Sailing & Catamaran Cruises in Crete: The 15 Best Days on Deck

Boat Tours in Heraklion, Cruises & Boat Tours, Dia Island Cruises, Heraklion Tours, Sailing & Catamaran Cruises, Sailing & Catamaran Cruises in Heraklion, Tour Reviews

Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

1.Sailing Cruise to Dia Island with Drinks and Meal

★★★★★★★★★★4.9 · 778 reviews · 6 hours · from $106Our pick

Sail from Heraklion to Dia Island for swimming, snorkeling, paddleboarding, a fresh Greek meal, drinks, and sunset views.

“Our Captain came to our hotel in Agia Pelagia to pick us up in the morning and he was lovely from the get-go. The boat ride to Dia Island was fun, and the island itself was amazing. We got to hike up the island and have a look around. The water was so blue and so clear we could see schools of small fish in it. There’s even a small beach which we had time to sunbathe on before going back to the boat (we chose the half day). Before we set off back towards Heraklion, we had some delicious Greek salad, fruits, cheese and bread. Our Captain also took…”

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Boat Tours in Heraklion, Cruises & Boat Tours, Dia Island Cruises, Diving & Snorkeling, Diving & Snorkeling in Heraklion, Heraklion Tours, Sailing & Catamaran Cruises, Sailing & Catamaran Cruises in Heraklion, Tour Reviews

Heraklion: Dia Island Sailing Cruise with Snorkeling

2.Dia Island Sailing Cruise with Snorkeling

★★★★★★★★★★4.7 · 742 reviews · 4.5 - 7 hours · from $82

Sail from Heraklion to uninhabited Dia Island for swimming, snorkeling, paddleboarding, Greek food, wine, and relaxed small-group sailing.

“The Sail Boat tour was extraordinary. We had such a beautiful sunny day. Both the Captains were very incredible. I booked for a Retreat I was hosting in Greece. We were 7 people and had the whole sailboat for ourselves. I booked the half day tour & honestly we loved it so much, that if I was doing it again, I would book the whole day! Highly recommend this experience! So worth it. 🤍 A big Thank you!!!!!! 🇬🇷 Best ever. Oh & the food was simple, but great! & we had lovely music for the whole tour, good ambiance!!!! +++5 stars ✨”

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Boat Tours in Heraklion, Cruises & Boat Tours, Dia Island Cruises, Heraklion Tours, Sailing & Catamaran Cruises, Sailing & Catamaran Cruises in Heraklion, Tour Reviews

Sailing Cruise to Dia Island with Meal and Water Activities

3.Sailing Cruise to Dia Island with Meal and Water Activities

★★★★★★★★★★4.5 · 526 reviews · 5 hours 30 minutes (approx.) · from $96

Sail from Heraklion to Dia Island for swimming, snorkeling, paddleboarding, a Cretan lunch, drinks, and a sunset return.

“Guide’s voice was quiet. Not all of us could hear him. Lunch was good. Snorkeling was not the best. Very little fish to see.”

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Balos Lagoon & Gramvousa Cruises, Boat Tours in Chania, Chania Tours, Cruises & Boat Tours, Sailing & Catamaran Cruises, Sailing & Catamaran Cruises in Chania, Tour Reviews, VIP

Kissamos: Balos & Gramvousa Luxury Catamaran Sailing Cruise

4.Balos & Gramvousa Luxury Catamaran Sailing Cruise

★★★★★★★★★★4.9 · 516 reviews · 7 - 8.5 hours · from $229

Review of DanEri Yachts’ luxury catamaran from Kissamos to Balos and Gramvousa, with meals, drinks, swimming, transfers, and practical tips.

“Such an amazing trip. The coast, the lagoon and the islands were beautiful. The boat was a perfect size, with space for everyone to move around a chill. Thank you to the crew for looking after us, keeping us well fed and watered! Very friendly and welcoming.”

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Dia Island Cruises, Half-Day, Private, Sailing & Catamaran Cruises, Tour Reviews

Heraklion: Private Half-Day Sailing Trip to Dia Island

5.Private Half-Day Sailing Trip to Dia Island

★★★★★★★★★★4.9 · 466 reviews · 4.5 hours

Review of a private Heraklion sailing trip to Dia Island, with swimming, snorkeling, fishing, fruit, drinks, optional lunch, and practical tips.

“It was a lovely sailing experience. It was beautiful and well organised. The staff was very friendly and kind. The overall experience was amazing and would 10/10 recommend it!”

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Boat Tours in Rethymno, Cruises & Boat Tours, Drinking Tours, Evening Experiences, Rethymno Tours, Sailing & Catamaran Cruises, Sunset Cruises, Tour Reviews

Rethymno: Sunset Catamaran Cruise – Sushi & Open Bar

6.Sunset Catamaran Cruise – Sushi & Open Bar

★★★★★★★★★★4.8 · 446 reviews · 3.5 hours · from $100

Sail from Rethymno for sushi, Greek wine, swimming, SUP, snorkeling, and a memorable Mediterranean sunset aboard a luxury catamaran.

“The crew was very experienced, communication was also great. It was a bit windy at first but the crew brought to an amazing area with quiet sea where we had a long pause and were able to swim. This little cruise was my mom’s birthday present and she was extremely happy.”

