Top 15 Luxury Island Tours in Greece

1.Heraklion Luxury Sailing Catamaran Dia Island | Gourmet Menu

★★★★★★★★★★4.9 · 312 reviews · 5.5 hours · from $141Our pick

Sail from Heraklion with Captain Thanasis and the EOS Yachts crew aboard a modern catamaran limited to 22 people. After a welcome snack and a view of Koules Fortress, spend about three hours near Dia Island swimming, snorkeling, paddling, fishing, and enjoying a chef-prepared seafood lunch with wine and beer.

“Great afternoon, unfortunately the conditions meant not so many activities were available, but the crew looked after us all really well.”

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2.Heraklion: Dia Island Luxury Catamaran Cruise with Meal

★★★★★★★★★★4.7 · 194 reviews · 5.5 hours · from $127

Sail from Heraklion’s Old Venetian Harbor to Dia Island aboard a Lagoon 450F catamaran. Swim, snorkel, fish, and use the SUP boards when conditions allow. Sophia and the crew serve a Mediterranean meal, unlimited drinks, and local stories about Dia. Choose a morning sailing or an afternoon trip with sunset views.

“This was by far one of the best experiences I’ve had on vacation. 9 of my closest friends joined me, and we had the time of our lives. Sophia, as well as the captain, were very knowledgeable, attentive to any needs we had, and they made an absolutely delicious lunch with the best Greek salad I’ve ever had. The catamaran is very spacious with plenty of room to move around. The unlimited wine or beer was a bonus! If you’re looking for a great private catamaranm experience, I highly recommend booking this one over any other!!”

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3.Kos Pearl 3 Island: Lounge in Luxury on the Aegean Waves

★★★★★★★★★★4.6 · 148 reviews · 7 hours · from $29Best value

Spend seven hours aboard the Kos Pearl visiting Pserimos, Vathi, and Blue Lagoon. You get a chicken or vegetarian lunch, swimming time, music, and a short Greek dance show. English-speaking crew members keep the day moving, with a chance to see dolphins and jump from the boat at the final stop.

“The boat was immaculate. The crew were very friendly and hard working. There was a great atmosphere on board and it was good value for money. Would definitely book again . We had a great day .”

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4.Luxury Catamaran Cruise, Dia Island –Open Bar & Lunch -Top Rated!

★★★★★★★★★★5.0 · 143 reviews · 5 hours 30 minutes (approx.) · from $145Top rated

Meet at Cafe Marina in Heraklion for a 5.5-hour catamaran cruise to Dia Island. EOS Yachts provides a professional English-speaking crew, fresh seafood or vegetarian and meat dishes, an open bar, snorkeling gear, SUPs, fishing equipment, and time to swim in a quiet bay. Groups are limited to 25 people.

“The best caramaran in the port and I'm sure is the crew. Amazing captain, chef and assistant. Beautiful and tasteful food, with dinner and snacks before and after. Everything is thought of, even SUPs and snorkel equipments. Captain anchored us in the best spot in the bay, close to the shore. Amazing experience, would reccomend to anyone.”

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5.Saronic Islands Full-Day Cruise with VIP Seats

★★★★★★★★★★4.7 · 111 reviews · 12 hours · from $304

Spend 12 hours sailing from Athens to Hydra, Poros, and Aegina in a VIP lounge with reserved seating, lunch, snacks, drinks, and fast-track boarding. You get about 90 minutes on Hydra, 50 minutes in Poros, and two hours in Aegina. Hosts such as Kostas, Katrina, and Jasper have been praised for attentive service.

“Amazing! I wish there was more time at Hydra. That island was the most beautiful. The middle island was less impressive. Overall it was wonderful and probably my favorite of the three boat excursions we went on in Greece”

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6.Heraklion: Dia Island Luxury Sailing Trip with Meal & Drinks

★★★★★★★★★★4.7 · 107 reviews · from $68

Sail from Heraklion’s Venetian harbor to Dia Island aboard TREATON or JACKPOT. You’ll have time to swim, snorkel, fish, paddleboard, and enjoy shrimp pasta, Greek salad, fruit, wine, beer, and soft drinks. Choose a shared morning or sunset cruise, or book a private trip with captain-led sailing and spacious decks.

“We loved this trip! Swimming in the emerald green crystal clear waters in the lagoon at Dia, followed by delicious meal! Joseph and Nikos were great hosts, recommended! 🙌🏼”

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7.Saronic Islands Cruise with VIP Area Seating & Lunch

★★★★★★★★★★4.1 · 45 reviews · 11 hours · from $276

Spend a full day sailing from Athens to Hydra, Poros, and Aegina aboard a large modern ship. Your package includes hotel pickup, a VIP lounge area, buffet lunch, drinks, a Hydra walking tour, and onboard entertainment. The VIP setup and meal service can vary, so confirm exactly what is included before paying $276.

“The tour guide was definitely not even reasonable. The tour is advertised as a private experience with food included and more, but in reality, it only offers unlimited soft drinks throughout the day. There’s no breakfast—I had to pay for that myself. Around 10 a.m. they served a few snacks, and at about 12 p.m. there was lunch, which was far from being enough to actually satisfy anyone. If you truly want a private area, it costs an extra one thousand euros to upgrade. I do not recommend this tour, not even if it cost a third of the price.”

