Our Top 15 Island Hopping Sailing Trips in Crete

1.Sailboat Cruise to Dia Island with Drinks & Lunch

★★★★★★★★★★4.8 · 1,405 reviews · 1 hour - 390 minutes · from $35Number one

Sail from Heraklion with an experienced crew on a luxury yacht, choosing a shared half-day trip to Dia Island, a private cruise, or a one-hour coastal sail. The island option includes swimming, snorkeling, fishing gear, paddleboards, lunch, fruit, and unlimited drinks. Crew members such as Stavroula and Dennis are noted for warm, capable service.

“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 per boat

Sail privately from Heraklion to Dia Island with a two-person crew, then spend 2.5 hours at Saint George Bay swimming, snorkeling, fishing, and using a paddleboard. Water, soft drinks, wine, fruit, and equipment are included. Add hotel transfers or an onboard meal for extra convenience.

“Sailing trip was great, guides gave a lot of explanation concerning the boat, island and history.”

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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 $72Highest rated

Set sail from Heraklion’s Old Venetian port with a certified crew, such as Costas, Mario, George, or Harry, for Dia Island’s quiet coves. You’ll have about 90 minutes for swimming, SUP, snorkeling, and sunbathing, followed by an organic lunch, fruit, soft drinks, and wine. Pickup is included within 10 kilometers.

“Friendly skipper and crew, great first time sailing experience for my friend and excellent anchorage choice as well. Would return to them again!”

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

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

From Cafe Marina in Heraklion, you sail with Eos Yachts to Dia Island for about three hours of swimming, snorkeling, SUP boarding, fishing, and canoeing. A certified English-speaking crew serves welcome coffee, Cretan treats, seafood or vegetarian lunch, fruit, dessert, beer, wine, and soft drinks. The catamaran returns to the same meeting point after roughly five and a half hours.

“What a day Amazing food as a first Amazing boat Amazing staff Amazing day and amazing trip 20/10 thanks again . Check out my page for some photos also @seriouslyscrumptiouseats”

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5.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 small yacht with a crew such as Markos, Alexandra, Magda, or Georges. Swim in calm St. George’s Bay, use the included snorkeling gear, enjoy a filling Cretan meal with wine and soft drinks, then return across the sea, with a sunset option available.

“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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6.Private Full-Day Sailing Trip to Dia Island

★★★★★★★★★★4.9 · 140 reviews · 6.5 hours · from $695 per boat

Sail privately from Heraklion to Dia Island with a two-person crew, stopping at Saint George Bay and another swimming spot. You can snorkel, fish, use a paddleboard, and relax with fruit, soft drinks, water, and local white wine. Boats range by group size and budget, with optional hotel transfers and onboard meals.

“We told the guides we were more interested in sailing than the excursions and they accommodated our request. The Elan 37 is a fun boat and she sailed well even in light winds. The lunch was delicious and we enjoyed it in an idyllic bay on Dia island. The captain and first mate were vey kind and helpful with our two kids. I highly recommend this excursion and will book again if we return to Crete.”

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

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

From Heraklion, sail with an English-speaking crew to Dia Island aboard a catamaran limited to 14 people. Expect a light brunch, fresh Mediterranean lunch, local beer and wine, swimming, snorkeling, paddleboarding, fishing, Wi-Fi, and time to relax in a sheltered bay.

“This is the company to use for a snorkel sailing adventure. Thomas, Anise, and Alexander took great care of us. Water was crystal clear. Plenty of time at Dia in a secluded cove. A wonderful day, high recommend! Dolphins were an added bonus.”

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8.Sailing Trip to Dia Island – All Inclusive

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

Set Sails Crete takes you from Heraklion’s Old Anchor to Dia Island for swimming, snorkeling, and stand-up paddleboarding. George and Niko are among the friendly crew members associated with the trip. Expect about three hours near the island, a fresh seafood pasta lunch, Greek salad, fruit, local beer, white wine, soft drinks, and water.

“Enjoyable morning “sailing” to the island. I was disappointed we actually did not sail! I expected 10 people and there were 14 so a bit crowded. Swimming in Aegean Sea was a treat. The crew made shrimp pasta and Greek salad for us! Lots of wine, beer, water and lemonade.”

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9.Catamaran Sailing to Dia with Lunch in Heraklion, Crete(EST 2024)

★★★★★★★★★★5.0 · 64 reviews · from $142

Spend about five and a half hours sailing from Heraklion to Dia Island aboard a Lagoon 46 catamaran. Swim in a quiet cove, snorkel, use the included SUP boards, sunbathe, and enjoy freshly made traditional Cretan pasta with fruit, soft drinks, wine, and beer. The crew serves a maximum of 17 people.

