GREECE

15 Sunset Sailing Cruises in Greece Worth Booking

35 sailing trips  ·  from $37 a head

Every trip has one spare afternoon in it. These 15 sunset sailing cruises in Greece are the ones that earn it, priced and timed so you can decide in minutes.

Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks - Hotel pickup makes the port connection easy
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Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling - Leaving Heraklion for Dia Island
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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

Santorini Caldera Sunset Sailing Cruise with Dinner and Wine - Getting to the boat without a stressful start
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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

Review of Santorini’s six-hour caldera sunset cruise, with a volcano hike, hot springs swim, Greek dinner, wine, and practical booking tips.

“This excursion is too notch. Make sure you arrange for return transport when the excursion is over. Our tour guide was fun and the meal was delicious. Loved swimming off the boat”

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Sailing Trip to Dia with Snorkeling, Dining & Sunset Option - Lunch on deck, with Cretan flavors
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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 Dia Island for snorkeling, a fresh meal, Cretan wine, and a sunset return on a small-group yacht.

“It was just beautiful. From pickup to drop-off, everything just worked out. The shuttle was very punctual, even a little early at the hotel, so we could start on time at the harbor. Alexandra and Markos were warm and inviting. They explained everything well and took care of everything we needed. The sailing trip was beautiful despite the very calm sea, and Markos did his best so that we could at least sail a little with the power of the wind. When we arrived at the island, there were explanations and assistance for the activities. We were very impressed by Markos' patience and calmness when he helped a fellow traveler…”

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Mykonos: Sunset Sail Cruise to Rhenia, Beach Hopping, Dinner - Starting near Paradise Beach and getting settled
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Mykonos: Sunset Sail Cruise to Rhenia, Beach Hopping, Dinner

Sunset Sail Cruise to Rhenia, Mykonos Beach Safari, Dinner&Drinks - Meeting the yacht at Agios Ioannis Diakoftis
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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

Sail from Mykonos to quiet Rhenia, swim and snorkel from a yacht, enjoy a Greek buffet, drinks, and sunset views for $114.89.

“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 - From your hotel to Vlychada Marina
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Santorini Caldera: Sunset Sailing Cruise with Meal

Kassandra: Sunset Sailing Boat Tour of Secluded Coves - Why the small group changes the experience
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Kassandra: Sunset Sailing Boat Tour of Secluded Coves

8.Kassandra: Sunset Sailing Boat Tour of Secluded Coves

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

See if Kassandra’s small-group sunset sail is worth $57, with secluded coves, swimming, snorkeling, paddleboarding, and sunset views.

“It was an amazing trip. We got coffee while exploring the local coast. Made a stop at a beautiful beach so we could jump from the boat and snorkel a bit. Then we saw dolphins and enjoyed the sunset on the way back. The captain was extremely polite and seemed very experienced.”

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Neos Marmaras: Sunset West Sithonia Islets Sailboat Tour - What the small group changes
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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

Review of Neos Marmaras’ small-group sunset sailing tour to Kelyfos Island, with swimming, snorkeling, SUP, sunset views, costs, and practical tips.

“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 - Vouliagmeni Beach when conditions cooperate
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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

Review of Athens’ five-hour luxury catamaran cruise with Greek food, swimming at Ydrousa, sunset views, drinks, and a small group.

“The experience was excellent! The boat was comfortable. We were able to move around & enjoy the beautiful surroundings & the calmness of the water. The food was perfect. Great experience! The sunset was amazing. The captain & his mate were perfect Thank you for a wonderful experience.”

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Agios Nikolaos: Golden Hour Sailboat Tour with Wine & Snacks - The first hour across Mirabello Bay
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Agios Nikolaos: Golden Hour Sailboat Tour with Wine & Snacks

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

SAILING DAY 4.5h-5h or SUNSET 3h-4.5h from Hersonissos CRETE - Lunch, wine, and raki on the five-hour trip
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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

Review of a small-group sailing trip from Gouves to Dia, with swimming, snorkeling, SUP, Cretan lunch, wine, and sunset options.

“Strattos our skipper was amazing from beginning to the end full of local knowledge and we had the best experience...all the best strattos from Alan judy grey lori Rob Alex abi and little judy. 😀”

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South Crete: Small group Full Day/ Sunset Sailing & Lunch - Agios Pavlos and Alatsonkremnoi
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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

Sail from Agia Galini to South Crete’s wild beaches with lunch, wine, snorkeling, SUP boards, and sunset views in a small group.

“Lovely way to end our week in Crete. It was an highlight that we will look back on fondly. Our group was my husband & I, plus 4 teenage/ young adult kids. On the boat we were joined by a charming mother and daughter of similar age from the NL. We went from Agia Galini to Paximadia and then to Agios Pavlos and back. Lunch was served at Agios Pavlos. Watermelon was served as a snack at Paximadia. Positives: Everyone enjoyed snorkelling. There weren't so many fish at Paximadia but a lot more at Agios Pavlos. The masks provided were a bit cloudy but luckily most of us had brought…”

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From Heraklion:Small group 5,5h Sunset Sailing trip to Dia Island - Heraklion’s Old Venetian Harbor from the water
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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

Review of a six-hour sunset sailing trip from Heraklion to Dia Island, with snorkeling, snacks, small groups, and practical booking advice.

“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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