The 10 Best Private Sailing Charters in Heraklion

1.Dia Island: Semi-Private Full Day Sailing Trip with meal

★★★★★★★★★★4.7 · 19 reviews · 6 hours · from $100Number one

Sail from Heraklion’s Venetian port to Dia Island aboard a comfortable boat with a crew of up to 10 people. You can swim, snorkel, fish, use the SUP, explore the bay, and enjoy a meal with local wine and fruit. Dimitri is part of the crew, and the return trip includes more sailing and sea views.

“Très bonne journée passée avec nos deux capitaines sur l'ile. Beaucoup de poissons à observer en snorkeling. Très bon repas fait maison. En amélioration, faire un 2eme spot de baignade ailleurs serait sympa.”

Check dates →Read our review →

2.Private sailing to Dia Island with Lunch

★★★★★★★★★★4.8 · 16 reviews · 4.5 hours · from $471 per boat

Set sail from Heraklion’s Old Venetian port with a private group of up to eight. Your English, Greek, or Italian-speaking crew guides you to Dia Island for quiet-bay swimming, snorkeling, SUP time, local stories, and an optional fresh Cretan lunch. Vang and Aphro have earned praise for warm, attentive hosting.

“Six of us were in Crete last week and we we booked this boat trip which was an exclusive sailing boat with crew. The trip was faultless and perfect. I was with my 70+ parents and they were catered for from their mobility issues to vegetarian requirements for the gorgeous lunch prepared for us. There was swimming in the sea and just taking in the scenery: we could not have asked for more. We were picked and dropped off from our hotel and the crew were knowledgeable of the history and questions we had about Crete. I would highly recommend this as a must-do! 🌟🌟🌟🌟🌟”

Check dates →Read our review →

3.Private Sailing Cruise to Dia Island with Meal & Water Activities

★★★★★★★★★★4.5 · 10 reviews · 5 hours 30 minutes (approx.) · from $951 per boat

Sail privately from Heraklion to Dia Island for about five and a half hours with guides such as Harry, Christina, Captain George, and Martina. Expect a clean yacht, a swim stop, snorkeling, SUP, fishing gear, shrimp linguini, Greek salad, fruit, and drinks. Pickup covers much of Crete’s north coast, but wind and departure delays can affect the day.

“We had a fantastic time on this private sailing cruise. The staff were welcoming and attentive, making the whole journey enjoyable and relaxing. The food was delicious and plentiful, and the boat itself was in excellent condition—clean, comfortable, and well maintained. The mix of sailing, swimming, and water activities made it both fun and memorable. Highly recommend for anyone looking for a perfect day at sea.”

Check dates →Read our review →

4.Dia Island Private Sailing Cruise with Full Meal

★★★★★★★★★★5.0 · 6 reviews · 5.5 hours · from $931 per boatHighest rated

Set sail from Heraklion’s Venetian harbor on a private yacht for up to 10 people. Cruise past Koules Fortress, swim and snorkel in Dia’s clear bay, try fishing or paddleboarding, and enjoy shrimp linguini, Greek salad, fruit, and unlimited drinks. Crew members may include Amalia, Zoey, Spiros, Christos, or Giannis.

“Great crew, great experience, truly appreciated them calling to advise to switch booking for a different day for better weather, and the food was AMAZING”

Check dates →Read our review →

5.Sunset Private Sailing Trip to Dia island

★★★★★★★★★★5.0 · 4 reviews · 4.5 hours · from $730 per boat

Join Avanti Sailing for a 4.5-hour private cruise from Heraklion with an experienced captain and crew. Sail to Dia island, swim and snorkel in clear water, try the SUP and fishing gear, enjoy local wine and snacks, then watch the sunset over Crete. George and Nick may be among the welcoming crew.

“One of the highlights of our entire trip to Greece!! George and Nick were a fantastic crew and they made us feel welcome and well taken care of. The trip itself offered the perfect combination of elements: gentle breezes, warm sun, cool water, great wine and snacks and a beautiful sunset. Could not ask for anything more from a sailing excursion. Highly recommend!!”

Check dates →Read our review →

6.Dia Island Private Sailing Trip

★★★★★★★★★★5.0 · 3 reviews · 5.5 hours · from $707 per boat

You will sail from Heraklion’s Old Port aboard the private yacht Maryline with an English- or Greek-speaking captain. Reach Dia Island in about 75 minutes, then spend roughly three and a half hours swimming, snorkeling, walking among cedar trees, enjoying snacks, and relaxing in Saint George Bay. The trip suits groups of up to 10.

Check dates →Read our review →

7.Private Catamaran Cruise to Dia with Meal&Drinks

★★★★★★★★★★5.0 · 2 reviews · 5 hours · from $2,121 per boat

Sail from Heraklion to Dia Island aboard a private catamaran for up to 10 people. You get coffee and pies on arrival, unlimited soft drinks, beer, and white wine, plus a fresh Mediterranean meal. Swim, snorkel, fish, paddleboard, or enjoy the sunset. English and Greek speaking crew, Wi-Fi, cabins, and children’s options are included.

Check dates →Read our review →

8.Private Catamaran Cruise, Dia Island with Lunch

★★★★★★★★★★5.0 · 2 reviews · 6.5 hours · from $2,239 per boat

Set sail from Hersonissos with a private English- or Greek-speaking crew, then spend 3.25 hours in a quiet Dia Island bay. Swim, snorkel, fish, paddleboard, and enjoy a freshly cooked Mediterranean lunch with unlimited soft drinks, beer, and white wine. The catamaran has Wi-Fi, music, cabins, toys, and shaded deck space.

Check dates →Read our review →

9.Private Sailing Trip from Heraklion to Dia with meal & SUP

★★★★★★★★★★5.0 · 2 reviews · 5 hours · from $353 per boat

Sail from Heraklion to uninhabited Dia with your private group, a skipper, and an assistant. Aris and Zjohn may be your crew. You will swim, snorkel, paddleboard, explore the island, enjoy snacks and soft drinks, and sail back as the sun sets. The boat holds up to three people for $353.

“Aris and Zjohn were very friendly and accommodating. It felt like a private boat tour for our party. They were very professional yet warming in their approach to let us know how the day will go, and some history of the places. We went to a private island and had a chance to snorkel, paddle board and get to explore a little of the island. What made it even more personal was that Aris and Zjohn made our food for us which was exceptional! Actually it was almost Michelin star level, made with love. We had a three course meal and then they escorted us back to the island. The…”

Check dates →Read our review →

10.Private Sailing Trip from Heraklion to Dia island

★★★★★★★★★★5.0 · 2 reviews · 4.5 - 6 hours · from $730 per boat

Join Avanti Sailing for a private 4.5 to 6-hour cruise from Heraklion to Dia Island. You can sunbathe, help with sailing, swim, snorkel, use the SUP, view marine life, and enjoy a meal with local wine and fruit. The boat carries up to 10 people, with hotel pickup available if selected.

Check dates →Read our review →