Greece · SUNSET SAILING CRUISES

Where to Watch the Sun Go Down: the 15 Best Sunset Sails in Greece

50 sailing trips  ·  from $37 a seat

From the water the sunset has no crowd in front of it. The 15 below are priced and timed, with a note on which serve a proper dinner at anchor and which pour a glass and call it catering.

Santorini Catamaran Cruise with Greek Meal, Open-Bar and Sunset - The hot springs at Palea Kameni
Catamaran Cruises, Catamaran Cruises in Santorini, Evening Experiences, Greece Sailing Trips, Sailing Trips with Lunch & BBQ, Sailing Trips with Lunch in Santorini, Santorini Sailing Trips, Sunset Sailing Cruises, Sunset Sailing Cruises in Santorini, Tour Reviews

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 $181Number one

Spend about five hours on a shared catamaran around Santorini, with hotel pickup, two swim stops, a Greek meal, white wine, Greek beer, soft drinks, and a towel. Choose a morning sailing or sunset cruise. Luxury options add views of Oia and Ammoudi Bay, though you stay aboard while passing them.

“Great mix of activities-sailing and stopping to swim. Crew very nice and hospitable. Not overcrowded”

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Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks - The hot springs near Palea Kameni
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Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

2.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 Santorini’s caldera, swimming near the hot springs, Red Beach, and White Beach, then eating a BBQ meal with wine, soft drinks, and water. Captain Sakis and crew members Giannis and Orestis have been praised for their warm service. Choose the later departure for the best chance of seeing Oia’s sunset.

“Amazing cruise - great crew, great atmosphere, the views, the stops at the bays and the food were all perfect. The wine was probably the only thing I didn’t rate too highly but not enough to put me off. The sunset was incredible - worth every penny to go o this trip! Definitely recommend.”

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Catamaran Day & Sunset Cruises with meals Drinks and transportation - BAOS Island and the View Toward Delos
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Catamaran Day & Sunset Cruises with meals Drinks and transportation

3.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 from Mykonos, with hotel pickup, homemade rosé wine, a freshly cooked Greek meal, snorkeling, and a two-hour swim stop at Rhenia. You’ll pass Delos for photos and history, then return by Little Venice. Crew members may include Dimitris, Iliana, Margarita, or Andreas.

“This trip was really amazing, we were with 6 other guests, the captain and 2 deckhands. The water was gorgeous, the staff was friendly and the food was amazing. I was really sad when the trip came to an end, it really was fantastic.”

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

4.Sunset Catamaran Cruise with Dinner Buffet & Drinks

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

Spend three hours aboard a sailing or power catamaran from Mandraki Harbor. Swim and snorkel at anchored Kallithea Bay, enjoy grilled chicken, salads, dips, feta, bread and unlimited drinks, then watch the sun drop over Rhodes with music on the return to port.

“The activity was very nice! Good ending to our holiday”

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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling - What makes Dia Island worth the crossing
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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

5.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 professional crew such as Andreas, Manos, or George. Swim and snorkel in a quiet bay, use the paddleboard, eat Greek food onboard, and sail home at sunset. Shared and private options are available, with hotel pickup offered from selected areas.

“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 - Leaving Ornos Bay under sail
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Mykonos Catamaran Premium Day-Sunset Tours 8-flavor Meal & Drinks

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

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

Spend about five hours on a catamaran from Ornos Bay, sailing toward Rineia and, when seas are calm, Delos. You get an onboard eight-flavor Greek meal, unlimited beer, wine, sodas, snorkeling gear, a paddleboard, and supervised sea scooters. Choose a daytime or sunset departure, with a south-coast Mykonos route available in windy weather.

“Crew and food was amazing!!! Great day on the water. 10/10 recommend!!! I can’t say enough about the delicious food. The cabin was very comfortable and plenty of places to relax and the sea scooters were so fun.”

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Rethymno: Sunset Catamaran Cruise - Sushi & Open Bar - Boarding at Rethymno Marina
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Rethymno: Sunset Catamaran Cruise – Sushi & Open Bar

7.Sunset Catamaran Cruise – Sushi & Open Bar

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

Sail from Rethymno Marina aboard the catamaran Karina for 3.5 hours of swimming, snorkeling, SUP, sushi, Cretan snacks, and sunset views near Geropotamos Beach. The English and Greek speaking crew, including Nana, Yannis, Banos, and Sepdos, keeps the mood friendly and attentive. A maximum of 25 people helps the cruise feel spacious rather than crowded.

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

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Hersonissos: Luxury Sunset Catamaran Cruise Sushi & Open Bar - From Hersonissos Port to the open sea
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Hersonissos: Luxury Sunset Catamaran Cruise Sushi & Open Bar

8.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 for 3.5 to 4.5 hours of swimming, snorkeling, paddleboarding, sushi, local wine, beer, and sunset views at Saint George Bay. The English-speaking crew serves welcome Prosecco, fruit, snacks, and soft drinks. Groups are limited to 20, with optional pickup from selected areas.

“Great trip and the Catamaran…the crew were superb and very accommodating Highly recommended”

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Romantic Sunset Catamaran Caldera Cruise incl. Meal & Drinks - Red Beach gives you the first volcanic views
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Romantic Sunset Catamaran Caldera Cruise incl. Meal & Drinks

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

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

Spend about five hours aboard a small catamaran along Santorini’s caldera, with stops near Red Beach, White Beach, the thermal springs, and Oia. You get hotel pickup, towels, Greek barbecue, wine, beer, and soft drinks. The crew, including Yannis on some departures, keeps the mood friendly and relaxed.

