Dia Island: The 15 Best Sailing Trips from Heraklion

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal - The smooth start: boarding at Cafe Marina in Heraklion

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

A small-group sail from Heraklion to Dia Island in Crete with swimming, snorkeling, paddleboarding, and a Mediterranean meal plus unlimited drinks.

“Perfect friendly Crew. Nice Katamaran. Good drinks and delicious food. It was my third time with this company. Sofia, Giannis and our Captain Petros are a super Crew. I will make the Dia Tour again. I love it sooooo much. Thank you Guys. Nicole”

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Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

2.Sailboat Cruise to Dia Island with Drinks & Lunch

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

Sail from Heraklion to Dia Island on a luxury yacht with snorkeling, unlimited drinks, and lunch, plus optional fishing.

“The trip was excellent and relaxing, especially because our captain and co-captain were very informative and friendly. Overall great experience and the food was amazing too!”

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Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

3.Sailing Cruise to Dia Island with Drinks and Meal

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

Sail from Heraklion to Dia Island for snorkeling, SUP, fishing, drinks, and a Greek meal, with optional sunset views.

“This was a fabulous trip. The staff were very friendly and committed to making sure everyone had a good time. They boat was fantastic and their were enough activities to keen everyone entertained during the cruise. Food was fantastic too. Highly recommend this tour to anyone in Heraklion for the day.”

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Heraklion: Dia Island Sailing Cruise with Snorkeling

4.Dia Island Sailing Cruise with Snorkeling

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

Sail from Heraklion to Dia Island for swimming, snorkeling, paddleboarding, drinks, and Greek food on a small group cruise.

“The Sail Boat tour was extraordinary. We had such a beautiful sunny day. Both the Captains were very incredible. I booked for a Retreat I was hosting in Greece. We were 7 people and had the whole sailboat for ourselves. I booked the half day tour & honestly we loved it so much, that if I was doing it again, I would book the whole day! Highly recommend this experience! So worth it. 🤍 A big Thank you!!!!!! 🇬🇷 Best ever. Oh & the food was simple, but great! & we had lovely music for the whole tour, good ambiance!!!! +++5 stars ✨”

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Sailing Cruise to Dia Island with Meal and Water Activities

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 Dia Island for swimming, snorkeling, SUP, and a shrimp linguini lunch with wine and beer included.

“Our excursion to Dia Island from the port in Heraklion was very enjoyable. About an hour from port, the captain anchored the boat in a small bay off the island. There were two small beaches there. Once arriving, we had 3-4 hours of free time for all sorts of water activities (snorkeling, paddle boarding, swimming off the boat in the bay) Lunch was served (pasta with shrimp, fresh fruit, etc). This was a great vacation activity, especially for kids. Thoroughly enjoyable.”

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Heraklion: Private Half-Day Sailing Trip to Dia Island

6.Private Half-Day Sailing Trip to Dia Island

★★★★★★★★★★4.9 · 466 reviews · 4.5 hours · from $459

Private 4.5-hour sail from Heraklion to Dia Island with snorkeling, fishing gear, paddleboards, drinks, fruit, and optional meal.

“It was a great experience. Best skipper team with Haris and Thomas. Thank you for an unforgettable trip! In August the sea is very rough from noon to afternoon, you should be a bit seaworthy ;)”

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Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

7.Sailing Trip to Dia Island with Lunch & Swimming

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

Sail from Heraklion to Dia Island for snorkeling, SUP, fishing, and a Mediterranean lunch with unlimited drinks in a small group.

“Ilis and Vaso were our guides and we were really pleased with their hospitality. They were very welcoming, ensured we were looked after and had the best possible experience. Food was really lovely and great variety of drinks available on board. They had a paddling board and snorkelling masks available for everyone for when we stopped off to swim. Would recommend, 10/10 experience.”

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Heraklion: Small-Group Sailing Trip to Dia Island with Lunch

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

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

Small-group sailing from Heraklion to Dia Island with crystal coves for snorkel, SUP and wildlife, plus organic lunch and wine.

“We had amazing time on this trip. Crew were very helpful and friendly. Amazing view from the sailing boat. We stopped in very beautiful shore, where we could swim in the sea and have relaxing time. Served food was also great. All in all 100 percent I would recommend this experience. Maybe I would suggest taking a day time trip, because it gets a bit chilly in the evening. But even in the cold weather I had a good time.”

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From Heraklion: Sunset Cruise to Dia Island

9.Sunset Cruise to Dia Island

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

Sail from Heraklion to Dia Island for a half-day cruise with snorkeling, snacks, and golden-bay relaxation, with clear-water swim time.

“Our trip was amazing! A big thank you for our Captain Alex and crew member Yannis from #Cretan yachts. Dia Island has clear, aqua blue, beautiful water. The sunset was so nice! Henk-jan, Diana and Daniel”

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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

10.Sunset Sailing Cruise Dia Island with Snorkeling

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

Heraklion to Dia Island sunset catamaran with snorkel time, paddleboard, food and drinks, and up to 7 hours on Crete.

“Amazing, lovely time in the water, the snorkelling kits and paddle board added to the fun. Great wine on deck too!”

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Heraklion: Dia Island Luxury Catamaran Cruise with Meal

11.Dia Island Luxury Catamaran Cruise with Meal

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

5.5-hour Dia Island catamaran from Heraklion with meal, unlimited drinks, snorkeling, fishing gear, and paddle boards when conditions allow.

“Excellent activity! Really nice boat (around 26 persons per boat) and the waters in dia island are amazing. A really special activity and great crew.”

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Dia island : Small Group Sailing Trip to Dia Island with Lunch

12.Dia island : Small Group Sailing Trip to Dia Island with Lunch

★★★★★★★★★★5.0 · 162 reviews · 4 hours 30 minutes (approx.) · from $72Top rated

Small-group sail to Dia Island from Heraklion with snorkeling, SUP, wildlife chances, and an organic lunch plus pickup.

“Small group tour was amazing; our family of 3 and 2 friends we didn't know - perfect! George and Harry are super knowledgeable and great chefs, each always interacting with one of us. The island taken to was beautiful with the most crystal blue water and it was amazing to watch them direct the boat almost all the way to the beach around other boats anchored in the bay to get us the best spot. They even accommodated one of the girls birthday with a song, hats, and coordinated the surprise with the friend having the cake picked up and brought on board. Boat had plenty of shaded and sunny…”

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Heraklion: Dia Catamaran Tour – Lunch, Open Bar & Snorkeling

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

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

5-hour catamaran from Heraklion to Dia Island with open bar, fresh Mediterranean lunch, snorkeling, SUP, and family-friendly sea fun.

“This excursion was amazing from the beginning. There was lots of places to sit (in and out of the sun), unlimited drinks and the fresh fish lunch was delicious. We had lots of time for activities once at Dia. We would recommend booking on the catamaran as it has more places to sit and was worth the extra money”

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Heraklion: Dia Island Catamaran Cruise with Dinner and Wine

14.Dia Island Catamaran Cruise with Dinner and Wine

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

Cruise from Heraklion to Dia Island on a luxury catamaran with snorkeling gear, unlimited drinks, and a Mediterranean dinner plus sunset views.

“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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