3 Days* in the GREEK ISLANDS


Greece’s archipelago (the word is actually derived from the ancient Greek name for the Aegean Sea) is made up of a staggering 6,000 individual islands, depending on your size categorization. Of these, as many as 227 are inhabited. From Crete to Rhodes, Mykonos to Corfu, the options are many and varied. Three days is barely enough time to scratch the surface, but scratch it we did – and here’s what we discovered:

Poolside in the Greek Islands, Greece - 3 Days*

Poolside in the Greek Islands, Greece - 3 Days*

Day 1* in the Greek Islands

Arrive in Paros late morning. The Blue Star Ferry from Athens takes about four hours and is a pleasant activity in itself. Find a comfortable seat on the outdoor deck near the stern and you can watch the white washed isles pass by, latte-in-hand.

Paros has a bit of everything you want from a Greek island: stunning beaches, a hip but sparse crowd, stylish, cheap accommodation and a splash of nightlife. We stayed at Saint Andrea Resort just outside Naousa, which I really can’t recommend enough. The minimal décor achieves a kind of Hamptons-in-Greece aesthetic, and the pool/ restaurant area is laid across a generous patio overlooking the bay. Not a bad place to plop yourself down in an oversized bean bag for some vitamin D and a glass of local white wine. When hunger pangs, shuffle over to a nearby table for a wrap or salad.  

Alternatively you can jump in a taxi and head over to the little beach down the road (Nikos, the affable - and handsome - hotel manager will organize transportation for you). Sunset is actually a wonderful time to splash around in the turquoise water. The crowds have departed and you can easily find a smooth boulder perch from which to watch the fading light dance across the waves.

Greek Islands, Greece - 3 Days*

Greek Islands, Greece - 3 Days*

Head to the town of Naousa for the evening. Quaint and stylish, you can spend hours wandering the narrow, car-free streets, popping into boutiques and galleries, stopping in seaside cafes for an aperitif; you know, exactly what you imagined you’d be doing on a Greek Island junket.

For dinner, try Yemeni Taverna, a fantastic little eatery on a cobblestoned street in old town. The cuisine is local and fresh. I highly recommend the Saganaki (fried cheese, basically) octopus with lemon and garlic and a big goblet of local red wine. 

Day 2* in the Greek Islands

Rise early, overindulge in Saint Andrea’s tremendous complimentary breakfast, rent a car and head to Antiparos. Antiparos is like Paros’s cool little sister, and a morning of motorized exploration will turn up a number of idyllic, deserted beaches. Pick one that suits your mood, pitch your umbrella and unleash your inner Bond girl; incidentally, Antiparos is a good place for topless sunbathing, if that’s your thing.

Boat Trails Ocean, Greek Islands Greece - 3 Days*

Boat Trails Ocean, Greek Islands Greece - 3 Days*

At this point no one would blame you for ditching the 3Day itinerary, quitting your job and moving to Antiparos for the rest of the year. If, however, you manage to tear yourself away:

Sunset on Santorini, Greek Islands Greece - 3 Days*

Sunset on Santorini, Greek Islands Greece - 3 Days*

Catch the afternoon ferry to Santorini. Fair warning: Santorini is crowded. And we’re talking crowds of the cruise ship/ tour bus variety. This is definitely a drawback. But! It’s also one of the most unbelievably beautiful places in the Mediterranean, maybe the world.

This dichotomy makes your choice of accommodation crucial. Through Airbnb, we were lucky enough to find an adorable cave house tucked into the spectacular Caldera cliffs in Oia. The winding pedestrian walks are arranged so the private patio feels totally isolated, the throngs of tourists a distant memory. Maria, the contact, also manages a number of similar properties.

After your journey, I recommend setting yourself up on said patio and tucking in to some spanakopita, cheese and honey from the local market.

Here you can watch the moon rise over the volcano across the bay. If you happen to be there during a full moon cycle, this can be an other-worldly experience. 

Day 3* in the Greek Islands

Fishing village, Amoudi Bay Greek Islands Greece - 3 Days*

Fishing village, Amoudi Bay Greek Islands Greece - 3 Days*

There are a number of worthwhile beaches on Santorini, if you’re okay with crowds. The red beach is especially stunning. But, if you’re not up for renting a car, there’s a lovely and somewhat undercover swimming spot near Amoudi Bay (just below the caldera cliffs) that I highly recommend. To get there, walk down the 300 steps from Oia to Amoudi. You’ll pass by a tiny fishing village and a cluster of upscale restaurants teetering over the sea. Follow the dirt path (wear appropriate footwear) until you see a rocky lump of island just off the coast. From there you can scout out a comfortable rock and spread yourself out. There are many safe places from which to plunge into the cool green water and float out to the rock island.

Fortify yourself for the walk back up to Oia at one of the seafood restaurants in Amoudi. They’re all pretty comparable, each serving the catch of the day on white tablecloths with overpriced wine. We had good luck at Sunset Restaurant with the lobster and octopus, both super fresh and cooked over an open fire in front of us.

After bathing and a siesta, it’s time to check out Oia’s high-end, eclectic shopping scene. The main drag, Nikolaou Nomikou, is packed with interesting galleries and boutiques for every budget. Turkish towels and sandals are easy wins, as are flowy frocks that travel well and will give you caftan bragging rights for years to come. Atlantis Books (http://atlantisbooks.org) also has a great expat collection if you’ve run out of reading material.

Wine and Food, Santorini Greek Islands, Greece - 3 Days*

Wine and Food, Santorini Greek Islands, Greece - 3 Days*

Sunset is a big deal on Santorini. And by big I mean literally thousands of selfie-stick-wielding tourists packing themselves into the narrow streets on the western cliffs on the edge of town, straining to catch a glimpse of the sun dipping directly into the sea, as it does there. Sure, it’s a beautiful sight. But the experience is 100% ruined by the Beatles-mania-style crowding. And, frankly, if you’ve seen a sunset in California or Portugal or the Caribbean or basically anywhere that faces west over the sea – it’s not going to change your life. Instead, take in magic hour at one of Oia’s spectacularly placed restaurants.

Pelekanos has sweeping views of the Caldera and the Mediterranean cuisine is fresh and approachable. We had a deep bowl of spaghetti with seasonal vegetables, dripping with local olive oil and crumbly fresh cheese… It was delicious and more effective than 2 Ambien and a bottle of whiskey.

Sweet dreams, weary traveler. 




  • Caftans
  • Sandals
  • Wine


  • Lightly in a backpack or easily managed bag, the ferry stairs and cobblestoned Oia streets are not kind to rolling suitcases.
  • Wide angle or panoramic lens
  • Turkish towels