The 14 Crete Sailing Trips That Earn Their Price

1.Sailboat Cruise to Dia Island with Drinks & Lunch

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

Choose a shared half-day sail to Dia Island with lunch, wine, soft drinks, snorkeling gear, paddleboards, and fishing equipment, or book a private trip. A one-hour coastal option stays near Heraklion and includes drinks but no lunch or water activities.

“It takes a conciderable while to get to the island and there isn't a lot to look at in the meantime, I wish the boat was faster. The island looks nice upclose, but it's unfortunatelly not allowed to take a look around from a hill - you can only stay on the beach and visit an old... church? On the other hand, staying in the water is perfectly fine, as it's crystall clear, you can see the sea floor and there's a lot of fish around. While I recommend bringing your own snorkel, the equipment is provided. Good thing they also have flippers. Beware the see urchins - the shore…”

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2.Private Half-Day Sailing Trip to Dia Island

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

Cruise privately from Heraklion to Dia Island with a two-person crew, stopping in Saint George Bay for swimming, snorkeling, fishing, paddleboarding, and lunch if added. The 4.5-hour trip includes drinks, wine, fruit, gear, and plenty of deck space for up to eight people.

“Amazing! We chose to be picked up from our resort, communication and transport great! The boat was private, with only the 5 of us plus Marius and Marisa (the two captains) and had lots of space. The ride was lovely, and when we got to Dia Island, we had over 2 and a half hours to swim, snorkel, and ate lovely fresh salad and sandwiches (made by the captains) which were incredible. They were so welcoming and made us feel so welcome. Amazing value for money, especially for such a private trip with a lovely, modern boat. Would 100% recommend and do it again.”

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3.Luxury Catamaran Cruise, Dia Island –Open Bar & Lunch -Top Rated!

★★★★★★★★★★5.0 · 143 reviews · 5 hours 30 minutes (approx.) · from $145Top rated

Sail from Heraklion to Dia Island aboard a luxury catamaran with a certified English-speaking crew. You get a seafood Mediterranean lunch, Cretan snacks, unlimited local wine and beer, plus snorkeling, SUP, fishing, canoe boards, and a peaceful three-hour stop in the bay.

“The best caramaran in the port and I'm sure is the crew. Amazing captain, chef and assistant. Beautiful and tasteful food, with dinner and snacks before and after. Everything is thought of, even SUPs and snorkel equipments. Captain anchored us in the best spot in the bay, close to the shore. Amazing experience, would reccomend to anyone.”

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

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

Sail from Heraklion to Dia Island aboard a yacht limited to 10 people. Swim and snorkel in St. George’s Bay, enjoy a fresh meal with Cretan wine, then choose the sunset return. Pickup is available from many Crete resort areas.

“Great trip!! When we arrived at Dia, we swam and went snorkelling. Lunch was average, but wasn’t there for the food. The sunset cruise on the way back was amazing. The family enjoyed this trip!!”

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

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

Join an English-speaking crew aboard a luxury catamaran from Heraklion for a 6.5-hour trip to Dia Island. Captain Spiro, George, Alexandra, Thomas, Anise, and other crew members have been praised for friendly service. Expect swimming, snorkeling, paddleboarding, fishing, fresh lunch, and drinks in a bay of clear water.

“Lovely relaxing day out visiting dia island , hosts were friendly and meal cooked onboard was exceptional. Whilst on board you can use snorkeling equipment, sup boards and floats. Highly recommend for a chilled day out Only issues we found was that a few clips were broken on the front of the boat seats at knee level...a few of us got scratched as they're quite sharp so could do with being replaced along with a lock on the toilet door which was missing”

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6.Balos & Gramvousa Luxury Catamaran Sailing Cruise from Kissamos

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

Sail from Kissamos with an English-speaking crew that may include Dimitri, Yannis, and Jessica. You’ll visit Balos Lagoon and Gramvousa, swim, snorkel, paddleboard, enjoy Greek snacks and a cooked Mediterranean lunch, and return after about 7.5 hours. The catamaran carries up to 22 people.

“Wonderful day on the water! The crew members (Demitri & Jessica) were awesome, ensuring that we were never without food and beverages, and were always there to entertain and explain the different sites! The food (prepared by Jessica) was absolutely delicious with plenty to go around! This tour definitely did not disappoint!! Highly recommend!”

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7.Luxury Catamaran Cruise with Lunch & Open Bar

★★★★★★★★★★5.0 · 80 reviews · 6 hours 30 minutes (approx.) · from $174

Set sail from Panormo at 9:30 am on a modern catamaran with an English-speaking crew. Enjoy a healthy breakfast, Cretan lunch, local wine and beer, swimming, SUP, snorkeling, fishing, shaded lounges, and a small group capped at 20 people.

“Great Experience. Crew was amazing. Had a really fun time. Couldn't fault the experience. The crew were great with the kids in the family too.”