“My family enjoyed a very memorable day on board this luxury Catamaran . Nothing more could have been done or provided by the professional crew. The only sad part of the day is that we had to leave. The crew is able to take you to very peaceful cove on the island, where you can paddle board and snorkel . Lunch was an added value to our day”

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

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

Sail from Heraklion to Dia Island on a Bavaria 51 with skippers Giannis and Alex. Spend time swimming, snorkeling, paddleboarding, fishing, and sunbathing, then enjoy fresh pasta, fruit, soft drinks, water, and wine. The shared trip carries up to 10 people and returns to Cafe Marina in about four hours.

“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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11.Sunset Dia Catamaran Cruise by Top-50 Greek Chef

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

Join Cyma Sails at 3 pm for a five-and-a-half-hour sunset cruise from Heraklion to Dia Island. George, Andy, and Costos are among the warm hosts you may meet on board. Expect Prosecco, swimming, paddleboarding, fishing, a chef-prepared Cretan dinner, unlimited drinks, and a return to the same harbor.

“This was our second catamaran trip on a Greek island. It was once again a highlight of our holiday. It's always so nice to drive across the sea with background music, a cool crew and damn delicious food. We got to know great people on the ship, with whom we really laughed a lot. Even today, a few days after the trip, we remember and think: That was so beautiful! Every holiday we take a catamaran ride and every time it is breathtaking, especially as it goes into the sunset.Auto-translated”

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

★★★★★★★★★★4.9 · 42 reviews · 6.5 - 8.5 hours · from $176

Spend 6.5 to 8.5 hours sailing from Crete to Dia Island aboard a new catamaran for up to 15 people. You’ll get espresso, brunch, an organic Mediterranean lunch, unlimited local wine and beer, and time to swim, snorkel, fish, or paddleboard. The crew speaks English and Greek, with hotel pickup available from selected areas.

“The Sunset Cruise was very enjoyable with plenty of space on board the catamaran, excellent service, a great crew and delicious food, highly recommended!!!”

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13.Dia Catamaran Cruise with Lunch by Top-50 Greek Chef

★★★★★★★★★★5.0 · 35 reviews · 5 hours 30 minutes (approx.) · from $131

Sail from Heraklion to Dia Island on a large catamaran with a 25-person limit. Start with coffee and Cretan treats, then swim, snorkel, fish, paddleboard, or relax by the private floating pool. Chef Giorgos Chronakis provides a fresh Mediterranean lunch, with wine, beer, soft drinks, and special menus available by request.

“It was one of the best trips we went on absolutely fantastic from start to finish The crew were amazing and the food was delicious would highly recommend this trip!”

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14.Ag. Nikolaos Catamaran to Spinalonga – Gourmet Meal & Water Toys

★★★★★★★★★★5.0 · 33 reviews · 5 hours (approx.) · from $150

Spend about five hours aboard a modern catamaran from Agios Nikolaos, cruising around Mirabello Bay and Spinalonga. You get a nutritionist-designed Mediterranean lunch, unlimited soft drinks, beer and white wine, plus swimming stops, snorkeling, SUPs, a sea scooter, kayak, water slide, and shaded seating. The English-speaking crew serves a maximum of 20 people.

“We had the pleasure of experiencing a catamaran charter on the Artemis in Agios Nikolaos, Crete, and it was an unforgettable adventure. The blend of comfort, stunning natural beauty, and attentive service made for an exceptional day on the water.”

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15.Catamaran Cruise to Dia with Sunset, Meal & Bar

★★★★★★★★★★5.0 · 30 reviews · 5 hours (approx.) · from $150

Join an English-speaking crew aboard a luxury catamaran from Heraklion to uninhabited Dia Island. Swim, snorkel, paddleboard, fish, and use the water toys before a fresh Mediterranean meal with dessert, open drinks, and a sunset sail back. Georges and Marina are among the friendly crew members, and the boat carries up to 20 people.

“Que dire de plus que la convivialité, l’équipage au top, les animations, l’apéritif et le dîner était grandiose! Si ce n’est le prix qui est un peu élevé, mais vous en serez pas déçu de cette excursion, dépaysement totale assuré ! J’ai oublié les magnifiques vues et super beau coucher de soleil. En résumé, je recommande”

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