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8.Heraklion: Luxury Catamaran Cruise to Dia Island with Lunch

★★★★★★★★★★4.8 · 36 reviews · from $144

Spend about 6.5 hours sailing from Heraklion to Dia Island aboard a comfortable DanEri Yachts catamaran. The crew serves coffee, local pies, unlimited beer, wine, and soft drinks, plus a fresh Mediterranean lunch with vegetarian, vegan, gluten-free, and children’s choices. Swim, snorkel, fish, paddleboard, or relax in a secluded bay.

“The catamaran cruise was amazing! The crew was fantastic—friendly and attentive. The food was perfect, with every meal exceeding expectations. Overall, it was a wonderful and relaxing experience. Highly recommend!”

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9.Private Luxury Sailing Trips to Dia Island

★★★★★★★★★★4.5 · 25 reviews · 6 hours (approx.)

Sail privately from Heraklion to Dia Island with a skipper and crew, then spend time at St. George’s Bay swimming, snorkeling, fishing, and relaxing. Your group of up to 10 gets equipment, fruit, soft drinks, water, and white wine. Ask about pickup, lunch, champagne, and whether Captain Mario is leading your trip.

“It was a wonderful and relaxing boat trip with friendly staff. Truly a delightful experience on the sea”

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10.From Ierapetra: Day Cruise with Luxury Yacht to Chrissi island

★★★★★★★★★★4.5 · 23 reviews · 6 hours (approx.) · from $155

Join a maximum of 15 people for a six-hour yacht trip from Ierapetra to Chrissi Island. The captain and his brother handle the day, with a beach stop, lunch served aboard, snorkeling, swimming, and time to relax. Bring towels and water shoes, since parts of the shore are rocky.

“Barca comoda, personale gentile ed efficiente, giornata piacevolissima anche perché i compagni di viaggio erano molto carini”

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11.Luxury Boat Trip to Symi Island with Swimming at St. George

★★★★★★★★★★4.5 · 22 reviews · 8 hours · from $81

Spend eight hours cruising from Rhodes to Symi Island, with a 1.5-hour swim stop at boat-access-only St. George’s Bay and three hours to explore Symi town. You can choose sun or shade aboard the boat, buy coffee at the bar, and taste Simiako Garidaki, the island’s small shrimp cooked in olive oil. Hotel transfers are optional.

“Activity was amazing. St George’s bay is just stunning and Symi was great to see!! Transfer was organised with ease, our hotel wasn’t listed but this wasn’t and issue and within minutes Half Price Tours had organised a pickup and gave a pick up time! They kept in touch, messaged later on after the activity to check how everything was. Driver was friendly and got everyone picked up and dropped off with ease! The boat was a good size for everyone, plenty of seats, clean boat. Honestly couldn’t fault it, really loved this activity and wouldn’t hesitate to go again! Ps… you will need to bring towels, or do what…”

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12.VIP Swimming Cruise to three islands

★★★★★★★★★★4.6 · 18 reviews · 9 hours · from $229

You’ll board a luxury cruise with hotel pickup, fast-lane boarding, private sun beds, a lounge, buffet lunch, unlimited soft drinks, coffee, wine, and beer, plus one cocktail. Swim at Agistri and Metopi, visit Aegina, then return along the Athens Riviera with a DJ and sunset views.

“O navio e muito velho e esta em mau estado. Sendo una reserva Vip era esperado mais conforto e mais serviços. A area reservada esta mal cuidada espreguiçadeiras Partidos e divisão com ar condicionado muito ma com Mobiliário antigo e cheirava mal. A comida era péssima e a dispensa de bebidas era tudo menos vip E definitivamente uma experiência a evitar.”

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13.Kos: Seanomad Private Luxury Yacht Full Day 2 Islands Cruise

★★★★★★★★★★5.0 · 8 reviews

Spend seven hours aboard Sea Nomad’s 2023 Sea Ray Sundancer 320, cruising from Kos Marina to Pserimos and Plati Island. Your English-speaking captain takes you to Vathi and Erinies beaches for swimming and snorkeling, with drinks, fruit, and mini sandwiches provided. Fuel and a full meal are not included.

“Amazing day. Booked for four people and everyone loved the whole experience. Can not recommend higher.”

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14.Ierapetra Chrissi Island Luxury Yacht Cruise with Meal

★★★★★★★★★★4.5 · 7 reviews · 5 hours 30 minutes (approx.) · from $180

Sail from Ierapetra to Chrissi Island for about four hours of swimming, snorkeling, and time ashore. A maximum of 20 people share the yacht, with SUP gear, snorkels, seafood pasta, Greek salad, Cretan appetizers, fruit, beer, wine, and soft drinks included. Pickup is available across southeastern Crete.

“Crew that takes care of the details and offers you an experience at sea to remember. Easy to recommend.Auto-translated”

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15.Corfu Grand Island VIP Tour

★★★★★★★★★★4.0 · 6 reviews

You’ll ride in an air-conditioned Mercedes van with an English-speaking driver, tasting Corfiot olive oil, olives, kumquat, honey, and other homemade treats before visiting Paleokastritsa, Lakones, Angelokastro, and either Canal D’Amour or Kassiopi. Hotel and port pickup are offered, and the tour is private for your group.

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