12 Sailing Yacht Charters in Greece Worth Booking

1.Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer

★★★★★★★★★★5.0 · 1,170 reviews · 5 hours (approx.) · from $133Our pick

Spend about five hours aboard a spacious catamaran with hotel pickup, swimming stops at Red and White beaches, volcanic hot springs, snorkeling, a freshly cooked Greek barbecue, and unlimited drinks. Choose the sunset sailing for sea views of Oia, with room for no more than 20 people.

“The trip was great! Good food, vine, beer and soft drinks. Nice and friendly staff. I wish the weather and water would be warmer, but hey its November...I highly recommend to take this tour. Especially sunset one.”

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2.Balos & Gramvousa Luxury Catamaran Sailing Cruise

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

Sail from Kissamos to Balos Lagoon and Gramvousa Island aboard a modern catamaran for up to 22 people. Expect sunbeds, shaded lounges, SUPs, snorkeling gear, local food, an open bar, and attentive English-speaking crew such as Dimitri, Jessica, and Yiannis. Transfers are included from Georgioupoli to Kissamos.

“The guide Captain Janus and his crew were very good! They provided our group of 8 an awesome day with swimming in beautiful waters and walking on beautiful beaches. They prepared lots of snacks and food, and the beer and vino were great! I will receive this trip and this crew to my clients!”

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3.Santorini Luxury Sailing Catamaran Cruise with BBQ, Drinks and Transfer

★★★★★★★★★★4.5 · 422 reviews · 5 hours (approx.) · from $133

Cruise Santorini’s caldera aboard a catamaran for about five hours, stopping near the hot springs, White Beach, and Red Beach. Your crew serves a Greek barbecue with wine, beer, and soft drinks, while towels, snorkeling gear, and hotel transfers simplify the day. Routes can change with weather.

“We had a great day with sunset Oia! Pick up and drop off from the hotel was made so easy and straightforward. The bbq on the boat was nice and authentic. The staff were great and explained the history of every stop on the boat. Great day overall! Highly recommended.”

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4.Heraklion Luxury Sailing Catamaran Dia Island | Gourmet Menu

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

Set sail from Heraklion with Captain Thanasis and the EOS Yachts crew aboard a modern catamaran for a 5.5-hour trip to Dia Island. Enjoy welcome treats, chef-prepared seafood or alternative meals, an open bar, snorkeling, SUPs, canoeing, fishing, and plenty of time in a calm bay.

“What can we say - what an absolutely outstanding experience! My partner and I had an amazing time, everything was exceptional. The staff were so friendly and welcoming and really looked after us. You have time to have a dip and use paddle boards after reaching Dia island, which was so much fun! Shoutout to the chef too, for the super tasty food! It was also my birthday so was surprised with a cake! Very sweet of them going the extra mile. Sailing back into the sunset is an unforgettable experience. 10/10 highly recommended!!!”

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5.Gulet Trip with Food, Drinks, SUP, Kayak & Swimming

★★★★★★★★★★4.6 · 288 reviews · 6 hours · from $104

Join El Greco Cruises at Mandraki Port for a six-hour gulet trip along Rhodes’ east coast. Swim at Anthony Quinn Bay, use kayaks and SUPs at Fun Island in Ladiko Bay, and stop at Kallithea Springs. Nikos and Stephanos are among the friendly crew members praised for their care and good advice.

“Our trip was on a very hot Friday, but we found some shade on the boat and were able to enjoy the day in and out of the sun. The trip was well planned with stops along the way allowing for swimming every hour or so. Having access to SUP boards and kayaks was the highlight, however the company could benefit from pumping up their SUP boards a bit more as some were flat. The tour guides were very informative and focused on safety.”

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6.Day sailing Skiathos Skopelos with lunch on Rainbow yacht

★★★★★★★★★★5.0 · 262 reviews · 7 hours (approx.) · from $163

Spend about seven hours aboard Rainbow yacht with hosts Yannis and Angelica, plus their dog Naya. Swim at Tsougria, Panormos, and other island stops, cruise past Mamma Mia beaches, eat a Greek meal cooked on board, and return to Skiathos around 5 pm.

