At the very best of times, planning a trip can be daunting. Island hopping however, is a whole other matter – ferry planning, flight coordination, hotels, how long to spend and where – a million questions that need to be answered… but it’s worth it.
Easily one of the best weeks I’ve spent in Europe was island hopping through the Greek Cyclades – a classic trip covering Santorini, Mykonos, and a hidden gem – Milos (full guide to Milos here).
With 8 days and 7 nights at our disposal, we decided to start in Santorini with some ultra-luxe R&R, exploring the classic streets of Oia and the amazing offerings of Fira, Imerovigli, and Ammoudi. Stop two was Mykonos, arriving relaxed enough to enjoy the buzzing nightlife this island is famed for. And finally, we made our way to Milos, a beautiful island at the southern end of the Cyclades justifiably renowned for Greece’s best beaches and turquoise waters that take your breath away.
Santorini – 2-3 days
Santorini makes a lovely escape into the surreal, with the Caldera at your feet and unbelievable views regardless of where on the island you’re based. While there aren’t any accessible beaches, the hikes between the towns like that from Fira to Oia via Imerovigli is lovely, and the views off the cliff are spectacular.
Spend a couple of days here to soak in the sun and explore the beautiful towns. Shoulder season is usually the best time to visit to avoid the massive crowds from tourists and cruise ships in the harbour. Spend a few days exploring Oia, getting lost in the picture perfect town, before taking a cruise to Nea Kameani from Fira’s old port and seeing the sunset from the sea with the light reflecting off Oia at golden hour. Catch a meal at Kamari Village for some of the best local cuisine on the island at very affordable prices.
Mykonos – 2-3 days
The ‘Ibiza of Europe,’ infamous for its celebrity visitors and 1930s claim to fame, this beautiful island does not disappoint. About a 2-3 hour ferry crossing from Santorini (with stops along the way at Ios and Naxos that you should absolutely stop to explore if you have the time) it is incredibly easy to hop over in the morning, well in time for when the island really buzzes to life post-4pm.
To make the most of Mykonos you need about 2-3 days here. In contrast however, to get the best feel of the place, a visit during the peak months of June-September are your best bet to catch the crowds and witness the atmosphere this island is known for. Catch all the landmarks of the island during the day, and spend the evenings dancing on the beach or at one of the many bars in the town, after local Greek taverna food at its many popular restaurants. PS – there are only 31 taxis on the entire island so for the most flexibility, rent a car or a quad bike to get yourselves around!
For the full Mykonos guide, click here.
Milos – 4-7 days
And finally, rest yourself and get some much-needed post-Mykonos down time in this beautiful island in the south. Surprisingly unknown, Milos has the best beaches in the country, and each day is a lovely new surprise. It is easiest to get here from Santorini (a 2 hour ferry) but if you’re traveling between June and September you’ll get a direct ferry from Mykonos – but be sure to double check!
You want to spend at least 4 days in Milos, 7 if you have the time to extend your trip. With over 70 beaches, in 4 days you might barely scratch the surface. This special island is home to the best food, most beautiful beaches, and wonderful Aegean hospitality. Check out my Milos guide here for the full scoop on how to spend your time.
So there you have it, an island-hopping itinerary laid out for you. Flying from almost anywhere in the world to Santorini or Mykonos is easy enough, and on the rarer occasion might include a stopover in Athens. My best recommendation would be to aim for a multi-city flight plan so you don’t waste any time on your last day attempting to ferry back to your starting point and can really make the most of all your time on the islands. Mykonos and Milos are best traversed by car, with almost minimal public transportation, while Santorini has a fantastic public bus service that serves all the villages. Reservations at restaurants in Santorini and Mykonos, especially during the busier months, are a must and your hotel will most definitely be able to help you with those.
And probably the most important… stay flexible! Ferry services can be unpredictable so you always need to double check, but remember, island hopping done right is all about impulsive decisions and not sticking to your plans, so enjoy it!