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YOLO Cruises - Mykonos to Santorini

Spend a week with Sail in Greece island hopping around the most spectacular islands in Europe discovering tiny islands and secluded bays hidden in the turquoise blue of Aegean sea.


Day 1 - Mykonos

Arrival day. Meet your group at 13:00 for a welcome meeting and enjoy your Greek lunch on board while you are getting to know each other. Your boat will stay overnight in Mykonos and in the afternoon will explore the old town. Walk around the famous sugar-cube houses, feel part of little venice, explore picturesque allies and say hi to the famous Pelican (mascot of the island). At night you will see why Mykonos is worldwide famous for its night!

Day 2 - Mykonos to Paros

Enjoy breakfast with friends on the vintage 30ft wooden ship and if needed take a refreshing dive or a brave jump of the boat when docked in the crystal waters of Mykonos to wake up from the last night’s hangover! We depart at 10:00 and arrive in Paros at 11:30. Walk around Paroikia town or relax in white sandy beaches. Paros is famous for its water sports and especially wind surfing but also for its crazy night life! The island catches the warm winds and breezes of the sea, so if you fancy some adventure water sports this is the place to do so.
Optional activity: This is “Greek night” !
Optional activity: Quad Safari

Day 3 Paros to Naxos

We will leave the island at 9:00 and sail to the enchanting island of Naxos famous for the locally produced liquer, called “Kitro”. Once you arrive the guide will take you to the old traditional white blue-doored houses of the old town. Once you have truly been lost in the little tiny streets of rock houses and terraces looking over the sea you will visit the castle of Kastra. Then to the beach before catching the best sunset in Naxos at the ancient portara which is a monument situated on a rocky island away from the rest of the island. Hidden gem: The best beach of the island our Greek “Hawaii”! Optional tour: Go Naxos! (Hiking tour)

Day 4 - Naxos to Koufonisia and final stop....IOS

Wave good bye to Naxos at 9:00 and arrive at Koufonisia around 11:00, the smallest of the Cyclades islands. An unknown island too many, the reason it still keeps its authenticity. Experience the best natural beaches of the Cyclades and feel the sense of calmness and peace. No bars, no clubs and maybe …no people! Just you and the sea! Enough quietness..? There we will set our party! Barbeque in a secluded beach, loud music and lots of alcohol will be parts of our private party! Later in the afternoon we will sail for the famous “party animal” island.….IOS. After passing through Heraklia and Schinousa, 2 “lost” islands in the Mediterranean sea, we arrive at Ios. Get ready for the real bar hoping!
Optional tour: relax on the beach!

Day 5 - Ios

Second day in Ios will start ( we guess..) at around 12:00, after Ios hangover. Get ready and will take you straight to the hottest beach on the island, Mylopotas, full of young people, refreshing cocktails and hot sand. Brave enough to join the water sports? Peter will by our host there! For those that want to meet the “Pirates of the Caribean” in Greece we have our famous pirate booze cruise! At night experience the famous night life of Ios with our bar crawl and get drunk with free shots and refreshing cocktails!
Optional activity: Pirate booze cruise

Day 6 - Ios to Santorini

We depart from Ios at around 10:00 and after sailing around 11:30 Santorini will arise for our eyes only! We will take a 15 min walk up the steep donkey path to the old town of Chora, called Thira. Thira is the central town, full of boutiques, markets, taverna’s and coffee shops. This worldwide famous destination, honeymoon dream for couples around the world, reveals its secrets us our tour leader will show you the hidden gems of the island. On the day a bus tour is available, that will get you around the island and at night we will dine at Caldera’s cliffs overlooking the volcano and watch Santorini sunset, maybe the most coveted sunset in the world! On our night everyone has a farewell party and heads into the famous clubs of Santorini. The night is ours!
Optional activities: Bus tour in Santorini

Day 7 - Around the Island of Santorini

Wake up from the smell of your Greek homemade breakfast and you will be dazzled by the breathtaking view of Thira. It’s time to explore the volcano as we will climb to the top, take a quick look of Santorini’s sister ‘’Thirasia’’ and after head for a refreshing swim to the hot springs of the island. Later in the afternoon watch exclusively from your private deck Oia’s worldwide famous sunset while sipping your cocktail on board. On our last night join our bar hopping led by your tour leader to the best bars of the island.

Day 8 - Departure Day

Have your breakfast, relax on the boat and say goodbye to your new friends. All the best stories have always an ending… Maybe next year?

YOLO cruises Greece's #1 PARTY CRUISES!. 

Spend a week with Sail in Greece island hopping around the most spectacular islands in Europe discovering tiny islands and secluded bays hidden in the turquoise blue of Aegean sea. Travelling with around 25 like-minded travellers aboard traditional Greek motor yachts ( called "Kaikia") we experience the true culture of the islands and people. Swim every day in a different bay, walk every evening in a dazzling town, experience every day another island and party hard as the sun goes down.

You will be island hopping on the world famous Cyclades, ie Mykonos, Santorini, Ios, Paros, Koufonisia, with travelers sharing the same passion like you. Join us to see spectacular sunsets, deep into crystal clear Mediterranean waters, explore the famous islands of Greece and enjoy every single night-out with a drink in your hands and local Philoxenia around you! That’s not enough?Exclusive parties at the pop-star Mykonos where everything is possible, breathtaking sunsets at Santorini, the black purl of Aegean sea, adventurous water sports and even donkey rides are here to make the BEST of your trip! Our ships offer double and triple cabins all en-suite, fully air-conditioned and wi-fi on board. While shipping on the day, you will experience what many people believe to be the best cuisine in the world and see on your own what Greek hospitality is about.

Itinerary Notes

The itinerary may need to change due to inclement weather conditions or difficulties at docking. This decision will be made solely at your captain’s discretion, based on the safety of the group and the ship.
Departure Day: Saturdays (May – Sep)
Departure Time: 13:00
Finish Time: 10:00 the following Saturday
Note it is possible to finish on Friday evening as the boats will dock in Santorini around 15:00

What's Included

World famous clubs and wild parties (Mykonos)
Memorable adventures
7 nights accommodation on board
Breakfast and Lunch included
Traditional vintage cruise ships
Experienced local tour leader
Free Wi-Fi
Free shots of OUZO on board!



Beth Kemp

YOLO cruise was great. Excellent people, epic nights, unlimited sunshine! GO back 100 %!

Sarah from Australia

We booked the YOLO cruise and it was the best experience ever. Amazing places, friendly crew and our rep had the best advices ever. Food was delicious and the parties at night unforgettable. I will highly recommend it to everyone.

David from New Zealand

We were thinking of booking the usual island hopping tours, but we are glad we DIDN’T! We had our own boat, no packing/unpacking, great service all the way, stop at secluded beaches, and amazing rep! Do not miss it!

Caitlin from Canada

It was an unexpected experience. Something different into my life with the islands of Mykonos and Santorini pleased as unique memories of nightlife. The sea of Aegean and the sights of Greek islands travel me and my company to another world. Everything was simply perfect!

Laura from UK

We were on Athens and had 1 day to kill. We booked the Booze cruise in order to fill our free day in Athens. The best BOOZE cruise ever! Free drinks, crazy travellers, barbeque on the beach and amazing beaches on the way! Highly recommended!

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