The Ultimate Itinerary For The Best Greece Trip

Just because our physical bodies may need to stay put and shelter in place for the time being, it doesn’t mean our souls can’t still do some dream-traveling.

I have had to cancel two amazing trips that I have been planning for the greater part of a year, because of the coronavirus. And while it has dampened my spirit a bit, if definitely hasn’t extinguished the travel-spark in me. For those of us who feel the incessant need to travel, within the depths of our bones, we know that we will definitely get out there and see more of the World again, as soon as we are able. When exactly, may currently be unclear, but nonetheless, it is the sparkling carrot dangling before us. It enables us to visualize and fantasize about future dreamy destinations, while we hunker in place right now, and do what we need to do, to keep our World, and fellow humans as safe as possible.

But while we practice sheltering in place, and social-distancing, it’s OK to let our minds do the wandering for us— so let’s allow ourselves to go ahead and dream up the next Fairytale trip that we will take, once the travel restrictions are lifted, and our wanderlust desires can once again pilot our decisions.

I chose to write this post now, about a trip I took a year and a half ago, at the end of June, 2018, because Greece is just one of those magical, fantasy-destinations that is on most people’s bucket list. And if you let your imagination take over and allow yourself to plan THE trip to celebrate a pandemic-free World, then let yourself imagine the playground of Gods and Goddesses.

I was lucky enough to experience the most magical places in Greece (after an exorbitant amount of research and planning), and I want to share them with you, because we all need a little Utopia right now.

When you think of Greece, your mind undoubtedly goes to romantic islands with turquoise waters and white washed little villages. And let me tell you- you’re envisioning it right! But that’s only a small sliver of the country of Greece, and there are so many other extraordinary destinations within Greece, that are unlike anything your mind can conjure up when thinking about this Mediterranean gem.

I had seen photos of places in Greece that seemed too impossible to be true, and so of course, I had to take it upon myself to see these fantasy spots with my own two eyes.

So, I took three full weeks to visit four amazing destinations in Greece, to make sure I had enough time to explore each one to the fullest. Each one of these destinations would be an awesome trip on their own as well, but I just feel like if I’m going to travel halfway around the world from Hawaii, I want to make it count. I also like to be in one place for enough time to really absorb the sights, tastes, and culture, without feeling rushed or like I’ve missed something. And I always crave variety (It’s the spice of life, right?) So, I put together an itinerary of four very different and unique Greecian destinations, and had the vacation of my life! (Once again!)

Santorini is one of those places you see in romance movies, or dotted all over your instagram feed from accounts like ‘Beautiful Destinations.’ I knew it was going to be incredible, with its white-washed architecture and blue-capped domes, perched above the glimmering aqua ocean, but in person, it far exceeded the fantasy. It’s a photo-lover’s Heaven, with picture-worthy spots at literally every corner, and so many varied parts of the island, that you could easily spend a week there, and discover new places each hour.

We hiked along the rim of the caldera one day, all the way from Fira (the Capital), to Oia, the iconic town on the far Northern tip, that makes Santorini recognizable around the world. It is about a six-mile hike, and can definitely get hot and tiring, so if you’re planning on doing it, make sure you are well hydrated, well fueled, and well footwear-ed. (I might’ve made up that last word, but it doesn’t make it any less true.) Also, make sure you pack snacks, if you need to eat frequently, as once you pass Imerovigli, there’s no other place to get food on the entire hike, until you reach Oia. The views are stunning though, and will give you the truest sense of the entire scope of Santorini and its sunken crater in the center.

The second day, we sailed directly through the center of the caldera, past red sand beaches, even swimming in the hot springs, created by the thermal vent of the still active portion of the volcano. It’s funny, I traveled halfway around the world to come from one volcano to another….

We used the catamaran company, Spiridakos, which has been in business for decades, sports a fleet of 20+ nicely equipped catamarans, and employs a very spirited team of friendly, lively, and fun attendants, who make sure your trip is comfortable and exciting, all in one. We had an amazing day, a nice dinner on board, and then a full-on dance party during the last half hour of our 4 hour-trip, as the gorgeous sun set over the ocean, and the captain brought us back to shore. It was a night to remember!

Fira was where we spent our first two nights, and walking around this town was a perfect, gorgeous introduction to Santorini! We hit the coastal walkway above the main town, closer to Imerovigli just before the sun set, and had the most amazing meal at the local eatery, Mama Thira (which is the other way that they say Fira here.) We also found the iconic blue dome that Santorini is famous for. It’s a bit hidden, and the view above it, that looks out across the entire caldera too, is not on any main road. You can ask any locals though, and they will point you in the right direction.

