The 5 Island Hopping Sailing Trips in Crete 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.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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5.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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