8 Heraklion Island Hopping Tours Worth Boarding

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 yacht limited to 14 people. Your English-speaking crew, including a certified captain, serves shrimp linguini, Greek salad, Cretan appetizers, and unlimited drinks, with time for swimming, snorkeling, paddleboarding, and sunset sailing.

“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 $106Top rated

Sail from Heraklion’s Venetian harbor to uninhabited Dia Island with a certified crew, snorkeling gear, SUP boards, fishing equipment, lunch, wine, soft drinks, and raki. You’ll hear island legends, swim in clear water, and return by sail, with sunset departures available.

“Literally so nice, personable and professional. We made friends with others on the tip facilitated by the captain. Not been cheesy but we will be lifelong friends.”

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3.Dia Island Sailing Cruise with Snorkeling

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

Sail from Heraklion with a small crew of up to 18 people to uninhabited Dia Island. Expect swimming, snorkeling, paddleboarding, drinks, and food onboard. Ernesto and George are among the crew members, and the half-day or full-day format lets you match the trip to your schedule.

“A beautiful day, great weather, calm sea. Crew were kind and great to talk with. Really enjoyed snorkelling, the water was magical!”

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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 professional crew, snorkeling gear, paddleboard, food, drinks, and time to swim. Full-day trips add a second bay and a seafood meal, while half-day trips focus on one cove and sunset sailing.

“Thoroughly enjoyed! nice crew and nice ppl on board”

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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 with a small crew and time to swim, snorkel, fish, paddleboard, and sunbathe. Lunch includes shrimp linguine, Greek salad, Cretan appetizers, and fruit, with beer, wine, soft drinks, and water. Pickup is available across much of Crete.

“Perfect day sailing and enjoying the sun and sea!!! The crew was great and the food was delicious!!!”

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6.Sailing Trip to Dia Island with Lunch & Swimming

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

Join a six-hour small-group sailing trip from Heraklion to Dia Island with up to 10 people. Captains George, Panos, and Vaso share local stories while you swim, snorkel, paddleboard, fish, and enjoy shrimp or vegetarian pasta with drinks on board.

“We are a family of 5 and were lucky to share the yacht with just another family of 3 and our lovely guides George and Marcos. It was a very hot, still day so we couldn’t actually sail but this meant for beautiful calm waters and exceptional swimming and snorkelling when we got to Dia Island. Lunch was delicious too. All in all a fabulous trip!”

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7.Heraklion Luxury Sailing Catamaran Dia Island | Gourmet Menu

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

Sail from Heraklion to Dia Island aboard EOS Yachts’ modern catamaran, limited to 22 people. The crew serves Cretan treats, seafood cooked by Chef Charis, local wine, beer, and dessert. You’ll have about three hours for swimming, snorkeling, fishing, canoeing, and paddleboarding in a sheltered bay.

“The yacht itself exceeded my expectations. It was very spacious with luxurious touches. The boat did not feel crowded. The crew were very attentive and welcoming. They were constantly offering us drinks or assistance. The meal was also delicious, gourmet quality. The sunset ride back was stunning. Highly recommend.”

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8.Sunset Cruise to Dia Island

★★★★★★★★★★4.8 · 259 reviews · 5.5 hours · from $82

Sail from Heraklion’s Old Port to Dia Island aboard the MARYLINE, with about 3.5 hours for swimming, snorkeling, snacks, and beach time. Captains and crew such as Alex, Yannis, Kosta, and Niko have hosted departures, with English and Greek guidance, music, and an introduction to sailing.

“We had such a fun afternoon! Alex and his partner were so funny and made for a comfortable trip to Dia! We had great conversation and food and drinks offered throughout. Everything was explained thoroughly including what to expect. It was my first time on a sailboat and the guides were incredible and so reassuring. Would 100% recommend if you’re looking for a fun day trip to Dia! Thank you so much for making our trip so fun and such an easy experience! We hope to come back again and will 100% be looking for you guys again - the best! Thank you!”

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