15 Island Hopping Sailing Trips in Crete Worth Casting Off For

1.Sailboat Cruise to Dia Island with Drinks & Lunch

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

Sail from Heraklion with an English-speaking crew to Dia Island for swimming, snorkeling, paddleboarding, fishing, lunch, and unlimited drinks. Shared trips include the meal, while private cruises let you add one. Stavroula, Dennis, and other crew members are praised for friendly, careful service. A one-hour coastal option skips Dia and water activities.

“Nice shorter activity 4 hr, Friendly crew! Good lunch with plenty of water and wine! Beautiful day! ❤️🥂”

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2.Private Half-Day Sailing Trip to Dia Island

★★★★★★★★★★4.9 · 466 reviews · 4.5 hours · from $459 whole boat, up to 8

Sail privately from Heraklion to Dia Island with a two-person crew such as Vassilis, Costa, or George. You get about 2.5 hours in Saint George Bay for swimming, snorkeling, fishing, paddleboarding, and relaxing, with drinks, wine, fruit, and gear included. Add hotel transfers or a full meal for a smoother half-day on the water.

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

★★★★★★★★★★5.0 · 162 reviews · 4 hours 30 minutes (approx.) · from $72Top rated

Sail from Heraklion’s Old Venetian port to uninhabited Dia Island with a certified crew, usually aboard a 43 to 45-foot yacht. You’ll swim, snorkel, use a SUP board, enjoy an organic lunch with drinks, and hear about Dia’s protected wildlife. Pickup is free within 10 kilometers of the port.

“A lovely day! The expert crew was very accommodating and friendly, sailing was delightful, food was unexpectedly good! & generous, swimming was fun- only improvement would be better snorkel equipment & perhaps kick boards to float on for others who are not as strong at swimming…. Cash only shuttles are putting a strain on our Euro supply & exchange is costly but overall we loved this experience. Thank you :)”

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4.Private Full-Day Sailing Trip to Dia Island

★★★★★★★★★★4.9 · 140 reviews · 6.5 hours · from $695 whole boat, up to 8

You’ll sail from Heraklion to Dia Island on a private yacht with a two-person crew, stopping in Saint George Gulf and another swimming cove. Use the included snorkeling gear, fishing kit, and paddleboards, then enjoy fruit, soft drinks, water, and local white wine. Boats suit different group sizes, with hotel transfers and lunch available for an extra charge.

“Magnifique journée avec un guide très sympathique et professionnel, on a adoré.”

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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

Set sail from Heraklion with an English-speaking crew, often including captains and hosts such as Spiro, George, Alexandra, or Thomas. You’ll spend about four hours anchored at Dia Island for swimming, snorkeling, paddleboarding, fishing, and a freshly prepared Mediterranean lunch. The catamaran carries up to 14 people and returns around mid-afternoon.

“Absolutely the highlight of our trip to Crete! The staff were so welcoming and thoughtful. Always checking in with us to make sure we were ok and had everything we could need. Food was abundant and so fresh and delicious. There were only 7 of us on the boat so it felt like a private experience. Would definitely recommend!”

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6.Sailing Trip to Dia Island – All Inclusive

★★★★★★★★★★5.0 · 67 reviews · 6 to 8 hours (approx.) · from $90

Join Set Sails Crete from Heraklion for a six to eight hour boat trip to Dia Island. George, Niko, or another English-speaking crew member guides the day, with swimming, snorkeling, stand-up paddleboarding, seafood pasta, Greek salad, fruit, beer, wine, soft drinks, and water included.

“A great day out! George and Niko were incrediblley friendly and I feel like we became fast friends through the day. The water was cool but clear as crystal, easy to see the fish! The sun was great at drying us off upon leaving the ocean for a fresh made meal which we enjoyed with our new found friends (including the other visitors) on the boat. The island is practically untouched and has only a few buildings. Stunning views all round, throughout the whole trip...”

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7.Sailing to Dia Island with lunch on Bavaria 51 Heraklion, Crete

★★★★★★★★★★5.0 · 58 reviews · from $116

Spend about four hours sailing from Heraklion to Dia Island aboard a Bavaria 51 yacht with Green Cruises. Swim, snorkel, try stand-up paddleboarding with free lessons, fish, or help manage the sailing route. Giannis and Alex may be your skippers, while lunch, fruit, drinks, and wine are included.

“It was a lot of fun snorkeling and hanging out on the boat and in the water. Also was served the most delicious pasta dish. The water was beautiful and the caption and guide was very good.”

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8.Heraklion | Half day Sailing cruise to Dia Island

★★★★★★★★★★4.5 · 30 reviews · from $80

Set sail from Cafe Marina in Heraklion for a 4.5-hour cruise to Dia Island aboard the comfortable Swell. Your certified crew teaches basic sailing, provides snorkeling gear and a paddle board, and serves snacks, coffee, tea, and soft drinks. Swim in Dragon Tail Bay, visit the island chapel, and return to Heraklion with a maximum of 10 people.

“We sailed with the Swell. Very comfortable boat. The captains were very nice and knowledgeable and steered us safely through rather choppy waters. The blue of the Aegean sea was the highlight of the trip, but swimming and snorkeling in the „dragon tail bay“ was great too.”

