ISLAND HOPPING SAILING TRIPS IN GREECE

The 15 Island Hopping Sailing Trips in Greece We Would Step Aboard

53 sailings  ·  from $35 a head

This is the shortlist you would send a friend: 15 island hopping sailing trips in Greece worth the money, each with its price, its verdict from the people who sailed it, and the one thing to know before you commit.

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal - Why 14 people changes the feel of the cruise
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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 Dia Island aboard a small yacht with up to 14 people. You’ll swim, snorkel, paddleboard, and eat shrimp linguini, Greek salad, and Cretan appetizers. English-speaking crew members such as Mariana, Manos, Sofia, Giannis, and Captain Petros have earned warm praise for friendly service, with afternoon trips offering sunset views.

“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: Sailboat Cruise to Dia Island with Drinks & Lunch - Dia Island: clear water and limited time ashore
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Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

2.Sailboat Cruise to Dia Island with Drinks & Lunch

★★★★★★★★★★4.8 · 1,405 reviews · 1 hour - 390 minutes · from $35Best value

Sail from Heraklion with an English-speaking crew to Dia Island for swimming, snorkeling, paddleboarding, fishing, lunch, and unlimited drinks. Shared trips include the meal, while private cruises let you add one. Stavroula, Dennis, and other crew members are praised for friendly, careful service. A one-hour coastal option skips Dia and water activities.

“Nice shorter activity 4 hr, Friendly crew! Good lunch with plenty of water and wine! Beautiful day! ❤️🥂”

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Gouvia: Corfu Island Sailing Trip with Snack and Soft Drinks - Barbati Beach and the first clear-water swim
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Gouvia: Corfu Island Sailing Trip with Snack and Soft Drinks

3.Gouvia: Corfu Island Sailing Trip with Snack and Soft Drinks

★★★★★★★★★★4.8 · 851 reviews · 5 - 10 hours · from $69

Cruise from Gouvia Marina along Corfu’s northeast coast aboard Ikaria or Eros 2, with a skipper such as Ari, Savvas, or Thassos. You’ll stop at Barbati Beach, Gialiskari, and a blue cave for swimming, snorkeling, and optional cliff jumping. Sandwiches, fruit, and soft drinks are included, while snorkeling gear and alcoholic drinks cost extra.

“This trip was a highlight of our holiday. Our skipper was friendly and informative . The boat was great with plenty of shade but also lots of space up front for sun lovers. Sandwiches and fruit were provided at one of the swimming stops and soft drinks were included. There was plenty of time for swimming at each of the 3 stops. I would do this trip again when next in Corfu.”

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Heraklion: Sailing Cruise to Dia Island with Drinks and Meal - Arriving at Dia Island’s clear-water cove
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Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

4.Sailing Cruise to Dia Island with Drinks and Meal

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

Sail from Heraklion’s Old Venetian Harbor to Dia Island with a certified crew, often including Captain Nick, Stelios, Celia, Kristina, or Iorgu. Swim, snorkel, fish, paddleboard, hike, and eat a fresh lunch onboard. Choose hotel pickup or meet beside Marina Café, and consider an afternoon departure for sunset.

“We had an amazing trip to Dia island with Stelios and Celia! We decided to try the full day trip over the half day and are so glad we did. Definitely pay the bit more if you can! The pickup from our hotel was right from the door and on time, we were welcomed on board at the harbour and at the island had a chance to try snorkelling and SUP for the first time. Lunch was prepared while we swam and we had plenty of chance to sunbathe without feeling under pressure to do anything to a schedule. The whole experience was so relaxing, we felt like welcomed guests…”

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Heraklion: Dia Island Sailing Cruise with Snorkeling - Arriving at Dia’s clear-water bays
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Heraklion: Dia Island Sailing Cruise with Snorkeling

5.Dia Island Sailing Cruise with Snorkeling

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

Sail from Heraklion with a professional crew to Dia Island, about an hour offshore. Swim in clear bays, use the included snorkeling and paddleboard gear, and enjoy drinks with either seafood pasta and Greek salad or a lighter half-day meal. Ernesto and George are among the crew members praised for their care and stories.

“Thank you for the nice sailing trip to Dia Island. We had a really great time, the staff has been super nice and caring! We had some nice food and our glutenfree and vegan wishes were considered. We would really recommend this trip and would love to come again one day.”

