The 13 Best Sailing Trips with an Open Bar in Crete

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

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

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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3.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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4.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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5.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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6.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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7.Luxury Sunset Catamaran Cruise Sushi & Open Bar

★★★★★★★★★★5.0 · 61 reviews · 3 hours 30 minutes (approx.) · from $96

Sail from Hersonissos toward Malia Bay and Agios Georgios Bay aboard a modern catamaran for about three and a half hours. Enjoy Prosecco, sushi, fruit, local beer, white wine, and soft drinks, with time for swimming, snorkeling, paddleboarding, and fishing. The English-speaking crew welcomes families, couples, and small groups.

“Great sunset sail! They message you on WhatsApp with any updates which was great. We sailed from about 4:15-7:45pm so definitely a nice, long sail! The staff were so friendly and kept filling our glasses up. They really try to get the crowd excited and into it. The views can’t be beat either! We loved it!”

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8.Ag. Nikolaos: Catamaran Trip with Sushi, Drinks, & Water Toys

★★★★★★★★★★4.5 · 43 reviews · 5 hours (approx.) · from $150

Join the Artemis catamaran from Agios Nikolaos for about five hours on Mirabello Gulf. You’ll see Spinalonga Island, stop in calm bays for swimming, snorkeling, SUP, kayaking, fishing, and a water slide, then enjoy a prepared meal, drinks, music, and Wi-Fi. The English-speaking crew serves a maximum of 20 people.

“Generally very good. Staff were excellent. But no sailing just motoring. The meeting point is vague so we spent a lot of time trying to find the boat. Food was good but limited. Swim stops were great. Overall more pluses than minuses”

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

★★★★★★★★★★4.9 · 42 reviews · 6.5 - 8.5 hours · from $176

Spend 6.5 to 8.5 hours sailing from Crete to Dia Island aboard a new catamaran for up to 15 people. You’ll get espresso, brunch, an organic Mediterranean lunch, unlimited local wine and beer, and time to swim, snorkel, fish, or paddleboard. The crew speaks English and Greek, with hotel pickup available from selected areas.

“The Sunset Cruise was very enjoyable with plenty of space on board the catamaran, excellent service, a great crew and delicious food, highly recommended!!!”

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10.Chania Morning Catamaran Cruise with Premium Lunch & Drinks

★★★★★★★★★★5.0 · 40 reviews · 5 hours (approx.) · from $167

Set sail from Kolymvari on a spacious DanEri catamaran for a five-hour morning cruise to Agioi Theodoroi. Swim, snorkel, fish, or paddleboard from a quiet bay, then enjoy a fresh Mediterranean lunch, snacks, protein drinks, local beer, and white wine. The crew may include Roman, Sakis, Francisco, Anna, or Kris, depending on the sailing.

“We had a wonderful cruise to Thodoroy Island on a beautiful sunny day. Anchored for over 2 hours, swam, snorkeled and paddleboarded….and had a great lunch with drinks. Crew was very accommodating and it was a perfect day.”

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11.Panormo: Luxury Sunset Catamaran Cruise Sushi & Open Bar

★★★★★★★★★★5.0 · 39 reviews · 3 hours 30 minutes (approx.) · from $101

From Panormo Port, you’ll sail for about 3.5 hours toward Bali Bay or Skaleta aboard a modern catamaran. Expect Prosecco, Greek wine, beer, sushi, fruit, swimming, snorkeling, SUP boards, and a sunset sail. An English-speaking crew serves up to 20 people, with shaded lounges, sunbeds, Wi-Fi, and an onboard WC.

“The trip was perfect from start to finish! Brilliant crew, spacious boat, not too many people, good quality food and drink. The sunset and Coast as we sailed were just magical.”

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12.Private Sailing Cruise, Balos and Gramvousa with meal and drinks.

★★★★★★★★★★5.0 · 38 reviews · 8 hours (approx.) · from $947 per boat

Spend about eight hours aboard Izabela, sailing from Kissamos to Balos Lagoon and Gramvousa. Your skipper chooses safe swim spots, serves a light Cretan lunch with beer, wine, and soft drinks, and points out the Venetian fortress. You also get snorkeling gear, a beach umbrella, a covered cabin, restroom, and shower.

“We all thoroughly enjoyed the day, an amazing experience. Beautiful sailing boat with plenty of opportunities to swim from the boat. George also provided a truly delicious lunch, catering for a vegetarian and also gluten free.”

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13.Afternoon Catamaran trip – Dinner, Drinks & Sunset

★★★★★★★★★★4.5 · 31 reviews · 5 hours (approx.) · from $168

Sail from Kolymvari on a modern catamaran to the calm bays of Agioi Theodoroi Islands. You’ll have time for swimming, snorkeling, fishing, and stand-up paddleboarding while the English-speaking crew prepares a Mediterranean meal. Beer, wine, soft drinks, Wi-Fi, shaded seating, and sunset views are included.

“This was a fantastic trip, worth every penny. The boat itself is amazing but it was the crew who really made our trip special. My wife is disabled and in a wheelchair but Captain Yannis and his crew safely got her on board and nothing was too much trouble. The drinks were free flowing and the food was absolutely delicious. After sailing to Theodora Island we anchored and had plenty of time to swim and snorkel and use the paddle boards (not as easy as it looks). A surprise lesson in Greek dancing before a final swim and a gentle cruise back to the port. As I boarded the craft…”

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