This summer we sailed through the Cyclades islands of Greece. We hired a boat with a friendly captain, Martin, and a warm hostess, Roxanne, through Yacht Getaways. Our immaculate and well-maintained four-bedroom, four-bath catamaran (plus staff quarters) was the ultimate way to summer. In fact, we can’t imagine ever vacationing during the summer than on the sea. A typical day began with a tasty prepared breakfast, followed by a sail to a secluded area to swim, snorkel, and SUP in the most aqua of waters. A bountiful lunch served with wine awaited our return to the boat and then commenced a spectacular sail to the next island on the itinerary. On each island, we had plenty of time to explore, shop, eat, and embrace the vibe of the Chora (town). We all slept better than we had in months being soothed to sleep by the subtle movements of the bay knowing that the next day would bring us another wonderful adventure at sea. The worst part of the trip was knowing that it would come to an end.
Day One Paros and Sail to Naoussa:
We were due to meet our boat at 4:00 p.m. at the dock in Paros. We purposefully took an early ferry on Blue Star Ferries from Athens to have plenty of time to explore Paros before our late afternoon embarkment.
Finding a taxi in Paros when the ferry docked was almost impossible. We went to a couple of car rental places and they were all sold out (so make sure to book ahead!). Luckily, we met Vasli, a charming, chipper, and overly energetic local who drove us to where we were headed, and by the end of our trip became our personal driver and new friend in Paros. His company name is Diego (named after his beloved dog who passed away). His phone number is 0030-6944580232. Call him when you find yourself on the island. Unexpectedly, he became a special part of our trip.
First on our agenda was lunch at Tsitsanis Restaurant, all the way up the mountain. Out of our almost two weeks in Greece, this was the most authentic Greek dining experience we had. Nestled in the middle of a tiny square, with older locals sitting on the patio smoking their cigarettes, this lesser-known restaurant serves incredibly delicious food at really inexpensive prices.
To walk off the loads of food we ingested, we decided to take the two-mile historic Byzantine Trail to the colorful town of Lefkes. In retrospect, this may have been ambitious, especially in the sweltering heat. However, if you are more prepared than we were (i.e. don’t wear flip-flops and bring along more water than you think you’ll need), you won’t regret the trek. It takes you through the delightful countryside with lovely landscapes.
After meeting our skipper and captain who settled us into our cabins, we sipped on local wine as we sailed to Naoussa, a vibrant, popular island with endless alleys and coastline eateries.
We had a decent dinner by the marina at Notos Aegean Restaurant which serves typical Greek cuisine in a pretty setting with unforgettable sunset views.
After dinner, we strolled some more in the Chora, and when our kids got tired, we dropped them off on the catamaran – another bonus to chartering a boat: free babysitting! We grabbed some cocktails and then headed to our heavenly quarters for a night of peaceful slumber on Monastiri Bay.
Day Two, Sail to Naxos:
Waking up each morning felt like a dream. This is an example of a typical view that will greet you each day…
followed by a delectable breakfast and a leisurely sail to the next destination…
One of the perks of being on a boat is that you can explore areas that very few people can access. And these places are extraordinary. Our newly trained daughter anchored us in Filizi Bay where we SUP’d endlessly and snorkeled through the crystal clear waters.
After a swim in Paradise, and a relaxed lunch, we headed to the island of Naxos with the wind in our hair, sunkissed and happy, nodding off under the bluest of skies.
The Portara, or city gate, is a famous site on the island. We decided to skip the hike to it and take a picture of the landmark from afar (see bottom left photo). Instead, we walked into the heart of the Chora to get lost in its alleyways and soak in the views as we ascended toward the top of the mountain. There is also a Castle on the island which was fun to walk through.
All that walking made us hungry early so we stopped at Meltemi for appetizers. The owner is so jovial and welcoming, especially happy to see customers during off-peak hours. We ordered more versions of croquettes than we could count and left feeling victorious for finding this gem.
The day was getting hotter and the kids needed a reprieve on the boat while we needed one with cold cocktails. Drinks at Honey & Cinnamon Cocktail Bar were perfectly crafted and presented beautifully in their boho-chic, well-shaded patio.
When I think of our dinner at Flamingo, I’m inclined to shout “Opa!”. Plate breaking, and dancing to the live music come along with epic views and an overly fun dinner.
Day Three, Sail to Koufonisia:
After another terrific night’s sleep and another glorious breakfast, we headed to Rhina Cave Bay for cave explorations and cliff jumps. We spent hours discovering other sides of the island and little nooks with the clearest waters. Heaven.
Friends ask me all the time which island was my favorite and Koufonisia wins the prize. It isn’t the largest or the most visited, which contributes to its winning factors. Yet it has the most striking waters and coastlines of any island I’ve been to.
Upon docking, we took the local water taxi to Pori Beach, on the other end of the island. The scenery at Pori took our breath away.
After a swim in one of the most memorable beaches we walked along the 3.5-mile coastal trail stopping along the way for quick dips in crystal waters and magnificent views. The most adventurous part of the trail was a plunge in Devil’s Eye (middle picture below). While three of us decided to slowly crawl in, the two daredevils in our group chose to jump into the naturally made pool formed by rocks.
This is an untouched, pristine trail that will lead you to an infinite number of grand beaches (make sure to have plenty of water with you as there are no vendors selling water along the way). As we entered Paralia Italida Beach, we walked through a nude beach, heads up to those who may be uncomfortable! On the other end of the sand is an area for those who prefer to be clothed while swimming in an unreal landscape.