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Shared Mykonos Sail Cruise to Delos and Rhenia Islands - Sailing toward Delos, Greece’s ancient island center
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Shared Mykonos Sail Cruise to Delos and Rhenia Islands

6.Shared Mykonos Sail Cruise to Delos and Rhenia Islands

★★★★★★★★★★5.0 · 705 reviews · 6 hours (approx.) · from $151Top rated

Spend about six hours sailing from Agios Ioannis to Delos and Rhenia aboard a spacious gulet with a friendly crew, including Dimitri and Thomas on some departures. Explore Delos for 90 minutes, swim and snorkel in clear water, and enjoy a buffet of grilled meats, vegetables, Greek salad, tzatziki, rice, fruit, and drinks.

“This is a must do / from the pick up to the drop off. It was perfectly executed. I’ve done a lot of boat tours at various destinations and this was by far the best. The crew -Dimitri and Thomas - were stand-up. They helped my mom who had some mobility issues throughout the day. Additionally, they were so patient and helpful with all of the guests. The captain was a class act. We loved the swimming spots -my kids enjoyed the day immensely. The lunch was the best lunch I have had yet in Mykonos, which says a lot.”

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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling - Leaving Heraklion for an hour at sea
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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

7.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 small crew of up to 18 people. Swim, snorkel near an old Minoan port, use the paddleboard, and enjoy Greek food onboard. Full-day trips include salad, tzatziki, and seafood pasta, while half-day trips include tomato pasta. Crew members such as Andreas and George add local stories and friendly help.

“We had a wonderful time! There were a lot of people on the boat but it didn’t feel crowded. The cove where we anchored was lovely — our only complaint was that a party boat anchored nearby and played loud (bad) house music the whole time. It made the experience slightly less idyllic, but we tuned it out eventually, food was delicious, guides were friendly and cooked a delicious dinner, and the sunset was dreamy. A perfect way to spend our afternoon/evening in Heraklion!”

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Sailing Cruise to Dia Island with Meal and Water Activities - Three hours for swimming, snorkeling, and paddleboarding
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Sailing Cruise to Dia Island with Meal and Water Activities

8.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 about three hours in a sheltered bay for swimming, snorkeling, paddleboarding, fishing, and sunbathing. Lunch, fruit, Greek appetizers, beer, wine, soft drinks, and equipment are included. The boat carries up to 14 people, though some departures may use a larger catamaran.

“Great day out ,everything was perfect from start to finish.If your coming to Crete on holiday don’t miss out on this trip”

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Heraklion: Sailing Trip to Dia Island with Lunch & Swimming - Meeting at Heraklion Port or using the minivan transfer
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Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

9.Sailing Trip to Dia Island with Lunch & Swimming

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

Sail six nautical miles from Heraklion to Dia Island with a maximum of 10 people. Captains George, Panos, and Vaso provide local stories, swimming time, SUP boards, snorkeling gear, fishing equipment, lunch, and unlimited drinks. Optional minivan pickup makes this a practical half-day escape from much of Crete’s north coast.

“George and Marco were friendly and informative and made the trip very enjoyable. We spent a good amount of time snorkelling using the equipment they provided and enjoyed a nice lunch of pasta, salad and fruit. It’s a small group of 10 so the boat isn’t overcrowded and you get to know the people well. Highly recommend”

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Heraklion: Private Half-Day Sailing Trip to Dia Island - Meeting the skipper at Heraklion Marina
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Heraklion: Private Half-Day Sailing Trip to Dia Island

10.Private Half-Day Sailing Trip to Dia Island

★★★★★★★★★★4.9 · 466 reviews · 4.5 hours · from $459 whole boat, up to 8

Sail privately from Heraklion to Dia Island with a two-person crew such as Vassilis, Costa, or George. You get about 2.5 hours in Saint George Bay for swimming, snorkeling, fishing, paddleboarding, and relaxing, with drinks, wine, fruit, and gear included. Add hotel transfers or a full meal for a smoother half-day on the water.

