SAILING WORLDWIDE
The best days on the water.
The 12 most popular crete sailing trips. What each sail costs, how long you are on the water, and which crews run it well.
Cruise from Heraklion to Dia Island on a luxury yacht with snorkeling and included lunch and drinks, plus optional private and short sails.
Most Popular“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 snorkeling, unlimited drinks, and lunch on a yacht, with easy pickup options available.
“Amazing! From the start to the end, the crew were wonderful and the meal was very tasteful! Dimitry was the co captain but I don’t remember the captain’s name! But thanks for that mid day cruise! I definitely recommend it 😁”
Private 4.5-hour sail from Heraklion to Dia Island: snorkel, swim, fish, paddleboards, unlimited drinks. $459 per group up to 8.
“We had a great time. If we ever get back to Crete we will do it again.”
Sail from Kissamos to Balos Lagoon and Gramvousa Island with a fresh on-board Cretan lunch, swimming stops, and castle views.
“One of the must do things in Crete! The Balos beach is one of the best beaches to visit and the Sailing cruise trip made it a great experience all together. Louis & Alex were great hosts and made it feel at home. Highly recommended 5/5”
Sail Crete’s south coast to Loutro, Glyka Nera, and Marmara caves with swimming, shade, snacks, and a local lunch for up to 9.
“Beautiful, non-touristy sailing trip. Swam in some amazing caves. Visited a village that you can only access by boat or hiking. A day we will never forget!!”
Sail from Heraklion to Dia Island for swimming, SUP, snorkeling, and an organic lunch, with a small-group feel and wildlife spotting.
“A crazy experience Very well organized The skipper and his team-mate very nice A perfect crossing Inoubliable I recommend 100%Auto-translated”
Sail from Kissamos to Balos and Gramvousa with real sailing, deck-cooked Cretan lunch, and snorkel time in clear lagoon waters.
“Activity was very good. Unfortunately, we did not sail very much. I suspect most of these trips via sailboat just use motors. Might as well call it a motor sail and charge less.”
Luxury catamaran to Dia Island with open bar, seafood lunch, snorkel/SUP gear, and a small-group vibe in Crete.
“We had an absolutely amazing experience! The skippers were the best – professional, friendly, and very attentive. The food was fantastic and the open bar with snacks made it a true all-inclusive, worry-free package. We booked the 3:30 pm tour and were rewarded with a breathtaking sunset right in the middle of the sea –…”
Sail from Heraklion to Dia Island for swimming, snorkeling, lunch, and optional sunset sailing, with pickup options and small-group comfort.
“This was a truly fantastic experience that my wife and I enjoyed thoroughly! First, we appreciated all the communication before the day of our trip, with all the practical information regarding the trip, which made the preparations and planning simple and easy. We felt the duration of 4.5 hours worked very well. The trip itself…”
Private 6.5-hour sailing from Heraklion to Dia Island with snorkeling, fishing gear, paddleboards, unlimited drinks, and optional lunch.
“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…”
Small-group catamaran to Dia Island from Heraklion with snorkeling, SUP, and a premium onboard lunch plus an open bar.
“Great day. Lovely food cooked on board. Very happy experience with a great crew and an exceptionally clean boat”
Luxury catamaran from Kissamos to Balos Lagoon and Gramvousa. Snorkel, SUP, skip crowds, and enjoy lunch plus unlimited drinks.
“Beautiful day at sea. This was a great way to see some of the most gorgeous beaches of Chania. The crew & boat was great. My only complaint is that the boat felt too crowded. There should have been about 15 people vs. the 25 that were on board. Also, lunch ran out as there…”
The sailing ports worth the trip, grouped by the sea they sit on.
