Where to Sail: the 4 Best Sailing Trips in Crete

1.Sailboat Cruise to Dia Island with Drinks & Lunch

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

Sail from Heraklion to Dia Island on a shared yacht trip with lunch, local wine, soft drinks, snorkeling gear, paddleboards, and optional fishing. You get about four to six hours on the water, with crew such as Stavroula, Dennis, or Mido. Private and one-hour coastal options are also available.

“The activity was very well organised (10/10) as well as the pick up and drop off service.”

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2.Private Half-Day Sailing Trip to Dia Island

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

You’ll sail from Heraklion with a two-person English or Greek-speaking crew to Dia Island’s Gulf of Saint George, once explored by Jacques Yves Cousteau. Expect a private boat for up to eight, clear water for swimming and snorkeling, fishing gear, paddleboards, fruit, wine, soft drinks, and about 2.5 hours at anchor. Hotel transfers and full meals cost extra.

“Sailing trip was great, guides gave a lot of explanation concerning the boat, island and history.”

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3.Balos Gramvousa Sailing Cruise with Lunch

★★★★★★★★★★4.9 · 257 reviews · 7.5 hours · from $229

Sail from Kissamos to Balos Lagoon and Gramvousa Island aboard a small shared or private boat with an experienced skipper. Swim, snorkel, hike to Gramvousa Castle, and enjoy a fresh Cretan lunch with drinks, fruit, and shaded deck seating. Guides such as Vasilis, Katarina, Jo, and Luis help make the day personal and relaxed.

“Vasilis and Katarina were amazing and we loved it! Delicious lunch and gorgeous views. We felt safe and enjoyed the ride. Definitely would recommend.”

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4.Balos & Gramvousa Luxury Catamaran Sailing Cruise from Kissamos

★★★★★★★★★★5.0 · 116 reviews · 7 hours 30 minutes (approx.) · from $235Top rated

Sail from Kissamos to Balos Lagoon and Gramvousa on a small catamaran limited to 22 people. Swim, snorkel, paddleboard, and enjoy Greek snacks, a Mediterranean lunch, drinks, and attentive crew such as Dimitri, Yannis, and Jessica. The early start helps you reach both stops before the large ferries arrive.

“Dimitri, Yanni and Jessica were amazing during our tour. It was an amazing day with my husband and two teens. Thank you!!”

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