“Amazing! We chose to be picked up from our resort, communication and transport great! The boat was private, with only the 5 of us plus Marius and Marisa (the two captains) and had lots of space. The ride was lovely, and when we got to Dia Island, we had over 2 and a half hours to swim, snorkel, and ate lovely fresh salad and sandwiches (made by the captains) which were incredible. They were so welcoming and made us feel so welcome. Amazing value for money, especially for such a private trip with a lovely, modern boat. Would 100% recommend and do it again.”

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Heraklion Luxury Sailing Catamaran Dia Island | Gourmet Menu - Meeting Captain Thanasis at Heraklion Port
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Heraklion Luxury Sailing Catamaran Dia Island | Gourmet Menu

11.Heraklion Luxury Sailing Catamaran Dia Island | Gourmet Menu

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

Sail from Heraklion with EOS Yachts aboard a modern catamaran limited to 22 people. Captain Thanasis and the English-speaking crew serve Cretan snacks, chef-prepared seafood, local wine, beer, and dessert while you swim, snorkel, fish, canoe, or paddleboard in a quiet Dia Island bay.

“We loved our day aboard the Catamaran! We try to do a boat trip every summer but this was a little more expensive than we usually pay. As we wanted a Catamaran and not a sailing boat, we decided to go for it and we couldn't have been happier with our choice. The captain gave us a briefing before we left and explained that it is an inclusive vessel where we are all valued equally and are a team for the day. It was done in such a way that really put everyone in good spirits and we, as a small group, enjoyed each others company throughout the day. There…”

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

12.Small-Group Sailing Trip to Dia Island with Lunch

★★★★★★★★★★4.7 · 277 reviews · 4.5 - 7 hours · from $94

Join a crewed sailing yacht from Heraklion’s Old Venetian port to Dia Island, seven nautical miles offshore. With a maximum of 10 people, you’ll swim, snorkel, paddleboard, hear local stories, and eat a fresh Greek lunch with drinks and wine. Crews may include skippers such as Stratos, Stefanos, Alex, or Aphrodite.

“Excellent boat trip, pick up on time, staff were brilliant, highly recommend”

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Dia island : Small Group Sailing Trip to Dia Island with Lunch - Dia Island and its protected coves
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Dia island : Small Group Sailing Trip to Dia Island with Lunch

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

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

Sail from Heraklion’s Old Venetian port to uninhabited Dia Island with a certified crew, usually aboard a 43 to 45-foot yacht. You’ll swim, snorkel, use a SUP board, enjoy an organic lunch with drinks, and hear about Dia’s protected wildlife. Pickup is free within 10 kilometers of the port.

“A lovely day! The expert crew was very accommodating and friendly, sailing was delightful, food was unexpectedly good! & generous, swimming was fun- only improvement would be better snorkel equipment & perhaps kick boards to float on for others who are not as strong at swimming…. Cash only shuttles are putting a strain on our Euro supply & exchange is costly but overall we loved this experience. Thank you :)”

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Heraklion: Private Full-Day Sailing Trip to Dia Island - Your first hours around Dia Island
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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 · from $695 whole boat, up to 8

You’ll sail from Heraklion to Dia Island on a private yacht with a two-person crew, stopping in Saint George Gulf and another swimming cove. Use the included snorkeling gear, fishing kit, and paddleboards, then enjoy fruit, soft drinks, water, and local white wine. Boats suit different group sizes, with hotel transfers and lunch available for an extra charge.

“Magnifique journée avec un guide très sympathique et professionnel, on a adoré.”

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Dia Island Catamaran – Premium Lunch, Open Bar, Small Group - Is $181.41 a fair price?
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Dia Island Catamaran – Premium Lunch, Open Bar, Small Group

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

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

Set sail from Heraklion with an English-speaking crew, often including captains and hosts such as Spiro, George, Alexandra, or Thomas. You’ll spend about four hours anchored at Dia Island for swimming, snorkeling, paddleboarding, fishing, and a freshly prepared Mediterranean lunch. The catamaran carries up to 14 people and returns around mid-afternoon.

“Absolutely the highlight of our trip to Crete! The staff were so welcoming and thoughtful. Always checking in with us to make sure we were ok and had everything we could need. Food was abundant and so fresh and delicious. There were only 7 of us on the boat so it felt like a private experience. Would definitely recommend!”

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Newest in Island Hopping Sailing Trips in Greece

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