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15 Island Hopping Sailing Trips in Crete to Build a Day Around

18 sailing trips  ·  from $35 a head

The 15 best island hopping sailing trips in Crete you can book right now, with the price a head, how long each one runs and whether the sails go up. Number one is first for a reason.

Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch - Dia Island’s clear water and quiet cove
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Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

1.Sailboat Cruise to Dia Island with Drinks & Lunch

★★★★★★★★★★4.8 · 1,405 reviews · 1 hour - 390 minutes · from $35Our pick

Review of Crete’s Dia Island sailing trip from Heraklion, with yacht views, swimming, snorkeling, lunch, drinks, costs, and practical tips.

“A very choppy crossing to the island. Very well handled by the skipper though The boat was comfortable and safety was well looked after Food was very good. Would have been nice to have beer as an option perhaps Time went very quickly”

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Heraklion: Private Half-Day Sailing Trip to Dia Island - Dia Island and Saint George Bay
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Heraklion: Private Half-Day Sailing Trip to Dia Island

2.Private Half-Day Sailing Trip to Dia Island

★★★★★★★★★★4.9 · 466 reviews · 4.5 hours

Review of Heraklion’s private Dia Island sailing trip, with snorkeling, fishing, lunch options, pricing, timing, and practical tips.

“It was a lovely sailing experience. It was beautiful and well organised. The staff was very friendly and kind. The overall experience was amazing and would 10/10 recommend it!”

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Dia island : Small Group Sailing Trip to Dia Island with Lunch - The one-hour sail to Dia Island
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Dia island : Small Group Sailing Trip to Dia Island with Lunch

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

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

Review of the Dia Island sailing trip from Heraklion, with lunch, swimming, snorkeling, wildlife, pickup details, value, and practical tips.

“Absolutely fantastic excursion! We ended up having the entire boat to ourselves and the team really accommodated us and ensured we really had an amazing time. Lunch/wine onboard was delicious and they were fantastic photographers making sure we got ample amount of photos”

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Heraklion: Private Full-Day Sailing Trip to Dia Island - Meeting the crew at Heraklion Marina
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Heraklion: Private Full-Day Sailing Trip to Dia Island

4.Private Full-Day Sailing Trip to Dia Island

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

Review of a private Heraklion sailing trip to Dia Island, with swimming, snorkeling, fishing, lunch options, drinks, and practical booking advice.

“We told the guides we were more interested in sailing than the excursions and they accommodated our request. The Elan 37 is a fun boat and she sailed well even in light winds. The lunch was delicious and we enjoyed it in an idyllic bay on Dia island. The captain and first mate were vey kind and helpful with our two kids. I highly recommend this excursion and will book again if we return to Crete.”

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Dia Island Catamaran – Premium Lunch, Open Bar, Small Group - What the small group really changes
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Dia Island Catamaran – Premium Lunch, Open Bar, Small Group

5.Dia Island Catamaran – Premium Lunch, Open Bar, Small Group

★★★★★★★★★★5.0 · 126 reviews · 6 hours 30 minutes (approx.) · from $181

Review of Crete’s Dia Island catamaran cruise, with a small group, fresh Mediterranean lunch, open bar, swimming, snorkeling, and SUPs.

“This was a great experience. The captain and the crew were awesome. Crew answered all questions and were very pleasant at all time. The captain was amazing. He engaged all passengers trying to teach us typical Greek dance and later put on a concert as Johnny Depp. The lunch was amazing. Made fresh as we were all swimming. It was great. This was truly a 5 star trip.”

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Sailing Trip to Dia Island - All Inclusive - A fresh lunch served on the boat
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Sailing Trip to Dia Island – All Inclusive

6.Sailing Trip to Dia Island – All Inclusive

★★★★★★★★★★5.0 · 67 reviews · 6 to 8 hours (approx.) · from $90

Review of Crete’s all-inclusive Dia Island sailing trip, with swimming, snorkeling, paddleboarding, seafood pasta, drinks, pricing, and practical tips.

“A great day out! George and Niko were incrediblley friendly and I feel like we became fast friends through the day. The water was cool but clear as crystal, easy to see the fish! The sun was great at drying us off upon leaving the ocean for a fresh made meal which we enjoyed with our new found friends (including the other visitors) on the boat. The island is practically untouched and has only a few buildings. Stunning views all round, throughout the whole trip...”

