The 15 Sailing Trips in Greece That Earn Their Price

1.Dia Island Sailboat Cruise with Swimming and Meal

★★★★★★★★★★4.8 · 2,579 reviews · 5.5 hours · from $95Our pick

Sail from Heraklion’s Venetian Harbour to Dia Island aboard a yacht limited to 14 people. Captain Petros and crew members such as Sofia and Giannis provide swimming, snorkeling, paddleboarding, a Mediterranean meal, and unlimited drinks during this 5.5-hour cruise.

“Perfect friendly Crew. Nice Katamaran. Good drinks and delicious food. It was my third time with this company. Sofia, Giannis and our Captain Petros are a super Crew. I will make the Dia Tour again. I love it sooooo much. Thank you Guys. Nicole”

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2.Milos & Polyaigos Full-Day Sailboat Tour with Lunch

★★★★★★★★★★4.9 · 1,646 reviews · 10 hours · from $147

Spend 10 hours aboard a small sailing boat with guides such as Dora, Niki, or Alexandra. Circle Milos, swim at Polyaigos and Gerakas, snorkel through Kleftiko, see Sykia Cave, and enjoy lunch, snacks, and drinks onboard. The boat uses motor power rather than sailing throughout.

“Such an amazing sailing day that I had. So worthy of the money. Every stops we got briefed so much on the sites. The guide she was knowledgeable and super funny. She made me feel so welcomed and included. She’s also a very good private photographer! So many snacks and finger foods as well!”

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3.Sailing Catamaran Cruise with BBQ and Drinks

★★★★★★★★★★4.7 · 1,452 reviews · 5 hours · from $117

Sail from Santorini’s Vlychada or Ammoudi Port aboard a polished catamaran, with three swim stops, hot springs, volcano views, snorkeling, and a BBQ. English and Greek hosts, hotel pickup, towels, and drinks are included. Sunset departures finish near Ammoudi.

“Amazing trip with great guide and crew. Food and drink were excellent too. We would highly recommend this trip! Thank you”

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4.Sailboat Cruise to Dia Island with Drinks & Lunch

★★★★★★★★★★4.8 · 1,405 reviews · 1 hour - 390 minutes · from $35Best value

Join a shared half-day yacht trip from Heraklion to Dia Island with lunch, wine, soft drinks, snorkeling gear, SUP boards, and fishing equipment. Private cruises and a shorter coastal sail are also available. Crew members including Stavroula, Dennis, and Mido help keep the trip relaxed and well organized.

“A memory for a lifetime. the staff were super professional and accommodating. the sailing was smooth and beautiful and the sea was Cristal clear and just the right temperature.”

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

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

Spend about five hours aboard a catamaran limited to 20 people. Swim at Red Beach and White Beach, visit the volcanic hot springs, enjoy a fresh Greek barbecue with wine and beer, then watch the sunset from the water if you choose the afternoon sailing.

“Amazing! A must do in Santorini. The staff were friendly and professional. The food was Excellent. The views of Santorini from the sea and the sunset are breathtaking !”

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6.Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

★★★★★★★★★★4.5 · 1,105 reviews · 5 hours (approx.) · from $95

Spend about five hours sailing Santorini’s caldera, with stops at the hot springs, Red Beach, and White Beach. Swim, snorkel, eat a BBQ, and enjoy Santorinian wine, soft drinks, and water. The later cruise may finish with sunset views near Oia. Hotel pickup and drop-off are included.

“Sunset cruise was great fun. Food was very tasty. Boat facilities were great, very clean, lots of shade. Music was a little loud, difficult to have a conversation with others on board. Great way to enjoy the afternoon and see the Santorini sunset.”

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7.Corfu Island Sailing Trip with Snack and Soft Drinks

★★★★★★★★★★4.8 · 851 reviews · 5 - 10 hours · from $69

Join skipper Ari, Savvas, Tasos, or another English-speaking local crew member for a relaxed half-day sail from Gouvia. You’ll stop at Barbati, Gialiskari, and the Blue Caves for swimming, snorkeling, and cliff jumping, with sandwiches, fruit, and soft drinks included.

“Amazing!!! Super relaxing and beutiful, it was the highlight of my trip to corfu! The water, the boat and the views were just amazing! Out captain, Naxo, was also very friendly and excited to be with us.”

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8.Sailing Cruise to Dia Island with Drinks and Meal

★★★★★★★★★★4.9 · 778 reviews · 6 hours · from $106

Join Sailing Grace for a six-hour cruise from Heraklion to uninhabited Dia Island. Captain Stelios, Celia, and the crew provide snorkeling, fishing, SUP gear, lunch, wine, raki, and time to swim or hike. Hotel pickup is available from selected areas.

