Best of · HERAKLION ISLAND HOPPING TOURS

15 Heraklion Island Hopping Tours Worth Boarding

22 tours  ·  from $70 a head

This is the shortlist you would send a friend: 15 heraklion island hopping tours worth the money, each with its price, its traveller verdict and the one thing to check before you pay.

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal - Why the 14-person limit changes the day
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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 Venetian Harbour to Dia Island aboard a yacht limited to 14 people. Your English-speaking crew, including a certified captain, serves shrimp linguini, Greek salad, Cretan appetizers, and unlimited drinks, with time for swimming, snorkeling, paddleboarding, and sunset sailing.

“The perfect day! Our guided were all so kind and accommodating. The boat was beautiful, spacious, and had plenty of fun equipment. The lunch was delicious and abundant, as well and the drinks! Overall, a fantastic experience. Would absolutely do it again!”

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Heraklion: Sailing Cruise to Dia Island with Drinks and Meal - Dia Island: quiet shores and clear water
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Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

2.Sailing Cruise to Dia Island with Drinks and Meal

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

Sail from Heraklion’s Venetian harbor to uninhabited Dia Island with a certified crew, snorkeling gear, SUP boards, fishing equipment, lunch, wine, soft drinks, and raki. You’ll hear island legends, swim in clear water, and return by sail, with sunset departures available.

“Literally so nice, personable and professional. We made friends with others on the tip facilitated by the captain. Not been cheesy but we will be lifelong friends.”

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Heraklion: Dia Island Sailing Cruise with Snorkeling - Dia Island’s quiet northern bays
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Heraklion: Dia Island Sailing Cruise with Snorkeling

3.Dia Island Sailing Cruise with Snorkeling

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

Sail from Heraklion with a small crew of up to 18 people to uninhabited Dia Island. Expect swimming, snorkeling, paddleboarding, drinks, and food onboard. Ernesto and George are among the crew members, and the half-day or full-day format lets you match the trip to your schedule.

“A beautiful day, great weather, calm sea. Crew were kind and great to talk with. Really enjoyed snorkelling, the water was magical!”

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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling - Five hours around Dia’s main cove
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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

4.Sunset Sailing Cruise Dia Island with Snorkeling

★★★★★★★★★★4.7 · 529 reviews · 4.5 - 7 hours · from $82

Sail from Heraklion to uninhabited Dia Island with a professional crew, snorkeling gear, paddleboard, food, drinks, and time to swim. Full-day trips add a second bay and a seafood meal, while half-day trips focus on one cove and sunset sailing.

“Thoroughly enjoyed! nice crew and nice ppl on board”

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Sailing Cruise to Dia Island with Meal and Water Activities - Dia’s church, wildlife, and old Minoan harbor
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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 with a small crew and time to swim, snorkel, fish, paddleboard, and sunbathe. Lunch includes shrimp linguine, Greek salad, Cretan appetizers, and fruit, with beer, wine, soft drinks, and water. Pickup is available across much of Crete.

“Perfect day sailing and enjoying the sun and sea!!! The crew was great and the food was delicious!!!”

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Heraklion: Sailing Trip to Dia Island with Lunch & Swimming - Dia Island and Saint George Bay
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Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

6.Sailing Trip to Dia Island with Lunch & Swimming

★★★★★★★★★★4.8 · 517 reviews · 6 hours · from $100

Join a six-hour small-group sailing trip from Heraklion to Dia Island with up to 10 people. Captains George, Panos, and Vaso share local stories while you swim, snorkel, paddleboard, fish, and enjoy shrimp or vegetarian pasta with drinks on board.

“We are a family of 5 and were lucky to share the yacht with just another family of 3 and our lovely guides George and Marcos. It was a very hot, still day so we couldn’t actually sail but this meant for beautiful calm waters and exceptional swimming and snorkelling when we got to Dia Island. Lunch was delicious too. All in all a fabulous trip!”

