Crete · CRETE SAILING TRIPS

The 15 Best Sailing Trips in Crete

26 tours  ·  from $37

A sailboat out of Heraklion buys you shade, a swim ladder and a meal cooked on deck. The 15 below compare the Dia island runs on group size, how long the engine stays off and what is really included.

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal - Why 14 People Makes a Difference
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Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

1.Dia Island Sailboat Cruise with Swimming and Meal

★★★★★★★★★★4.8 · 2,579 reviews · 5.5 hours · from $95Our pick

Sail from Heraklion’s Old Venetian Harbour to protected Dia Island aboard a small yacht for up to 14 people. Captain Petros and crew members such as Sofia, Giannis, Mariana, and Manos may host your trip, with swimming, snorkeling, paddleboarding, a Mediterranean meal, unlimited drinks, and sunset options.

“Fantastic few hours in the Greek sea, lovely crew DELICIOUS food and gorgeous sunset! Love love love”

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Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch - Saint George Bay and Dia Island
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Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

2.Sailboat Cruise to Dia Island with Drinks & Lunch

★★★★★★★★★★4.9 · 1,287 reviews · from $90

Join a small shared cruise or private sailing trip from Heraklion to Dia Island. Swim and snorkel in Saint George Bay, try fishing, enjoy lunch and unlimited drinks, and sail back with an attentive crew such as Marcos, Vasilis, Dimitris, or Alexandra.

“A beautiful and relaxed boat trip including a lovely little meal. I enjoyed it a lot. Thanks to captain and skipper and also the other travelers.”

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Heraklion: Sailing Cruise to Dia Island with Drinks and Meal - What the crossing feels like in changing weather
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Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

3.Sailing Cruise to Dia Island with Drinks and Meal

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

You’ll sail from Heraklion’s Old Venetian Harbor to Dia Island with a certified crew, often including Stelios, Celia, Captain Nick, Kristina, or Iorgu. Swim, snorkel, paddleboard, fish, hike, and enjoy shrimp spaghetti, salad, fruit, wine, soft drinks, and raki aboard a small-group yacht.

“Lovely chilled boat cruise with two swimming stops… the island is uninhabited just some goats but it’s all about boat life!! Lush food, beer and wine and soft drinks flowing all day and raki shots for the hard-core”

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Heraklion: Dia Island Sailing Cruise with Snorkeling - What Dia Island gives you after the crossing
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Heraklion: Dia Island Sailing Cruise with Snorkeling

4.Dia Island Sailing Cruise with Snorkeling

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

Sail from Heraklion with a professional crew, often including Ernesto and George, to uninhabited Dia Island. Swim in clear bays, snorkel, paddleboard, and enjoy Greek salad, tzatziki, seafood pasta, fruit, wine, and soft drinks. Choose a half-day or full-day trip, with small groups of up to 18.

“A really enjoyable and relaxing day. The group was small and everyone chatted with eachother and also with the two crew who were great. It was my first time on a sailing boat which I really enjoyed as well. Would highly recommend!”

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Sailing Cruise to Dia Island with Meal and Water Activities - Swimming, snorkeling, paddleboarding, and fishing
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Sailing Cruise to Dia Island with Meal and Water Activities

5.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 uninhabited Dia Island aboard a yacht or catamaran, with swimming, snorkeling, SUP, fishing, lunch, wine, beer, and soft drinks included. Expect about an hour at sea each way and three hours in a sheltered bay. Boats and crew may vary.

“We were collected from our hotel and taken to the port. Our first experience in a sail boat and really enjoyed it. Food and drinks were included. The water at Dia island was gorgeous to swim in. Then a journey back watching the sunset was the perfect ending.”

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Heraklion: Private Half-Day Sailing Trip to Dia Island - Leaving Heraklion after a one-hour sail
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Heraklion: Private Half-Day Sailing Trip to Dia Island

6.Private Half-Day Sailing Trip to Dia Island

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

Spend 4.5 hours on a private sailing boat from Heraklion to Dia Island, with a two-person crew, drinks, fruit, snorkeling gear, fishing equipment, and paddleboards. Anchor in Saint George Bay, the setting once explored by Jacques Yves Cousteau, and add a fresh onboard meal if you wish.

