The 15 Best Dia Island Boat Trips in Crete

1.Dia Island Sailboat Cruise with Swimming and Meal

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

Sail from Heraklion’s Old Venetian Harbour to protected Dia Island on a yacht limited to 14 passengers. Captain Petros and crew members such as Sofia, Giannis, Mariana, and Manos provide a relaxed day of swimming, snorkeling, paddleboarding, Greek food, unlimited drinks, and optional sunset views.

“Amazing experience!! The food and staff were amazing, the location is stunning, we had the most beautiful day”

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2.Sailboat Cruise to Dia Island with Drinks & Lunch

★★★★★★★★★★4.9 · 1,287 reviews · from $90

Sail about an hour from Heraklion to Dia Island on a shared or private yacht. Swim and snorkel in Saint George Bay, try fishing, enjoy lunch, fruit, local wine, and soft drinks, then return by sea. Crew members such as Marcos, Vasilis, Alexandra, and Dimitry have helped make these cruises warm and personal, though the crew can vary.

“Great activity. Thoroughly enjoyed and the crew were amazing. Food was excellent, couldn’t have asked for better”

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3.Sailing Cruise to Dia Island with Drinks and Meal

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

Spend six hours sailing from Heraklion to Dia Island with an English- and Greek-speaking crew. Swim, snorkel, fish, paddleboard, hike, and eat a fresh Mediterranean lunch onboard. Hotel pickup is available, and afternoon departures can include a sunset sail back to port.

“FANTASTIC!!! HIGHLY RECOMMENDED!!! the trip to and Dia was an iregular trip(rough sea) ( but very safe) but the interaction with the crew was out of this world! we have spent 3 hrs (or so) by the Island of Dia snorkeling, paddling, diving... drinking. nice company as well beautiful meal plenty drinks Thank you Captain Nick "BARBOSSA" 1ST MATE KRISTINA 1ST MATE IORGU”

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4.Dia Island Sailing Cruise with Snorkeling

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

From Heraklion’s Venetian harbor, sail with a professional crew toward uninhabited Dia Island. You’ll swim, snorkel, paddleboard, and enjoy drinks onboard, with seafood pasta on the full-day trip or sandwiches and tomato pasta on the half-day option. Recent sailings have featured friendly guides such as Ernesto and George.

“It was a beautiful experience and the guys were very polite and helpful towards us”

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

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

Spend about five and a half hours sailing from Heraklion to uninhabited Dia Island. Swim from the boat, snorkel, paddleboard, fish, and eat shrimp linguini with Greek sides. Pickup covers many Crete resorts, and the boat may be a sailing yacht or catamaran, depending on the booking.

“Well worth the expedition if you want to sail, swim, sunbath, eat, drink and nap in an iconic Greek settling. The sailboat held 12 and traveled for an hour to anchor in a protected cove in Dia. With an adorable church on the hill as a backdrop, swimming in clear and initially cool clear water was refreshing. Not much to look at snorkeling but the water clear. Inflatable SUP fun with the wind much stronger and the current non-exsisitant. A delightful Mediterranean meal served along with endless wine beer and water. Knowledgeable captain and crew stayed out of the way allowing the passengers to mingle and play.”

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6.Private Half-Day Sailing Trip to Dia Island

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

Sail privately from Heraklion to Dia Island with a two-person crew such as Ilias and Nikiforas, Vassilis and Costa, or another assigned team. You get 2.5 hours at Saint George Bay for swimming, snorkeling, fishing, paddleboarding, and relaxing, plus drinks and fruit. Add hotel transfers or a full meal for extra convenience.

“Brilliant trip, crew were lovely and so helpful. Highly recommend”

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7.Sailing Trip to Dia Island with Lunch & Swimming

★★★★★★★★★★4.8 · 414 reviews · from $67

Set Sails takes you from Heraklion to Dia Island on a small-group yacht cruise with captains such as George, Vaso, Spiros, and Marina. Expect an 80-minute sail each way, a three-hour stop at Saint George Bay, seafood pasta, Greek salad, unlimited drinks, snorkeling, fishing, and SUP boarding.

“Trip was really good, so relaxing. Our crew goerge and marina were fantastic hosts. Great conversation & the lunch they provided was lovely. If you can request to have them, I 100% would!!”

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

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

Sail from Heraklion’s Old Venetian port to protected Dia Island aboard a comfortable yacht with up to 10 people. Your crew handles the boat while you swim, snorkel, paddleboard, watch for falcons and dolphins, and enjoy a freshly prepared Greek lunch with wine. Morning, afternoon, and sunset departures may be available.

