Under sail · ISLAND HOPPING SAILING TRIPS
Two or three islands in a day, most of it spent on the water rather than in a port queue. These 15 set out which islands each boat actually reaches, how long you get ashore, and what it costs.
Sail from Heraklion to protected Dia Island for swimming, snorkeling, a Mediterranean meal, unlimited drinks, and sunset views.
“Amazing experience!! The food and staff were amazing, the location is stunning, we had the most beautiful day”
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”
Cruise Corfu’s northeast coast from Gouvia, with three swim stops, snorkeling, cliff jumping, snacks, drinks, and a blue cave visit.
“The itinerary was well-paced and full of variety: we swam in three beautiful swimming holes, snorkeled in a little cave spot, and even got to jump off a small cliff—definitely a thrill! One of the stops included a beach with a charming café, perfect for a quick refreshment and some downtime. Our skipper, Savvas, was a standout. He was chill, informative, and incredibly kind. A fun moment was when he let us feed leftover sandwiches to the fish—watching them swarm was surprisingly entertaining! We also arranged van transportation from the cruise port to the marina, which was smooth and affordable at just €11 per person for a 15-minute ride. Highly…”
Sail from Mykonos to Delos and Rhenia for ancient ruins, a guided tour, clear-water swimming, Greek lunch, and wine.
“The crew was extremely friendly and fun. The boat was perfect. Everything was amazing”
Sail from Heraklion to Dia Island for swimming, snorkeling, SUP, a Mediterranean lunch, drinks, and a sunset return.
“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 Dia Island for swimming, snorkeling, paddleboarding, Greek food, wine, and a relaxed small-group day at sea.
“The team,the activities snd spots with clear water”
Review the Mykonos sail to Delos and Rhenia, with ruins, swimming, snorkeling, BBQ lunch, costs, timing, and practical tips.
“Wonderful crew and the food was fantastic. We enjoyed the entire trip and would highly recommend this activity for anyone who wants to spend a day relaxing in the sun while enjoying good food, views and swimming.”
Sail from Mykonos to Rhenia for swimming, lunch, and a guided Delos tour, with wine, Wi-Fi, snorkeling gear, and a Greek toast.
“In beautiful calm sunny weather a fantastic experience. Staff helpful and friendly. We had a fab time. Captain Stellios.and Marios were so lovely and friendly and helpful. Mario's created beautiful food for us all dietary requirements taken care of.”
Sail from Heraklion to quiet Dia Island for snorkeling, paddleboarding, Greek food, swimming, and a sunset return cruise.
“A lovely experience, very relaxing. Just the right number of people to make it enjoyable. A nice dinner and snorkeling near Dia Island. Thanasis and Panagiotis were super nice and kind, also sharing curiosity and answering questions”
Review of the Dia Island sailing cruise from Heraklion, with swimming, snorkeling, paddleboarding, lunch, drinks, pickup, and practical tips.
“Amazing crew, so warm and welcoming. Food was all home made and delicious. Fishing, padel boarding and snorkelling was available plus jumping off the boat. So fun and so worth the money.”
Sail from Heraklion to Dia Island for swimming, snorkeling, SUP, fresh Cretan lunch, unlimited drinks, and warm small-group hospitality.
“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!”
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”
Sail Milos and Poliegos on a small catamaran with swim stops, snorkeling, Greek food, open bar, photography, and expert weather routing.
“The crew was absolutely awesome, we got to go to the best swimming spots in Milos! bbq lunch was incredibly tasty and we had such a great time. I would highly recommend booking this tour. Wear your swim trunks!!”
Review of Crete’s Dia Island sailing cruise, with swimming, SUP, snorkeling, sunset views, fresh food, wine, transfers, and practical tips.
“Loved it. Everyone made to feel very welcome. Food was simple but very tasty. 10 out of 10. I would highly recommend it. I would recommend offering the guests a drink while they wait to leave the marina as it’s really hot and some of us had to travel a bit to get there. If I ever return I would definitely take the trip with them again.”
Sail from Agios Nikolaos to Spinalonga and Kolokytha on a small catamaran with swim stops, lunch, drinks, and SUP gear.
“It was a wonderful trip that we wished it would never end.. the beaches we visit was perfect! It is also quite nice that the catamaran was not that big so that the trip was not so crowded & it helped enjoying even more. Food could be a bit better but nothing worth to complain there, fantastic times!”
Pick an island, a boat, or a kind of day aboard.
