The 15 Sunset Sailing Cruises in Greece That Earn Their Price

1.Santorini Catamaran Cruise with Greek Meal, Open-Bar and Sunset

★★★★★★★★★★5.0 · 1,694 reviews · 5 hours (approx.) · from $181Our pick

Spend about five hours on a shared Santorini catamaran with hotel pickup, volcanic hot springs, Red Beach, swimming stops, a Greek meal, wine, beer, and soft drinks. Choose a morning or sunset sailing, with luxury options adding Oia and Ammoudi Bay views.

“Such an amazing experience with a friendly and knowledgeable crew. We would definitely recommend this sunset cruise to any of our friends who may come to Santorini in the future.”

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

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

Cruise Santorini’s coast aboard a catamaran for up to 20 people, with stops at Red Beach, White Beach, the hot springs, and the volcano. You’ll get hotel transfers, snorkeling gear, towels, a fresh Greek BBQ, drinks, and a sunset sail if you select the afternoon departure.

“Very peaceful cruise with great views and good food. Even though the weather was not the best the cruise was still a lot of fun”

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3.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 from Ammoudi or Athinios Port past the volcano, swimming near the hot springs, Red Beach, and White Beach, then enjoying a BBQ and drinks aboard a catamaran. The later departure may include sunset views near Oia. Expect music and a social group atmosphere.

“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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4.Catamaran Day & Sunset Cruises with meals Drinks and transportation

★★★★★★★★★★5.0 · 760 reviews · 5 hours (approx.) · from $133

Spend about five hours aboard a modern catamaran with a skipper and crew such as Dimitris, Iliana, or Margarita. Sail past Delos, swim and snorkel at Rhenia, enjoy a fresh Greek meal and homemade rose wine, and return by hotel van.

“Crew is amazing. They made the catamaran experience so wonderful. Margarite met us within walking distance from the cruise port and was so informative and helpful throughout the entire experience. The lunch they served was delicious! We had an amazing time. So happy we booked this excursion!”

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5.Sunset Catamaran Cruise with Dinner Buffet & Drinks

★★★★★★★★★★4.8 · 644 reviews · 3 hours · from $58

Sail from Mandraki Harbor to Kalithea Bay for swimming and snorkeling, then enjoy a Greek buffet with unlimited wine, beer, soft drinks, and water as the catamaran returns beneath Rhodes’ sunset. Choose a sailing or power catamaran, with toilets, an outdoor shower, and swim gear onboard.

“This was our favourite event of our trip! The staff were so welcoming, the views were stunning and the unlimited local drinks and food were incredible. We wish we could have done this every night!”

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6.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, paddleboard, eat Greek food, and watch the sunset on the return journey. The crew, including guides such as Andreas and Ianos on some departures, adjusts the plan to wind and sea conditions.

“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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7.Mykonos Catamaran Premium Day-Sunset Tours 8-flavor Meal & Drinks

★★★★★★★★★★5.0 · 500 reviews · 5 hours (approx.) · from $181

Sail from Ornos Bay toward Rineia and, weather permitting, Delos on a small-group catamaran cruise limited to 16 people. Expect swimming, snorkeling, paddleboarding, supervised sea scooters, an eight-flavor Greek meal, an open bar, and a choice of daytime or sunset departure.

“It's awesome, the small group is the way to do this, the crew is always on point, the food was amazing.”

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8.Sunset Catamaran Cruise – Sushi & Open Bar

★★★★★★★★★★4.8 · 446 reviews · 3.5 hours · from $100

Spend 3.5 hours aboard DanEri Yachts’ catamaran Karina with Prosecco, sushi, Cretan snacks, an open bar, SUP boards, snorkeling gear, and a sunset stop at Geropotamos Beach. The English and Greek speaking crew keeps the mood relaxed, with space for up to 25 people.

“The crew was so lovely and friendly. We recommend this trip 100%!”

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9.Luxury Sunset Catamaran Cruise Sushi & Open Bar

★★★★★★★★★★4.8 · 442 reviews · 3.5 - 4.5 hours · from $94

Set sail from Hersonissos on a modern catamaran bound for Saint George Bay. You’ll get Prosecco, sushi, local snacks, unlimited beer, wine, soft drinks, and time for swimming, snorkeling, SUP, and sunset views. The group is limited to 20, with hotel pickup available from selected areas.

