11 Dining Cruises in Greece That Earn the Fare

1.Catamaran Tour with BBQ Dinner, Drinks, and Music

★★★★★★★★★★4.6 · 5,886 reviews · 5 hours · from $93Number one

Spend five hours aboard the 74-foot Ocean Voyager or 80-foot Tahiti catamaran, with hotel pickup, hot-spring swimming, Red and White Beach stops, a fresh barbecue, unlimited white wine and soft drinks, and music. Choose morning light or a sunset sail through Santorini’s caldera.

“This was so fun. It is more of a boat trip rather than a boat party which I mistaked it for. We made it a party boat though and was so fun with no restrictions. The music was playing either, think ABBA! The drink selection was great and the food was amazing. You stop at a couple of places you get to jump in the sea. The food comes out about 3 hours into the trip so eat before you go but there is plenty food when served. So delicious proper Greek selection.”

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2.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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3.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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4.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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5.Sailing Trip to Dia with Snorkeling, Dining & Sunset Option

★★★★★★★★★★5.0 · 142 reviews · 4 hours 30 minutes (approx.) · from $36Cheapest deck

Sail from Heraklion to Dia Island aboard a small yacht with a crew such as Markos, Alexandra, Magda, or Georges. Swim in calm St. George’s Bay, use the included snorkeling gear, enjoy a filling Cretan meal with wine and soft drinks, then return across the sea, with a sunset option available.

“Fabulous trip and experience, great food and friendly staff made the experience special. We travelled as two couples and one vegetarian and accommodated”

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

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

Spend five hours on a sailing yacht off Mykonos, passing Ornos, Psarou, Platis Gialos, Paraga, and Paradise beaches before swimming and snorkeling from the boat at quiet Rhenia. Your crew serves a Greek buffet, wine, beer, soft drinks, and a farewell shot. Captain Stelios and crew member Anastasis have earned warm praise, though the boat size varies.

“Such lovely staff, everyone was very well looked after, beautiful sunset and views !!”

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

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

Set sail from Agios Ioannis along Mykonos’ famous south coast, then spend about two hours swimming and snorkeling from the yacht near uninhabited Rhenia. The crew serves a Greek buffet with wine, beer, soft drinks, and coffee or tea before the return sail at sunset. Pickup costs extra.

“Unbelievable trip, fantastic crew, great sites, everything was top notch. So much fun and great Greek meal included as well. Highly recommend!”

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8.3-Hours Sunset Catamaran Cruise with Dinner all Inclusive

★★★★★★★★★★5.0 · 39 reviews · 3 hours (approx.) · from $83

Set sail from Mandraki Harbor for a 45 to 60-minute swim and snorkel stop at Kallithea Bay, then watch the sunset from the water and cruise past Rhodes Old Town. Dinner, beer, wine, and soft drinks are included. The catamaran carries up to 25 people and returns to the harbor after roughly three hours.

“It is smart to go in the evening, not only for sunset, but also its not so hot anymore. Although hot enough for swimming. They have swimming noodles' and I felt perfectly save with it, even if I am not a great swimmer. It was small group of people, not crowded - so this helped to feel cozy and comfortable. The sunset was spectacular. Wonderful experience over all.”

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9.Motor Yacht Sunset Cruise with 5-Course Dinner

★★★★★★★★★★4.5 · 35 reviews · from $80

Sail from Vlihada through Santorini’s caldera on the Oniro yacht, passing red and white beaches, the lighthouse, and both volcanoes. You’ll swim near the volcano and Mesa Pigadia, then enjoy a five-course meal with wine, beer, soft drinks, coffee, and tea. Hotel pickup and small groups are included.

“Staffs were very attentive expecially Spyros who did a great job explaining us about the sites and chilling with us whenever he could. Food was delicious, there was no music but we carried a speaker and played it through out. Sunset isn't from Oia but this was majestic and beautiful.”

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10.Afternoon Catamaran trip – Dinner, Drinks & Sunset

★★★★★★★★★★4.5 · 31 reviews · 5 hours (approx.) · from $168

Sail from Kolymvari on a modern catamaran to the calm bays of Agioi Theodoroi Islands. You’ll have time for swimming, snorkeling, fishing, and stand-up paddleboarding while the English-speaking crew prepares a Mediterranean meal. Beer, wine, soft drinks, Wi-Fi, shaded seating, and sunset views are included.

“This was a fantastic trip, worth every penny. The boat itself is amazing but it was the crew who really made our trip special. My wife is disabled and in a wheelchair but Captain Yannis and his crew safely got her on board and nothing was too much trouble. The drinks were free flowing and the food was absolutely delicious. After sailing to Theodora Island we anchored and had plenty of time to swim and snorkel and use the paddle boards (not as easy as it looks). A surprise lesson in Greek dancing before a final swim and a gentle cruise back to the port. As I boarded the craft…”

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11.Dreamy Sails – Sunset Tour With Dinner And Wine

★★★★★★★★★★5.0 · 5 reviews · 4 hours (approx.) · from $65

Set out from Argostoli at 6:30 pm with Dreamy Sails for a four-hour evening cruise led by Vaseli, Vaso, and Vageli. Swim at Vardiani, eat dinner in a small island gulf, watch the sunset, then stop for a night swim at Xi Beach. Wine, drinks, music, and a bar add to the easygoing mood.

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