CRETE

Best Sailing In Crete

Crete’s best days out.

The 15 most popular sailing on Crete — what each day actually involves, what it costs, and the operator running it.

15 Best Sailing In Crete

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal - Meeting at Cafe Marina and getting on the yacht without stress

Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch - Meeting up near Marina Cafe: small timing details that matter

2Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

Heraklion to Dia Island sailing with snorkeling gear, unlimited drinks and local wine, and a filling onboard lunch on a small yacht.

★ 4.9

“This activity was amazing, great communication from the get-go, staff were lovely and very knowledgeable, the transport shuttle was on time and quick, the boat and Dia Island were stunning and the food and drinks were great - especially if you like a sweeter white wine!”

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Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

Heraklion: Sailing Cruise to Dia Island with Drinks and Meal - The Onboard Meal and Drinks: What a Mediterranean Lunch Feels Like at Sea

3Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

Sail from Heraklion to Dia Island for snorkeling, SUP, dolphins stories, and a full onboard Mediterranean meal with drinks.

★ 4.9

“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

Heraklion: Dia Island Sailing Cruise with Snorkeling - Dia Island: the swimming, snorkeling, wine, and photo stop package

Sailing Cruise to Dia Island with Meal and Water Activities

Sailing Cruise to Dia Island with Meal and Water Activities - Getting on board: pickup, meeting point, and what to expect

5Sailing Cruise to Dia Island with Meal and Water Activities

Sail to Dia Island from Heraklion for snorkeling, SUP, swimming, and a full lunch with drinks, plus time on board to relax.

★ 4.5

“Very pleasant cruise out to Dia Island. The crew was wonderful and provided excellent service. We did have to wait to dock, but it was pleasant to chat with other passengers while waiting. Would definitely recommend this trip.”

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Heraklion: Private Half-Day Sailing Trip to Dia Island

Heraklion: Private Half-Day Sailing Trip to Dia Island - The private yacht setup: comfort, shade, and real “vacation mode”

Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

Heraklion: Sailing Trip to Dia Island with Lunch & Swimming - Getting on board: Old Anchor meeting point and optional transfers

7Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

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

★ 4.8

“The boat ride was amazing! sit went very smoothly and our guides were great! George and Vaso. It was very relaxing, the shrimp pasta and greek salad were very good. They also had pesto pasta as a substitute. Snorkeling, swimming, paddle board, and laying in the sun were all a blast. I recommend it 100%”

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Kolimvari: Sailing Cruise with Meal & Water Activities

Kolimvari: Sailing Cruise with Meal & Water Activities - The sailing hour along Chania’s north coast (and what it’s good for)

Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling - Half-Day vs Full-Day: Choosing the Right Amount of Sea Time

Sailing trip to the Top Coasts of Crete, Daily/Multi-day

Sailing trip to the Top Coasts of Crete, Daily/Multi-day - Your boat setup for a 7-hour day (shade, cabin, and downtime)

Heraklion: Dia Island Luxury Catamaran Cruise with Meal

Heraklion: Dia Island Luxury Catamaran Cruise with Meal - From Cafe Marina to the Catamaran: Getting There Without Panic

11Heraklion: Dia Island Luxury Catamaran Cruise with Meal

Heraklion to Dia Island on a Lagoon catamaran: snorkeling, SUP and swim time plus a Mediterranean meal and unlimited drinks.

★ 4.7

“This was by far one of the best experiences I’ve had on vacation. 9 of my closest friends joined me, and we had the time of our lives. Sophia, as well as the captain, were very knowledgeable, attentive to any needs we had, and they made an absolutely delicious lunch with the best Greek salad…”

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Heraklion: Dia Island Catamaran Cruise with Water Toys

Heraklion: Dia Island Catamaran Cruise with Water Toys - Price and value: why $151.23 can make sense

12Heraklion: Dia Island Catamaran Cruise with Water Toys

Half-day catamaran cruise from Heraklion to Dia Island with tons of water toys, nutritionist-made lunch, and unlimited drinks in a small group.

★ 5.0

“Great activity to relax in Heraklion! Great staff, safe ride and a lot of food for everyone. We had a great time in the water the location was great and not too crowded.”

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Chania: Afternoon Catamaran trip – Dinner, Drinks & Sunset

Chania: Afternoon Catamaran trip - Dinner, Drinks & Sunset - The catamaran setup: space to lounge, music to keep it light

13Chania: Afternoon Catamaran trip – Dinner, Drinks & Sunset

5-hour catamaran from Kolymvari with dinner and unlimited drinks, snorkeling and SUP, plus a sunset sail near Agioi Theodoroi in Crete.

★ 4.9

“We had the best time on our catamaran cruise in Chania! From start to finish, the experience was incredible. The captains and crew were amazing, so friendly, professional, and clearly passionate about what they do. They provided everything you could need for a fun and relaxing time in the bay, snorkeling gear, paddle boards, floaties,…”

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

Dia island : Small Group Sailing Trip to Dia Island with Lunch - The protected cove stop: snorkeling, SUP, and wildlife chances

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

Heraklion: Dia Catamaran Tour - Lunch, Open Bar & Snorkeling - Boarding at Marina Café: Arrive Early, Then Get Comfortable

15Heraklion: Dia Catamaran Tour – Lunch, Open Bar & Snorkeling

Heraklion to Dia Island on a spacious catamaran with open bar, snorkeling, SUP, and a Mediterranean lunch. 5 hours of sea time.

★ 4.9

“I had the pleasure of experiencing a catamaran cruise to Dia Island, and it was spectacular. This trip provided a perfect blend of relaxation, adventure, and breathtaking scenery. The catamaran itself was modern, spacious, and well-maintained. The seafood was just perfect. Big bravo to the chef Konstantinos. The boat had plenty of sea toys like…”

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More Sailing In Crete