“Our group was 2 adults, a teenager and a ten year old. We all loved the trip! It ended up being quite choppy 🌊 on the day of our trip, which I personally enjoyed. Definitely listen to the skipper when he tells you to sit up top with him if there is any chance you may feel sea sick and do it on the way back too! The sup boards had no fins which made them tricky to manoeuvre. Plenty of ’noodle’ floats and snorkeling gear. We enjoyed our swim in the sea. The crew were lovely. A good selection of drinks were available and the snacks were as expected…”

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

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

Cruise from Santorini’s coast to Red Beach, White Beach, the volcano hot springs, and Oia’s sunset. You’ll swim or snorkel, eat Greek appetizers and barbecue, and enjoy wine, beer, ouzo, and soft drinks. Pickup is available, and the boat carries up to 16 people, weather permitting.

“Ok, given the choice I would not do this trip again. Major confusion about the pick up location. Then 3 buses arrived all together- it was very confusing to figure out who was collecting who, and they were 15 minutes late. The food was ok but not great. The “ hot springs “ !!! Very over rated, as were the red and white beaches. And eventually not even a sunset ( and yes - I know that’s pot luck) At the end of the cruise, you then had to climb out of the catamaran and into a little row boat to get to shore. Overall disappointing”

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11.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 Dia Island aboard a yacht limited to 10 people. Swim and snorkel in St. George’s Bay, enjoy a fresh meal with Cretan wine, then choose the sunset return. Pickup is available from many Crete resort areas.

“Great trip!! When we arrived at Dia, we swam and went snorkelling. Lunch was average, but wasn’t there for the food. The sunset cruise on the way back was amazing. The family enjoyed this trip!!”

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

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

Spend five hours aboard a sailing yacht with an English-speaking crew, passing Mykonos beaches before swimming and snorkeling off uninhabited Rhenia. A Greek buffet, wine, beer, soft drinks, Wi-Fi, and sunset views are included. Transfers cost extra, and the boat is reached barefoot.

“Had a lovely time on this cruise it was very well planned and we was looked after from start to finish. The perfect end to our holiday.”

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13.Kleftiko Sunset Catamaran Cruise with Meal & Drinks

★★★★★★★★★★4.9 · 121 reviews · 5.5 - 7 hours · from $182

Sail from Adamantas on a modern catamaran to Klima, Cape Vani, Sykia Cave, and Kleftiko. You get swimming, snorkeling, SUP, Mediterranean food, an open bar, shaded lounges, and a sunset return. The group is capped at 20, with optional pickup and private bookings available.

“This was a fun afternoon however the sea did not completely play ball with strong winds and a good wind chop. Kleftiko bay was beautiful and we enjoyed a swim here followed by a fabulous dinner. A very enjoyable trip and would highly recommend.”

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

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

Spend about five hours on a sailing yacht off Mykonos, passing the south-coast beaches before swimming and snorkeling from the boat near quiet Rhenia. Enjoy a Greek buffet, wine, beer, soft drinks, and a sunset return. Crew members may include Costas, Joanna, Bobi, or Foti.

“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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15.Luxury Sunset Catamaran Cruise Sushi & Open Bar

★★★★★★★★★★5.0 · 61 reviews · 3 hours 30 minutes (approx.) · from $96

Sail from Hersonissos toward Malia Bay and Saint George Bay on a luxury catamaran with an English-speaking crew. You get Prosecco, sushi, fruit, an open bar, snorkeling, paddleboards, fishing, and sunset views. The boat holds up to 20 people and returns to the same marina.

“The boat was very nice and lots of room for everyone to sit & spread out which felt luxurious. I might have gone in with higher expectations however I felt that we were left to our own devices for the whole trip. We all got less than half a glass of bubbly on boarding then were told it was a bit choppy at sea so spent an hour or so sailing until we pulled up somewhere calmer for swimming but there was no communication that this would be our only stop we made an assumption as was too choppy. There were some snacks put out & it was a help…”

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