“What an afternoon of fun! Stratos was an excellent skipper and full of knowledge. First mate Soultana (i hope I’ve spelt your name correctly) gave us outstanding hospitality and food. All of us had a great time sunbathing, swimming, paddle boarding, eating and having the odd glass of wine. I think it was our most favourite trip of the holiday. I highly recommend it and ask for Stratos 🙂”

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9.Sunset Cruise to Dia Island

★★★★★★★★★★4.8 · 259 reviews · 5.5 hours · from $82

Spend 5.5 hours sailing from Heraklion to Dia Island aboard the yacht MARYLINE. Swim and snorkel in Saint George Bay, enjoy fruit, sandwiches, drinks, music, and sailing instruction, then watch the sun set over the Cretan coast. Captains and crew such as Alex, Kosta, Yannis, and Niko are known for a warm, easygoing style.

“Good relationship between the guides, humourous, but professional, but entertaining. We sailed approx one hour each way and stayed 2.5-3 hrs at the island. We got fruit, sandwiches, and drinks. Was surprised that there's no sun cover on the boat, but it was OK”

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10.Sunset Sailing Cruise Dia Island with Snorkeling

★★★★★★★★★★4.6 · 242 reviews · from $63Best value

Sail from Heraklion to uninhabited Dia Island with a small group of up to 18 people. Swim in clear water, snorkel, use the paddleboard, and enjoy food, drinks, and raki onboard. The return journey is timed for sunset, with optional hotel pickup and Greek and English speaking crew.

“The guides were so lovely and accommodating. The whole experience was extremely enjoyable from start to finish. We had a really lovely time! Thank you”

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11.Dia Island Luxury Catamaran Cruise with Meal

★★★★★★★★★★4.7 · 194 reviews · 5.5 hours · from $127

Sail from Heraklion’s Old Venetian Harbor to Dia Island aboard a Lagoon 450F catamaran with an English- or Greek-speaking crew. Swim, snorkel, fish, and use the SUP board before a meal of pasta, Greek salad, Cretan appetizers, fruit, and unlimited drinks. Choose a morning sailing or a sunset return.

“Excellent activity! Really nice boat (around 26 persons per boat) and the waters in dia island are amazing. A really special activity and great crew.”

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12.Dia Island Catamaran Cruise with Dinner and Wine

★★★★★★★★★★4.8 · 147 reviews · from $120

Spend five hours on a semi-private sailing catamaran from Heraklion to Dia Island. You get coffee, Cretan snacks, swimming, snorkeling, SUP boards, fishing, an onboard Mediterranean dinner, unlimited drinks, and a sunset sail. Hotel pickup is available from several resort areas, and private groups can be arranged.

“It was fantastic trip. Nice catamaran, friendly staff, very good food. We were very happy! Thanks again)”

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13.Dia Island Romantic Sunset Cruise with Wine

★★★★★★★★★★4.8 · 144 reviews · from $86

Sail from Heraklion to Dia Island aboard a semi-private catamaran for 3.5 hours. You’ll get Prosecco, snacks, unlimited Cretan wine and Greek beer, swimming, snorkeling, paddleboarding, and sunset views. The English-speaking crew, including Sergei on some sailings, keeps the mood relaxed and attentive. Hotel transfers and private groups are available as booking options.

“Sergei and his crew were fantastic hosts from the second we met them at the port, until we left the boat. My wife and myself felt very welcome, comfortable and relaxed. The crew did not stop working to ensure that everyone had everything that they needed, constantly coming back to ask if people needed more drinks or something to eat etc. A fantastic experience from start to finish!”

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14.Private Full-Day Sailing Trip to Dia Island

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

Spend 6.5 hours on a private sailing boat from Heraklion to Dia Island with a two-person crew. Swim at Saint George Bay, snorkel with provided gear, try fishing, use a paddleboard, and enjoy fruit, water, soft drinks, and wine. Add hotel transfers and a full onboard meal for an easier day.

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

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

Leave Heraklion at 9:30 a.m. aboard a luxury catamaran limited to 14 people, with an English-speaking crew such as Spiro, George, Alexandra, or Thomas. Spend about four hours in a Dia Island cove swimming, snorkeling, paddleboarding, fishing, and eating a fresh Mediterranean lunch. Drinks, Wi-Fi, and water gear are included.

“Despite a choppy sea, the crew (Sergey & George) were excellent and reassuring. George was a fantastic crew man, full of stories, charm and funny. Excellent food as well from both and an all round relaxing, enjoyable and memorable. trip.”

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