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8.Luxury Sunset Catamaran Cruise Sushi & Open Bar

★★★★★★★★★★5.0 · 61 reviews · 3 hours 30 minutes (approx.) · from $96

Sail from Hersonissos toward Malia Bay and Saint George Bay on a luxury catamaran with an English-speaking crew. You get Prosecco, sushi, fruit, an open bar, snorkeling, paddleboards, fishing, and sunset views. The boat holds up to 20 people and returns to the same marina.

“The boat was very nice and lots of room for everyone to sit & spread out which felt luxurious. I might have gone in with higher expectations however I felt that we were left to our own devices for the whole trip. We all got less than half a glass of bubbly on boarding then were told it was a bit choppy at sea so spent an hour or so sailing until we pulled up somewhere calmer for swimming but there was no communication that this would be our only stop we made an assumption as was too choppy. There were some snacks put out & it was a help…”

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9.Sunset Dia Catamaran Cruise by Top-50 Greek Chef

★★★★★★★★★★5.0 · 43 reviews · 5 hours 30 minutes (approx.) · from $144

Join George, Andy, and Costos for a five-and-a-half-hour sunset sail from Heraklion to Dia Island. Swim, paddleboard, fish, and enjoy seafood, Cretan dishes, unlimited drinks, and sunset views aboard the area’s largest catamaran.

“We were attended to the moment we arrived, being greeted before we could even open the doors to our van. Kindly and safely welcomed us aboard and we had a personal hiccup that we were unsure how to solve but were helped so quickly and efficiently after a suggestion from George. The ride was smooth and entertaining the whole way through. And the attention to our needs was fantastic. We got to hear an interesting story of the history of Dia island and enjoy some games and laughter too. The snacks were so simple but so delicious but the sea bass in the main, stole the show. We had the…”

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10.Balos and Gramvousa Private Sailing Trip with Meal

★★★★★★★★★★4.8 · 41 reviews · 8 hours

Spend eight hours aboard the private sailboat Izabela, cruising from Kissamos to Balos Lagoon and Imeri Gramvousa. Swim, snorkel, hike to a Venetian fortress, and enjoy Cretan food, wine, beer, and soft drinks with your group and crew.

“We had a brilliant experience! We were a family of 10 and it was perfect! Just the right amount of time, the lunch was excellent and Skipper was very accommodating. The family have all agreed that it was the best! Highly recommend!!”

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11.Luxury Sunset Catamaran Cruise Sushi & Open Bar

★★★★★★★★★★5.0 · 39 reviews · 3 hours 30 minutes (approx.) · from $101

From Panormo Port, you’ll sail toward Bali Bay or Skaleta aboard a luxury catamaran with a maximum of 20 people. Expect Prosecco, sushi, Greek wine, swimming, SUP boards, snorkeling, and a sunset return, all with an English-speaking crew.

“The trip was perfect from start to finish! Brilliant crew, spacious boat, not too many people, good quality food and drink. The sunset and Coast as we sailed were just magical.”

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12.Private Sailing Cruise, Balos and Gramvousa with meal and drinks.

★★★★★★★★★★5.0 · 38 reviews · 8 hours (approx.)

Spend about eight hours aboard the private sailing boat Izabela, cruising from Kissamos to Balos and Gramvousa. Skippers such as Christopher, George, Yanni, and Alex tailor the day to your group, with Cretan lunch, beer, wine, snorkeling gear, umbrellas, and time for swimming.

“This was a family trip and if you come to Crete I highly recommend this trip. The captain Cristopher was very knowledgeable and always ready to help you out. We felt safe and we enjoyed every part of the trip. Don’t miss this experience… it was amazing.”

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13.Private Sailing Cruise from Heraklion to Dia Island

★★★★★★★★★★5.0 · 22 reviews · 6 hours (approx.)

Join Captain Greg and first mate Demetri for a private sailing trip from Heraklion to Dia Island. Swim in clear water, use the paddleboard and snorkel gear, explore an ancient harbor site, and enjoy fruit, snacks, drinks, and lunch on the longer cruise option.

“Very good sailing trip. Personalized for our group of four people. Relaxing, and activities when we arrived at Dia Island. Lunch was very good.”

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14.Fully Private Sailing Cruise with Meal & Drinks

★★★★★★★★★★5.0 · 18 reviews · 7 hours

Spend seven hours aboard the private yacht BE HAPPY with skipper Nikos and a hostess, sailing from Souda past forts, villages, and small islands. Swim in clear coves, snorkel, try the helm, and enjoy a fresh three-course Cretan lunch with wine, beer, and soft drinks.

“Excellent day. Swam in beautiful clear waters. Sailed in open waters. It would have been good to have had some snorkelling gear, but other than it was superb. Lunch was delicious. It was cooked on the boat with local food. The skipper and his crew were lovely.”

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