Island hopping · LUXURY ISLAND CRUISES IN GREECE

The 15 Luxury Island Cruises in Greece That Earn Their Price

16 tours  ·  from $29 a head

Every trip has one free day too few. These 15 luxury island cruises in Greece justify the slot, priced and timed so you can decide in minutes and get back to packing a dry bag.

Greece Island Hopping Tours, Island Hopping Tours, Kos Island Hopping Tours, Luxury & VIP Island Cruises, Luxury Island Cruises in Greece, Tour Reviews, VIP

3 Island Luxury Cruise with 4 Swimming Stops with Captain Morgan

1.3 Island Luxury Cruise with 4 Swimming Stops with Captain Morgan

★★★★★★★★★★5.0 · 931 reviews · 7 hours (approx.) · from $32Our pick

Spend about seven hours at sea with Captain Morgan, visiting Pserimos, Vathi, Kalymnos, and Plati from Kos. You get four swimming stops, a fresh BBQ lunch, dolphin watching, music, and an entertaining crew led in part by Ariel. The boat can carry up to 200 people, so expect a lively rather than intimate cruise.

“Lovely day out, with some fantastic swimming locations in picturesque settings. Added bonus of being lucky enough to see the dolphins. Lunch that was included was also tasty.”

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Heraklion Luxury Sailing Catamaran Dia Island | Gourmet Menu - Sailing one hour toward mythical Dia Island
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Heraklion Luxury Sailing Catamaran Dia Island | Gourmet Menu

2.Heraklion Luxury Sailing Catamaran Dia Island | Gourmet Menu

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

Sail from Heraklion to Dia Island aboard EOS Yachts’ modern catamaran, limited to 22 people. The crew serves Cretan treats, seafood cooked by Chef Charis, local wine, beer, and dessert. You’ll have about three hours for swimming, snorkeling, fishing, canoeing, and paddleboarding in a sheltered bay.

“The yacht itself exceeded my expectations. It was very spacious with luxurious touches. The boat did not feel crowded. The crew were very attentive and welcoming. They were constantly offering us drinks or assistance. The meal was also delicious, gourmet quality. The sunset ride back was stunning. Highly recommend.”

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Santorini: Southern Island Luxury Catamaran Cruise with Meal - White Beach and Mesa Pigadia
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Santorini: Southern Island Luxury Catamaran Cruise with Meal

3.Southern Island Luxury Catamaran Cruise with Meal

★★★★★★★★★★4.9 · 201 reviews · from $141

You’ll sail from Vlichada Marina to Red Beach, White Beach, Mesa Pigadia, Akrotiri Lighthouse, and Nea Kameni. The crew serves a fresh Greek BBQ with unlimited local wine, beer, soft drinks, and water. Choose a sunset sailing or daytime return with music and sunbathing.

“The best excursion I have ever had on my many trips!! The numbers and helpers are so caring and fun that I will never forget them. Thank you, Philip ( If I remember correctly) If you are alone, you are nervous but he made me relax and made effort to mix with people and so kind !!”

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Heraklion: Dia Island Luxury Catamaran Cruise with Meal - Why the Lagoon 450F makes a difference
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Heraklion: Dia Island Luxury Catamaran Cruise with Meal

4.Dia Island Luxury Catamaran Cruise with Meal

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

Join Cretan Sailing Cruises from Heraklion’s Old Venetian Harbor for a 5.5-hour cruise to Dia Island aboard a Lagoon 450F catamaran. Swim, snorkel, fish, paddleboard, and enjoy a Mediterranean meal with unlimited drinks. Morning and sunset departures are available, with Sophia and the crew looking after you.

“Excellent activity! Really nice boat (around 26 persons per boat) and the waters in dia island are amazing. A really special activity and great crew.”

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Kos Pearl 3 Island: Lounge in Luxury on the Aegean Waves - Pserimos: a gentle first stop
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Kos Pearl 3 Island: Lounge in Luxury on the Aegean Waves

5.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. Swim from sandy shores or the boat, enjoy chicken or a vegetarian lunch, and listen to music with the crew. Arrive early for top-deck seats, bring water shoes, and watch for dolphins beside the boat.