“Literally so nice, personable and professional. We made friends with others on the tip facilitated by the captain. Not been cheesy but we will be lifelong friends.”

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9.Dia Island Sailing Cruise with Snorkeling

★★★★★★★★★★4.7 · 742 reviews · 4.5 - 7 hours · from $82

Sail from Heraklion’s Venetian harbor to Dia Island with a small crew of up to 18 people. Ernesto, George, or another experienced crew member guides the trip, with swimming, snorkeling, paddleboarding, drinks, and a meal included. Choose a shorter half-day cruise or stay longer for a second bay.

“A beautiful day, great weather, calm sea. Crew were kind and great to talk with. Really enjoyed snorkelling, the water was magical!”

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10.Kleftiko Sailing Day Trip with Snorkeling and Lunch

★★★★★★★★★★4.8 · 713 reviews · 8 hours · from $170

Spend eight hours with Excellent Yachting sailing from Adamas along Milos’s west coast. Swim at Kalogries and Agios Dimitrios, explore Kleftiko by snorkel gear and RIB, and enjoy Greek food, drinks, and underwater photos with a friendly multilingual crew.

“Trust the reviews!! Fantastic day, so well organised with quick and easy communication. Staff were incredible and really made the day. We laughed from start to end, met some great people, ate well and drank better! Really made the last day in Milos the perfect ending”

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11.Sailing Catamaran Cruise in Santorini with BBQ, Drinks and Transfer

★★★★★★★★★★4.5 · 568 reviews · 5 hours (approx.) · from $95

Spend about five hours sailing Santorini’s caldera from Ammoudi or Athinios, with hotel pickup, swimming at the hot springs, Red Beach, and White Beach, plus snorkeling gear, a BBQ lunch, Santorinian wine, soft drinks, and an English-speaking crew.

“The catamaran excursion was mine and my husbands favorite thing we did in Santorini. The volcanic hot springs were amazing as well as the delicious lunch they served.”

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12.Sunset Sailing Cruise Dia Island with Snorkeling

★★★★★★★★★★4.7 · 529 reviews · 4.5 - 7 hours · from $82

Sail from Heraklion to uninhabited Dia Island with a small group of up to 18 people. Swim, snorkel near an old Minoan port, paddleboard, eat Greek food, and return beneath the sunset with crew members such as Manos, Andreas, Stella, or Elena.

“This was one of the best experiences I’ve ever had!! Stella and Elena are two wonderful hosts who did everything to make the trip amazing! Thank you to them! We had a delicious dinner with pasta, salad, and fruit, the chance to enjoy the beauty of the sea, and saw an incredible sunset! I highly recommend it to everyone!”

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13.Sailing Trip to Dia Island with Lunch & Swimming

★★★★★★★★★★4.8 · 517 reviews · 6 hours · from $100

Sail six nautical miles from Heraklion to Dia Island with up to 10 people, a warm local crew, swimming, snorkeling, SUP, fishing, and a fresh lunch. Captain George, Panos, Vaso, and the team bring Cretan stories, music, and easygoing hospitality to this six-hour outing.

“So amazing, the crew were so fun and so nice and they took us to aqua water coves. So beautiful !!”

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14.Balos & Gramvousa Luxury Catamaran Sailing Cruise

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

Sail from Kissamos to Balos Lagoon and Gramvousa on a semi-private catamaran limited to 22 people. Expect attentive crew such as Dimitri, Jessica, Yannis, or Spiros, plus breakfast, Cretan snacks, lunch, drinks, snorkeling, SUPs, and time to swim.

“The crew was fun, kind, and most importantly emphasized our safety. Everything was timed perfectly and pick up and drop off was prompt! Jessica’s cooking was superb and the beaches were beautiful! It was a great day!”

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15.Private Half-Day Sailing Trip to Dia Island

★★★★★★★★★★4.9 · 466 reviews · 4.5 hours

Spend 4.5 hours on a private sailing boat from Heraklion to Dia Island with a two-person crew. Swim and snorkel in Saint George Bay, try fishing, use the paddleboards, and enjoy fruit, drinks, and wine. Add a full meal, or bring snacks of your own.

“Communication with the provider was excellent from point of booking to the day of the event. They answered my many questions and was helpful with facilitating a cake delivery for my daughters birthday. The round trip taxi service was fairly priced, the driver arrived in time & was very friendly and accommodating. The boat was lovely & the crew Ilias & Nikiforas were fantastic. Really friendly& welcoming guys. Dia Island was beautiful & the journey to and from the island was equally as enjoyable. All round a perfect excursion and well worth the money. Thank you”

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