Sailing Trips in Greece: Our 15 Best

1.Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

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

Sail from Heraklion’s Old Venetian Harbour to protected Dia Island aboard a yacht limited to 14 people. Captain Petros and crew members such as Sofia, Giannis, Mariana, and Manos provide the sailing, safety guidance, food, and drinks. You’ll swim, snorkel, paddleboard, and eat shrimp linguini with Greek salad before sailing back.

“Fantastic few hours in the Greek sea, lovely crew DELICIOUS food and gorgeous sunset! Love love love”

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

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

Spend 10 hours on a motor-assisted sailboat circling Milos and visiting Polyaigos. Swim at Gerakas and Kleftiko, snorkel through sea caves, see Sarakiniko and Sykia, and learn island stories from guides such as Dora and Niki. Lunch, snacks, drinks, masks, and flippers are included.

“What a fantastic experience from start to finish! Very welcoming and friendly crew. Attentive to every detail and accommodating. Very knowledgable on the whole tour with great insights to each site. Ticked off every spot that you can only visit by boat. The best way to see the south coast of the beautiful Milos island! Would definitely do again!”

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3.Sailing Catamaran Cruise with BBQ and Drinks

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

You’ll sail from Vlychada or Ammoudi aboard a polished catamaran with an English-speaking crew, stopping at Red Beach, Palea Kameni, and Mesa Pigadia for swimming and snorkeling. A BBQ, Greek salad, wine, soft drinks, towels, and hotel pickup are included. Sunset departures finish near Ammoudi, weather permitting.

“I booked this trip at the very last minute, and the team stepped forward in the most awesome ways. First, the woman at the office was very helpful, she quickly arranged transportation after we landed at the airport (they picked us up in 9 minutes!) My friend is 83 years old and walks a little slower than others, but they made a point to accomodate him at every juncture. This 3-person team worked in tandem throughout the trip. They helped another guest who was sick the entire trip, while making sure all other guests were having a great experience. We went to three different locations, where we could jump in…”

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4.Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

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

Set out from Heraklion on a luxury sailing yacht with an English or Greek-speaking crew. The shared half-day trip reaches Dia Island for swimming, snorkeling, fishing, lunch, wine, and soft drinks. Private cruises offer meal choices, while the one-hour coastal sail skips Dia, lunch, and water activities. Crew members may include Stavroula, Dennis, Miso, or Mido.

“A very choppy crossing to the island. Very well handled by the skipper though The boat was comfortable and safety was well looked after Food was very good. Would have been nice to have beer as an option perhaps Time went very quickly”

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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

Sail Santorini’s caldera aboard a catamaran for up to 20 people. Swim at Red Beach and White Beach, visit the hot springs, enjoy a freshly cooked Greek BBQ with wine and beer, and watch the sunset from the sea. Hotel pickup, snorkeling gear, towels, and return transport are included.

“Sunset tour with drinks and lovely dinner. The boat is very nice and the crew. Downside to the tour is the weather can change easily on the islands and we did not end up being able to go to some of the places on the tour. We spent over an hour sitting in one location with not much to see at all. The bus pickup also never arrived for me and to call the business directly for the driver to come back. I was then almost late for the boat departing”

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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

Sail from Ammoudi or Athinios Port past the volcano, swim near the hot springs, Red Beach, and White Beach, then enjoy a BBQ and drinks aboard a large catamaran. The later departure may include sunset views near Oia, though timing can vary. Hotel pickup, snorkeling gear, and vegetarian food are included.

“Great crew, very friendly and helpful staff, beautiful trip. The BBQ food was EXCELLENT and lots of it. Bring your own towel!”

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7.Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

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

Sail from Heraklion’s Old Venetian Harbor to uninhabited Dia Island with a certified crew. You’ll have time for snorkeling, SUP, fishing, swimming, and a short walk, followed by salad, tzatziki, shrimp spaghetti, fruit, wine, soft drinks, and raki. Hotel pickup is available, and afternoon trips may finish with sunset views.

