SUNSET SAILING CRUISES IN GREECE

15 Sunset Sailing Cruises in Greece for the Logbook

35 sailings  ·  from $37 a head

The 15 best sunset sailing cruises in Greece you can get aboard today, with what each costs, how long it stays out and who it suits. Number one is first for a reason; start there.

Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks - Hot springs near the volcano
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Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

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

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

Spend about five hours on a spacious Santorini catamaran, with hotel pickup, caldera views, hot springs, Red Beach, White Beach, swimming, snorkeling, and a BBQ meal. Complimentary water, soft drinks, and Santorinian Nychteru wine are included. The later sailing aims for sunset near Oia, though the final viewing point can change.

“Overall it was ok. The food was good along with the views. Music was load and it could’ve been shorter. Those looking for a quiet ride around seeing the sites this is not for you.”

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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling - Leaving Heraklion for an hour at sea
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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

2.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 crew of up to 18 people. Swim, snorkel near an old Minoan port, use the paddleboard, and enjoy Greek food onboard. Full-day trips include salad, tzatziki, and seafood pasta, while half-day trips include tomato pasta. Crew members such as Andreas and George add local stories and friendly help.

“We had a wonderful time! There were a lot of people on the boat but it didn’t feel crowded. The cove where we anchored was lovely — our only complaint was that a party boat anchored nearby and played loud (bad) house music the whole time. It made the experience slightly less idyllic, but we tuned it out eventually, food was delicious, guides were friendly and cooked a delicious dinner, and the sunset was dreamy. A perfect way to spend our afternoon/evening in Heraklion!”

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Santorini Caldera Sunset Sailing Cruise with Dinner and Wine - Starting at Fira’s old port
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Santorini Caldera Sunset Sailing Cruise with Dinner and Wine

3.Santorini Caldera Sunset Sailing Cruise with Dinner and Wine

★★★★★★★★★★4.5 · 208 reviews · 6 hours (approx.) · from $96

Spend about six hours sailing Santorini’s caldera with a shared group of up to 130 people. Hike the volcano, swim to Palea Kameni’s warm springs, eat a Greek buffet with wine, and watch sunset near Oia. Guides including Tito, Toto, and Cesar have led departures, while pickup is available for an added cost.

“This tour was great. Everything from the pickup to the stops was excellent. The guide was really amazing too. You should totally do it.”

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Sailing Trip to Dia with Snorkeling, Dining & Sunset Option - St. George’s Bay, Dia’s quiet swimming stop
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Sailing Trip to Dia with Snorkeling, Dining & Sunset Option

4.Sailing Trip to Dia with Snorkeling, Dining & Sunset Option

★★★★★★★★★★5.0 · 142 reviews · 4 hours 30 minutes (approx.) · from $36Best value

Sail from Heraklion to uninhabited Dia Island with a small group of up to 10 people. Swim and snorkel in sheltered St. George’s Bay, try fishing, enjoy a filling Cretan meal with soft drinks, water, and white wine, then choose a sunset return. Captains including Markos, Magda, Alexandra, and Yorgé are praised for warm, personal service.

“This was an excellent sailing experience. The 45ft sailboat was outstanding, as were the crew and captain. The lunch was terrific and the day to Dia exceeded all our expectations. Highly recommend this excursion. Our only regret, is that we did not have time to do the sunset sail.”

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Mykonos: Sunset Sail Cruise to Rhenia, Beach Hopping, Dinner - Leaving Mykonos and passing the famous beaches
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Mykonos: Sunset Sail Cruise to Rhenia, Beach Hopping, Dinner

5.Sunset Sail Cruise to Rhenia, Beach Hopping, Dinner

★★★★★★★★★★4.8 · 122 reviews · 5 hours · from $111

Spend five hours sailing past Mykonos beaches to quiet Rhenia, where you swim from the yacht, snorkel, and eat a Greek buffet with wine, beer, and soft drinks. The crew, sometimes including Captain Stelios or Anastasis, finishes the trip with sunset views and a farewell drink. Pickup costs extra.

“We really liked it and the Captain Stelios along with Anastasis were so kind and willing to help , explain and show us the beauty of this island. Totally recomended!!!”

