The 15 Sailing and Yacht Charters in Greece That Earn Their Price

1.Dia Island Sailboat Cruise with Swimming and Meal

★★★★★★★★★★4.8 · 2,579 reviews · 5.5 hours · from $95Our pick

Sail from Heraklion’s Venetian Harbour to Dia Island aboard a yacht limited to 14 people. Your English-speaking crew, including a certified captain, serves shrimp linguini, Greek salad, Cretan appetizers, and unlimited drinks, with time for swimming, snorkeling, paddleboarding, and sunset sailing.

“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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2.Sailboat Cruise to Dia Island with Drinks & Lunch

★★★★★★★★★★4.8 · 1,405 reviews · 1 hour - 390 minutes · from $35Best value

Choose a 3.5 to 6.5-hour shared or private yacht trip from Heraklion to Dia Island, with swimming, snorkeling, paddleboards, fishing gear, lunch, and drinks. The one-hour coastal option stays near Heraklion and includes drinks but no island stop or water activities.

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

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3.Gouvia: Corfu Island Sailing Trip with Snack and Soft Drinks

★★★★★★★★★★4.8 · 851 reviews · 5 - 10 hours · from $69

Set out from Gouvia Marina with a skipper such as Ari, Savvas, or Tasos for a relaxed five-hour cruise along Corfu’s northeast coast. Swim at Barbati and Gialiskari, try a supervised cliff jump, explore a blue cave, and enjoy sandwiches, fruit, and soft drinks aboard a small yacht for up to 12 people.

“Amazing day out! A small sail boat with only 12 people and an amazing guide”

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4.Sailing Cruise to Dia Island with Drinks and Meal

★★★★★★★★★★4.9 · 778 reviews · 6 hours · from $106

Sail from Heraklion’s Venetian harbor to uninhabited Dia Island with a certified crew, snorkeling gear, SUP boards, fishing equipment, lunch, wine, soft drinks, and raki. You’ll hear island legends, swim in clear water, and return by sail, with sunset departures available.

“Literally so nice, personable and professional. We made friends with others on the tip facilitated by the captain. Not been cheesy but we will be lifelong friends.”

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5.Dia Island Sailing Cruise with Snorkeling

★★★★★★★★★★4.7 · 742 reviews · 4.5 - 7 hours · from $82

Sail from Heraklion with a small crew of up to 18 people to uninhabited Dia Island. Expect swimming, snorkeling, paddleboarding, drinks, and food onboard. Ernesto and George are among the crew members, and the half-day or full-day format lets you match the trip to your schedule.

“A beautiful day, great weather, calm sea. Crew were kind and great to talk with. Really enjoyed snorkelling, the water was magical!”

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6.Shared Mykonos Sail Cruise to Delos and Rhenia Islands

★★★★★★★★★★5.0 · 705 reviews · 6 hours (approx.) · from $151Top rated

Spend about six hours sailing from Agios Ioannis to Delos and Rhenia. Explore Delos with an optional guide, then swim, snorkel, and eat a fresh BBQ lunch aboard a spacious gulet. Crew members Dimitri and Thomas are noted for attentive help, while hotel transfers cost extra.

“The sailing trip to Delos and Renia was maybe our favorite activity of our time in Mykonos. It was a good mix of relaxation and activity — enjoying a relaxing drink and lunch on the boat, exploring on our own in Delos, and a refreshing swim at Renia. I would have liked a little bit more time on Delos, but other than that, it was perfect. Staff/crew was very attentive to the needs of all passengers.”

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7.Sunset Sailing Cruise Dia Island with Snorkeling

★★★★★★★★★★4.7 · 529 reviews · 4.5 - 7 hours · from $82

Sail from Heraklion to uninhabited Dia Island with a professional crew, snorkeling gear, paddleboard, food, drinks, and time to swim. Full-day trips add a second bay and a seafood meal, while half-day trips focus on one cove and sunset sailing.

“Thoroughly enjoyed! nice crew and nice ppl on board”

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8.Sailing Cruise to Dia Island with Meal and Water Activities

★★★★★★★★★★4.5 · 526 reviews · 5 hours 30 minutes (approx.) · from $96

Sail from Heraklion to uninhabited Dia Island with a small crew and time to swim, snorkel, fish, paddleboard, and sunbathe. Lunch includes shrimp linguine, Greek salad, Cretan appetizers, and fruit, with beer, wine, soft drinks, and water. Pickup is available across much of Crete.

