The 8 Best Sunset Sails for Two in Greece

1.Romantic Sunset Catamaran Caldera Cruise incl. Meal & Drinks

★★★★★★★★★★4.5 · 328 reviews · 5 hours (approx.) · from $114Our pick

Sail Santorini’s Caldera aboard a small catamaran, stopping at Red Beach, White Beach, and the volcanic hot springs. Enjoy swimming, snorkeling, Greek barbecue, Santorinian wine, beer, and soft drinks before watching the sunset near Oia. Hotel pickup and drop-off are available.

“The crew was thoughtful and would provide tips on where we were and a bit of history. The meal served was adequate and we were provided with a gluten free chicken breast and cold salads. I would recommend this excursion to everyone.”

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2.Heraklion: Dia Island Romantic Sunset Cruise with Wine

★★★★★★★★★★4.8 · 144 reviews · from $86

Sail from Heraklion to Dia Island on a semi-private catamaran with a Prosecco welcome, cheese and cold-cut platters, unlimited Cretan wine and Greek beer, snorkeling, SUPs, and sunset views. Sergei has been praised for warm hosting, but service depends on the crew assigned to your sailing.

“Awesome trip! The team was very friendly and cared a lot about our needs. The bay at Dia island was greatful and the water was very clear. The sunset was also beautiful. It was a special experience which we can recommend to everyone.”

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3.Private Beautiful Day or Romantic Sunset Cruise with Meal and Drinks

★★★★★★★★★★5.0 · 122 reviews · 5 hours (approx.) · from $574Top rated

Sail privately around Santorini for about five hours with up to 12 people. Swim at the volcanic hot springs, Red Beach, and White Beach, then enjoy a BBQ, Greek appetizers, open drinks, snorkeling, and SUP. Day and sunset departures are available, with hotel pickup arranged in advance.

“Our sunset private boat tour in Santorini was absolutely magical. From the moment we stepped on board, our two lovely hosts made us feel so welcome and relaxed. They were warm, attentive, and made the whole experience feel incredibly personal and special. The food served on board was absolutely delicious, fresh, beautifully prepared, and full of local flavour. As we cruised along the coast, the views were simply breathtaking, with the iconic cliffs and white-washed villages glowing in the golden light. And the sunset - what can we say? It was truly one of the most beautiful we’ve ever seen. Watching it from the water, with a glass of wine…”

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4.Panormo: Luxury Sunset Catamaran Cruise Sushi & Open Bar

★★★★★★★★★★5.0 · 39 reviews · 3 hours 30 minutes (approx.) · from $101

Sail from Panormo with an English-speaking crew on a luxury catamaran toward Bali Bay or Skaleta. Enjoy Prosecco, sushi, local wine and beer, swimming, snorkeling, SUP boards, and a sunset at sea. The cruise lasts about 3.5 hours and carries no more than 20 people.

“The trip was perfect from start to finish! Brilliant crew, spacious boat, not too many people, good quality food and drink. The sunset and Coast as we sailed were just magical.”

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5.Kissamos: Romantic Sunset Sailing Catamaran Cruise

★★★★★★★★★★4.9 · 15 reviews · from $73Best value

Join DanEri Yachts for a three-hour semi-private sunset cruise from Kissamos Port. You’ll sip Prosecco, swim or snorkel near Agios Sozon, use a SUP, enjoy Cretan cheese and fruit, and watch the sunset with beer, wine, soft drinks, music, and Wi-Fi included.

“The cruise was amazing! There was just perfect amount of people, not too many so it didn’t feel crowded. The boat was luxorius and the crew was professional and fun! It was 10/10 experience!”

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6.Romantic Luxury Sunset sailing

★★★★★★★★★★4.5 · 3 reviews

Sail from Heraklion with Magda’s LuxuryCrete team, pass Rocca al Mare and the old Venetian shipyards, then cross to Dia Island. Expect a four-hour private cruise for two with wine, soft drinks, snacks, snorkeling gear, fresh-linen cabins, and sunset time in a sheltered bay.

“Bulk handling. Snorkeling is not nice as everything is full and the floor totally broken. Drinking would save a lot, mood really modest.”

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7.Romantic Sunset Sail Cruise

★★★★★★★★★★5.0 · 2 reviews · from $92

Set sail from Rhodes’ Platia Neoriou at 5:30 pm for about three hours. You’ll enjoy fruit salad, beer, wine, soft drinks, water, and snorkeling equipment while watching the sun sink behind the horizon. The boat carries no more than 10 people and returns to the starting point.

“It was an unique experience! We had great time. We totally recommend it! The crew was so polite, friendly and made us have so much fun! Don’t miss the chance to include it in your vacation schedule!”

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8.Shared Catamaran Romantic Sunset Cruise from Santorini via Volcano

★★★★★★★★★★3.0 · 2 reviews · 5 hours (approx.) · from $235

Join a shared catamaran cruise from Santorini at 3:30 pm, with pickup, snorkeling gear, Wi-Fi, Greek mezedes, an onboard barbecue, drinks, and a sunset stop near Oia. The 16-person limit keeps the boat social but not crowded.

“The experience was very pleasant. The staff were very professional and the meal was good. The views were great and sunset was the perfect ending!”

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