“FANTASTIC!!! HIGHLY RECOMMENDED!!! the trip to and Dia was an iregular trip(rough sea) ( but very safe) but the interaction with the crew was out of this world! we have spent 3 hrs (or so) by the Island of Dia snorkeling, paddling, diving... drinking. nice company as well beautiful meal plenty drinks Thank you Captain Nick "BARBOSSA" 1ST MATE KRISTINA 1ST MATE IORGU”

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8.Heraklion: 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. You’ll swim, snorkel, paddleboard, and eat onboard while the captain and host explain Crete’s coast. Full-day trips include seafood pasta and Greek salad, while half-day trips offer sandwiches or tomato pasta. Ernesto and George are among the crew members guests may meet.

“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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9.Adamas: Kleftiko Sailing Day Trip with Snorkeling and Lunch

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

Spend eight hours sailing west from Adamas with an experienced crew such as Giannis, Christos, and Dionysis. Visit Kalogries, Kleftiko, Sykia Cave, and Agios Dimitrios, with snorkeling gear, underwater photos, a RIB cave tour, breakfast snacks, Greek lunch, and drinks included.

“Had the best time on this excursion!! Cannot recommend it enough!”

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

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

Spend about five hours aboard a catamaran from Ammoudi or Athinios, sailing past the volcano and Palea Kameni. Swim near the hot springs, Red Beach, and White Beach, then enjoy a generous BBQ with Santorinian wine, water, and soft drinks. Hotel pickup and return transport are included, but bring a towel and warm layer.

“The sea was a little choppy given the time of year we were visiting but even that didn’t take away from the brilliant experience we had. The crew were so friendly and informative, and the food was excellent, and obviously the unlimited drinks helped boost our experience a little too. We were a group of 3 adults and 2 children, and every one of us said how brilliant the trip was.”

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11.Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

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

Sail from Heraklion with a small crew of up to 18 people to Dia Island, where you can snorkel, paddleboard, swim, and eat Greek food aboard a catamaran. Crew members including Manos, Andreas, Stella, and George have hosted recent sailings. Choose a half-day or full-day trip, shared or private.

“A pleasant sail with lovely hosts who are very skilled sailors.”

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12.Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

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

Join Captain George, George the Fisherman, Panos, or Vaso for a six-hour cruise from Heraklion to Dia Island. With up to 10 people aboard, you’ll sail to Saint George Bay for swimming, snorkeling, SUP, fishing, and a Cretan lunch of pasta, salad, and fruit. Transfers may be available from nearby resorts.

“Amazing half a day trip, good views, good food and drinks, a must do if you visit Crete, very enjoyable for a small group of people.”

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13.Kissamos: 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 a nutritionist-designed brunch and lunch, local wine and beer, SUPs, snorkeling gear, fishing, shaded seating, and attentive English-speaking crew such as Dimitri, Yannis, Jessica, and Spiros. Pickup may be available from Georgioupoli to Kissamos.

“Amazing day on the water. Crew were fantastic, really friendly. Great food lots of drinks. 2 beautiful swimming stops. Highly recommend.”

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14.Heraklion: Private Half-Day Sailing Trip to Dia Island

★★★★★★★★★★4.9 · 466 reviews · 4.5 hours · from $459 per boat, seats 8

You’ll spend 4.5 hours on a private sailing boat from Heraklion to Dia Island, with a two-person crew, snorkeling gear, fishing rods, paddleboards, wine, soft drinks, and fruit. Anchor in Saint George Bay for swimming and lunch. Hotel transfers and a full meal cost extra.

“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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15.Dia Sailing Cruise With All-inclusive Meal And Drinks

★★★★★★★★★★4.6 · 422 reviews · 5.5 hours · from $76

Sail from Heraklion’s Old Venetian Port to protected Dia Island on a 5.5-hour cruise. Swim, snorkel, paddleboard, and enjoy shrimp pasta, Greek salad, fruit, wine, soft drinks, and water. Crew members such as Alex, Nikolas, Mel, and Fabio are praised for warm service, while the sunset departure adds a fine finish.

“We had an amazing day sailing with Alex and Mel! There were 8 people in total on our cruise, which felt very comfortable for the size of the boat. Mel cooked us a delicious lunch. The water was crystal clear and perfect for swimming. The only thing that would have improved our experience would have been to let us know sooner about the pick up time, as we were only informed after 7 pm in the evening before the 9 am cruise, so we were a bit worried we had been forgotten about!”

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