“Communication with the provider was excellent from point of booking to the day of the event. They answered my many questions and was helpful with facilitating a cake delivery for my daughters birthday. The round trip taxi service was fairly priced, the driver arrived in time & was very friendly and accommodating. The boat was lovely & the crew Ilias & Nikiforas were fantastic. Really friendly& welcoming guys. Dia Island was beautiful & the journey to and from the island was equally as enjoyable. All round a perfect excursion and well worth the money. Thank you”

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Heraklion: Sailing Trip to Dia Island with Lunch & Swimming - Transfers from Hersonissos, Malia, and Nearby Resorts
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Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

7.Sailing Trip to Dia Island with Lunch & Swimming

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

Set Sails takes you from Heraklion to Dia Island on a small-group yacht cruise with swimming, snorkeling, fishing, SUP, and lunch. The crew may include George, Vaso, Spiros, or Marina. Choose port departure or selected transfers, then spend about three hours anchored at Saint George Bay.

“My partner and I loved this trip! Vaso & Spiros were fantastic guides. Snorkeling at Dia Island was super fun and the water was nice and warm. We enjoyed chatting with the others guests on the boat - had some wine together which was fun. Highly recommend this experience!”

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Kolimvari: Sailing Cruise with Meal & Water Activities - Agioi Theodoroi and the Kri-Kri goats
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Kolimvari: Sailing Cruise with Meal & Water Activities

8.Kolimvari: Sailing Cruise with Meal & Water Activities

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

Join a small-group sailing cruise from Kolymvari with crew such as Lucas and Jason. After coastal views and a safety briefing, swim near Agioi Theodoroi, snorkel, paddleboard, watch for Kri-Kri goats, and enjoy shrimp linguine, Greek salad, local appetizers, fruit, and unlimited drinks.

“The crew on board were very hospitable and the scenery was beautiful. A generous amount of time was given at each location and very decent food included also!”

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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling - Dia Island’s quiet main bay
Crete Sailing Trips, Crete Snorkeling Trips, Crete Sunset Cruises, Cruises & Boat Tours, Dia Island Cruises, Evening Experiences, Heraklion Tours, Sailing, Sailing Trips in Heraklion, Snorkeling, Snorkeling Trips in Heraklion, Sunset Cruises in Heraklion, Tour Reviews

Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

9.Sunset Sailing Cruise Dia Island with Snorkeling

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

Sail from Heraklion to uninhabited Dia Island with a small crew, swimming, snorkeling, paddleboarding, food, wine, and raki. Depending on the boat and departure, you may meet crew members such as Alex, Kostas, Emanuel, Constantine, Thanos, or Eleanor. Choose a shared or private catamaran and a half-day or full-day outing.

“This experience was the cherry on the cake for our trip here. For a cheap price a 4 hour boat-trip with food, amazing view on the sea and sunset, snorkling and swimming. The guides/captains were all very kind. 10/10 would recommend.”

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Sailing trip to the Top Coasts of Crete, Daily/Multi-day - Loutro, the village without road access
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Sailing trip to the Top Coasts of Crete, Daily/Multi-day

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

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

Spend about seven hours on a private sailing trip from Sfakia Port with your group of up to nine. Visit Loutro, Sweet Water Beach, and Marmara Beach, swim in clear coves, explore sea caves, and enjoy lunch, snacks, water, and soft drinks.

“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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Dia island : Small Group Sailing Trip to Dia Island with Lunch - Choosing between Agios Georgios and Panagia Bay
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Dia island : Small Group Sailing Trip to Dia Island with Lunch

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

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

You sail from Heraklion’s Old Venetian port to Dia Island with a certified crew, usually in a group of no more than 10. Expect a calm bay, swimming, SUP boards, snorkeling gear, an organic lunch, fruit, soft drinks, and wine. Pickup is free within 10 kilometers.

