The 15 Sailing Trips in Crete That Earn Their Price

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal - Why 14 people changes the day

★★★★★★★★★★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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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 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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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 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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Heraklion: Dia Island Sailing Cruise with Snorkeling

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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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 $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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Kissamos: Balos & Gramvousa Luxury Catamaran Sailing Cruise

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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Heraklion: Private Half-Day Sailing Trip to Dia Island

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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Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

8.Sailing Trip to Dia Island with Lunch & Swimming

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

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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Kolimvari: Sailing Cruise with Meal & Water Activities

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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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

10.Sunset Sailing Cruise Dia Island with Snorkeling

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

Sail from Heraklion to quiet Dia Island for snorkeling, paddleboarding, Greek food, drinks, and a beautiful sunset return.

“This experience was the cherry on the cake for our trip here. For a cheap price a 4 hour boat-trip with food, amazing view on the sea and sunset, snorkling and swimming. The guides/captains were all very kind. 10/10 would recommend.”

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

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

★★★★★★★★★★5.0 · 221 reviews · 7 hours (approx.) Top rated

Sail Crete’s car-free southern coast to Loutro, Sweet Water, and Marmara Beach, with swimming, lunch, snacks, and time to relax.

“Beautiful, non-touristy sailing trip. Swam in some amazing caves. Visited a village that you can only access by boat or hiking. A day we will never forget!!”

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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 $73

Review of Crete’s small-group sailing trip to Dia Island, with swimming, snorkeling, SUP boards, organic lunch, drinks, and hotel pickup.

“Awesome sailing trip thanks to friendly and passionate about their job skippers. Picking up was really chaos, we were said to remain at Marina Cafe at 16h and 16h30 we still didn’t know what was happening. Other companies staff came and asked to people about their sailing activities but not our contact. After running from one side to another, we found by ourselves the boat. Somethig to be corrected, for sure. After that bad moments, everything changed thanks to Costas and Mario Young skippers, explaining interesting things and very professional. We had time to swim as snorkelling, a lovely and tasty dinner and we were enjoying sunset coming back.”

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From Kissamos: Balos Gramvousa Sailing Cruise with Lunch

13.Balos Gramvousa Sailing Cruise with Lunch

★★★★★★★★★★4.8 · 153 reviews · from $615

Review of the 8-hour Kissamos sailing cruise to Balos and Gramvousa, with Cretan lunch, snorkeling, castle views, and practical booking tips.

“The Itinerary/time plan was just perfect! You have some time to explore both Gramvousa and Balos (I could definitely spend the more time at both stops just because the waters are so lovely. the time plan was very reasonable, so no rush or anything very chill). More importantly, you can kinda avoid/miss the crowds (who are coming with the big boats) and enjoy the stunning view more peacefully. Super friendly and helpful staff! nicely prepared fresh lunch. Would definitely recommend.”

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Sailing Trip to Dia with Snorkeling, Dining & Sunset Option

14.Sailing Trip to Dia with Snorkeling, Dining & Sunset Option

★★★★★★★★★★5.0 · 142 reviews · 4 hours 30 minutes (approx.) · from $36Best value

Sail from Heraklion to Dia Island for snorkeling, a fresh Cretan lunch, wine, and a sunset return aboard a small yacht.

“Fabulous trip and experience, great food and friendly staff made the experience special. We travelled as two couples and one vegetarian and accommodated”

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Heraklion: Private Full-Day Sailing Trip to Dia Island

15.Private Full-Day Sailing Trip to Dia Island

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

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

“Our sailing trip to Dia Island was an unforgettable experience! From the moment we stepped aboard, the crew made us feel right at home. They were exceptionally accommodating, ensuring that every detail was perfect for our family. The boat was well-maintained, and the journey was smooth and scenic. We were able to relax, swim in crystal-clear waters, and even snorkel around the island. The crew's knowledge of the area and genuine hospitality made the trip even more special. If you're in Crete and looking for a unique adventure, this is an absolute must-do. We'll definitely be back for another voyage!”

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