6 Sunset Sailing Cruises in Heraklion Worth a Whole Day

1.Sunset Sailing Cruise Dia Island with Snorkeling

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

Sail from Heraklion to uninhabited Dia Island with a professional crew such as Andreas, Manos, or George. Swim and snorkel in a quiet bay, use the paddleboard, eat Greek food onboard, and sail home at sunset. Shared and private options are available, with hotel pickup offered from selected areas.

“This was one of the best experiences I’ve ever had!! Stella and Elena are two wonderful hosts who did everything to make the trip amazing! Thank you to them! We had a delicious dinner with pasta, salad, and fruit, the chance to enjoy the beauty of the sea, and saw an incredible sunset! I highly recommend it to everyone!”

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2.Luxury Sunset Catamaran Cruise Sushi & Open Bar

★★★★★★★★★★4.8 · 442 reviews · 3.5 - 4.5 hours · from $94

Set sail from Hersonissos on a modern catamaran for 3.5 to 4.5 hours of swimming, snorkeling, paddleboarding, sushi, local wine, beer, and sunset views at Saint George Bay. The English-speaking crew serves welcome Prosecco, fruit, snacks, and soft drinks. Groups are limited to 20, with optional pickup from selected areas.

“Great trip and the Catamaran…the crew were superb and very accommodating Highly recommended”

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

★★★★★★★★★★4.9 · 181 reviews · 5 - 6.5 hours · from $132

Spend a relaxed afternoon sailing from Heraklion to protected Dia Island aboard a semi-private catamaran for up to 20 people. You’ll get espresso, healthy Cretan food, unlimited water, soft drinks, beer, and white wine, plus swimming, snorkeling, kayaking, SUPs, a sea scooter, and a slide before sailing home at sunset.

“Seamless organisation, spotless boat and the team were amazing. Highly recommend!”

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4.Sunset Catamaran Trip – Sushi & Open Bar

★★★★★★★★★★4.5 · 77 reviews · 3 hours 30 minutes (approx.) · from $102

Set sail from Rethymno on a luxury catamaran for about three and a half hours. You’ll have Prosecco, sushi, fruit, local wine and beer, plus time for swimming, snorkeling, SUP, fishing, and relaxing on deck. The English-speaking crew may include Vito, Slavik, George, or Sergei, though crew assignments can change.

“We loved this cruise so much! The time of day was perfect for the sail & sea swim & activities. The crew were all so lovely and we felt right at home on the boat. Would recommend this to anyone in the area - we traveled and it was so worth it! The views are stunning and the swimming location is amazing, and on top of that the all inclusive drinks and snacks made it a perfect activity, thank you guys!!”

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5.Sunrise Balloon Flight & Sunset Catamaran Cruise

★★★★★★★★★★5.0 · 45 reviews · 8 - 9 hours · from $353Highest rated

Spend one remarkable day seeing Crete from sky and sea. Fly over the Lassithi Plateau at sunrise, help inflate the balloon, enjoy a Greek breakfast, then board a semi-private catamaran from Heraklion or Hersonissos. Swim, snorkel, paddleboard, fish, eat sushi, and watch the sunset with unlimited local beer, wine, soft drinks, and water.

“The hot air balloon trip was amazing. It was such an awesome experience as well with helping to set the air balloon up for take off! Was totally worth it! Thanks for the experience!”

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6.SAILING DAY 4.5h-5h or SUNSET 3h-4.5h from Hersonissos CRETE

★★★★★★★★★★4.5 · 30 reviews · 3 to 5 hours (approx.) · from $108

Join Eye Travel for a small-group sailing trip from Gouves, near Hersonissos. Day cruises visit Dia Island, while some sunset trips use Saint George Bay. Expect swimming, snorkeling, SUP, fishing gear, a Cretan meal on the five-hour option, and a friendly crew that may include captains such as Manos, Dimitris, or Stratos.

“We had a wonderful day on the water with just about enough wind to sail. Boat was well maintained, our skipper Dimitrios is a great guy, very knowledgeable about the area and Greek mythology. Lunch was prepared on board and was delicious. We will definitely sail with Dimitrios again.”

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