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Sunset Sail Cruise to Rhenia, Mykonos Beach Safari, Dinner&Drinks - What you eat and drink on board
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Sunset Sail Cruise to Rhenia, Mykonos Beach Safari, Dinner&Drinks

6.Sunset Sail Cruise to Rhenia, Mykonos Beach Safari, Dinner&Drinks

★★★★★★★★★★4.5 · 116 reviews · 5 hours (approx.) · from $114

Join Sunfos Alessia Yachting for a five-hour sail from Agios Ioannis to Rhenia, with a beach safari along Mykonos’ southern coast. Expect swimming from the yacht, free snorkeling gear, a Greek buffet, wine, beer, soft drinks, and a sunset return. Crew names vary, with Costas, Joanna, Bobi, Foti, and Sofia among those reported on board.

“Super fun trip! The boat was great and there wasn’t too many people onboard- something I had been a bit worried about. We stopped to swim a couple of times and the views as you sail around are incredible. Lunch was pretty tasty but quite late in the day so I was quite hungry by that point- maybe take some snacks ! The booze was unlimited but I wouldn’t say free flowing. We had to keep asking for a drink/ trying to find the guy to ask but all in all a very fun day with ALOT of sun and even some dolphins!”

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Santorini Caldera: Sunset Sailing Cruise with Meal - Red Beach, White Beach and Aspronisi
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Santorini Caldera: Sunset Sailing Cruise with Meal

7.Santorini Caldera: Sunset Sailing Cruise with Meal

★★★★★★★★★★4.8 · 68 reviews · 5 hours · from $147

Join a small sailing group of up to 10 for a five-hour Santorini cruise from Vlychada Marina. You’ll pass Red Beach, White Beach and Aspronisi, swim near Mesa Pigadia and Palea Kameni, see the caldera villages from the water, and eat a crew-prepared seafood barbecue with Greek wine and beer. Hotel pickup is included.

“Chris & Mariangela made this Experience perfect for us! I can recommend it 100 %”

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Kassandra: Sunset Sailing Boat Tour of Secluded Coves - A quiet cove instead of another crowded beach
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Kassandra: Sunset Sailing Boat Tour of Secluded Coves

8.Sunset Sailing Boat Tour of Secluded Coves

★★★★★★★★★★4.7 · 57 reviews · 3 hours · from $57

From Chrousso Marina, sail with a skipper toward Halkidiki’s southeast coast aboard a boat for up to 8 to 11 people. You’ll stop at quiet coves for swimming, snorkeling, and paddleboarding before watching the sunset from the water. Captain Grigorious, known as Greg, and Georgia have crewed recent sailings.

“Beautiful calm boat ride, benefitted from only having 10 people aboard. I'd recommend this excursion, absolutely.”

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Neos Marmaras: Sunset West Sithonia Islets Sailboat Tour - The route toward Kelyfos Island
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Neos Marmaras: Sunset West Sithonia Islets Sailboat Tour

9.Neos Marmaras: Sunset West Sithonia Islets Sailboat Tour

★★★★★★★★★★4.7 · 50 reviews · 3 hours · from $57

Set sail from Neos Marmaras with a skipper such as Captain Giorgos for a three-hour sunset trip toward Kelyfos Island. Swim, snorkel, or use the SUP in a quiet cove before watching the sun sink over the Aegean. The boat carries up to 8 to 11 people, with water, coffee, tea, and a refrigerator for your own food.

“12-jähriger Sohn durfte zeitweise das Boot steuern, es gab Wein, eine hübsche Bucht wurde angesteuert, wir konnten angebotene Tauchermasken und Schnorchel benutzen, freundlicher Seebär als Skipper. Wunderschöner Sonnenuntergang. Man sollte einigermaßen trittsicher sein für die Tour. --”

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Luxury Catamaran Sunset Semi-Private & Greek Gastronomy in Athens - Leaving Alimos Marina at 3:30 p.m.
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Luxury Catamaran Sunset Semi-Private & Greek Gastronomy in Athens

10.Luxury Catamaran Sunset Semi-Private & Greek Gastronomy in Athens

★★★★★★★★★★5.0 · 45 reviews · 5 hours (approx.) · from $156

Join a five-hour catamaran cruise from Alimos Marina with Alex and Veronica, or another experienced crew team, for swimming near Ydrousa, possible time at Vouliagmeni Beach, Greek food, drinks, SUP, snorkeling, and an Athens Riviera sunset. The boat holds no more than 10 people, with pickup available within 8 kilometers for an extra fee.

“The sunset tour was fantastic. The host was so friendly and despite the overcast weather we were able to swim and have a really good trip. Very accommodating to vegetarian diet as well. Highly recommend!”

