The Mediterranean · SAILING TRIPS IN GREECE

Sailing Trips in Greece: Our 15 Picks for Clear Water

27 tours  ·  from $35 a head

Good sailing trips in Greece fill up weeks ahead in high season and the great ones go first. Below: the 15 to book early, what each fare covers and how they differ.

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal - The one-hour sail to Dia Island
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Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

1.Dia Island Sailboat Cruise with Swimming and Meal

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

Sail from Heraklion to Dia Island for swimming, snorkeling, paddleboarding, a Mediterranean meal, unlimited drinks, and sunset views.

“Here’s a smoother, more natural version of your text: This was the last day of our trip through Crete, and we ended it in the best way possible. The cruise was incredible, the weather was perfect, and the crew and food were fantastic. It was everything I wanted and more. We were having so much fun that we didn’t even have enough time to try all the activities - which is actually a good thing!”

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Adamas: Milos & Polyaigos Full-Day Sailboat Tour with Lunch - Starting in Adamas and crossing the Gulf
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Adamas: Milos & Polyaigos Full-Day Sailboat Tour with Lunch

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

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

Review of Milos and Polyaigos full-day boat tour with Kleftiko caves, swimming stops, lunch, drinks, snorkeling, and practical tips.

“Thankyou for such a fabulous day!! Kate our guide, and the rest of the team took great care of us. We were so well fed, with brekkie, lunch and multiple snacks! As well as unlimited drinks including wine! One member of our party is coeliac and they were very accomodating to her dietaries! All three swim spots were magical blue water, and the boat provided snorkels, pool noodles etc for activities. All six of us loved it so much!!! Thankyou for creating one of our trip highlights!”

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Santorini: Sailing Catamaran Cruise with BBQ and Drinks - From Thera pickup to Vlychada Port
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Santorini: Sailing Catamaran Cruise with BBQ and Drinks

3.Sailing Catamaran Cruise with BBQ and Drinks

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

Sail Santorini’s caldera by luxury catamaran, swim at volcanic beaches and hot springs, enjoy a BBQ, and watch an Aegean sunset.

“This was excellent!!!! We wished there was an all day option. The crew on board, our driver, the people answering all my crazy questions on WhatsApp, were fantastic. They were even able accommodate a vegan diet which we were so thankful for as well. This is a top notch company and it shows. For anyone visiting Santorini looking for a great cruise look no further.”

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Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch - Meeting the skipper at Heraklion Port
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Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

4.Sailboat Cruise to Dia Island with Drinks & Lunch

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

Sail from Heraklion to Dia Island for swimming, snorkeling, lunch, drinks, and beautiful Crete views on a flexible yacht trip.

“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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Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks - Sailing beside the volcano and Palea Kameni
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Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

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

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

Review of Santorini’s 5-hour sunset catamaran cruise with swimming, hot springs, BBQ, drinks, hotel pickup, and practical booking tips.

“Not sure this was the right trip for us. Didn't know was a party catamaran. However the company running this do have a more semi private opinion The BBQ was very good, actually enjoyed it and the crew was very good too Just the experience was not enough. A bit more could have been better The snorkeling equipment was not clean”

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Gouvia: Corfu Island Sailing Trip with Snack and Soft Drinks - Barbati Beach brings the first clear-water stop
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Gouvia: Corfu Island Sailing Trip with Snack and Soft Drinks

Heraklion: Sailing Cruise to Dia Island with Drinks and Meal - Stories, sea air, and the chance of dolphins
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Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

7.Sailing Cruise to Dia Island with Drinks and Meal

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

Sail from Heraklion to Dia Island for swimming, snorkeling, paddleboarding, a Greek meal, drinks, and sunset views.

“This was truly an incredible day! So relaxing in such a beautiful place. They made lunch on the boat and it was amazing. Swimming, walking the beach and soaking up the sun on the deck - absolute perfection.”

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Heraklion: Dia Island Sailing Cruise with Snorkeling - Dia Island after the crossing
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Heraklion: Dia Island Sailing Cruise with Snorkeling

8.Dia Island Sailing Cruise with Snorkeling

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

Review of Heraklion’s Dia Island sailing cruise, with snorkeling, paddleboarding, meals, prices, transport tips, and honest advice.

