Crete · SAILING

Top 15 Sailing Days in Crete

40 tours  ·  from $37

Good sailing days fill up weeks ahead and the great ones go first. Below: the 15 to book early, what each includes and how they differ.

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
Crete Sailing Trips, Cruises & Boat Tours, Dia Island Cruises, Heraklion Tours, Lunch Experiences, Sailing, Sailing Trips in Heraklion, Tour Reviews

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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Rethymno: Sunset Catamaran Cruise - Sushi & Open Bar - The First Hour: Open Sea, Shade, and Snacks
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Rethymno: Sunset Catamaran Cruise – Sushi & Open Bar

7.Sunset Catamaran Cruise – Sushi & Open Bar

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

Sail from Rethymno on the 25-person catamaran Karina for 3.5 hours of swimming, SUP, snorkeling, sushi, Cretan snacks, and Greek wine. The English-speaking crew, including Nana, Yannis, Banos, and Sepdos, finishes the trip with sunset views near Geropotamos Beach.

“Host was incredible, atmosphere was amazing. Could not recommend this trip more!!!”

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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

8.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

9.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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Hersonissos: Sunset Catamaran Cruise with Snacks and Drinks - Boarding at Hersonissos Port
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Hersonissos: Sunset Catamaran Cruise with Snacks and Drinks

10.Sunset Catamaran Cruise with Snacks and Drinks

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

Sail from Hersonissos with an attentive English and Greek-speaking crew, unlimited soft drinks, beer, white wine, local snacks, Wi-Fi, and water gear. Swim at Agios Georgios Bay, try a SUP board, float with the pink flamingo, then watch the sunset from the sea.

“Brilliant. Secluded cove swim was really nice, just about caught the sun set on the way back. They changed to departure to Heraklion due to choppy seas but also picked us up and dropped us back at the hotel so we weren't put out. Finger food was pretty none existent so don't be expecting much, and drinks didn't exactly flow but the scenary was great, the guide was spot on, good music and vibes. Would recommend.”

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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling - Dia Island’s quiet main bay
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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

11.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

12.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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Heraklion: Dia Island Luxury Catamaran Cruise with Meal - One hour across the Cretan Sea
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Heraklion: Dia Island Luxury Catamaran Cruise with Meal

13.Dia Island Luxury Catamaran Cruise with Meal

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

From Heraklion’s Old Venetian Harbor, you sail to Dia Island aboard a Lagoon 450F catamaran with an English or Greek-speaking crew. Swim, snorkel, fish, or use the SUP board before a Mediterranean meal, unlimited drinks, and a relaxed return, with morning and sunset departures.

“The sunset on the boat, I truly recommend the evening trip.”

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Chania: Afternoon Catamaran trip - Dinner, Drinks & Sunset - Leaving Kolymvari with snacks and a safety briefing
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Chania: Afternoon Catamaran trip – Dinner, Drinks & Sunset

14.Afternoon Catamaran trip – Dinner, Drinks & Sunset

★★★★★★★★★★4.9 · 168 reviews · 5 hours · from $165

Sail from Kolymvari to the Agioi Theodoroi Islands on the Vesselina, with swimming, snorkeling, SUP boards, fishing gear, dinner, and unlimited drinks. The crew, including Angelo, Nana, Peach, and Yianni, keeps the five-hour cruise relaxed, social, and well organized before the sunset return.

“We had the best day on the boat. We were a group of 11. Food was amazing, drinks flowing. We were allowed to request any song we wanted. Was just overall an amazing day”

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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

15.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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New in Sailing

★ 3.9Spinalonga and Kolokitha Island Sailing Trip3 reviews
★ 5.0Private Catamaran Cruise with Meal & Drinks6 reviews
★ 5.0Small Group Sailing Cruise from Agios Nikolaos in Mirabello BayFrom $13221 reviews
★ 5.0Crete Yacht Cruises 5 Hours Private Guided Cruise in Ag Nikolaos13 reviews
★ 4.7Mirabello Bay Sailing Cruise with MealFrom $11230 reviews
★ 4.9Golden Hour Sailboat Tour with Wine & SnacksFrom $11235 reviews
★ 5.0Catamaran Sailing to Dia with Lunch in Heraklion, Crete(EST 2024)From $14264 reviews
★ 4.5Day Cruise with Luxury Yacht to Chrissi islandFrom $15523 reviews
★ 4.6Chrissi Island Yacht Cruise with Lunch & SnorkelingFrom $2265 reviews
★ 5.0Panormo: Luxury Catamaran Cruise with Lunch & Open BarFrom $17480 reviews
★ 4.5Rethymno Catamaran Cruise: Healthy Lunch & Open BarFrom $17479 reviews
★ 4.9Spinalonga AM Catamaran Cruise with LunchFrom $13483 reviews
★ 4.9Morning Catamaran Cruise with Premium Lunch & DrinksFrom $15890 reviews
★ 4.8Spinalonga PM Catamaran Cruise with DinnerFrom $13488 reviews
★ 4.6Agia Galini: South Crete Sailing Trip with Optional LunchFrom $10692 reviews

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