CRETE

The 15 Crete Sailing Tours That Earn Their Price

47 sailing trips  ·  from $35 a head

The good crete sailing tours fill up weeks ahead and the small boats go first. Below: the 15 to book early, what each includes and how they differ.

Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch - Dia Island’s clear water and quiet cove
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Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

1.Sailboat Cruise to Dia Island with Drinks & Lunch

★★★★★★★★★★4.8 · 1,405 reviews · 1 hour - 390 minutes · from $35Our pick

Review of Crete’s Dia Island sailing trip from Heraklion, with yacht views, swimming, snorkeling, lunch, drinks, costs, and practical tips.

“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”

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Heraklion: Private Half-Day Sailing Trip to Dia Island - Dia Island and Saint George Bay
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Heraklion: Private Half-Day Sailing Trip to Dia Island

2.Private Half-Day Sailing Trip to Dia Island

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

Review of Heraklion’s private Dia Island sailing trip, with snorkeling, fishing, lunch options, pricing, timing, 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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From Kissamos: Balos Gramvousa Sailing Cruise with Lunch - Leaving Kissamos for the open sea
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From Kissamos: Balos Gramvousa Sailing Cruise with Lunch

3.From Kissamos: Balos Gramvousa Sailing Cruise with Lunch

★★★★★★★★★★4.9 · 257 reviews · 7.5 hours · from $229

Sail from Kissamos to Balos Lagoon and Gramvousa for swimming, castle views, and a fresh Cretan lunch on a small boat.

“An Unforgettable Experience! We booked a sailing boat tour in Crete while traveling with my husband and our 4-year-old daughter. From start to finish, everything was absolutely perfect. The crew was incredibly friendly, kind, and welcoming and taking time to explain things we were curious about and made us feel completely at ease, especially with a young child on board. They were so accommodating, and our daughter truly had the time of her life: she still talks about it! Every part of the journey was fantastic. They prepared an incredible traditional Cretan lunch cooked right on the boat (we honestly couldn’t get enough of it!) and later served fresh fruit,…”

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Sailing trip to the Top Coasts of Crete, Daily/Multi-day - Loutro, the Village Without Roads
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Sailing trip to the Top Coasts of Crete, Daily/Multi-day

Dia island : Small Group Sailing Trip to Dia Island with Lunch - The one-hour sail to Dia Island
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Dia island : Small Group Sailing Trip to Dia Island with Lunch

5.Dia island : Small Group Sailing Trip to Dia Island with Lunch

★★★★★★★★★★5.0 · 162 reviews · 4 hours 30 minutes (approx.) · from $72

Review of the Dia Island sailing trip from Heraklion, with lunch, swimming, snorkeling, wildlife, pickup details, value, and practical tips.

“Absolutely fantastic excursion! We ended up having the entire boat to ourselves and the team really accommodated us and ensured we really had an amazing time. Lunch/wine onboard was delicious and they were fantastic photographers making sure we got ample amount of photos”

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Sailing Trip to Dia with Snorkeling, Dining & Sunset Option - Lunch on deck, with Cretan flavors
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Sailing Trip to Dia with Snorkeling, Dining & Sunset Option

6.Sailing Trip to Dia with Snorkeling, Dining & Sunset Option

★★★★★★★★★★5.0 · 142 reviews · 4 hours 30 minutes (approx.) · from $36

Sail from Heraklion to Dia Island for snorkeling, a fresh meal, Cretan wine, and a sunset return on a small-group yacht.

“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…”

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Heraklion: Private Full-Day Sailing Trip to Dia Island - Meeting the crew at Heraklion Marina
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Heraklion: Private Full-Day Sailing Trip to Dia Island

7.Private Full-Day Sailing Trip to Dia Island

★★★★★★★★★★4.9 · 140 reviews · 6.5 hours

Review of a private Heraklion sailing trip to Dia Island, with swimming, snorkeling, fishing, lunch options, drinks, and practical booking advice.

“We told the guides we were more interested in sailing than the excursions and they accommodated our request. The Elan 37 is a fun boat and she sailed well even in light winds. The lunch was delicious and we enjoyed it in an idyllic bay on Dia island. The captain and first mate were vey kind and helpful with our two kids. I highly recommend this excursion and will book again if we return to Crete.”

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Dia Island Catamaran – Premium Lunch, Open Bar, Small Group - What the small group really changes
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Dia Island Catamaran – Premium Lunch, Open Bar, Small Group

8.Dia Island Catamaran – Premium Lunch, Open Bar, Small Group

★★★★★★★★★★5.0 · 126 reviews · 6 hours 30 minutes (approx.) · from $181

Review of Crete’s Dia Island catamaran cruise, with a small group, fresh Mediterranean lunch, open bar, swimming, snorkeling, and SUPs.

