Skip Santorini...and Other Secrets for the Ultimate Greek Vacation

Our plan was to elope at City Hall, days before jetting off to the Cyclades in Greece - a circular group of over 200 tiny islands in the Aegean sea, characterized by the country's iconic turquoise blue water, white washed buildings and vibrant fuchsia bougainvillea. A place that makes anyone with an mobile phone feel like Ansel Adams.

We had booked this vacation months before we even got engaged - to make up for a cancelled trip to Nicaragua in January, when we found ourselves confronted with a new apartment and two new jobs all at once. Perhaps it was the goddess Clotho herself spinning the threads of our fates, because six months later we were engaged and on our way to one of the most romantic places on earth, full of love birds and honeymooners. 

It’s such a beautiful little corner of the world that it’s hard not to enjoy yourself. But as with any region focused exclusively on tourism, it takes just a few "insider" tips to transform a nice trip into an extraordinary one.

Having traveled to the islands of Naxos, Folegandros and Santorini via Athens, I have six secrets for having the perfect vacation in Greece.

1. Go in the offseason.

The weather in the Cyclades is so perfect that you barely notice it (this is coming from a girl with a minimum of three weather apps on her phone at all times). Wake up and it’s another 80 degree sunny day, with low humidity and a light breeze.

Fortunately, that doesn’t just apply to summer, but also the shoulder months of June and September. We booked our trip for the second week of September - a time when it’s busy enough that restaurants and beaches are still lively, but the crowds don’t feel oppressive as you might expect during peak travel season. 

For instance, our sailboat toured Naxos with just four guests (including us!) - compared with the usual 20 people - affording us a bit of privacy and allowing us to get to know the owner and crew, two Greek brothers who recently returned after years of living in Northern Europe to start their sailing business. Later in the week, we even snagged a cheaper “low season” rate the last two nights at our absolute gem of a hotel - Anemomilos Apartments - in Folegandros.

  A beach all to ourselves in Naxos

A beach all to ourselves in Naxos

2. Know your beach goals.

When I first started my research, I naively assumed our dreams of white sand, crystal-clear waters, and lounge chairs were standard Greek fare. But turns out that the Cyclades have incredibly diverse beaches; and with the right itinerary you can get a little taste of them all. Starting on Naxos, we stayed at the boho chic hotel Naxian on the Beach and enjoyed the island’s classic stretch of full-service - yet surprisingly easy going - seaside living. We then traveled on to Folegandros, an island with barren hills and dramatic cliffs, where any small alcove with pebbly sand and water is deemed a beach. But what these secluded seashores lack in amenities, they more than make up for in charm. Finally, we ended the trip in Santorini - known for its striking red and black sand beaches, which may be appealing to look at, but not so much for swimming. I’d recommend starting with the traditional white sand beaches - to deliver on any instagram-fueled expectations - and then venture to others throughout the course of your trip to experience the full range Greece has to offer.

  Agios Nikolaos Beach in Folegandros

Agios Nikolaos Beach in Folegandros

3. Visit at least one island that doesn’t have an airport.

Navigating the Cyclades takes some careful planning. There are multiple ferry companies and routes, often with only one or two pickups per island each day. This makes it tempting to just hop on a cruise ship and sail from Mykonos to Santorini; or fly into one of the other large islands and plop down for the entire week. If you do, you’ll still have a fine time; but if you can manage to squeeze in one remote island (for us, it was Folegandros), I promise it will be worth the extra effort.

Folegandros is a gracious and intimate island - offering us a much needed respite from our life on the island of Manhattan (a place so bustling that you need to actively avoid engaging with others). At every turn, we saw the same Spanish family of five who would give us a nod hello, along with a glimpse into our imaginary future. And on our last night, we watched a wedding celebration in the town square, lit up by fairy lights in the trees - an affair that had the whole island buzzing for days. And while waiting for the island's single bus to return to the port from the only bus station in the town center (or Chora), we even managed to stumble upon an authentically hipster bar, Dal Capo Del Porto - with great craft beer from the region and an even better playlist.