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Dia Island Cruises, Heraklion Tours, Sailing & Catamaran Cruises, Sailing & Catamaran Cruises in Heraklion, Tour Reviews

Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

7.Sailing Trip to Dia Island with Lunch & Swimming

★★★★★★★★★★4.8 · 414 reviews · from $67

Sail from Heraklion to Dia Island for swimming, snorkeling, SUP, fishing, a Greek lunch, unlimited drinks, and sunset views.

“Ilis and Vaso were our guides and we were really pleased with their hospitality. They were very welcoming, ensured we were looked after and had the best possible experience. Food was really lovely and great variety of drinks available on board. They had a paddling board and snorkelling masks available for everyone for when we stopped off to swim. Would recommend, 10/10 experience.”

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Boat Tours in Chania, Chania Tours, Cruises & Boat Tours, Sailing & Catamaran Cruises, Sailing & Catamaran Cruises in Chania, Tour Reviews

Kolimvari: Sailing Cruise with Meal & Water Activities

8.Kolimvari: Sailing Cruise with Meal & Water Activities

★★★★★★★★★★4.7 · 390 reviews · 5 hours · from $129

Review of a five-hour Crete sailing cruise from Kolymvari with swimming, snorkeling, SUP, a fresh meal, unlimited drinks, and sunset views

“Lovely cruise. Everyone was very friendly and the host very helpful. Beautiful scenery. Enjoyed the swim. The food was delicious. Was fun to have the drinks. I would highly recommend.”

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Boat Tours in Heraklion, Cruises & Boat Tours, Evening Experiences, Heraklion Tours, Sailing & Catamaran Cruises, Sailing & Catamaran Cruises in Heraklion, Sunset Cruises, Sunset Cruises in Heraklion, Tour Reviews

Hersonissos: Sunset Catamaran Cruise with Snacks and Drinks

9.Sunset Catamaran Cruise with Snacks and Drinks

★★★★★★★★★★4.8 · 328 reviews · from $90

Review of Hersonissos sunset catamaran cruise with swimming, snorkeling, SUP boards, snacks, drinks, and golden-hour views of Crete.

“Great experience, i think the hosts need to mention the islands as we pass or enter so we are aware”

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Boat Tours in Rethymno, Cruises & Boat Tours, Rethymno Tours, Sailing & Catamaran Cruises, Tour Reviews

Rethymno: Sailing Catamaran Cruise with Meal & Drinks

10.Sailing Catamaran Cruise with Meal & Drinks

★★★★★★★★★★4.7 · 285 reviews · from $164

Review of a six-and-a-half-hour Rethymno catamaran cruise with swimming, SUP, snorkeling, fresh Mediterranean lunch, and unlimited drinks.

“I liked being out on the water and everyone was so nice.”

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Dia Island Cruises, Heraklion Tours, Sailing & Catamaran Cruises, Sailing & Catamaran Cruises in Heraklion, Tour Reviews

Heraklion: Small-Group Sailing Trip to Dia Island with Lunch

11.Small-Group Sailing Trip to Dia Island with Lunch

★★★★★★★★★★4.7 · 277 reviews · 4.5 - 7 hours · from $94

Sail from Heraklion to protected Dia Island for clear-water swimming, snorkeling, a local lunch, and a relaxed small-group day at sea.

“Everthing was very Nice :) Maybe the Trips should be a Bit longer.”

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Boat Tours in Heraklion, Cruises & Boat Tours, Dia Island Cruises, Diving & Snorkeling, Diving & Snorkeling in Heraklion, Evening Experiences, Heraklion Tours, Sailing & Catamaran Cruises, Sailing & Catamaran Cruises in Heraklion, Tour Reviews

Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

12.Sunset Sailing Cruise Dia Island with Snorkeling

★★★★★★★★★★4.6 · 242 reviews · from $63

Sail from Heraklion to quiet Dia Island for snorkeling, paddleboarding, Greek food, drinks, and a sunset return cruise.

“Absolutely amazing experience ! I recommend and for sure we would repeat it in the future when we visit Greece again . It was the best value for money !”

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Sailing & Catamaran Cruises, Tour Reviews

Sailing trip to the Top Coasts of Crete, Daily/Multi-day

13.Sailing trip to the Top Coasts of Crete, Daily/Multi-day

★★★★★★★★★★5.0 · 221 reviews · 7 hours (approx.) Top rated

Sail Crete’s car-free southern coast to Loutro, Marmara, and Sweet Water Beach with swimming, snorkeling, lunch, and local snacks.

“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!!”

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Boat Tours in Heraklion, Cruises & Boat Tours, Dia Island Cruises, Heraklion Tours, Sailing & Catamaran Cruises, Sailing & Catamaran Cruises in Heraklion, Tour Reviews, VIP

Heraklion: Dia Island Luxury Catamaran Cruise with Meal

14.Dia Island Luxury Catamaran Cruise with Meal

★★★★★★★★★★4.7 · 194 reviews · 5.5 hours · from $127

Cruise from Heraklion to Dia Island on a spacious catamaran with swimming, snorkeling, paddle boarding, a Cretan meal, and drinks.

“We were very happy and glad during and after the trip, the staff was friendly, smiling and helpful. I especially want to note the attitude towards passengers from the crew, we felt comfortable and safe. Just simply had a great time 👌. I can confidently recommend others to also enjoy spending time on board with this company and their crew 🫶”

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