Where to Book Chania Sailing Trips: the 11 Best

1.Balos & Gramvousa Luxury Catamaran Sailing Cruise

★★★★★★★★★★4.9 · 516 reviews · 7 - 8.5 hours · from $229Number one

Sail from Kissamos to Balos Lagoon and Gramvousa Island aboard a modern catamaran limited to 22 people. The crew, often including Giannis, Dimitri, Jessica, Peter, or Spiros, serves Cretan food, beer, wine, and soft drinks while you swim, snorkel, paddleboard, or relax on deck. Transfers are available from Georgioupoli to Kissamos.

“We really enjoyed the full day sailing - the beaches were beautiful, the food served on board was delicious, we felt like there was sufficient time at each beach to really enjoy ourselves, and the boat was luxurious and nice. Our only grievance was that Kissamos (where the tour started) is an expensive cab ride away from Chania, where everyone was coming from, and it would have been nice if the tour provided transportation or at least helped everyone coordinate cabs to save money.”

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2.Sailing Cruise with Meal & Water Activities

★★★★★★★★★★4.7 · 390 reviews · 5 hours · from $129

Set out from Kolymvari with a small group and an experienced crew such as captain Loukas and chef Jason. Sail about an hour to Agioi Theodoroi, swim in clear water, snorkel, paddle board, and look for the island’s Kri Kri goats. A three-course meal, unlimited drinks, music, and a sunset option make this a relaxed five-hour outing.

“Excellent five hours on a 44 ft sailing boat - we enjoyed the full experience and the captain and the chef did very well 🙏🏽🇬🇷 just go and enjoy!”

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3.Balos & Gramvousa Luxury Catamaran Cruise

★★★★★★★★★★4.6 · 240 reviews · 7 hours · from $190

Sail from Kissamos to Gramvousa and Balos on a modern catamaran with a small-group feel. You get time to swim, visit Gramvousa Fortress, use SUP and snorkeling gear, and enjoy shrimp linguine, Greek salad, Cretan appetizers, and unlimited drinks. Crew members including Tina, Yannis, Stellios, and Michael help make the day easy and friendly.

“We had such a wonderful time on this sailing trip! The atmosphere on board was great, with a fun group of people. Yannis and Olga were very friendly and welcoming, and it was lovely to talk with them throughout the day. The food was delicious, and they regularly offered drinks, making sure everyone felt comfortable. The stops at Gramvousa and Balos were absolutely beautiful. Thanks to Yannis’ advice on timing, we were able to enjoy the places before the big tourist boats arrived, which made the experience even more special. Overall, an unforgettable day and a truly fantastic experience. We highly recommended!”

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4.Chania Old Port:Luxury Sunset Catamaran Cruise with Prosecco

★★★★★★★★★★4.9 · 177 reviews · 3.5 - 4.5 hours · from $100Cheapest deck

Sail from Chania Old Port to Agioi Theodoroi aboard a modern catamaran with up to 20 people. Enjoy welcome Prosecco, sushi, fruit, Greek wine, beer, SUP boards, snorkeling gear, and a sunset over the sea. Crew member Irini is known for bringing extra energy to the trip.

“We had an incredible time on this excursion. The activities were a blast, the views were absolutely stunning, and the guides were fantastic.”

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5.Afternoon Catamaran trip – Dinner, Drinks & Sunset

★★★★★★★★★★4.9 · 168 reviews · 5 hours · from $165

Join the DanEri Yachts crew for a five-hour catamaran cruise from Kolymvari. Swim and snorkel in a quiet bay, use the SUP boards and inflatables, then enjoy seafood, meat, salads, wine, beer, and soft drinks. Crew members including Angelo, Nana, and Yianni have helped make this a warm, sociable evening on the Cretan coast.

“We have just got back from a fantastic trip on one of the DanEri catamarans. Beautiful boat/yacht, friendly staff who done everything they could to make our trip enjoyable and great food with lots of wine, beer and soft drinks. Lots of spots to sit and relax, really clean and comfortable. We had a good amount of time to swim, snorkel and paddle board. The sunset on the way back was beautiful. A perfect trip.”

