15 Sailing Trips in Heraklion That Survive a Close Look

1.Dia Island Sailboat Cruise with Swimming and Meal

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

Sail from Heraklion’s Venetian Harbour to Dia Island aboard a small yacht with up to 14 people. Captain Petros and crew members such as Sofia, Giannis, Mariana, and Manos have been praised for friendly service. Swim, snorkel, paddleboard, and enjoy shrimp linguini, Greek salad, Cretan appetizers, and unlimited drinks.

“This was a top notch experience: I strongly recommend this sunset boat trip!”

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2.Sailboat Cruise to Dia Island with Drinks & Lunch

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

Set sail from Heraklion with an English- or Greek-speaking crew for Dia Island, about an hour offshore. Swim and snorkel in Saint George Bay, try fishing, enjoy lunch and unlimited drinks, then relax on deck. Shared cruises include the meal, while private trips let you select meal add-ons.

“Pick up from cruise ship was on time, comfortable and a friendly driver. This was a great shore excursion-loved the journey to Dia which is a beautiful bay, gorgeous sea to swim and snorkel in!”

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3.Sailing Cruise to Dia Island with Drinks and Meal

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

Spend six hours sailing from Heraklion with a certified crew, stopping at Dia Island for snorkeling, paddleboarding, fishing, swimming, and a Mediterranean meal. Captains and crew may include Nick, Kristina, Iorgu, Stelios, or Celia. Hotel pickup is optional, and afternoon departures can include sunset views.

“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’s Venetian harbor to uninhabited Dia Island with a small crew and no more than 18 people aboard. Ernesto, George, and other professional crew members provide sailing, swimming, snorkeling, paddleboarding, drinks, and food. Choose a half-day or full-day trip, with hotel transfers available from selected areas.

“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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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 small yacht or, on some departures, a larger catamaran. Spend about three hours in a sheltered bay swimming, snorkeling, paddleboarding, fishing, and eating shrimp linguini with Greek sides. Crew members including Petros, Yannis, Katrinia, Amalia, and Mariana have been praised for friendly service.

“Guide’s voice was quiet. Not all of us could hear him. Lunch was good. Snorkeling was not the best. Very little fish to see.”

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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, time in Saint George Bay, snorkeling gear, fishing equipment, paddleboards, fruit, and unlimited water, soft drinks, and wine. Optional hotel transfers and onboard meals are available.

“Had the best time with my family on the boat. Our captain Kostas was personable and informative. We all had a wonderful time in his hands! The food was great as well, simple sandwiches and a fresh salad plus the fruit platter was a perfect meal on the water.”

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7.Sailing Trip to Dia Island with Lunch & Swimming

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

Spend six hours sailing from Heraklion to Dia Island aboard a small yacht limited to eight people. Swim and snorkel in Saint George Bay, try SUP and fishing, and enjoy shrimp pasta, Greek salad, fruit, and unlimited drinks. Crew members may include George, Vaso, Spiros, or Marina.

“Trip was really good, so relaxing. Our crew goerge and marina were fantastic hosts. Great conversation & the lunch they provided was lovely. If you can request to have them, I 100% would!!”

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8.Hersonissos: Sunset Catamaran Cruise with Snacks and Drinks

★★★★★★★★★★4.8 · 328 reviews · from $90

Set out from Hersonissos on a 3.5-hour semi-private catamaran cruise. You’ll get Prosecco, local cheeses, fruit, wine, beer, and soft drinks, then stop at Agios Georgios Bay for swimming, snorkeling, SUP boarding, and photos with a pink flamingo float. The crew may include Thomas, Sasch, Anise, Yannis, or Prodromos.

“Loved everything about this trip! Wonderful experience from start to finish, something we will never forget! Hosts were lovely and friendly, food/drink was great, music was awesome too! We had enough time to jump and swimming in the sea and also enough time to enjoy the beautiful sunset! The most relaxing boat trip I’ve ever been on, highly recommend to anyone don’t hesitate to book it! Thanks for the wonderful experience, Monika,Tim &Oliver”

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9.Small-Group Sailing Trip to Dia Island with Lunch

★★★★★★★★★★4.7 · 277 reviews · 4.5 - 7 hours · from $94

Sail with up to 10 people from Heraklion’s Old Venetian port to protected Dia Island. Your crew handles the boat while you swim, snorkel, paddleboard, and eat a fresh Greek lunch with wine. Morning trips offer more daylight and warmth, while afternoon departures can bring sunset views. Hotel pickup in Heraklion is included.