“Perfect day sailing and enjoying the sun and sea!!! The crew was great and the food was delicious!!!”

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9.Sailing Trip to Dia Island with Lunch & Swimming

★★★★★★★★★★4.8 · 517 reviews · 6 hours · from $100

Join a six-hour small-group sailing trip from Heraklion to Dia Island with up to 10 people. Captains George, Panos, and Vaso share local stories while you swim, snorkel, paddleboard, fish, and enjoy shrimp or vegetarian pasta with drinks on board.

“We are a family of 5 and were lucky to share the yacht with just another family of 3 and our lovely guides George and Marcos. It was a very hot, still day so we couldn’t actually sail but this meant for beautiful calm waters and exceptional swimming and snorkelling when we got to Dia Island. Lunch was delicious too. All in all a fabulous trip!”

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10.Private Half-Day Sailing Trip to Dia Island

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

Sail from Heraklion to Dia Island on a private boat for up to eight people, with two crew members, drinks, fruit, snorkeling gear, fishing equipment, and paddleboards. You get about two and a half hours in Saint George Gulf, with an optional onboard meal and hotel transfers.

“Amazing half day trip. Skippers Vassilis and Costa were informative and friendly. Such a lovely day. Transport was door to door no waiting and also fab. Totally worth the money! Recommend!”

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11.Heraklion Luxury Sailing Catamaran Dia Island | Gourmet Menu

★★★★★★★★★★4.9 · 312 reviews · 5.5 hours · from $141

Sail from Heraklion to Dia Island aboard EOS Yachts’ modern catamaran, limited to 22 people. The crew serves Cretan treats, seafood cooked by Chef Charis, local wine, beer, and dessert. You’ll have about three hours for swimming, snorkeling, fishing, canoeing, and paddleboarding in a sheltered bay.

“The yacht itself exceeded my expectations. It was very spacious with luxurious touches. The boat did not feel crowded. The crew were very attentive and welcoming. They were constantly offering us drinks or assistance. The meal was also delicious, gourmet quality. The sunset ride back was stunning. Highly recommend.”

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12.Small-Group Sailing Trip to Dia Island with Lunch

★★★★★★★★★★4.7 · 277 reviews · 4.5 - 7 hours · from $94

Join a crewed sailing yacht from Heraklion’s Old Venetian port and cruise to protected Dia Island. With a maximum of 10 people, you can swim, snorkel, use a SUP, enjoy a fresh local lunch, and hear about Crete’s wildlife, myths, and seafaring traditions from guides such as Stratos, Stefanos, and Aphrodite.

“We had a beautiful day, great skipper and crewmate. Lovely sail too and from Dia Island. Some lovely swimming in a crystal clear cove. Nice lunch with lovely company”

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

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

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

“It’s was a great experience to my children and to me Unfortunately, the boat was small and there was another family with 5 children So we had to move to the bow”

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14.Private Full-Day Sailing Trip to Dia Island

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

Sail privately from Heraklion to Dia Island with a two-person crew, stopping at Saint George Bay and another swimming spot. You get snorkeling gear, fishing gear, paddleboards, fruit, wine, soft drinks, and water. Crews have included Kostas, Magda, Nikos, and Vasilis.

“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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15.Half Day Cruise on a Sailing Yacht in Corfu Island

★★★★★★★★★★5.0 · 108 reviews · 4 hours (approx.)

Sail Corfu’s northeast coast for four hours on a private yacht for up to 10 people. Expect swimming near Strogylo, Barbati, Kalami, or Kerasia, plus snorkeling gear, SUP, snacks, drinks, WiFi, and a crew that can help plan celebrations.

“We are a family of 5 who visited corfu on a cruise ship. We had a 2 week vacation in Italy and on the cruise and each of us listed this as one of our top 1-2 experiences of our trip. Panos our captain and Veronika our stewardess were outstanding. they went above and beyond to ensure we had a great time, were fun and very personable. the sailing yacht was wonderful and spacious. We were able to find 2 separate swimming sites with crystal clear water and coves to swim into This is not the cheapest option, but provided excellent value and exceeded our expectations”

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