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6.Morning Catamaran Cruise with Premium Lunch & Drinks

★★★★★★★★★★5.0 · 128 reviews · 5 hours · from $164Highest rated

Sail from Kolymvari on Vesselina, a modern catamaran limited to 20 people. Enjoy espresso, a nutritionist-designed brunch and lunch, unlimited local drinks, swimming, snorkeling, SUP, and time near Agioi Theodoroi. The English and Greek-speaking crew, including Anna, Kristos, and Roman, can arrange transfers from Chania and nearby resorts.

“It was amazing! It was my first time on this type of tour. The food was amazing. The captain was very kind and chef was very informative. This deck crew is the best.”

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7.Shared Balos and Gramvousa Sailing Trip with Meal and Drinks

★★★★★★★★★★4.9 · 50 reviews · 8 hours · from $153

Spend eight hours sailing from Kissamos to Balos Lagoon and Imeri Gramvousa aboard Izabela or Poseidon, two small boats with gray biminis. You get two hours at Balos, a traditional Cretan lunch with drinks, and two hours at Gramvousa for swimming, snorkeling, and the 20-minute walk to its Venetian Castle.

“We had the best time. Gramvousa is amazing. Beautiful water and swimming. Food on the boat was delicious! Would recommend this to anyone!”

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8.Catamaran Balos Sunset Cruise with Sushi & Drinks

★★★★★★★★★★5.0 · 41 reviews · 3.5 - 5.5 hours · from $147

Sail from Kissamos toward Balos Lagoon on a semi-private catamaran with a maximum of 22 people. You’ll get Prosecco, sushi, fruit, local wine and beer, swimming, snorkeling, SUP, and a sunset at sea. A tender boat brings you closer to the lagoon, while the crew handles transfers, food, and safety details.

“Esperienza bellissima Perfetta la sosta nella caletta dalle acque limpide ai piedi di una suggestiva chiesetta greca Poi verso il tramonto con una lenta navigazione che crea uno stato di attesa inebriante e poi all'improvviso i colori abbaglianti di uno splendido tramonto in un tripudio di colori dal rosso al giallo più intenso, una sfera perfetta che si inabissa nel mare che dà la pittoresca consapevolezza di un altro giorno che finisce E poi il rientro avvolti dal buio della sera romantico più che mai Grazie guys”

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9.Chania Old Port: All-inclusive Catamaran Trip Agioi Theodori

★★★★★★★★★★4.9 · 28 reviews · 6h 30m · from $170

Set sail from Chania Old Port aboard a modern DanEri catamaran for about six and a half hours. You get a nutritionist-designed brunch and lunch, unlimited selected drinks, a shaded lounge, sunbeds, SUP boards, snorkeling gear, and time to swim near protected Agioi Theodoroi. Crew members including Kalliopi and Stavros have helped make recent trips especially welcoming.

“Relaxing boat trip with great food and drinks and some good swimming and snorkelling - very enjoyable.”

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10.Private Day Catamaran Cruise with Swimming and Meal

★★★★★★★★★★4.9 · 12 reviews · 5 hours · from $2,121 per boat

Board the Vesselina at Kolymvari for a private five-hour sail to Agioi Theodoroi. DanEri Yachts provides swimming, snorkeling, SUP boards, fishing gear, a Mediterranean meal, unlimited beer, wine, and soft drinks, plus Wi-Fi and music. Choose a morning cruise or an afternoon sail timed for sunset.

“The crew went above and beyond for us. A great day out.”

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11.Private Sailing Cruise with Snorkel, Lunch & Drinks

★★★★★★★★★★5.0 · 2 reviews · 7 hours · from $589

Spend 10am to 5pm on a private 40-foot sailboat with Yannis and Costas, sailing from Chania’s Venetian Harbour to Agios Theodoros and Maherida Bay. Swim, snorkel, sunbathe, and eat homemade Mediterranean food onboard. The boat holds up to eight people, making this a relaxed choice for families or friends.

“The boat was in pristine condition and absolutely beautiful. Yannis & Costas were so welcoming and made sure our day was nothing short of amazing. They prepared great snacks and lunch along with serving us drinks when needed. Their hospitality was very much appreciated and made the day on the water that much better! Thank you both for an unforgettable day in Chania & in Greece!!”

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