Sailing trips · SUNSET SAILING CRUISES IN GREECE

The 15 Sunset Sailing Cruises in Greece That Earn Their Price

40 trips  ·  from $37 a head

Good sunset sailing cruises in Greece fill up weeks ahead and the small-group boats go first. Below: the 15 to book early, what each includes on board and how they differ.

Santorini Catamaran Cruise with Greek Meal, Open-Bar and Sunset - Sailing Across Santorini’s Caldera
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Santorini Catamaran Cruise with Greek Meal, Open-Bar and Sunset

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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Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer - Pickup from your hotel to Vlychada Port
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Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer

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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Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks - Swimming near Santorini’s hot springs
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Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

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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Catamaran Day & Sunset Cruises with meals Drinks and transportation - Leaving Tourlos Port with Mykonos behind you
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Catamaran Day & Sunset Cruises with meals Drinks and transportation

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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Rhodes: Sunset Catamaran Cruise with Dinner Buffet & Drinks - Forty-five minutes at Kalithea Bay
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Rhodes: Sunset Catamaran Cruise with Dinner Buffet & Drinks

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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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling - The one-hour crossing from Heraklion
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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

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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Mykonos Catamaran Premium Day-Sunset Tours 8-flavor Meal & Drinks - The south coast backup route
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Mykonos Catamaran Premium Day-Sunset Tours 8-flavor Meal & Drinks

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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Rethymno: Sunset Catamaran Cruise - Sushi & Open Bar - The First Hour: Sea Views and a Gentle Start
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Rethymno: Sunset Catamaran Cruise – Sushi & Open Bar

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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Hersonissos: Luxury Sunset Catamaran Cruise Sushi & Open Bar - The welcome drink and first hour at sea
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Hersonissos: Luxury Sunset Catamaran Cruise Sushi & Open Bar

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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Romantic Sunset Catamaran Caldera Cruise incl. Meal & Drinks - Red Beach and the first look at the caldera
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Romantic Sunset Catamaran Caldera Cruise incl. Meal & Drinks

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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Heraklion: Catamaran Cruise to Dia with Sunset, Meal & Bar - Dia Island and its protected bay
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Heraklion: Catamaran Cruise to Dia with Sunset, Meal & Bar

11.Catamaran Cruise to Dia with Sunset, Meal & Bar

★★★★★★★★★★4.9 · 181 reviews · 5 - 6.5 hours · from $132

Spend 5 to 6.5 hours sailing from Heraklion to Dia Island aboard a semi-private DanEri Yachts catamaran. Swim, snorkel, kayak, paddleboard, ride the slide and sea scooter, then enjoy a nutritionist-designed Cretan meal, open bar, and sunset sail back.

“It was fantastic trip. Nice catamaran, friendly staff, very good food. We were very happy! Thanks again)”

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Chania Old Port:Luxury Sunset Catamaran Cruise with Prosecco - The 75-minute cruise toward Agioi Theodoroi
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Chania Old Port:Luxury Sunset Catamaran Cruise with Prosecco

Chania: Afternoon Catamaran trip - Dinner, Drinks & Sunset - Agioi Theodoroi and the long swim stop
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Chania: Afternoon Catamaran trip – Dinner, Drinks & Sunset

13.Afternoon Catamaran trip – Dinner, Drinks & Sunset

★★★★★★★★★★4.9 · 168 reviews · 5 hours · from $165

Join DanEri Yachts for a five-hour afternoon cruise from Kolymvari to Agioi Theodoroi. The crew, including names such as Angelo, Nana, Peach, and Yianni on some sailings, serves dinner, drinks, and local snacks while you swim, snorkel, paddleboard, and watch the sunset.

“This experience is incredible! The crew was so friendly and created a safe and fun environment for everyone to enjoy the beautiful scenery (and the food was delicious)! From the moment we were picked up at our hotel to the entire time we were on the boat and returned again to our hotel, everything was well organized and professional. Highly recommend!”

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Athens: Half-Day Sunset Catamaran Cruise with Meal & Drinks - Swimming in Clear Saronic Gulf Water
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Athens: Half-Day Sunset Catamaran Cruise with Meal & Drinks

14.Half-Day Sunset Catamaran Cruise with Meal & Drinks

★★★★★★★★★★5.0 · 167 reviews · 4 hours · from $159

Sail from Alimos Marina with an English-speaking skipper and crew aboard a modern catamaran. Expect a small-group cruise, swimming and snorkeling stops, seafood pasta, Greek appetizers, wine, beer, and water. Sunset timing can vary, so confirm the departure hour when booking.

“I had an amazing time. I booked it as it was my birthday with one of my friends and had a really nice time. The group wasn't too big, I think it was about 11 or 12 max but there was more than enough space on the boat. The crew was amazing and even surprised me with a small birthday song and dessert.”

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Rhodes: Sunset Catamaran Cruise with Snack, Fruits & Drinks - Kallithea Springs: the main reason to book
Catamaran Cruises, Catamaran Cruises in Greece, Evening Experiences, Greece Sailing Trips, Sailing Trips with an Open Bar in Greece, Sailing Trips with Open Bar & Drinks, Sunset Sailing Cruises, Sunset Sailing Cruises in Greece, Tour Reviews

Rhodes: Sunset Catamaran Cruise with Snack, Fruits & Drinks

15.Sunset Catamaran Cruise with Snack, Fruits & Drinks

★★★★★★★★★★4.6 · 142 reviews · 3 hours · from $58

Set out from Mandraki Harbour at 5:00 PM on a comfortable catamaran for Kallithea Springs Bay. You’ll have about an hour for swimming, snorkeling, kayaking or paddleboarding, then cruise toward Elli Beach for sunset. Greek and English speaking crew, fruit and chilled drinks are included.

“Amazing. staff were lovely and the catamaran was beautiful. We were able to stop off for around an hour of snorkelling and were also provided with drinks and snacks. We caught the sunset on the way back which was the perfect end to an evening out on the water.”

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Milos: Kleftiko Sunset Catamaran Cruise with Meal & Drinks - Starting at Adamantas Port
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Milos: Kleftiko Sunset Catamaran Cruise with Meal & Drinks

Sunset Sail Cruise to Rhenia, Mykonos Beach Safari, Dinner&Drinks - Greek food served while the yacht rests
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Sunset Sail Cruise to Rhenia, Mykonos Beach Safari, Dinner&Drinks

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