“This was a great experience. The captain and the crew were awesome. Crew answered all questions and were very pleasant at all time. The captain was amazing. He engaged all passengers trying to teach us typical Greek dance and later put on a concert as Johnny Depp. The lunch was amazing. Made fresh as we were all swimming. It was great. This was truly a 5 star trip.”

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Balos & Gramvousa Luxury Catamaran Sailing Cruise from Kissamos - Starting in Kissamos at 8:30 am
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Balos & Gramvousa Luxury Catamaran Sailing Cruise from Kissamos

9.Balos & Gramvousa Luxury Catamaran Sailing Cruise from Kissamos

★★★★★★★★★★5.0 · 116 reviews · 7 hours 30 minutes (approx.) · from $235

Review of the Balos and Gramvousa luxury catamaran cruise from Kissamos, with food, swimming, timing, price, crowds, and practical tips.

“Absolutely lovely staff. The main guy, Dimitri??? ( could be getting his name wrong) he was absolutely amazing. He made the trip. Food was soooo good too. The wind was awful and we were so Cole and couldn’t get into the water, or do much but the experience of the company made it still great considering.”

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Sailing Trips with Cretan Sailing - The first hour and St. George Bay
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Sailing Trips with Cretan Sailing

10.Sailing Trips with Cretan Sailing

★★★★★★★★★★4.0 · 99 reviews · 4 hours (approx.) · from $54

Review of Cretan Sailing from Hersonissos, with swimming, snorkeling, BBQ lunch, costs, timing, crowd notes, and practical booking advice.

“Experience is great, we had 2 stops, first one just to swim and second one with different places you could swim to and different activities. Me as a not strong swimmer was given a floatie so could fully participate. We chose to do snorkeling at second stop, it is just the goggles they give but we were able to see so many fish it was amazing. We had the chicken for the food which was a cooked bit of chicken, salad and a couple slices of bread, nothing fancy but did the job and we threw some bread for the fishes as was no butter so a bit dry for…”

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Sailing Cruises Chania - Swimming and snorkeling near the Island of Ag
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Sailing Cruises Chania

11.Sailing Cruises Chania

★★★★★★★★★★5.0 · 93 reviews · 4 to 7 hours (approx.) · from $437

Sail Chania’s Gulf, swim by the Island of Ag, spot KRI KRI goats, and enjoy Cretan food and drinks on a private cruise.

“We highly recommend spending the day on this boat. We have done a lot of day cruises in the pacific and the Mediterranean. We have been on some great boats and sailed with some great crews. This is by far the best crew we have sailed with. The boat is impeccably maintained as well.”

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Rethymno Catamaran Cruise: Healthy Lunch & Open Bar - Georgioupoli Bay and the water activities
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Rethymno Catamaran Cruise: Healthy Lunch & Open Bar

12.Rethymno Catamaran Cruise: Healthy Lunch & Open Bar

★★★★★★★★★★4.5 · 79 reviews · 6 hours 30 minutes (approx.) · from $174

Spend 6.5 hours sailing Crete’s north coast with healthy Cretan food, open bar, swimming, SUP, snorkeling, and attentive crew.

“Everything was on time as they said. The captain, assistant and deckhand (both women 😁) were all very friendly and knowledgeable. We felt completely safe and taken care of. The boat was clean, well organized and well set up. We were welcomed on board with food and drinks. The captain explained everything about the trip and made us laugh and feel at ease. The girls kept asking if we needed or wanted anything and brought it to us. The appetizers, lunch and dessert were delicious. 100% we would do this again and Highly Recommend This Exact Boat, Captain, Assistant and Deckhand!! From the 6 of us who live near the…”

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Sailing Trip to Dia Island - All Inclusive - A fresh lunch served on the boat
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Sailing Trip to Dia Island – All Inclusive

13.Sailing Trip to Dia Island – All Inclusive

★★★★★★★★★★5.0 · 67 reviews · 6 to 8 hours (approx.) · from $90

Review of Crete’s all-inclusive Dia Island sailing trip, with swimming, snorkeling, paddleboarding, seafood pasta, drinks, pricing, 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...”

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Catamaran Sailing to Dia with Lunch in Heraklion, Crete(EST 2024) - Swimming, snorkeling, and free SUP time
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Catamaran Sailing to Dia with Lunch in Heraklion, Crete(EST 2024)

Sailing to Dia Island with lunch on Bavaria 51 Heraklion, Crete - Leaving Heraklion aboard Bavaria 51
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Sailing to Dia Island with lunch on Bavaria 51 Heraklion, Crete

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