  Charming streets in the town center of Folegandros

Charming streets in the town center of Folegandros

4. Pack light.

One of the perks of the beach jaunt is that summer clothes fold up real well, which can come in handy for an island hopping adventure, where you’ll have lots of tight ferry and flight connections between islands. I am a self proclaimed over-packer, despite having traveled a ton for both work and fun. But I was determined on this trip to bring only a carry on, and I was thankful I did. Turns out having an airport on your island may seem like a luxury but still poses some risks. Our flight from Santorini to Athens ended up being canceled due to "wind" and we missed our flight back home to NYC (and my fiance’s first day at a new job). Luckily, since I hadn’t checked my bag, we were able to quickly make our way over to the ferry station, where we jumped on the first boat back to Athens. Even with my small carry on, though, I still brought far too much stuff. Most of our days were spent sailing or swimming, so ditch your dressy duds and pack that extra bikini instead.

  All you really need is your bikini

All you really need is your bikini

5. Fit in a little history.

Although we both love art, culture, books, history...for this trip, we just wanted to fulfill our basic need of sun and sand. And we did. But believe it or not, there comes a day when your brain craves a step up on the hierarchy of vacation needs - when another day of sun worshiping, with the latest multiverse thriller and a glass of Santorini white wine just doesn’t cut it. That was us on the sixth day. As our ferry approached the port of Santorini, we started reading up on the island’s ancient archaeological site, Akrotiri, which some even believe to be the inspiration behind the lost city of Atlantis myth - and made that our first stop after checking in at the hotel. While the site doesn’t have much context or signage due to funding issues, it still gave us some much needed mental stimulation. Plus, in general, Greece is not lacking in ancient ruins that make you ponder your place in the world and history - so don’t miss them, even if it's just an for an hour. 

  Greek church in the Cyclades

Greek church in the Cyclades

6. Skip Santorini.

If you google “Santorini - most beautiful place on earth,” nearly 500,000 search results appear. But as the great artists tell us time and again, beauty is relative. We saved Santorini for last, mainly because we wanted to start with some white sand and end with an easy connection back to Athens. So after seven glorious days of easy Greek living - sailing around Naxos on a catamaran; watching the sunset from our private balcony in Folegandros - Santorini just felt like more of the same. But more crowded, more expensive and harder to navigate (pro tip: when people suggest renting a car or ATV, rather than relying on taxis, trust them!).

Most of the hotels and restaurants are clustered along the western coast in the villages of Oia and Fira which offer prime sunset viewing - their narrow whitewashed trails bursting with cruise-ship clans searching for that postcard money shot and honeymooners ready to splurge on a trip of a lifetime. At nearly a thousand dollars a night, we couldn’t justify the price of staying in a luxury hotel in Oia and decided to stay at a boutique spot on the other coast for a fraction of the cost. The concierge did his best to get us excited about the rising moon as opposed to the setting sun, like a man on Canal street peddling off-brand Gucci bags. “It’s like nothing you’ve ever seen,” he told us. “Trust me.”

We did. And while the vibrant moon was certainly special to watch, it wasn't the iconic Santorini sunset we were expecting. The next day, determined to catch a glimpse before heading home, we took another catamaran sailing tour that guaranteed us a front-row seat. Of course, we had a blast, as one tends to do on a fancy sailboat excursion in Greece, but it still felt different than our sailing tour around Naxos: shorter, less personal and once again, more expensive. And when it came time for the show to begin, a huge cloud rolled in - the sky and weather Gods once again asserting their authority over us mortals.

Thankfully, Folegandros and Naxos gave us enough memories to face a lifetime of obscured sunsets - and the best un-honeymoon two nearly newlyweds could ask for.    

  Our sunset in Folegandros from our hotel terrace

Our sunset in Folegandros from our hotel terrace