Crete by Boat: 15 Sailings From Its Two Coasts

1.Sailboat Cruise to Dia Island with Drinks & Lunch

★★★★★★★★★★4.8 · 1,405 reviews · 1 hour - 390 minutes · from $35Number one

Sail from Heraklion with an experienced crew on a luxury yacht, choosing a shared half-day trip to Dia Island, a private cruise, or a one-hour coastal sail. The island option includes swimming, snorkeling, fishing gear, paddleboards, lunch, fruit, and unlimited drinks. Crew members such as Stavroula and Dennis are noted for warm, capable service.

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

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2.Private Half-Day Sailing Trip to Dia Island

★★★★★★★★★★4.9 · 466 reviews · 4.5 hours · from $459 per boat

Sail privately from Heraklion to Dia Island with a two-person crew, then spend 2.5 hours at Saint George Bay swimming, snorkeling, fishing, and using a paddleboard. Water, soft drinks, wine, fruit, and equipment are included. Add hotel transfers or an onboard meal for extra convenience.

“Sailing trip was great, guides gave a lot of explanation concerning the boat, island and history.”

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3.Balos Gramvousa Sailing Cruise with Lunch

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

Sail from Kissamos with an experienced skipper to Balos Lagoon and Gramvousa Island. You’ll have time to swim, snorkel, hike to the Venetian castle, and eat a fresh Cretan lunch cooked aboard. Small-group and private options are available, with beer, soft drinks, fruit, towels, and snorkeling gear included.

“Was great overall experience. Crew were amazing. Lunch was delicious. Would do it again!!!”

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

★★★★★★★★★★5.0 · 221 reviews · 7 hours (approx.) · from $1,198 per boatHighest rated

Spend about seven hours on a private sailing yacht from Sfakia, visiting car-free Loutro, Sweet Water Beach, and Marmara Beach. You can swim, snorkel, explore sea caves, relax in the cabin or shade, and enjoy lunch, snacks, water, and soft drinks. The boat holds up to nine people.

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

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

Set sail from Heraklion’s Old Venetian port with a certified crew, such as Costas, Mario, George, or Harry, for Dia Island’s quiet coves. You’ll have about 90 minutes for swimming, SUP, snorkeling, and sunbathing, followed by an organic lunch, fruit, soft drinks, and wine. Pickup is included within 10 kilometers.

“Friendly skipper and crew, great first time sailing experience for my friend and excellent anchorage choice as well. Would return to them again!”

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6.Luxury Catamaran Cruise, Dia Island –Open Bar & Lunch -Top Rated!

★★★★★★★★★★5.0 · 143 reviews · 5 hours 30 minutes (approx.) · from $145

From Cafe Marina in Heraklion, you sail with Eos Yachts to Dia Island for about three hours of swimming, snorkeling, SUP boarding, fishing, and canoeing. A certified English-speaking crew serves welcome coffee, Cretan treats, seafood or vegetarian lunch, fruit, dessert, beer, wine, and soft drinks. The catamaran returns to the same meeting point after roughly five and a half hours.

“What a day Amazing food as a first Amazing boat Amazing staff Amazing day and amazing trip 20/10 thanks again . Check out my page for some photos also @seriouslyscrumptiouseats”

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

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

Sail from Heraklion to Dia Island aboard a small yacht with a crew such as Markos, Alexandra, Magda, or Georges. Swim in calm St. George’s Bay, use the included snorkeling gear, enjoy a filling Cretan meal with wine and soft drinks, then return across the sea, with a sunset option available.

“Fabulous trip and experience, great food and friendly staff made the experience special. We travelled as two couples and one vegetarian and accommodated”

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8.Private Full-Day Sailing Trip to Dia Island

★★★★★★★★★★4.9 · 140 reviews · 6.5 hours · from $695 per boat

Sail privately from Heraklion to Dia Island with a two-person crew, stopping at Saint George Bay and another swimming spot. You can snorkel, fish, use a paddleboard, and relax with fruit, soft drinks, water, and local white wine. Boats range by group size and budget, with optional hotel transfers and onboard meals.

