The 9 Sailing Trips in Crete That Earn Their Price

1.Dia Island Sailboat Cruise with Swimming and Meal

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

Review of Crete’s Dia Island sailing cruise from Heraklion, with swimming, snorkeling, paddleboarding, a Greek meal, drinks, and sunset options.

“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.Sailboat Cruise to Dia Island with Drinks & Lunch

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

Sail from Heraklion to Dia Island for swimming, snorkeling, lunch, unlimited drinks, and relaxed yacht time on Crete’s clear waters.

“I loved the sailing trip and the time we had to swim. The skipper and first mate were friendly and professional. The meal was healthy and delicious. The crew provided a quick safety talk, rules of the vessel, and tips for a successful sailing trip. This was a great afternoon that I was sad to see end.”

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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 swimming, snorkeling, SUP, Greek food, drinks, and sunset views on a six-hour yacht cruise.

“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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4.Dia Island Sailing Cruise with Snorkeling

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

Review of the Heraklion to Dia Island sailing cruise, with snorkeling, paddleboarding, meals, drinks, crew details, costs, and practical tips.

“The crew was super friendly. Even the weather condition was not the best, the travel went quite smooth. The bays are there just amazing. Only dis thing was, I was expecting to swim in more spots (we did 2), but the places we swam was fantastic 🥰 The food was not great but it tastes good since you became super hungry 😁”

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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 $97

Sail from Heraklion to Dia Island for swimming, snorkeling, paddleboarding, a Cretan lunch, drinks, and a relaxed small-group day at sea.

“Very confusing figuring out who the contact people were, ours wasn't very friendly and hard to understand..boat MUCH smaller than pic and NO island, stuck in windy spot w/ warm beer and little rooom.”

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6.Balos & Gramvousa Luxury Catamaran Sailing Cruise

★★★★★★★★★★4.9 · 516 reviews · 7 - 8.5 hours · from $229

Review of the Balos and Gramvousa luxury catamaran cruise from Kissamos, including food, stops, costs, transfers, and practical booking tips.

“Great day out on the water, great crew who looked after us all day.”

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7.Private Half-Day Sailing Trip to Dia Island

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

Sail from Heraklion to Dia Island on a private yacht with swimming, snorkeling, fishing, fruit, drinks, and optional lunch.

“The guys were great! They knew what they were doing and we’re super accommodating! Definitely recommend 😁”

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8.Sailing Trip to Dia Island with Lunch & Swimming

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

Review of Crete’s Dia Island sailing trip from Heraklion, with lunch, swimming, snorkeling, SUP, fishing, drinks, transport, and practical tips.

“Niko and Dmitri were brilliant! They couldn’t do enough for us and were very attentive. The food was great and the whole experience was the highlight of our trip! They were very friendly and I would give them 10/10 for the trip! Thank you guys!”

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9.Kolimvari: Sailing Cruise with Meal & Water Activities

★★★★★★★★★★4.7 · 390 reviews · 5 hours · from $129

Sail from Kolymvari to Agioi Theodoroi for clear-water swimming, snorkeling, SUP, a fresh meal, and unlimited drinks on a small yacht.

“A great experience combining sailing, swimming, paddle boarding and delicious lunch in a stunning part of the Mediterranean”

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