Under sail · ISLAND HOPPING SAILING TRIPS IN CRETE
The 15 best island hopping sailing trips in Crete you can book today, with what each costs, how long the boat is out and who it suits. Number one is first for a reason; start there.
Sail from Heraklion to Dia Island for swimming, lunch, drinks, and Crete views, with shared, private, and one-hour cruise choices.
“A very choppy crossing to the island. Very well handled by the skipper though The boat was comfortable and safety was well looked after Food was very good. Would have been nice to have beer as an option perhaps Time went very quickly”
Sail privately from Heraklion to Dia Island for swimming, snorkeling, fishing, fresh fruit, drinks, and optional lunch in a beautiful Cretan bay.
“very friendly guide, bad luck with the weather, but nevertheless definitely recommended”
Review of Crete’s small-group sailing trip to Dia Island, with snorkeling, SUP, lunch, wildlife, hotel pickup, and practical booking advice.
“- Captain and staff including pick up driver were really nice - water is really clear - boat is clean - captain brought a sea urchin to show to everyone. That was cute. BUT - the Equipment is the worst snorkeling Equipment We ever had on such a trip - at first they just had 8 snorkels for 12 ppl. So the Captain handed me his private one. That one was good. Later he found some more and said i have to change. Then i had to Deal with the rubish everyone had. Water came with EVERY breath. I didnt make it 2 meters of the boat on second attempt.…”
Review of Crete’s luxury Dia Island catamaran cruise, with seafood lunch, open bar, snorkeling, SUPs, and practical booking advice.
“The best caramaran in the port and I'm sure is the crew. Amazing captain, chef and assistant. Beautiful and tasteful food, with dinner and snacks before and after. Everything is thought of, even SUPs and snorkel equipments. Captain anchored us in the best spot in the bay, close to the shore. Amazing experience, would reccomend to anyone.”
Sail from Heraklion to Dia Island for snorkeling, a fresh onboard meal, Cretan wine, and an optional sunset return.
“It was just beautiful. From pickup to drop-off, everything just worked out. The shuttle was very punctual, even a little early at the hotel, so we could start on time at the harbor. Alexandra and Markos were warm and inviting. They explained everything well and took care of everything we needed. The sailing trip was beautiful despite the very calm sea, and Markos did his best so that we could at least sail a little with the power of the wind. When we arrived at the island, there were explanations and assistance for the activities. We were very impressed by Markos' patience and calmness when he helped a fellow traveler…”
Review of the private Heraklion to Dia Island sailing trip, with swimming, snorkeling, lunch options, drinks, crew details, and value advice.
“Magnifique journée avec un guide très sympathique et professionnel, on a adoré.”
Sail from Heraklion to Dia Island on a small catamaran with fresh lunch, open drinks, snorkeling, paddleboards, and a relaxed bay stop.
“The crew was really nice and did everything for its customers. It was a blast on the boat and very fun. Would go again.”
Review of Crete’s all-inclusive sailing trip to Dia Island, with seafood lunch, drinks, snorkeling, paddleboarding, timing, value, and practical tips.
“A great day out! George and Niko were incrediblley friendly and I feel like we became fast friends through the day. The water was cool but clear as crystal, easy to see the fish! The sun was great at drying us off upon leaving the ocean for a fresh made meal which we enjoyed with our new found friends (including the other visitors) on the boat. The island is practically untouched and has only a few buildings. Stunning views all round, throughout the whole trip...”
Sail from Heraklion to Dia Island on a Lagoon 46 catamaran with snorkeling, SUP, swimming, lunch, drinks, and free cancellation.
“It was a great trip with a great captain and crew. I highly recommend it! One of the highlights of our trip.”
Review of a four-hour Bavaria 51 sailing trip from Heraklion to Dia Island, with lunch, swimming, SUP, snorkeling, fishing, and wine.
“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.”
Review of Crete’s sunset catamaran cruise to Dia Island, with a Top-50 Greek chef, swimming, SUP, seafood, wine, and sunset views.
“Beautiful boat. Extremely comfortable with many seating choices. Hosts are very friendly and hospitable.”
Review the Dia Island catamaran from Crete, with a small group, open bar, gourmet lunch, swimming, snorkeling, and paddleboarding.
“It was the beast sailing cruise in my life. Everything was perfect! I enjoyed the food, the sea. Crew was really nice and welcoming! Highly recommend!”
Review of Crete’s Dia Island catamaran cruise from Heraklion, with breakfast, chef-prepared lunch, drinks, swimming, SUP, and snorkeling.
“Super katamaran,duży i komfortowy,przemiła załoga i fantastyczne jedzenie.Przerwa w zatoce na wyspie Dia fajnie zorganizowana:padel,sprzęt do nurkowania,leżaki na brzegu,przekąski,napoje(wino,piwo,cola,fanta,herbata mrożona).Gorąco polecam,przeżycia bezcenne.”
Review of Crete’s 5-hour catamaran cruise from Agios Nikolaos to Spinalonga, with lunch, drinks, swimming stops, and water toys.
“Absolutely perfect trip. Drinks flowed and we had a lovely swim in the sea. Lunch was delicious and plentiful. Would totally recommend this trip”
Sail from Heraklion to Dia Island for swimming, SUP, snorkeling, a fresh Mediterranean meal, open bar, and sunset views.
“Journée incroyable grâce à vous ! L'équipage bienveillant, souriant, avenant, rigolo ! Un catamaran splendide, parfaitement propre et cosy ! Un repas fabuleusement bon ! De la musique parfaitement bien choisie pour vous faire rêver !”
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