Crete · SAILING
Every week on Crete has one free day too few. These 15 sailing trips justify the slot, priced and timed so you can decide in minutes and get back to the fun part.
Small-group sail from Heraklion to Dia Island with snorkeling, paddleboarding, and a Mediterranean meal plus unlimited wine, beer, and drinks.
“It was amazing experience. Definitely a highlight of my vacation. Mariana and Manos was fun and helpful. Good food and beautiful views.”
Cruise Heraklion waters to Dia Island on a luxury yacht with snorkeling, unlimited drinks, and lunch, plus options for private or a shorter sail.
“A memory for a lifetime. the staff were super professional and accommodating. the sailing was smooth and beautiful and the sea was Cristal clear and just the right temperature.”
Sail from Heraklion to Dia Island for clear-water swimming, snorkeling, SUP, and an included Greek meal with wine and raki.
“The most magical and romantic experience to end our trip in Crete. Hosts were delightful, the snacks and drinks were excellent, the equipment and amenities provided for snorkelling, fishing and paddle boarding were amazing! The sights on the way and from the island were incredible - recommend the evening trip for the sunset. 100/10 couldn’t recommend more! So so worth the money!”
Sail from Heraklion to uninhabited Dia Island for snorkeling, paddleboarding, drinks, and Greek meals on a small-group sailing cruise.
“Ernesto and George are very lovely, informative and overall, A great experience!”
Sunset catamaran from Heraklion to Dia Island: snorkel clear water, paddleboard, Greek food and drinks, then sail back at sunset.
“The sailboat had the perfect atmosphere—spacious and comfortable with just the right number of people. Great music set the mood, and the skippers were not only professional but also genuinely pleasant, making the whole experience even better.”
Sail from Heraklion to uninhabited Dia Island for swimming, snorkeling, SUP, and a full lunch with drinks included, with pickup options.
“We had such a fun time on this excursion. From the driver who picked us up to our sailboat host to the captain - everyone was so welcoming and accommodating. We had a perfect day on the water with plenty of time to swim, snorkel and paddle board. The lunch of shrimp linguine and Greek Salad with fruit plus beer and water were excellent. This was one of the highlights of our trip to Greece. I highly recommend.”
Sail from Heraklion to Dia Island for swimming, snorkeling, SUP, and a real Cretan lunch with unlimited drinks, in a max 10-guest crew.
“It was overal a really nice experience. the pickup was well managed and the Boats were really clean. The crew did an amazing job to provide an amazing trip. thanks!”
Private 4.5-hour sail from Heraklion to Dia Island for snorkeling, paddleboards, fishing, unlimited drinks, and optional meal.
“Fantastic trip on our own little boat to Dia Island. The hosts were super friendly and really attentive, we felt very well looked after. The boat was wonderful and really clean. We had a lovely smooth sail there, plenty of time for a swim and snorkel and then lunch on board. We went for the sandwich option and it was so good! Would definitely recommend, fabulous trip.”
Rethymno sunset catamaran with sushi, an open bar, SUP and snorkeling, plus a Cretan sunset finish. 3.5 hours in Crete.
“The staff were all friendly and accommodating, making sure that our experience was special. The view was amazing and the sunset was spectacular.”
Sail from Heraklion to Dia Island for a 5.5-hour Crete cruise with snorkeling gear, SUP, sunset views, and unlimited Greek wine.
“You know those nights that just feel… perfect? This was one of them. We set sail for Dia Island, hoping for one of those crazy-colorful sunsets. The sun was a little shy, but honestly? It didn’t even matter. The crew was amazing, making us feel so at home, and the food and wine were delicious. It was just one of those magical, simple moments that you never want to end.”
Sail from Kolimvari to Agioi Theodoroi for swimming, snorkeling, SUP, Kri-Kri sightings, and a 3-course meal with unlimited drinks.
“Taking a yacht out to a snorkelling spot was the perfect activity for us on our holiday to Chania. Trip was professionally run with the skipper Lucas giving a good safety briefing at the start and explained what we’d be doing. We chose the option with food and drink and it was well worth it , with a constant supply of drinks from a cooler with plenty of ice. The snorkelling at Thodoroy Beach was fun with plenty of sea life to see, and the food served after a swim was excellent. The trip run by Cretan Sailing Cruises was a real highlight of our week. One tip we have…”
Catamaran sail from Agios Nikolaos to Spinalonga and Kolokytha with snorkeling, SUP, and an included meal plus unlimited drinks.
“Whole day was great although a lot of us on the boat ; our trip was made by the people we met and all had a laugh”
Heraklion to Dia Island on a luxury catamaran with chef-cooked Mediterranean lunch, snorkeling gear, SUP, open bar, and golden hour views.
“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.”
Sail from Kissamos to Balos Lagoon and Gramvousa, swim and snorkel, hike to the castle, and enjoy a traditional Cretan lunch onboard.
“Fun with lots of beautiful swimming spots, great crew!”
Heraklion to Dia Island catamaran with lunch, snorkeling gear, water toys, and open bar, plus calm views in 5.5-7 hours.
“My partner and I had a lovely time. Stunning views, the boat was immaculate. Plenty of equipment for the swimming portion. A real highlight was the food, and was makes this trip stand out from previous boat trips I’ve been on. Highly recommend!”
Every kind of day on the island, and the best of each.