“honestly this was incredible! the pick up bus was perfect, lovely and cool. well appointed. the skipper and deckhand were friendly engaging and knowledgeable. we were lucky and had the calmest weather so the journey was ideal. I occasionally get sea sick but not even a little. we pulled up to the less visited cove and had total privacy. equipment perfect. food outstanding. sea creatures were amazing. couldn't be happier”

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10.Sunset Sailing Cruise Dia Island with Snorkeling

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

Sail from Heraklion to uninhabited Dia Island with a small group of 10 to 18 people. Swim and snorkel in a quiet bay, use the paddleboard, enjoy a fresh Greek meal or tomato pasta, and return beneath a Cretan sunset. Crew members have included Alex, Kostas, Emanuel, Constantine, Thanos, and Eleanor.

“We had a great time sailing to Dia Island. The sail back at sunset was breath taking. We also were attracted by the snorkeling. Unfortunately there were very few fish and the sea bed was badly scoured by anchors”

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11.Dia Island Luxury Catamaran Cruise with Meal

★★★★★★★★★★4.7 · 194 reviews · 5.5 hours · from $127

Sail from Heraklion’s Old Venetian Harbor to Dia Island aboard a Lagoon 450F catamaran. You’ll swim, snorkel, fish, try a paddle board, and enjoy Greek salads, Cretan appetizers, pasta, fruit, and unlimited drinks. Choose a morning outing or an afternoon cruise with sunset views. Sophia and the crew handle the details in English or Greek.

“Amazing! Couldn’t fault a thing. 100% recommend. We had a great day”

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12.Dia Catamaran Tour – Lunch, Open Bar & Snorkeling

★★★★★★★★★★4.9 · 161 reviews · from $141

Spend five hours sailing from Heraklion to Dia Island with DanEri Yachts. Captain Giannis, Gianna, Konstantinos, and the crew provide coffee, pies, a Mediterranean lunch, unlimited soft drinks, beer, and white wine. Swim, snorkel, paddleboard, fish, and relax aboard a semi-private catamaran.

“Everything was perfect, the boat is beautiful and very well equipped, the team members are very nice and friendly The food was very good, and the sunset on the way back to Heraklion is just stunning I had a great time thank you !”

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13.Dia Island Catamaran Cruise with Dinner and Wine

★★★★★★★★★★4.8 · 147 reviews · from $120

Join DanEri Yachts for a five-hour afternoon catamaran cruise from Heraklion to Dia Island. Expect welcome coffee, Cretan snacks, swimming, snorkeling, SUP boards, fishing, an onboard Mediterranean dinner, unlimited drinks, and sunset views on the way back. Hotel pickup is available from several resort areas.

“I had an extraordinary experience with the yacht company Daneri. The evening trip was unforgettable. The captain was extremely kind and professional, and his vast experience was evident. The cook delighted us with delicious and very tasty dishes, and the deckhand served us impeccably. Although the sea was a bit rough initially, in less than 40 minutes we arrived at a location with calm, turquoise blue water. The experience of captain perfectly combined adrenaline with relaxation, offering everything one could wish for. On our return, the driver waited for us to ensure we got back safely, avoiding any inconvenience. We were impressed by the comfort, elegance, and the crew’s willingness…”

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14.Private Full-Day Sailing Trip to Dia Island

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

You’ll sail from Heraklion to Dia Island on a private boat with a two-person crew, stopping at Saint George Bay for swimming, snorkeling, fishing, and paddleboarding. Unlimited water, soft drinks, wine, fruit, and equipment are included. Add hotel transfers and a full meal for an extra cost.

“Best sailing trip ever! Nikos and Vasilis made our day a wonderful experience !”

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15.Dia Island Luxury Sailing Trip with Meal & Drinks

★★★★★★★★★★4.7 · 107 reviews · from $68

Sail from Heraklion’s Venetian port to protected Dia Island aboard TREATON or JACKPOT. You’ll have time to swim, snorkel, paddleboard, fish, and enjoy shrimp pasta, Greek salad, fruit, beer, wine, and soft drinks. Choose a shared or private morning, sunset, or full-day cruise, with crew such as Joseph, Thanos, Nikos, or Cosmos on selected trips.

“Overall was an amazing experience, definitely worth the money. Would do it again in a heartbeat. The guides were fantastic and very knowledgable about the island. They also made us an amazing lunch and served fruit afterwards! Thank you for an amazing day!!”

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