“Fantastic, friendly and attentive crew. Lovely stops, good food, value for money”

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Luxury Catamaran Cruise, Dia Island –Open Bar & Lunch -Top Rated! - Three hours in Dia’s peaceful bay
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Luxury Catamaran Cruise, Dia Island –Open Bar & Lunch -Top Rated!

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

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

Set sail from Heraklion with Eos Yachts for about five and a half hours aboard a luxury catamaran. You will spend roughly three hours in Dia’s calm bay, with snorkeling gear, SUPs, fishing equipment, lunch, Cretan snacks, and an open bar included.

“Absolutely amazing and would give 10/5 stars if I could. Wonderful crew, luxury high end catamaran, delicious food.”

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Dia Island Catamaran – Premium Lunch, Open Bar, Small Group - Starting in Heraklion and leaving the harbor
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Dia Island Catamaran – Premium Lunch, Open Bar, Small Group

7.Dia Island Catamaran – Premium Lunch, Open Bar, Small Group

★★★★★★★★★★5.0 · 126 reviews · 6 hours 30 minutes (approx.) · from $181

Leave Heraklion at 9:30 am for a six-and-a-half-hour catamaran trip to Dia Island. With a maximum of 14 people, an English-speaking crew, fresh lunch, open bar, SUPs, snorkeling gear, and onboard Wi-Fi, you spend about four hours swimming and relaxing in a sheltered bay.

“Best boar experience in Crete by far! Friendly crew, amazing service, beautiful water. The vibe and energy are always incredible on this catamaran.”

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From Athens: Saronic Islands Full-Day Cruise with VIP Seats - The Athens pickup and start of the sailing
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From Athens: Saronic Islands Full-Day Cruise with VIP Seats

8.Saronic Islands Full-Day Cruise with VIP Seats

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

Spend a full day sailing from Athens to Hydra, Poros, and Aegina in a VIP cabin with reserved seating, drinks, snacks, lunch, and fast boarding. You will have 90 minutes in Hydra, 50 minutes in Poros, and about two hours in Aegina, with hotel pickup and multilingual staff included.

“The trip was excellent in all areas. Highly recommend paying to go VIP. It made a huge difference to the trip which was a long day. The staff and guides that looked after us where fantastic including the onboard meals (and drinks). The places visited was also great, giving us a different perspective to Greece - a true view beyond Athens (which we also found to be very good) and the usual tourists beeches / locations.”

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Heraklion: Dia Island Luxury Sailing Trip with Meal & Drinks - Dia Island, an offshore stop without a beach landing
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Heraklion: Dia Island Luxury Sailing Trip with Meal & Drinks

9.Dia Island Luxury Sailing Trip with Meal & Drinks

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

Sail from Heraklion to Dia Island aboard TREATON or JACKPOT, with crew such as Cosmos, Joseph, Thanos, or Nikos. Swim, snorkel, paddleboard, fish, and enjoy shrimp pasta, Greek salad, fruit, wine, beer, and soft drinks. Choose a shared, private, sunset, morning, or full-day cruise.

“This tour was the highlight of our holiday. The captain and cabin boy were first rate! Very knowledgeable and entertaining. Their love of the island was evident and they took joy in sharing it with us. We were innitially worried when it said "groups up to 22" however we only had 8 on board. I think the smaller number of fellow passengers made the experience so much better. Many more and it would be too cramped, it would risk spoiing the experience and atmosphere. All the other passengers were lovely too and should also get 5 stars!Read more”

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Athens: Saronic Islands Cruise with VIP Area Seating & Lunch - Hydra: the best stop for atmosphere
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Athens: Saronic Islands Cruise with VIP Area Seating & Lunch

10.Saronic Islands Cruise with VIP Area Seating & Lunch

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

Spend 11 hours sailing from Athens to Hydra, Poros, and Aegina aboard a large cruise ship with VIP-area seating, buffet lunch, drinks, hotel transfers, and island visits. Kostas has been singled out for excellent service, but confirm exactly what your VIP ticket includes before paying $276.