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Heraklion Luxury Sailing Catamaran Dia Island | Gourmet Menu - Sailing one hour toward mythical Dia Island
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Heraklion Luxury Sailing Catamaran Dia Island | Gourmet Menu

7.Heraklion Luxury Sailing Catamaran Dia Island | Gourmet Menu

★★★★★★★★★★4.9 · 312 reviews · 5.5 hours · from $141

Sail from Heraklion to Dia Island aboard EOS Yachts’ modern catamaran, limited to 22 people. The crew serves Cretan treats, seafood cooked by Chef Charis, local wine, beer, and dessert. You’ll have about three hours for swimming, snorkeling, fishing, canoeing, and paddleboarding in a sheltered bay.

“The yacht itself exceeded my expectations. It was very spacious with luxurious touches. The boat did not feel crowded. The crew were very attentive and welcoming. They were constantly offering us drinks or assistance. The meal was also delicious, gourmet quality. The sunset ride back was stunning. Highly recommend.”

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From Heraklion: Sunset Cruise to Dia Island - Three and a half hours around Saint George Bay
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From Heraklion: Sunset Cruise to Dia Island

8.Sunset Cruise to Dia Island

★★★★★★★★★★4.8 · 259 reviews · 5.5 hours · from $82

Sail from Heraklion’s Old Port to Dia Island aboard the MARYLINE, with about 3.5 hours for swimming, snorkeling, snacks, and beach time. Captains and crew such as Alex, Yannis, Kosta, and Niko have hosted departures, with English and Greek guidance, music, and an introduction to sailing.

“We had such a fun afternoon! Alex and his partner were so funny and made for a comfortable trip to Dia! We had great conversation and food and drinks offered throughout. Everything was explained thoroughly including what to expect. It was my first time on a sailboat and the guides were incredible and so reassuring. Would 100% recommend if you’re looking for a fun day trip to Dia! Thank you so much for making our trip so fun and such an easy experience! We hope to come back again and will 100% be looking for you guys again - the best! Thank you!”

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Heraklion:Dia Island Catamaran Cruise with Lunch, Water Toys - Meeting the crew at Marina Café
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Heraklion:Dia Island Catamaran Cruise with Lunch, Water Toys

9.Dia Island Catamaran Cruise with Lunch, Water Toys

★★★★★★★★★★5.0 · 229 reviews · 5.5 - 7 hours · from $132Top rated

Join DanEri Yachts for a 5.5 to 7-hour catamaran cruise from Heraklion to Dia Island. Expect espresso, shaded lounges, paddleboards, snorkeling gear, an inflatable slide, a chef-prepared Cretan lunch, and attentive crew members such as Jana and Wesley.

“Wonderful day on a luxury boat . Team was great and beautiful island.”

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Heraklion: Dia Island Luxury Catamaran Cruise with Meal - Why the Lagoon 450F makes a difference
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Heraklion: Dia Island Luxury Catamaran Cruise with Meal

10.Dia Island Luxury Catamaran Cruise with Meal

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

Join Cretan Sailing Cruises from Heraklion’s Old Venetian Harbor for a 5.5-hour cruise to Dia Island aboard a Lagoon 450F catamaran. Swim, snorkel, fish, paddleboard, and enjoy a Mediterranean meal with unlimited drinks. Morning and sunset departures are available, with Sophia and the crew looking after you.

“Excellent activity! Really nice boat (around 26 persons per boat) and the waters in dia island are amazing. A really special activity and great crew.”

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Heraklion: Dia Island Catamaran Cruise with Dinner and Wine - One hour across the Cretan Sea
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Heraklion: Dia Island Catamaran Cruise with Dinner and Wine

11.Dia Island Catamaran Cruise with Dinner and Wine

★★★★★★★★★★4.8 · 147 reviews · from $120

Join DanEri Yachts for a five-hour afternoon cruise from Heraklion to Dia Island. Enjoy coffee and Cretan snacks, swim in a calm bay, use SUPs and snorkeling gear, and eat a fresh seafood and meat dinner with unlimited drinks as the sun sets.