“We told the guides we were more interested in sailing than the excursions and they accommodated our request. The Elan 37 is a fun boat and she sailed well even in light winds. The lunch was delicious and we enjoyed it in an idyllic bay on Dia island. The captain and first mate were vey kind and helpful with our two kids. I highly recommend this excursion and will book again if we return to Crete.”

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

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

From Heraklion, sail with an English-speaking crew to Dia Island aboard a catamaran limited to 14 people. Expect a light brunch, fresh Mediterranean lunch, local beer and wine, swimming, snorkeling, paddleboarding, fishing, Wi-Fi, and time to relax in a sheltered bay.

“This is the company to use for a snorkel sailing adventure. Thomas, Anise, and Alexander took great care of us. Water was crystal clear. Plenty of time at Dia in a secluded cove. A wonderful day, high recommend! Dolphins were an added bonus.”

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10.Balos & Gramvousa Luxury Catamaran Sailing Cruise from Kissamos

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

Set sail from Kissamos with an English-speaking crew such as Dimitri, Yannis, and Jessica, and reach Balos before the big ferries. Swim, snorkel, paddleboard, and enjoy Greek snacks, a Mediterranean lunch, beer, wine, and soft drinks aboard a catamaran limited to 22 people.

“This is the best Boat Tour we have ever been on. From the start of the trip to the end, you are treated by Dimitri and Jessica like you are so special. The homecooked Greek meal created by Jessica was stupendous. Meanwhile, Dimitri made personal contact with every member of the passengers on board. The scenery was wonderful too,especially snorkeling in the aqua waters.”

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11.Sailing Trips with Cretan Sailing

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

Join Cpt. Panos, George, and Leftheris aboard an 18-meter traditional wooden boat from Hersonissos. After sailing, swim and snorkel at St. George Bay and near Stalis, with grilled chicken, pork, or a vegetarian burger, salad, bread, and fruit included. Snorkel gear and life jackets are provided, though equipment may be limited to swim goggles.

“We love it!!! The smimming spots are very beautiful. The Crew ist friendly and helpfully. The lunch was simpel but tasty.”

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12.Sailing Cruises Chania

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

Set out from Chania’s Old Venetian Harbor with Yannis and Kostas for a private 4 to 7-hour sailing cruise. You’ll circle the Gulf of Chania, stop to swim near the Island of Ag, look for birds and KRI KRI goats near Maherida Beach, and enjoy Cretan snacks, drinks, and lunch on the longer sailing.

“An exceptional yacht cruise to witness the evening sunset in Chania. Recommend this experience to any couple!!”

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13.Panormo: Luxury Catamaran Cruise with Lunch & Open Bar

★★★★★★★★★★5.0 · 80 reviews · 6 hours 30 minutes (approx.) · from $174

Sail from Panormo Port on a six-and-a-half-hour catamaran cruise for up to 20 people. You’ll get a light breakfast, gourmet Mediterranean lunch, unlimited soft drinks, Greek beer, Cretan white wine, snorkeling gear, SUP boards, and time to swim in a quiet bay. Mario may also take memorable photos on board.

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14.Rethymno Catamaran Cruise: Healthy Lunch & Open Bar

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

Sail from Rethymno to Georgioupoli Bay aboard a modern catamaran with a professional English-speaking crew. Enjoy a light breakfast, nutritionist-designed Cretan lunch, unlimited beer, wine, soft drinks, and water. Swim, snorkel, paddleboard, fish, or relax on a sunbed during this six-and-a-half-hour cruise for up to 25 people.

“Excellent accommodation and service. Crew was professional and attentive. They were ready to go on time. Very friendly and helpful.”

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15.Sailing Trip to Dia Island – All Inclusive

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

Set Sails Crete takes you from Heraklion’s Old Anchor to Dia Island for swimming, snorkeling, and stand-up paddleboarding. George and Niko are among the friendly crew members associated with the trip. Expect about three hours near the island, a fresh seafood pasta lunch, Greek salad, fruit, local beer, white wine, soft drinks, and water.

“Enjoyable morning “sailing” to the island. I was disappointed we actually did not sail! I expected 10 people and there were 14 so a bit crowded. Swimming in Aegean Sea was a treat. The crew made shrimp pasta and Greek salad for us! Lots of wine, beer, water and lemonade.”

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