8 Best Heraklion Tours Worldwide

Cruises & Boat Tours, Heraklion, Heraklion Sailing Trips, Island-Hopping Sails, Sailing, Swim-Stop Cruises, Tall Ships & Sailing Boats, Tour Reviews

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

/ June 12, 2026

1.Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

Small-group Dia Island sail from Heraklion with swimming, snorkeling, SUP, a Mediterranean meal, and unlimited drinks on board.

Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

/ June 12, 2026

2.Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

Heraklion to Dia Island by yacht for snorkeling, SUP, drinks, and a Mediterranean meal. Dolphins if lucky. 6 hours.

★ 4.9

“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”

778 reviews6 hoursFrom $106by Sailing Grace

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Cruises & Boat Tours, Heraklion, Heraklion Sailing Trips, Island-Hopping Sails, Sailing, Snorkel Sailing Trips, Snorkeling, Tour Reviews

Heraklion: Dia Island Sailing Cruise with Snorkeling

/ June 12, 2026

3.Heraklion: Dia Island Sailing Cruise with Snorkeling

Sail from Heraklion to uninhabited Dia Island for snorkeling and paddleboarding, plus drinks and Greek seafood meals on a small group yacht.

★ 4.7

“The team,the activities snd spots with clear water”

742 reviews4.5 - 7 hoursFrom $82by Sailing Crete

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Cruises & Boat Tours, Evening Experiences, Heraklion, Heraklion Sailing Trips, Island-Hopping Sails, Sailing, Snorkel Sailing Trips, Snorkeling, Sunset Sails, Tour Reviews

Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

/ July 26, 2026

4.Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

Heraklion to Dia Island at sunset: snorkel, paddleboard, and enjoy Greek food and drinks on a small catamaran.

★ 4.7

“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…”

529 reviews4.5 - 7 hoursFrom $82by Sailing Crete

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Cruises & Boat Tours, Heraklion, Heraklion Sailing Trips, Island-Hopping Sails, Sailing, Tour Reviews

Sailing Cruise to Dia Island with Meal and Water Activities

/ July 26, 2026

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

5.5-hour Dia Island sailing from Heraklion with swimming, snorkeling, SUP, and an on-board lunch plus drinks in a small group.

★ 4.5

“Amazing experience, a very relaxed activity, the vive , the staff, everything was great. A day to remember.”

526 reviews5 hours 30 minutes (approx.)From $96.74by Cretan Sailing Cruises

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Cruises & Boat Tours, Heraklion, Heraklion Sailing Trips, Island-Hopping Sails, Lunch Experiences, Sailing, Swim-Stop Cruises, Tour Reviews

Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

/ July 26, 2026

6.Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

Small-group sailing from Heraklion to Dia Island with lunch, unlimited drinks, snorkeling and SUP, plus dolphin-spotting at sea.

★ 4.8

“We had an absolutely wonderful time. Our captain, Nick was excellent. Mike made a delicious pasta and shrimp dinner and the other young crew member (I can’t remember his name) was very sweet and friendly. All of the crew was very knowledgeable and took good care of all of us. We loved swimming at Dia…”

517 reviews6 hoursFrom $100by Set Sails

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Cruises & Boat Tours, Heraklion, Heraklion Sailing Trips, Sailing, Tour Reviews

Dia Sailing Cruise With All-inclusive Meal And Drinks

/ July 31, 2026

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

5.5-hour Dia Island sailing from Heraklion with snorkeling and SUP, plus an all-inclusive Mediterranean meal and unlimited Greek wine.

★ 4.6

“It was the best thing we did all trip. I was nervous because when I asked for direction, a local said that these tours only run the the summer. it just runs less frequently. It was amazing. Food and drinks were lovely. The host were great too. The water was perfect for swimming. It was…”

422 reviews5.5 hoursFrom $76by Rocca a Mare sailing adventures

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