“I had the pleasure of traveling with the Daneri yacht company, and it was an extraordinary experience. Everything was perfectly organized, and I was impressed by the quality of the services provided. First of all, the food was delicious and very tasty. We had a variety of dishes at our disposal that delighted our taste buds. Also, the drinks were plentiful and of very good quality. The music on the yacht was pleasant and created a relaxing and cheerful atmosphere. The sea was calm and had an absolutely stunning color, which made the trip even more enjoyable. A big plus was our driver, George. A friendly and very nice person…”

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Heraklion: Cruise to Chrissi Island Natural Park with Pickup - Setting sail across the Libyan Sea
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Heraklion: Cruise to Chrissi Island Natural Park with Pickup

12.Cruise to Chrissi Island Natural Park with Pickup

★★★★★★★★★★4.1 · 124 reviews · 10 - 12 hours · from $70Best value

Take a full-day coach and boat trip from Heraklion to Chrissi Island Natural Park. You will have free time in Ierapetra, cruise around the island for about 4.5 hours, and swim from the boat to Belegrina Beach. Guides speak English, French, and German. Lunch costs extra.

“Une île paradisiaque !!! J’ai vraiment aimé, pour ceux qui ne sont pas à l’aise de nager du bateau à la plage ( environs 80m) il y a des gilet de sauvetage, planches et frites pour aider. Prenez des masques ou des lunettes pour voir les poissons j’ai vu pu apercevoir beaucoup d’espèces.”

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Heraklion: Dia Island Sunset Boat Tour with Dinner - Saint George Bay and three hours at Dia Island
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Heraklion: Dia Island Sunset Boat Tour with Dinner

13.Dia Island Sunset Boat Tour with Dinner

★★★★★★★★★★4.8 · 116 reviews · 6 hours · from $100

Sail from Heraklion with the Set Sails crew toward Dia Island, about 6 nautical miles away. Choose a catamaran or monohull, swim at Saint George Bay, use the SUP and fishing gear, and enjoy Greek salad, shrimp pasta, fruit, and drinks before the sunset sail home.

“We had a wonderful experience on the boat trip to Dia Island! The crew was very friendly and welcoming, making us feel comfortable from the very beginning. The boat was clean and well maintained, and everything was perfectly organized. The views around Dia Island were stunning, and we had plenty of time to swim, relax, and enjoy the beautiful sea. It was both relaxing and fun – a great way to spend the day. What made the trip even more special was catching the sunset on the boat – it was absolutely magical! I definitely recommend this trip to anyone visiting Crete!”

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Heraklion: Dia Island Morning Sailing Trip with Snorkeling - The 75-minute sail to Dia Island
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Heraklion: Dia Island Morning Sailing Trip with Snorkeling

14.Dia Island Morning Sailing Trip with Snorkeling

★★★★★★★★★★4.9 · 100 reviews · 6 hours · from $82

Meet Cretan Yachts at Heraklion’s Old Port for a six-hour sailing trip to Dia Island. Captain Nikolas, Dimitris, Alexandros, or another local crew member may lead your outing, with snorkeling, swimming, fruit, snacks, wine, refreshments, and sailing time included.

“It was such a great experience, our guide was very friendly and kind, he created a really nice atmosphere for us, he gave us sandwiches, grapes and wine. This cruise worth every penny.”

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Heraklion: Nature Reserve Dia Island Full-Day Cruise & Lunch - Why Dia Island is more than a swimming stop
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Heraklion: Nature Reserve Dia Island Full-Day Cruise & Lunch

15.Nature Reserve Dia Island Full-Day Cruise & Lunch

★★★★★★★★★★4.7 · 33 reviews · 7 hours · from $115

Join a certified English- or Greek-speaking crew for a seven-hour sailing trip from Heraklion to Dia Island. Swim at three coves, use snorkel gear and SUP boards, hear about local wildlife and Minoan history, and enjoy a fresh lunch with drinks. Free Heraklion pickup is included.

“It was a wonderful day. Everything was perfect. We had great guiders. Food was amazing. The view was breath taking, peace.”

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★ 5.0Private Sailing Trip from Heraklion to Dia island2 reviews

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