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9.Small group 5,5h Sunset Sailing trip to Dia Island

★★★★★★★★★★4.5 · 26 reviews · 6 hours (approx.) · from $84

Set sail from Heraklion at 3:15 pm for a roughly six-hour cruise toward Dia Island and Agios Georgios. You’ll pass the Old Venetian Harbor and Koules Fortress, swim or snorkel in clear water, and enjoy snacks, bottled water, and soft drinks aboard a well-equipped yacht. The group is limited to 10 people.

“Our young skipper was delightful and spoke excellent English. We really enjoyed our cruise to Dia Island. The water where we snorkeled was a beautiful turquoise, and you could see to the bottom.”

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10.Private Luxury Sailing Trips to Dia Island

★★★★★★★★★★4.5 · 25 reviews · 6 hours (approx.) · from $639 whole boat, up to 10

Spend about six hours on a private sailboat from Heraklion to Dia Island. Your skipper handles the boat while you sail for about an hour, then swim, snorkel, fish, and relax at St. George’s Bay. Masks, fins, fishing gear, fruit, soft drinks, water, and white wine are included. Hotel transport and meals cost extra.

“It was a wonderful and relaxing boat trip with friendly staff. Truly a delightful experience on the sea”

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11.Private Sailing Cruise from Heraklion to Dia Island

★★★★★★★★★★5.0 · 22 reviews · 6 hours (approx.) · from $625 whole boat, up to 10

Set sail from central Heraklion with Captain Greg and his crew for a private six-hour cruise to Dia Island. Swim in clear water, snorkel, paddleboard, explore an ancient harbor site, and enjoy fruit, snacks, drinks, and a meal. The boat takes only your group, up to 10 people.

“We enjoyed our trip to Dia Island. The crew was great and we enjoyed some good sandwiches and fresh fruit and drinks after we got to the island. The kids loved jumping from the boat and swimming around and exploring on the shore. Definitely recommend!”

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12.All-inclusice Catamaran Day Cruise from Hersonissos to Dia Island

★★★★★★★★★★5.0 · 22 reviews · 6 hours 30 minutes (approx.) · from $174

Leave Hersonissos at 9 a.m. aboard a luxury catamaran limited to 20 people, bound for uninhabited Dia Island. You’ll have time for swimming, snorkeling, stand-up paddleboarding, and gentle fishing, with a healthy brunch, Mediterranean lunch, and open bar served onboard. The crew may include captains Tomas or Alex and cook Annais.

“Fantastic experience. Gorgeous boat and spotlessly clean. The location was great to use the paddle board and snorkel equipment. Lunch was delicious but most importantly Captain Alex and his crew mate Aleksandr were wonderful. They were so kind to our 14 year old making it the highlight of his holiday.”

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13.Small Group Sailing Cruise from Heraklion to Dia Island

★★★★★★★★★★5.0 · 15 reviews · 6 hours (approx.) · from $102

Sail from central Heraklion to uninhabited Dia Island aboard a luxury boat with a maximum of 10 people. You can swim, snorkel, explore the remains of an ancient Minoan-era port, relax on deck, and enjoy a meal during the approximately six-hour outing. Sunset departures are available.

“We had a wonderful time with the excellent team. All of us were excited to pass giant sea turtles as we were sailing and we saw a few different types of fish whilst snorkeling at Dia. We went on the sunset tour, which meant no early start and a fabulous end to the day watching the sunset on our way back to the harbour. Thank you for a fantastic trip. 100% recommended!”

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14.Sailing day to Dia island

★★★★★★★★★★4.5 · 13 reviews · 7 hours (approx.) · from $102

Sail from Heraklion to Dia island on a seven-hour trip limited to 10 people. Swim and snorkel in clear Cretan water, use the paddle board, and enjoy seafood pasta, Greek salad, bread, tzatziki, drinks, and wine prepared and served aboard. Transfers are available along Crete’s coastal zone.

“A great trip on the water… The captain and host did a great job in coordinating and creating a welcoming experience. The wind caused the waves in the sea to be a bit rough but the captain did a great job controlling everything to feel comfortable! Once at Dia, we were able to swim, use snorkeling gear, lounge on the boat while the hostess made us a really nice homemade like meal. On other sailing experiences I’ve gone on, it’s always been a pre made meal. This was a pasta with seafood and tomato sauce, Greek salad, bread/breadsticks, and tzatziki. Wine, orange juice, water, cola were served on board. Thank…”

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15.Small Group 5,5 hours Sailing Trip to Dia Island

★★★★★★★★★★5.0 · 11 reviews · 6 hours (approx.) · from $84

Join Dimitri and Alexandros for a roughly six-hour sailing trip from Heraklion to Dia Island. You will sail in a group of no more than 10, use the provided snorkeling gear, and enjoy snacks, soft drinks, and bottled water. The boat returns to the Old Venetian Harbor meeting point.

“Très belle sortie en mer, le personnel est top.. A amezing boat... It's a very good trip with Dimitri et Alexandre”

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