“We booked this tour in the afternoon the day before the booking and was recommended it by Viator when we called them. And after booking Viator said the tour was confirmed in our confirmation. We arrived at the port (after a 1.5 hour drive) the next morning, at the meeting point but the Aftersails team were nowhere to be seen. After waiting 30 minutes we gave them a call and they had no record of our booking. Their explanation was that the tours for the previous day were cancelled because of the windy weather and moved to our day. This is understandable, but there is obviously an issue with them…”

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From Kissamos: Balos Gramvousa Sailing Cruise with Lunch - The cruise from Kissamos: about 90 minutes of open water
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From Kissamos: Balos Gramvousa Sailing Cruise with Lunch

12.Balos Gramvousa Sailing Cruise with Lunch

★★★★★★★★★★4.8 · 153 reviews · from $615

Set sail from Kissamos with an experienced skipper, swim and snorkel at Balos, hike Gramvousa’s Venetian castle, and eat a fresh Cretan lunch cooked aboard. Private and small-group options are available, with crews such as Vasilis, Jo, George, and Alice depending on the departure.

“It was an amazing experience! Our skipper and his first mate were absolutely wonderful and made us feel very safe and welcome on their boat. The two locations we visited were like a dream, even though we had a little shorter visit to them as planned (because of weather conditions). The lunch that we were served, which was cooked on the boat, was some of the tastiest food we've had while in Crete. The sailing part was the star of the show, sitting on the edge of the boat enjoying the view, the sun, and the ocean spray made for an unforgettable day. Would recommend!Read more”

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Sailing Trip to Dia with Snorkeling, Dining & Sunset Option - Lunch, Cretan drinks, and time to slow down
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Sailing Trip to Dia with Snorkeling, Dining & Sunset Option

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

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

Sail from Heraklion to Dia Island aboard a 45-foot yacht with a small group of up to 10 people. Swim and snorkel in St. George’s Bay, enjoy a generous onboard meal with drinks, and choose a sunset return. Crew members such as Markos, Alexandra, Magda, and Georges provide warm, attentive service.

“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 is awesome in all respects and definitely something one should do if they visit the area of Heraklio. The sailing experience is exciting, the water at Dia is marvelous, the meal is delicious, and the staff is amazing! Our captain and co-captain were Markos and Magda and each of them was the perfect combination of…”

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Heraklion: Private Full-Day Sailing Trip to Dia Island - The first hour: sailing with Heraklion behind you
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Heraklion: Private Full-Day Sailing Trip to Dia Island

14.Private Full-Day Sailing Trip to Dia Island

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

Take a private sailing boat from Heraklion to Dia Island with a two-person crew, swimming stops, snorkeling gear, fishing equipment, paddleboards, fruit, drinks, and local white wine. Add hotel transfers or an onboard meal for a more polished day.

“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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Balos & Gramvousa Luxury Catamaran Sailing Cruise from Kissamos - The morning departure from Kissamos
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Balos & Gramvousa Luxury Catamaran Sailing Cruise from Kissamos

15.Balos & Gramvousa Luxury Catamaran Sailing Cruise from Kissamos

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

Join DanEri Yachts for a 7.5-hour cruise from Kissamos to Balos and Gramvousa. With a maximum of 22 people, captains such as Yannis and Dimitri, a chef-prepared lunch, snorkeling, paddleboards, and early arrival before the ferries, this is a polished way to see Crete’s famous northwest coast.

“Dimitri, Yanni (sp) and Jessica delivered a first class experience. We were sorry it had to end! The boat, food, music, meeting fellow travelers, the beach and views made for a perfect day. Highly recommend adding this to your holiday.”

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New in Crete Sailing Trips

★ 5.0Small Group Sailing Cruise from Agios Nikolaos in Mirabello BayFrom $13221 reviews
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★ 4.5Day Cruise with Luxury Yacht to Chrissi islandFrom $15523 reviews
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