“Marcan 25 min antes de hora enviada por correo, salimos en 2min.Marcamos para avisar que no estaba la van, no nos dieron el punto de salida del muelle, nos colgaron.Acabo ayudandonos el personal del hotel,3a llamada, fueron a otro hotel.Llgamos en uber, corriendo,nadie nos recibió.En marcha comentamos del paquete vip, revisaron y nos cambiaron.En un sofa junto a la unica puerta de acceso,siendo otras parejas ocupaban dos sofas,en areas no transitadas, nos negaron el cambio.Un grupo entro y salio,para supervisar adolecentes en la otra area,desagradable.Avise antes de bajar del incidente de la recogida con 3 personas, quedaron en revisar.Nos llevaron de vuelta a otro hotel,aun que al chofer en...”

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Dia Island Catamaran – Premium Lunch, Open Bar, Small Group - Starting in Heraklion and leaving the harbor
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Dia Island Catamaran – Premium Lunch, Open Bar, Small Group

11.Dia Island Catamaran – Premium Lunch, Open Bar, Small Group

★★★★★★★★★★4.9 · 42 reviews · 6.5 - 8.5 hours · from $176

Spend 6.5 to 8.5 hours sailing from Heraklion to Dia Island aboard DanEri Yachts’ new catamaran. You get shaded lounges, sunbeds, a chef-prepared Cretan lunch, local wine and beer, snorkeling, SUPs, fishing gear, and a small group capped at 15 people.

“It was the beast sailing cruise in my life. Everything was perfect! I enjoyed the food, the sea. Crew was really nice and welcoming! Highly recommend!”

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Private Luxury Sailing Trips to Dia Island - St George Bay: clear water and a quiet anchor
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Private Luxury Sailing Trips to Dia Island

12.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 mate, reaching St George Bay after about an hour. Swim in clear water, try fishing, snorkel, and relax with fruit, soft drinks, bottled water, and white wine. Hotel pickup, lunch, champagne, and cake cost extra.

“Mario the captain made sure our day was fantastic from start to finish. We also arranged our hotel pick up and drop off which made the trip stress free. The snacks, salad and fruit were delicious! This is a must do when visiting Crete! Thank you Mario for making this a very memorable day! Much love from Canada”

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Luxury Boat Trip to Symi Island with Swimming at St. George - Starting at Mandraki Harbor in Rhodes
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Luxury Boat Trip to Symi Island with Swimming at St. George

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

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

Sail from Rhodes to Symi on an eight-hour boat trip with a 1.5-hour swim stop at St. George’s Bay and three hours to explore Symi Town. Choose sun or shade, buy coffee on board, and add hotel transfers if needed. Bring a towel, cash, sun protection, and your own snorkel gear.

“Had a great day today and a very prompt transfer which was great as we was travelling from lindos”

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Athens: VIP Swimming Cruise to three islands - Agistri: the first real swim
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Athens: VIP Swimming Cruise to three islands

14.VIP Swimming Cruise to three islands

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

Join Athens Swimming Cruise for a nine-hour VIP boat day from Athens. Swim at Agistri and Metopi, spend time around Aegina, enjoy a Greek buffet with wine and soft drinks, and return along the Athens Riviera with a DJ and sunset views. Hotel pickup and drop-off are included.

“Jordan was excellent! He was very kind and patient with all guests. He made the trip! Having the option to swim or shop was nice. Overall great experience”

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Kos: Seanomad Private Luxury Yacht Full Day 2 Islands Cruise - Vathi Beach on Pserimos: cliffs, calm water, and a quiet start
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Kos: Seanomad Private Luxury Yacht Full Day 2 Islands Cruise

15.Seanomad Private Luxury Yacht Full Day 2 Islands Cruise

★★★★★★★★★★5.0 · 8 reviews

Join Sea Nomad from Kos Marina for a private seven-hour cruise aboard the 2023 Sea Ray Sundancer 320. Your English-speaking captain takes you to Vathi Beach and Erinies Beach on Pserimos and Plati Island for swimming, snorkeling, drinks, fruit, and Greek-style snacks.

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

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