The Chora of Koufonisia is charming, unpretentious, and full of color. I adore this little town.
Following our stroll we found ourselves back by the water and stopped for pre-dinner drinks at Bar Sorokos . They’re known to have one of the best views of the sunset on the island.
Mikres Cyclades is an upscale, fine-dining restaurant that requires reservations. It was packed with well-dressed patrons ready to have a meal that strays from the traditional Greek menu. We loved every bite.
Day Four, Sail to Schouinoussa (pronounced ski-know-oosa):
I was hoping to get stranded on Leonidas Bay. Being with just my family, in the middle of
nowhere, in a surreal setting with an arresting beauty that was hard to comprehend, I never wanted to leave. We spent hours here paddling, snorkeling, running the white sand through our hands, and counting our lucky stars.
Schouinoussa is a very small island and the Chora has very few cafes and shops compared to the other islands. We were surprised to learn that the bars stay open until 3:00 a.m.
Cafe Stou Peri is a cute spot to enjoy a glass of afternoon wine and hide from the sun for a while.
We were skeptical to eat at Deli Restaurant and Cafe Bar because their reviews aren’t that great but our skipper insisted we dine here (another big plus for having a skipper – they make excellent suggestions!). Not only was the ambiance phenomenal, but we also enjoyed one of our best meals on the trip here.
Myrsini Bay was our home for the night.
Day Five, Sail to Ios:
It was quite the change coming from a teeny island to a rather massive one. Ios is huge with lots to see and do. I suggest you rent a car for the day, which only costs sixty euros for 24 hours, from Road Runner Rentals, and includes parking spots throughout the island.
Yes, Homer who wrote The Iliad and The Odyssey was buried in the northernmost part of Ios. The drive to get there is picturesque with breathtaking views and high climbs. Once on-site, you’ll need to walk approximately 1,000 feet to get to his tomb which overlooks the vast, blue seas.
From Homer’s Tomb, you’ll continue along on roads with unbelievable vistas; part of the climb felt a little treacherous but certainly added to the excitement. After a twenty-five-minute drive, you’ll arrive at the family-owned cheese factory and be greeted in their well-shaded outdoor patio. A lovely selection of honey and cheeses are displayed in pretty pottery and wooden boards. A staff member will walk you through the tasting, which is also served with homemade wine. Advance reservations are required.
Lunch at Salt Restaurant
Salt is on the complete other side of the island and is worth the effort. The food was fantastic, the drive was enjoyable, and swimming in the calm, clear waters of Salt Bay was serene. We especially enjoyed the upscale, yet casual, atmosphere and well-balanced, creative cocktails. This one is a must. Make sure to make a reservation.
Post-lunch swim at Salt Bay
After all the sightseeing, eating, and swimming we took a drive to the Chora, one of the biggest towns out of all the islands we have visited. Like most of the islands on our itinerary, the Chora in Ios pops with color, full of windy alleys that are lined with cafes and stores, and lots of people meandering around.
This nightclub also serves as a day club with a DJ booth, an infinity pool, and an outrageous seascape. We made 7:00 p.m. reservations at a VIP table to watch the sunset, as Pathos is known to have the best sunset views on the island. The crowd, scene, and DJ were so enticing, that we decided to cancel our dinner reservations and spend the night dancing to the beats that blended with the breeze. As the sun was setting, an homage, like no other, proceeded with blaring opera music and a fire show once it got lost in the horizon.
Day Six, Sail to Antiparos:
After breakfast, we sailed to the Blue Lagoon (its official name is Turquoise Bay). Words nor photos can describe this magical place. We stayed in the wondrous waters for as long as we could, in awe of the natural beauty around us.
After quite some time in the Blue Lagoon, followed by another mouthwatering lunch whipped up by Roxanne, we docked in Antiparos – a glamorous, glitzy, miniature island. Tom Hanks and Rita Wilson own a summer home here and are said to visit frequently. I can see why. Although it is very small, the island is very ritzy with luxury retail shops and extremely well-dressed visitors. As they say, “good things come in small packages”
Dinner at Kalokeri was enjoyed on their pretty patio, with great people-watching access. The food we ordered was exceptionally good; the menu is an upscale version of traditional Greek food. Gosh, we ate well in Greece.
Day Seven, Sail Back to Paros:
On our last morning, we sadly packed our suitcases after breakfast, reminisced with Martin and Roxanne about our journey, and lazily lounged in the front of the boat grasping onto every last moment before we had to debark.
Throughout our trip, the meals prepared for us were fresh and favorable, and the staff taught the kids how to tie knots, drive the boat, and even anchor it. They also made great restaurant reservations, and as I mentioned earlier, happily watched the kids each night so that my husband and I could enjoy some alone time together. I honestly can’t imagine a better way to spend my summer than to sail through the seas.
Once we arrived in Paros, we spent two more nights on the island at The Summer Senses Luxury Resort. Remember our friend Vasli? He was there to pick us up and drive us around the island whenever we needed him. What a guy!
The dotting staff, gorgeous grounds, impeccable rooms, access to a scene-y beach club, an expansive breakfast buffet displayed so proudly with elegance, and its great location, make staying at this resort a no-brainer. This was the perfect place to gently push us toward the reality that our summer vacation was ending.
One of the property’s best aspects is Galazia Hytra, a sister restaurant to the
Michelin- star Hytra in Athens. Eating here was one of the highlights of our entire trip and the perfect ending to a perfect summer vacation.