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Sailing to Dia Island with lunch on Bavaria 51 Heraklion, Crete - Leaving Heraklion aboard Bavaria 51
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Sailing to Dia Island with lunch on Bavaria 51 Heraklion, Crete

Heraklion | Half day Sailing cruise to Dia Island - What the boat ride feels like
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Heraklion | Half day Sailing cruise to Dia Island

From Heraklion:Small group 5,5h Sunset Sailing trip to Dia Island - Heraklion’s Old Venetian Harbor from the water
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From Heraklion:Small group 5,5h Sunset Sailing trip to Dia Island

9.Small group 5,5h Sunset Sailing trip to Dia Island

★★★★★★★★★★4.5 · 26 reviews · 6 hours (approx.) · from $84

Review of a six-hour sunset sailing trip from Heraklion to Dia Island, with snorkeling, snacks, small groups, and practical booking advice.

“Our young skipper was delightful and spoke excellent English. We really enjoyed our cruise to Dia Island. The water where we snorkeled was a beautiful turquoise, and you could see to the bottom.”

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Private Luxury Sailing Trips to Dia Island - St. George’s Bay on Dia Island
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Private Luxury Sailing Trips to Dia Island

Private Sailing Cruise from Heraklion to Dia Island - A little archaeology beside the swimming stop
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Private Sailing Cruise from Heraklion to Dia Island

All-inclusice Catamaran Day Cruise from Hersonissos to Dia Island - The catamaran is part of the experience
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All-inclusice Catamaran Day Cruise from Hersonissos to Dia Island

12.All-inclusice Catamaran Day Cruise from Hersonissos to Dia Island

★★★★★★★★★★5.0 · 22 reviews · 6 hours 30 minutes (approx.) · from $174

Review of the all-inclusive Hersonissos to Dia Island catamaran cruise, with snorkeling, lunch, drinks, family tips, price, and practical details.

“Thomas and the crew were fabulous! So kind and welcoming. Very organized while providing refreshments throughout a wonderful afternoon cruise as well as a second sunset cruise that we purchased. Both were spectacular. Highly recommend Daneri Yacht cruises while visiting Crete.”

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Small Group Sailing Cruise from Heraklion to Dia Island - Swimming and snorkeling in clear Cretan water
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Small Group Sailing Cruise from Heraklion to Dia Island

13.Small Group Sailing Cruise from Heraklion to Dia Island

★★★★★★★★★★5.0 · 15 reviews · 6 hours (approx.) · from $102

Sail from Heraklion to quiet Dia Island for swimming, snorkeling, ruins, a meal, and sunset views in a small group of ten.

“We had a wonderful time with the excellent team. All of us were excited to pass giant sea turtles as we were sailing and we saw a few different types of fish whilst snorkeling at Dia. We went on the sunset tour, which meant no early start and a fabulous end to the day watching the sunset on our way back to the harbour. Thank you for a fantastic trip. 100% recommended!”

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Sailing day to Dia island - The one-hour crossing to Dia island
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Sailing day to Dia island

14.Sailing day to Dia island

★★★★★★★★★★4.5 · 13 reviews · 7 hours (approx.) · from $102

Sail from Heraklion to Dia island for swimming, snorkeling, paddleboarding, and a homemade meal in a small 10-person group.

“A great trip on the water… The captain and host did a great job in coordinating and creating a welcoming experience. The wind caused the waves in the sea to be a bit rough but the captain did a great job controlling everything to feel comfortable! Once at Dia, we were able to swim, use snorkeling gear, lounge on the boat while the hostess made us a really nice homemade like meal. On other sailing experiences I’ve gone on, it’s always been a pre made meal. This was a pasta with seafood and tomato sauce, Greek salad, bread/breadsticks, and tzatziki. Wine, orange juice, water, cola were served on board. Thank…”

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From Heraklion : Small Group 5,5 hours Sailing Trip to Dia Island - A yacht prepared for a half-day on the water
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From Heraklion : Small Group 5,5 hours Sailing Trip to Dia Island

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