Greece · SAILING TRIPS IN CRETE
The best sailing trips in Crete in Greece fill up weeks ahead and the very best go first. Here are 11 to book early, what each includes and how they differ.
Sail from Heraklion to protected Dia Island for swimming, snorkeling, paddleboarding, a Greek meal, unlimited drinks, and sunset sea views.
“Amazing experience!! The food and staff were amazing, the location is stunning, we had the most beautiful day”
Review of Heraklion’s Dia Island sailing cruise, with snorkeling, lunch, unlimited drinks, yacht comfort, timing, and practical booking tips.
“This activity was amazing, great communication from the get-go, staff were lovely and very knowledgeable, the transport shuttle was on time and quick, the boat and Dia Island were stunning and the food and drinks were great - especially if you like a sweeter white wine!”
Sail from Heraklion to Dia Island for swimming, snorkeling, SUP, a Mediterranean lunch, drinks, and sunset views aboard a small yacht.
“We had an amazing trip to Dia island with Stelios and Celia! We decided to try the full day trip over the half day and are so glad we did. Definitely pay the bit more if you can! The pickup from our hotel was right from the door and on time, we were welcomed on board at the harbour and at the island had a chance to try snorkelling and SUP for the first time. Lunch was prepared while we swam and we had plenty of chance to sunbathe without feeling under pressure to do anything to a schedule. The whole experience was so relaxing, we felt like welcomed guests…”
Sail from Heraklion to uninhabited Dia Island for swimming, snorkeling, paddleboarding, Greek food, wine, and small-group sailing.
“A beautiful day, great weather, calm sea. Crew were kind and great to talk with. Really enjoyed snorkelling, the water was magical!”
Sail from Heraklion to Dia Island for swimming, snorkeling, paddleboarding, a Cretan lunch, drinks, and a small-group sea day.
“Very pleasant cruise out to Dia Island. The crew was wonderful and provided excellent service. We did have to wait to dock, but it was pleasant to chat with other passengers while waiting. Would definitely recommend this trip.”
Sail from Kissamos to Balos and Gramvousa on a small luxury catamaran with Cretan food, open-bar drinks, water toys, and transfers.
“Great day out on the water, great crew who looked after us all day.”
Sail privately from Heraklion to Dia Island for swimming, snorkeling, fishing, fruit, drinks, and optional lunch on the Cretan Sea.
“The booking aftercare via text is so reassuring. Our driver was fantastic, the crew Harris and Dennis were brilliant and yacht was amazing. Dia island and is beautiful and the lunch on board was sooo tasty. Wine was great too!! We had a fantastic time”
Review of Rethymno’s 3.5-hour sunset catamaran cruise with sushi, open bar, swimming, SUP, snorkeling, and practical booking tips.
“We had the most unforgettable sunset trip with the catamaran in Rethymno! It was also my daughter’s birthday, and the hostess went above and beyond to make it special—she even prepared a cake and sang happy birthday for her. Truly, she was the most amazing hostess I have ever met. The atmosphere was warm and welcoming, food and drinks were always available and of top quality, and everything was arranged with such care. Watching the sun set over the sea with my family while celebrating my daughter’s birthday made this experience priceless. I highly recommend this trip to anyone visiting Rethymno—you won’t just enjoy the views, you’ll feel genuinely cared…”
Sail from Heraklion to Dia Island for swimming, SUP, snorkeling, fishing, lunch, unlimited drinks, and a six-hour Greek island escape.
“Very nice experience, and friendly host on the boat.”
Review of Crete’s Kolymvari sailing cruise, with Agioi Theodoroi swimming, snorkeling, SUP, a fresh meal, and unlimited drinks.
“It was a wonderful mini morning trip, with great guides. The water was beautiful and hosts were very attentive. Definitely recommend.”
Sail from Hersonissos at sunset with unlimited drinks, local snacks, swimming, SUPs, snorkeling, music, and a friendly crew.
“Prefect. The host were nice ! They made us confortable. I will recommend this for sure !”
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