical half-day escape from much of Crete’s north coast.

“George and Marco were friendly and informative and made the trip very enjoyable. We spent a good amount of time snorkelling using the equipment they provided and enjoyed a nice lunch of pasta, salad and fruit. It’s a small group of 10 so the boat isn’t overcrowded and you get to know the people well. Highly recommend”

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7.Dia Sailing Cruise With All-inclusive Meal And Drinks

★★★★★★★★★★4.6 · 422 reviews · 5.5 hours · from $76Best value

Sail from Heraklion’s Old Venetian Port to protected Dia Island on a 5.5-hour cruise with Alex, Nikolas, Mel, or Fabio and their crew. You’ll have time to swim, snorkel, paddleboard, eat shrimp pasta and Greek salad, and enjoy unlimited wine, soft drinks, and water. Choose a daytime sailing or return beneath the sunset.

“Wonderful day! The food was amazing, we had a lovely time!”

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8.Heraklion Luxury Sailing Catamaran Dia Island | Gourmet Menu

★★★★★★★★★★4.9 · 312 reviews · 5.5 hours · from $141

Sail from Heraklion with EOS Yachts aboard a modern catamaran limited to 22 people. Captain Thanasis and the English-speaking crew serve Cretan snacks, chef-prepared seafood, local wine, beer, and dessert while you swim, snorkel, fish, canoe, or paddleboard in a quiet Dia Island bay.

“We loved our day aboard the Catamaran! We try to do a boat trip every summer but this was a little more expensive than we usually pay. As we wanted a Catamaran and not a sailing boat, we decided to go for it and we couldn't have been happier with our choice. The captain gave us a briefing before we left and explained that it is an inclusive vessel where we are all valued equally and are a team for the day. It was done in such a way that really put everyone in good spirits and we, as a small group, enjoyed each others company throughout the day. There…”

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9.Dia Island Morning Sailing Trip with Snorkeling

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

Join Cretan Yachts at Heraklion’s Old Port for a six-hour sailing trip to Dia Island. With an English-speaking captain and crew, you’ll cruise for about 75 minutes each way, then enjoy 3.5 hours of swimming, snorkeling, sailing, snacks, fruit, wine, and refreshments in the island’s clear bays. Snorkeling gear and sailing instruction are included.

“It was amazing !! Such a nice experience !! Very small group which made it more special !! The captain Nickolas was so great - welcoming, funny , helpful , caring - we really appreciate how professional he was !! The trip was so fun, the water where we stopped for bathing and snorkelling was out of this world ! So many fish and such a clear water ! Highly recommended ! Great value for money and great memories for life !!”

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10.Nature Reserve Full day sailing to Dia Island & Lunch

★★★★★★★★★★5.0 · 64 reviews · 7 hours (approx.) · from $118Top rated

Set sail from Heraklion’s Old Venetian port with a certified crew such as Stephanos, Petros, or Nikos. Spend the day swimming and snorkeling in three Dia Island coves, use the included SUP boards, enjoy a fresh Greek lunch with vegetarian options, and return by sail. Pickup is available near the port, and the boat holds no more than 10 people.

“I can't say enough about how wonderful this trip was. Petros and Aphrodite were a great team. Very accommodating and great sailors. The food was amazing. They were very informative. Of course the snorkeling was fantastic. Beautiful water. Wonderful day.”

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11.SAILING DAY 4.5h-5h or SUNSET 3h-4.5h from Hersonissos CRETE

★★★★★★★★★★4.5 · 30 reviews · 3 to 5 hours (approx.) · from $108

Set sail from Gouves with a small crew aboard a boat limited to 14 travelers. Choose a 4.5 to 5-hour day trip to Dia Island, or a shorter sunset cruise to Saint George Bay during summer. Expect swimming, snorkeling, SUP, fishing gear, Cretan food on the longer trip, and guides such as Stratos, Manos, or Dimitrios.

“This was an amazing tour. Our captain was awesome and Maria made us a delicious lunch. We swam, met new people, and had a wonderful time. A beautiful way to see Crete and Dia!”

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12.Dia Island: Semi-Private Full Day Sailing Trip with meal

★★★★★★★★★★4.7 · 19 reviews · 6 hours · from $100

Set sail from Heraklion’s Venetian port with an English-speaking crew and no more than 10 people aboard. You’ll spend about four hours at Dia Island swimming, snorkeling, fishing, paddleboarding, eating, and relaxing. Dimitri may be part of the crew, and the return trip often includes hands-on sailing.

“A Perfect Day on the Water – Unforgettable Trip to Dia Island! ⭐⭐⭐⭐⭐ Our boat trip to Dia Island was absolutely incredible – the highlight of our holiday! From the moment we stepped on board, everything was perfectly organized and relaxed. The crew was warm, professional and made us feel completely at ease. The boat itself was spotless, spacious and comfortable, with plenty of shaded areas and sunbathing spots. The journey to Dia Island offered stunning views of the Cretan coastline, and once we arrived the crystal-clear turquoise waters were just breathtaking. We anchored in a bay where we had time to swim, snorkel , fish and paddleboard – all…”

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13.Private Sailing Cruise to Dia Island with Meal & Water Activities

★★★★★★★★★★4.5 · 10 reviews · 5 hours 30 minutes (approx.) · from $952 whole boat, up to 10

Set sail from Heraklion with your own group of up to 10 people for Dia Island. You’ll swim, snorkel, paddleboard, fish, and eat shrimp linguini with Greek salad and fruit. Guides including Harry, Christina, Captain George, and Martina have led recent cruises, though wind can affect water activities and departure times.

“Would highly recommend this trip. We were a group of 8 ladies. Lot's of fun had with the paddle boarding and sea scooter. The skippers really looked after us, the food and drink were very good.”

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14.Dia Island Private Sailing Cruise with Full Meal

★★★★★★★★★★5.0 · 6 reviews · 5.5 hours · from $931 whole boat, up to 10

Sail from Heraklion’s Venetian harbor to Dia Island aboard a private yacht for up to 10 people. Swim, snorkel, fish, paddleboard, and enjoy shrimp linguini, Greek salad, fruit, and unlimited drinks. Crew members have included Amalia, Zoey, Spiros, Christos, and Giannis, with morning and sunset departures available.

“This is an absolutely incredible experience that you should book immediately if you're looking for a boat in Crete. Zoey and Spiros were our captains and made the day one to remember! They gave us options of where we wanted to spend the day (places that were popular but crowded or less popular and secluded), provided amazing service and made delicious food! They are genuinely amazing individuals and were a joy to spend time with. Spiros and I had amazing conversations about sports and he went out of his way after the boat trip with a very kind gesture. I cannot say enough good things about our time on the…”

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15.Sunset Private Sailing Trip to Dia island

★★★★★★★★★★5.0 · 4 reviews · 4.5 hours · from $730 whole boat, up to 10

Set sail from Heraklion’s Venetian port with an experienced crew, heading to uninhabited Dia island. You’ll have time for swimming, snorkeling, fishing, SUP, snacks, local wine, and sea views before sailing back beneath a changing sunset sky. George and Nick are among the friendly crew members praised for making the trip comfortable and well organized.

“One of the highlights of our entire trip to Greece!! George and Nick were a fantastic crew and they made us feel welcome and well taken care of. The trip itself offered the perfect combination of elements: gentle breezes, warm sun, cool water, great wine and snacks and a beautiful sunset. Could not ask for anything more from a sailing excursion. Highly recommend!!”

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