“My boyfriend and I did this cruise tour at the end of April and overall had a great experience. Although it was extremely windy, a bit cold, and rainy at times, the crew made sure everyone had plenty of wine and was having fun. (They also supplied blankets, if needed.) The barbecue dinner was delicious and my boyfriend was grateful for the vegetarian option. It was too cold and drizzly for us to do the stop at the hot/tepid springs or swim much (I think only two or three people from the entire group opted to go for a short swim, and they reported it was chilly), but we still…”

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Santorini Caldera Sunset Sailing Cruise with Dinner and Wine - Boarding, pickup, and the first practical hurdle
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Santorini Caldera Sunset Sailing Cruise with Dinner and Wine

10.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, stopping at the volcano for a guided hike, Palea Kameni for warm spring swimming, and Thirassia Bay for a Greek buffet and wine. Guides such as Tito and Cesar add energy, while the sunset near Oia closes the day.

“Loved swimming at the warm springs but it did ruin my white bathing suit. Pays to read the notes! Sober was delicious. Be aware that you do pay for all drinks other than wine at dinner.”

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Heraklion: Catamaran Cruise to Dia with Sunset, Meal & Bar - Boarding at Marina Café in Heraklion
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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 a relaxed afternoon sailing from Heraklion to protected Dia Island aboard a semi-private catamaran for up to 20 people. You’ll get espresso, healthy Cretan food, unlimited water, soft drinks, beer, and white wine, plus swimming, snorkeling, kayaking, SUPs, a sea scooter, and a slide before sailing home at sunset.

“Seamless organisation, spotless boat and the team were amazing. Highly recommend!”

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Chania Old Port:Luxury Sunset Catamaran Cruise with Prosecco - Agioi Theodoroi and the swimming stop
Catamaran Cruises, Chania Sailing Trips, Evening Experiences, Greece Sailing Trips, Sailing Trips with an Open Bar, Sunset Sailing Cruises, Tour Reviews

Chania Old Port:Luxury Sunset Catamaran Cruise with Prosecco

12.Chania Old Port:Luxury Sunset Catamaran Cruise with Prosecco

★★★★★★★★★★4.9 · 177 reviews · 3.5 - 4.5 hours · from $100

Sail from Chania Old Port to Agioi Theodoroi aboard a modern catamaran with up to 20 people. Enjoy welcome Prosecco, sushi, fruit, Greek wine, beer, SUP boards, snorkeling gear, and a sunset over the sea. Crew member Irini is known for bringing extra energy to the trip.

“We had an incredible time on this excursion. The activities were a blast, the views were absolutely stunning, and the guides were fantastic.”

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Chania: Afternoon Catamaran trip - Dinner, Drinks & Sunset - One hour along the Cretan coast
Catamaran Cruises, Chania Sailing Trips, Dining Experiences, Dinner Experiences, Evening Experiences, Greece Sailing Trips, Sailing Trips with an Open Bar, Sailing Trips with Lunch & BBQ, Sunset Sailing Cruises, Tour Reviews

Chania: Afternoon Catamaran trip – Dinner, Drinks & Sunset

13.Afternoon Catamaran trip – Dinner, Drinks & Sunset

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

Join the DanEri Yachts crew for a five-hour catamaran cruise from Kolymvari. Swim and snorkel in a quiet bay, use the SUP boards and inflatables, then enjoy seafood, meat, salads, wine, beer, and soft drinks. Crew members including Angelo, Nana, and Yianni have helped make this a warm, sociable evening on the Cretan coast.

“We have just got back from a fantastic trip on one of the DanEri catamarans. Beautiful boat/yacht, friendly staff who done everything they could to make our trip enjoyable and great food with lots of wine, beer and soft drinks. Lots of spots to sit and relax, really clean and comfortable. We had a good amount of time to swim, snorkel and paddle board. The sunset on the way back was beautiful. A perfect trip.”

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Athens: Half-Day Sunset Catamaran Cruise with Meal & Drinks - Sailing the Saronic Gulf
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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

Spend four hours aboard a modern catamaran sailing from Alimos Marina along the Athenian Riviera. Your English-speaking crew prepares seafood pasta, salads, and Greek appetizers, with wine, beer, and water included. Expect a quiet small-group cruise, swimming stops, snorkel gear, and sunset views, though departure times can affect how much sunset you see.

“I really enjoyed the hospitality by niki our guide she was amazing and very helpful I was very at ease and comfortable definitely recommended sailing with her!”

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Rhodes: Sunset Catamaran Cruise with Snack, Fruits & Drinks - Leaving Mandraki Marina at 5 PM
Catamaran Cruises, Catamaran Cruises in Rhodes, Evening Experiences, Greece Sailing Trips, Rhodes Sailing Trips, Sailing Trips with an Open Bar, Sailing Trips with an Open Bar in Rhodes, Sunset Sailing Cruises, Sunset Sailing Cruises in Rhodes, 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

Join a small catamaran from Mandraki Harbour at 5 PM for a relaxed three-hour cruise to Kallithea Springs. You get about an hour for swimming, snorkeling, kayaking, or paddleboarding, followed by sunset views near Elli Beach. Greek and English-speaking crew, fruit, snacks, and drinks are included.

“Great adventure, very friendly staff and overall a wonderful time spent on the Prometheus boat. The crew ensures everyone is feeling great, provide unlimited drinks and we had a geek lunch at one of the bays. You need to know that the boat goes all the way on the engine and we did not go under sail.”

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Athens Semi Private Sunset Catamaran Cruise with meal & drinks - Vouliagmeni: the first clear-water stop
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Athens Semi Private Sunset Catamaran Cruise with meal & drinks

Sunset Sail Cruise to Rhenia, Mykonos Beach Safari, Dinner&Drinks - Rhenia: two hours of swimming from the yacht
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Sunset Sail Cruise to Rhenia, Mykonos Beach Safari, Dinner&Drinks

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