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Agios Nikolaos: Golden Hour Sailboat Tour with Wine & Snacks - Sailing across Mirabello Bay
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Agios Nikolaos: Golden Hour Sailboat Tour with Wine & Snacks

11.Golden Hour Sailboat Tour with Wine & Snacks

★★★★★★★★★★4.9 · 35 reviews · 4.5 hours · from $112

Join a semi-private 4.5-hour sailing trip from Agios Nikolaos for views of Spinalonga, swimming and snorkeling at Kolokitha, SUP, fishing, local wine, fruit, and deli-style snacks. With room for only 10 people, you get a relaxed boat day rather than a crowded excursion. Bring your own towel.

“Det var en rigtig skøn tur og der var god komfort på båden. Venlig besætning.”

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Corfu: Sunset Cruise on a Traditional Wooden Sailing Yacht - Finding the wooden yacht at Benitses Marina
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Corfu: Sunset Cruise on a Traditional Wooden Sailing Yacht

12.Sunset Cruise on a Traditional Wooden Sailing Yacht

★★★★★★★★★★5.0 · 34 reviews

Join the traditional wooden yacht Odysseia at Benitses Marina for a two-hour sunset cruise toward Pontikonisi. You’ll see Corfu’s old fortress, Garitsa Bay, Mon Repos, and the coast from the water, with a cocktail, wine, beer, juice, water, local finger foods, and soft music. The small group keeps the evening relaxed.

“One of the best activities we did in Corfu! The boat was spacious with lots of seating, the snacks were delicious, the hosts were amazing and very informative about this part of the island, and the views were breathtaking. Well worth the money for a great boat excursion! 100/10 would recommend to others and would do again!”

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SAILING DAY 4.5h-5h or SUNSET 3h-4.5h from Hersonissos CRETE - The sailing itself: wind, views, and a little spray
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SAILING DAY 4.5h-5h or SUNSET 3h-4.5h from Hersonissos CRETE

13.SAILING DAY 4.5h-5h or SUNSET 3h-4.5h from Hersonissos CRETE

★★★★★★★★★★4.5 · 30 reviews · 3 to 5 hours (approx.) · from $108

Set sail from Gouves with a small crew aboard a boat limited to 14 travelers. Choose a 4.5 to 5-hour day trip to Dia Island, or a shorter sunset cruise to Saint George Bay during summer. Expect swimming, snorkeling, SUP, fishing gear, Cretan food on the longer trip, and guides such as Stratos, Manos, or Dimitrios.

“This was an amazing tour. Our captain was awesome and Maria made us a delicious lunch. We swam, met new people, and had a wonderful time. A beautiful way to see Crete and Dia!”

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South Crete: Small group Full Day/ Sunset Sailing & Lunch - Leaving Agia Galini for the open water
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South Crete: Small group Full Day/ Sunset Sailing & Lunch

14.South Crete: Small group Full Day/ Sunset Sailing & Lunch

★★★★★★★★★★4.5 · 28 reviews · 5 to 7 hours (approx.) · from $108

Set sail from Agia Galini with a certified crew for a small-group cruise to Paximadia or Agios Pavlos. You get lunch, wine, soft drinks, snorkeling gear, SUP boards, swimming time, and a sunset return. The boat carries no more than 10 people, and the route changes with the weather.

“Although there wasn’t much wind, the sailing trip was unforgettable. The crew was warm and welcoming and along the way we even spotted dolphins. We stopped to snorkel around a charming little island before ending the day with a breathtaking sunset. The whole atmosphere was magical. A definite 10/10, I would highly recommend it.”

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From Heraklion:Small group 5,5h Sunset Sailing trip to Dia Island - Passing Koules Fortress and Castello del Molo
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From Heraklion:Small group 5,5h Sunset Sailing trip to Dia Island

15.Small group 5,5h Sunset Sailing trip to Dia Island

★★★★★★★★★★4.5 · 26 reviews · 6 hours (approx.) · from $84

Set sail from Heraklion at 3:15 pm for a roughly six-hour cruise toward Dia Island and Agios Georgios. You’ll pass the Old Venetian Harbor and Koules Fortress, swim or snorkel in clear water, and enjoy snacks, bottled water, and soft drinks aboard a well-equipped yacht. The group is limited to 10 people.

“Our young skipper was delightful and spoke excellent English. We really enjoyed our cruise to Dia Island. The water where we snorkeled was a beautiful turquoise, and you could see to the bottom.”

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