Sailing in the Cyclades
Greece is a special place. The birthplace of western civilization no less. Every part of the country is beautiful and fascinating. The Cyclades Islands are justifiably famous as they offer some of the most spectacular deep blue Mediterranean water, dramatic landscapes, sublime beaches, and beautiful sun-kissed villages dotting the sea coast of anywhere in the world. There are four other island chains in Greece to see (to say nothing of the mainland), but the 24 inhabited islands of the Cyclades in the Aegean Sea require their own guide.
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I'll get some of the superlatives out of the way early, but it's difficult to keep them from slipping into every sentence. The islands are truly "magical" and each little village, tucked away cove, or cliff hugging cafe is a "gem." But if I keep repeating that with every description, it may start to water down the truth of it.
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Everyone has their favorite islands. There is the jaw dropping visual scenery of Thera (Santorini) that backdrop "pre-wedding" photos every day along with billions of instagram posts. There are the chic night clubs of Mykonos favored by ravers and bachelorette parties flying in from all over the world. Some of the other islands feel practically undiscovered by comparison, though every available room is booked solid from mid-June to the end of August. Yet, on these somewhat lesser-know islands, you can still find a reasonably unspoiled Greece, or at least what that looks like to me. Better still if you travel in the shoulder season of May (and maybe in September), you can still breeze through them with total spontaneity, living the good life for a fraction of what a comparable experience might cost in most parts of the world (certainly the U.S.).
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If you can, travel in May. The weather is great, but not too hot yet. Many, if not most, of the hotels and restaurants are open for the season. But there is still a degree of quiet and solitude possible that make it all the more enjoyable. July and August are hot, crowded and expensive. You will need to book far in advance for most islands and even the ferries between them. And you will pay vastly more for the same hotels as earlier. June is somewhat in between these points.
Island Hopping
Start somewhere such as Thera, Mykonos or Athens (all places you can fly to) and then utilize the wonderful ferry system to go island to island as spontaneously as possible. Make decisions about when and where to go next a day or two before. This may be an unfamiliar way to travel but it's possible and wonderful (if you travel a little off season). If you are enjoying an island, stay longer. If your curiosity about the next island gets the best of you after a conversation with someone at a cafe the night before, then book a ferry on Ferry Hopper, book a room on Booking.com and go. Use Ferry Hopper to figure out routes that makes sense. You can't connect every island with every other, so doing a little looking ahead isn't a bad idea, but in general if you have a few weeks, you can just go with your own flow – something modern life almost never affords us a chance to do. If summer is your only option to visit, then you can still Island Hop, but just plan the whole trip out ahead of time, booking your rooms and ferry reservations well in advance.
Thera (Santorini)
It has to be seen to be believed. For all the photos you've seen online, the actual experience takes your breath away, over and over. And far from being spoiled, it retains a wonderful charm and authenticity despite 2 million tourists per year. It is even still affordable if you don't go high season and are willing to sleep without a front row seat to the caldera (though if going for your honeymoon, by all means splurge for the view with infinity pool). Dining out, with a world-class view from your table will cost you less than a mediocre meal in Manhattan. Walk down to the old port and have a drink. Hike the 6 mile donkey path to Oia and have another. You've earned it.
Eating & Drinking
As with many Mediterranean countries, Greece takes the cafe life seriously. Every port and village is full of cafes, restaurants, bars and tavernas with tables perched on balconies, quays and charming walking streets, to maximize the beauty and enjoyment of the moment.
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And somehow, despite the scenery it doesn't cost that much (though this does vary from island to island). We have amazing meals with drinks, wine, and dessert and still manage to spend much less than a basic pub meal that offers only flat screens for scenery back home. We rarely eat out at home or when camping in Stanley. We eat out every meal in Greece.
Naxos & Paros
These are the largest islands in the chain and next door neighbors. Many people just visit one or the other but they are really quite different from one another.
Naxos is full of beaches and interesting villages to explore. Or you can just stay in the port of Chora and walk to everything it has to offer including a lovely beach, a castle, an ancient Greek Temple of Apollo. If you want to see more of the island, there are many villages that can be reached by car. We rented a car for 24 Euro for the day. Much less than a tour bus and way more fun to drive. We particularly enjoyed the Aperathos high in the hills for its historic charm. For hotels, try the area in Chora right next to Agios Georgia's (St. George) beach. It's an easy 5 minute walk from the ferry.
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Paros has much more of a Mykynos vibe than Naxos. It's way more chic, has lots of expensive boutiques, and it draws a younger and more glamorous tourist. Lots of yachts. It also costs more than most other islands. But if you like upscale, Paros, Mykonos and Thera are good bets.
Naxos
Paros
Koufinisia
Small Cyclades
Koufinisia & Amorgos
These were probably our favorite islands. They are less populated and quieter. There are fewer cars. Both are exceptionally beautiful.
Koufinisia is so small it has only a single taxi cab and you can easily walk the entire island
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Amorgos is larger, and even has 2 ferry ports, both of which are lovely and worth several days. We sailed into one, took a bus to the other, and sailed away from that one. Amorgos is the most mountainous in the chain and offers excellent hiking as well along with the very impressive Panagia Hozoviotissa Monastery.
Milos, Sifnos, Serifnos
We had planned to hit all three of these islands. But in the end, we got to Sifnos and stayed 12 nights instead. It was our favorite of all the islands we visited. It has a really nice blend of things: there are great villages both in the middle of the island and on incredible beaches to stay in. We stayed in 3 different villages. It's laid back but still has great night life. The hiking is probably the best in all the Cyclades. It's fairly small and easy to get from place to place by car or bus. There are 365 churches and monasteries on the island, all located in remarkable settings.
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Milos and Serifnos are right next door (easily visible from several great hikes) and have great reps as well. We will definitely visit them the next time around.
Sifnos
(Kamares port from Agios Symeon monastery)
Cats of the Cyclades
Aegean Cats are a breed unique to this part of the world and they are everywhere in the islands. They are mostly strays and hardy survivors. Few of them don't sport at least a few scars from battles won or lost. They have been here a long time. There is a burial site on Cyprus where a man was interned with a beloved cat, 9500 years ago.
If you are unnerved by cats (my friend Feigs believes them to be messengers of the Devil) you might find dining a bit uncomfortable as there might be 2 or 3 of them patiently sitting next to you at dinner with a hopeful expression on their faces. But if you're a cat person, you will enjoy finding them having a siesta in just about every possible place you go. Several have adopted us as soon as we move into a hotel room. They respectfully stay outside, but just become our pets for the length of our stay by lounging on our veranda with us expecting only company in return.