CRETE SAILING TOURS

15 Crete Sailing Tours Worth Casting Off For

47 sailings  ·  from $35 a head

This is the shortlist you would send a friend: 15 crete sailing tours 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: 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

1.Sailboat Cruise to Dia Island with Drinks & Lunch

★★★★★★★★★★4.8 · 1,405 reviews · 1 hour - 390 minutes · from $35Our pick

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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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

2.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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From Kissamos: Balos Gramvousa Sailing Cruise with Lunch - Leaving Kissamos for the open water
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From Kissamos: Balos Gramvousa Sailing Cruise with Lunch

3.Balos Gramvousa Sailing Cruise with Lunch

★★★★★★★★★★4.9 · 257 reviews · 7.5 hours · from $229

Sail from Kissamos to Balos Lagoon and Gramvousa Island on a shared or private boat with an English- or Greek-speaking skipper. Swim, snorkel, hike to Gramvousa Castle, and enjoy a traditional Cretan lunch cooked onboard. Crews may include Vasilis, Katarina, Jo, or Luis, depending on the date.

“The captain and Jo were wonderful. They took good care of our family. The tasty foods, the company, and Balos/Gramvousa Island were all great. We really enjoyed seeing their sailing experiences. You can definitely trust their sailing capabilities. Highly recommend this excursion.”

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Sailing trip to the Top Coasts of Crete, Daily/Multi-day - Loutro, a village reached by sea
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Sailing trip to the Top Coasts of Crete, Daily/Multi-day

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

★★★★★★★★★★5.0 · 221 reviews · 7 hours (approx.) · from $1,198 whole boat, up to 9Top rated

Sail South Crete’s quiet coast on a private yacht for up to nine people. From Sfakia Port, you’ll reach Loutro, Glyka Nera Beach, and Marmara Beach, all places without roads or cars. Swim, snorkel, explore sea caves, relax in the cabin, and enjoy local lunch, snacks, water, and soft drinks while sailing conditions allow.

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

5.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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Sailing Trip to Dia with Snorkeling, Dining & Sunset Option - St. George’s Bay, Dia’s quiet swimming stop
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Sailing Trip to Dia with Snorkeling, Dining & Sunset Option

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

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

Sail from Heraklion to uninhabited Dia Island with a small group of up to 10 people. Swim and snorkel in sheltered St. George’s Bay, try fishing, enjoy a filling Cretan meal with soft drinks, water, and white wine, then choose a sunset return. Captains including Markos, Magda, Alexandra, and Yorgé are praised for warm, personal service.

“This was an excellent sailing experience. The 45ft sailboat was outstanding, as were the crew and captain. The lunch was terrific and the day to Dia exceeded all our expectations. Highly recommend this excursion. Our only regret, is that we did not have time to do the sunset sail.”

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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

7.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

8.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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Balos & Gramvousa Luxury Catamaran Sailing Cruise from Kissamos - Balos Lagoon: Two Hours of Clear Water
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Balos & Gramvousa Luxury Catamaran Sailing Cruise from Kissamos

9.Balos & Gramvousa Luxury Catamaran Sailing Cruise from Kissamos

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

Spend about 7.5 hours aboard DanEri Yachts’ catamaran from Kissamos, visiting Balos Lagoon and Gramvousa. The crew, often including Dimitri, Yannis, and Jessica, serves Greek snacks, a Mediterranean lunch, beer, wine, and soft drinks. You’ll have time for swimming, snorkeling, paddleboarding, and Gramvousa’s castle.

“If you’re looking for a way to explore Balos and Gramvousa, but want to avoid having to trek there or taking the ferry, do this!! It was such a stress free day and the boat was lovely. Balos and Gramvousa were absolutely stunning. It was so nice to basically explore it all alone. This trip is timed to avoid the ferry onslaught of people at both locations. Also, the food is stellar! I would definitely do this trip again and totally recommend it! Also, I love swimming and this trip gave me plenty of time to swim and snorkel in the Aegean!”

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Sailing Trips with Cretan Sailing - What sailing really means on this route
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Sailing Trips with Cretan Sailing

10.Sailing Trips with Cretan Sailing

★★★★★★★★★★4.0 · 99 reviews · 4 hours (approx.) · from $54

From Hersonissos, Cpt. Panos, George, and Leftheris take you out on an 18-meter traditional wooden boat for two swimming stops at St. George Bay and Stalis. You get snorkel gear, a grilled chicken, pork, or vegetarian lunch, salad, bread, and fresh fruit. Expect a relaxed shared cruise rather than guaranteed sailing.

“Experience is great, we had 2 stops, first one just to swim and second one with different places you could swim to and different activities. Me as a not strong swimmer was given a floatie so could fully participate. We chose to do snorkeling at second stop, it is just the goggles they give but we were able to see so many fish it was amazing. We had the chicken for the food which was a cooked bit of chicken, salad and a couple slices of bread, nothing fancy but did the job and we threw some bread for the fishes as was no butter so a bit dry for…”

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Sailing Cruises Chania - The Lighthouse and the Gulf of Chania
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Sailing Cruises Chania

11.Sailing Cruises Chania

★★★★★★★★★★5.0 · 93 reviews · 4 to 7 hours (approx.) · from $437

You’ll sail from Chania’s Old Venetian Harbor with hosts Yannis and Kostas, stopping to swim and relax near the Island of Ag and Maherida Beach. Expect city views from the water, snorkeling gear, Cretan snacks, drinks, and lunch on the seven-hour cruise. The private format lets your group shape the day.