“The Sail Boat tour was extraordinary. We had such a beautiful sunny day. Both the Captains were very incredible. I booked for a Retreat I was hosting in Greece. We were 7 people and had the whole sailboat for ourselves. I booked the half day tour & honestly we loved it so much, that if I was doing it again, I would book the whole day! Highly recommend this experience! So worth it. 🤍 A big Thank you!!!!!! 🇬🇷 Best ever. Oh & the food was simple, but great! & we had lovely music for the whole tour, good ambiance!!!! +++5 stars ✨”

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Adamas: Kleftiko Sailing Day Trip with Snorkeling and Lunch - Setting out from Adamas and passing Klima
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Adamas: Kleftiko Sailing Day Trip with Snorkeling and Lunch

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

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

Review of Milos’s 8-hour Kleftiko yacht cruise, with snorkeling, cave safari, Greek lunch, swimming stops, and practical booking tips.

“We had a wonderful day out on the boat!! Juliano, George and George had great energy and made sure we had a great time. Even thought it was a little bit windy they got us into some really nice sheltered spots for swimming with amazing clear water. We also got a great lunch!! Would highly recommend this day trip ☺️”

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Shared Mykonos Sail Cruise to Delos and Rhenia Islands - Rhenia: Clear Water, Snorkeling, and a Long Lunch
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Shared Mykonos Sail Cruise to Delos and Rhenia Islands

10.Shared Mykonos Sail Cruise to Delos and Rhenia Islands

★★★★★★★★★★5.0 · 705 reviews · 6 hours (approx.) · from $151Top rated

Sail from Mykonos to ancient Delos and quiet Rhenia for ruins, swimming, snorkeling, a fresh Greek lunch, and friendly crew care.

“The boat was fantastic, the crew wonderful and the swimming divine. The lunch was also delicious. Delos was quite striking and it’s a very significant city but it was very hot. We learned helpful information and I’d do it again as I believe the guide provides context you wouldn’t have otherwise. Just a heads up that it does get a bit exhausting.”

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Mykonos Sail Cruise to Rhenia, Guided Tour of Delos, Lunch&Drinks - Sailing across the Aegean Sea
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Mykonos Sail Cruise to Rhenia, Guided Tour of Delos, Lunch&Drinks

11.Mykonos Sail Cruise to Rhenia, Guided Tour of Delos, Lunch&Drinks

★★★★★★★★★★4.5 · 608 reviews · 6 hours (approx.) · from $145

Sail from Mykonos to Rhenia and Delos for swimming, lunch, Greek ruins, and a guided archaeological visit in one day.

“Very informative Delos Island tour with an archaeologist. Swimming at Rhenia was fabulous. The boat was well equipped and also intimate, with 8 guests total. It was too windy to actually sail, and the seas were fairly rough - we all got at least a little wet; be prepared! Regardless it was a beautiful day on the water and the food was amazing.”

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Santorini Sailing Dream Catcher with BBQ Lunch and Drinks - Red Beach, White Beach, and the swimming stops
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Santorini Sailing Dream Catcher with BBQ Lunch and Drinks

Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling - Dia Island’s quiet cove and clear water
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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

13.Sunset Sailing Cruise Dia Island with Snorkeling

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

Review of Heraklion’s Dia Island sunset cruise, with snorkeling, sailing, Greek food, paddleboarding, prices, timing, and practical tips.

“Andreas and Ianos (hope I am spelling it correctly) were great guides, answering a lot of questions about the island. The place is a pretty good place for snorkel activities but you have to venture a bit far out, especially by the old remains of a minoan port underwater. Food was really good, drinks at your discretion. Amazing experience overall!”

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Heraklion: Private Half-Day Sailing Trip to Dia Island - Leaving Heraklion by sailboat
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Heraklion: Private Half-Day Sailing Trip to Dia Island

Kolimvari: Sailing Cruise with Meal & Water Activities - One hour along the north coast of Chania
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Kolimvari: Sailing Cruise with Meal & Water Activities

15.Kolimvari: Sailing Cruise with Meal & Water Activities

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

Review of Crete’s Kolimvari sailing cruise, with swimming, snorkeling, SUP, a generous meal, unlimited drinks, and practical booking tips.

“This was such a fun day! Highly recommend. I’ve done multiple boat tours during my travels and this was a good one. Small group, lovely boat and catered for with food. Really nice crew, would definitely recommend for a relaxed boat day!”

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Santorini Caldera Sailing Tour with BBQ Lunch and Drinks - Red Beach and White Beach from the water
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Santorini Caldera Sailing Tour with BBQ Lunch and Drinks

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