“We had a lovely day in beautiful places, with nice food and nice company! We absolutely recommend this experience”

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7.Day Cruise by a Sailing Yacht to the most beautiful bays or Rhodes (Small Group)

★★★★★★★★★★5.0 · 197 reviews · 6 hours (approx.) · from $120

Spend about six hours on the water from Rhodes, stopping at Anthony Quinn Bay, Traganou Beach, and Ladiko Beach for swimming, snorkeling, and sun. The crew serves Greek-style food, fruit, wine, beer, soft drinks, and water. Captains such as George, Dimitri, Luca, and Yannis may lead the trip.

“Best part of our trip to Rhodes. Our captains George and Maria were so friendly and welcoming. They really made it even more special. The food is amazing, I have a few dietary restrictions and they were able to work around that and let me know what I could and couldn't eat which was great. Drinks whenever you want and the best part was seeing the fish while we were snorkelling in the bays. We went on a really windy day so it was a little choppy but you get used to it after 30 mins or so. I would definitely definitely recommend!”

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8.From Skiathos Marina: Yacht Sailing Day Trip with Lunch

★★★★★★★★★★4.8 · 180 reviews · 8 hours · from $175

Join Perfect Sailing for an eight-hour yacht trip from Skiathos New Port. Lambros and the crew take you toward Skiathos and Skopelos for swim stops, snorkeling, SUP, cave visits, Greek taverna lunch, and onboard snacks, drinks, towels, and breakfast.

“Brilliant day - great guides, beautiful locations, wonderful swimming spots. Food and drink provided was fantastic, would highly recommend to anyone visiting Skiathos, well worth the money! Thank you! 😊”

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9.Balos & Gramvousa Luxury Catamaran Sailing Cruise from Kissamos

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

Sail from Kissamos to Balos Lagoon and Gramvousa with an English-speaking crew such as Dimitri, Yannis, and Jessica. You get two hours at each stop, snorkeling, SUP boards, Greek snacks, a cooked Mediterranean lunch, open drinks, and a maximum group size of 22.

“What a fabulous day! Thank you to the entire crew, Jessica, Demitri and Yani. If you are in the chania area this is a must book this day trip!”

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10.Half Day Cruise on a Sailing Yacht in Corfu Island

★★★★★★★★★★5.0 · 108 reviews · 4 hours (approx.)

You’ll spend four hours on a private sailing yacht from Gouvia Marina, cruising Corfu’s northeast coast with swim stops near Strogylo, Barbati, Kalami, or Kerasia. The crew provides drinks, snacks, snorkeling gear, SUP equipment, towels, and music, with space for celebrations or quiet time.

“We are a family of 5 who visited corfu on a cruise ship. We had a 2 week vacation in Italy and on the cruise and each of us listed this as one of our top 1-2 experiences of our trip. Panos our captain and Veronika our stewardess were outstanding. they went above and beyond to ensure we had a great time, were fun and very personable. the sailing yacht was wonderful and spacious. We were able to find 2 separate swimming sites with crystal clear water and coves to swim into This is not the cheapest option, but provided excellent value and exceeded our expectations”

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11.Dia Island Luxury Sailing Trip with Meal & Drinks

★★★★★★★★★★4.7 · 107 reviews · from $68Cheapest seat

Sail from Heraklion’s Venetian Port to protected Dia Island aboard TREATON or JACKPOT. Swim, snorkel, paddleboard, fish, and enjoy shrimp pasta, Greek salad, fruit, beer, wine, and soft drinks. Choose a shared, private, morning, sunset, or full-day cruise.

“Overall was an amazing experience, definitely worth the money. Would do it again in a heartbeat. The guides were fantastic and very knowledgable about the island. They also made us an amazing lunch and served fruit afterwards! Thank you for an amazing day!!”

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12.Full-Day Sailing Yacht Cruise

★★★★★★★★★★4.8 · 88 reviews · 9 hours · from $259

Set sail from Piso Livadi with an English-speaking skipper and crew for a nine-hour cruise to Rina’s Cave, Schoinousa or Koufonissia, and southern Naxos. You’ll swim, snorkel, learn sailing basics, and enjoy lunch, snacks, wine, beer, and water aboard a modern yacht.

“The day was well structured and expectations were clearly set at briefing during the first 10 minutes. Lunch and snacks were very good. The only negative was another boat full of vacationers, about 100 people, were at our first swimming spot and it got very crowded and loud.”

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