“We highly recommend spending the day on this boat. We have done a lot of day cruises in the pacific and the Mediterranean. We have been on some great boats and sailed with some great crews. This is by far the best crew we have sailed with. The boat is impeccably maintained as well.”

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Rethymno Catamaran Cruise: Healthy Lunch & Open Bar - Georgioupoli Bay: Swim, Paddle, Snorkel, or Fish
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Rethymno Catamaran Cruise: Healthy Lunch & Open Bar

12.Rethymno Catamaran Cruise: Healthy Lunch & Open Bar

★★★★★★★★★★4.5 · 79 reviews · 6 hours 30 minutes (approx.) · from $174

Sail from Rethymno Port aboard a modern catamaran with a professional English-speaking crew. Enjoy a nutritionist-designed brunch and Cretan lunch, unlimited beer, wine, soft drinks, and water, plus SUP boards, snorkeling gear, fishing equipment, and shaded deck space. The cruise runs about 6.5 hours and carries up to 25 people.

“Great food, friendly staff, beautiful boat and a nice secluded spot to swim. The music was great, a fun group of people and not too many which was great. A really nice way to spend a relaxing day!”

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Sailing Trip to Dia Island - All Inclusive - The boat ride to Dia Island
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Sailing Trip to Dia Island – All Inclusive

13.Sailing Trip to Dia Island – All Inclusive

★★★★★★★★★★5.0 · 67 reviews · 6 to 8 hours (approx.) · from $90

Join Set Sails Crete from Heraklion for a six to eight hour boat trip to Dia Island. George, Niko, or another English-speaking crew member guides the day, with swimming, snorkeling, stand-up paddleboarding, seafood pasta, Greek salad, fruit, beer, wine, soft drinks, and water included.

“A great day out! George and Niko were incrediblley friendly and I feel like we became fast friends through the day. The water was cool but clear as crystal, easy to see the fish! The sun was great at drying us off upon leaving the ocean for a fresh made meal which we enjoyed with our new found friends (including the other visitors) on the boat. The island is practically untouched and has only a few buildings. Stunning views all round, throughout the whole trip...”

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Catamaran Sailing to Dia with Lunch in Heraklion, Crete(EST 2024) - Swimming, Snorkeling, and Stand-Up Paddleboarding
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Catamaran Sailing to Dia with Lunch in Heraklion, Crete(EST 2024)

14.Catamaran Sailing to Dia with Lunch in Heraklion, Crete(EST 2024)

★★★★★★★★★★5.0 · 64 reviews · from $142

Join Green Cruises from Cafe Marina in Heraklion for a five-and-a-half-hour sailing trip to Dia Island aboard a new Lagoon 46 catamaran. You get time to swim, snorkel, paddleboard, fish, sunbathe, and enjoy traditional Cretan pasta with fruit, soft drinks, wine, and beer included.

“It was a great trip with a great captain and crew. I highly recommend it! One of the highlights of our trip.”

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Sailing to Dia Island with lunch on Bavaria 51 Heraklion, Crete - The sail to Dia Island
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Sailing to Dia Island with lunch on Bavaria 51 Heraklion, Crete

15.Sailing to Dia Island with lunch on Bavaria 51 Heraklion, Crete

★★★★★★★★★★5.0 · 58 reviews · from $116

Spend about four hours sailing from Heraklion to Dia Island aboard a Bavaria 51 yacht with Green Cruises. Swim, snorkel, try stand-up paddleboarding with free lessons, fish, or help manage the sailing route. Giannis and Alex may be your skippers, while lunch, fruit, drinks, and wine are included.

“It was a lot of fun snorkeling and hanging out on the boat and in the water. Also was served the most delicious pasta dish. The water was beautiful and the caption and guide was very good.”

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Private Sailing Cruise, Balos and Gramvousa with meal and drinks. - Two hours at Balos Lagoon
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Private Sailing Cruise, Balos and Gramvousa with meal and drinks.

17★ 5.0Private Sailing Cruise, Balos and Gramvousa with meal and drinks.From $947 whole boat, up to 1038 reviews

Newest in Crete Sailing Tours

★ 5.0Small Group Sailing Cruise from Agios Nikolaos in Mirabello BayFrom $13221 reviews
★ 5.0All-inclusice Catamaran Day Cruise from Hersonissos to Dia IslandFrom $17422 reviews
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★ 5.0Private Sailing Cruise from Agios Nikolaos around Mirabello BayFrom $1,022 whole boat, up to 108 reviews
★ 5.0Full Day Private Luxury Escape SailingFrom $1,165 whole boat, up to 44 reviews
★ 5.0Small Group Sailing Cruise from Heraklion to Dia IslandFrom $10215 reviews
★ 5.0Sailing trip to DIA in Heraklion,Crete(4H)From $11815 reviews
★ 4.5Private Luxury Sailing Trips to Dia IslandFrom $639 whole boat, up to 1025 reviews
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