Fira, during the day, is bustling with tourists. There are sooo many little shops and places to grab a bite, along the meandering skinny walkways between buildings. The main road can get very hot & crowded, but we stopped there for some excellent Fro Yo at ChillBox, to cool off. We stayed in a small and quirky hotel called, Sweet Pop, with a bright 80’s color theme, but it was in a great central Fira location, and clean, and cute. And the price was good.

In the evening, the views of and from Fira, looking out over the Aegean sea, are beyond spectacular. I just couldn’t stop taking photos. And even those, did not do it justice.

We spent plenty of time exploring the fairytale-like streets of OIA. (Pronounced ‘Eeee-ahh)— which, I’ve concluded stands for, Oh! It’s Amazing. This town is the epitome of the Greece-travel fantasy. It is truly pristine, and will without a doubt leave a lifelong impression on anyone who steps foot through its exquisite streets. Everything is so clean and bright and the juxtaposed colorful shops against the white -washed facades of all the buildings is eye candy in itself, before you’ve even seen what goodies are for sale inside. There is amazing jewelry and fabrics around every corner, but my favorite shop was without a doubt, the Atlantis Book store on the main street. It is a spectacle itself, and you can’t miss it on a walk around Oia. The balcony above is also a wonderful little hidden gem.

The biggest piece of advice I can give you, is to hit Oia in the morning! You definitely want to get there before the masses of crowds arrive at around 10:00/11:00am. It gets unbelievably packed during the tourist seasons, and the town is so much more enjoyable without hordes of people to push through. Make sure you go all the way to the end of the town, to see the windmills- beautiful!

We used the quad to take a half-day trip to Pyrgos and the black sand Kamari Beach. Pyrgos is the more unruffled, untouched, subdued sister to Oia’s glamour. The colors are real. And the flavors, unreal! Hop on your quad, and take a trip to Pyrgos. You won’t regret seeing this beautiful little town. And the best part, no crowds! Most people that visit Santorini don’t veer away from Fira or Oia as much, so you’ll find Pyrgos to be pleasantly empty, except for maybe a few people meandering around, here and there.

After strolling through Pyrgos for a few hours, we hopped on our quad again, and headed down to the black sands of Kamari Beach. I loved this little area! It’s like the Playa del Carmen of Santorini- tons of beach-side cafes and little thatched umbrellas, and the glistening mediterranean sea lapping against the contrasting black sand beach. Such an awesome scene! We only stayed for a coffee, because we couldn’t miss our lunch reservation at the BEST restaurant on Santorini……..

This tiny, unassuming and unbelievably affordable restaurant (located in Naxos town, not far from Fira, and close to Pyrgos), serves up some of the best atmosphere, service, and delectable home-cooked food you will eat while on this island! I had read a bunch about it, and everyone said that despite its casual ambiance, you should DEFINITELY make reservations. I made one for us for lunch two days prior, and was so glad I did, as we watched them turn away person after person, wanting to dine there, because they were full. Not only was the meal so delicious, but they greet you at your table with complimentary mini individuals bottle of Ouzo, for each of you. This famous Greek liquor will knock your socks right off- it ain’t no joke! And they give you a lot! Maybe that’s why their food tasted so good! (Haha j/k). They also brought complimentary dessert, which was one of the BEST tasting cheesecakes I have ever had, with fresh blackberry sauce. Holy cow! Do yourself a favor, and make a reservation at Metaxi Mas.

Oh, my sweet, sweet Amoudi Bay… what can I say about you that will truly parlay your vibe and flavors? Well first off, I mean look at the photos! Those colors are undoctored. I most definitely edit most my photos, but these did not need any doctoring- the water was that blue and clear! But the octopus was not at all sucky! Haha! Seriously though- the food was incredible, and incredibly fresh. There are a handful of restaurants to choose from, right on the edge of the water. And when I say right on the edge, I mean make sure you don’t drink too much Ouzo, or you’ll easily end up in it, when standing up after your meal.

You can access Amoudi Bay via a winding staircase down from Oia, that sits directly above the Bay on the cliffs. While this looked like a fun jaunt down, we weren’t relishing the climb back up in the heat, so we decided to ride our quad down. Good choice! It was easy to find parking for it, and we were grateful to have the ride back up after spending hours down there, eating and swimming, and cliff jumping.

If you go down to Amoudi, be sure to bring a swimsuit, and be sure to walk around the bend (past all the restaurants) to the left. There’s a pathway over rocks, and over a rock bridge, that leads to a hidden swim area, and tiny island with a perfect picturesque white church, that you can easily swim to and jump off from. It’s about a 20 foot jump, and it was a popular spot for locals and visitors who found it, and a fun way to cool off and spend some time after lunch.

Where Santorini captivates with its beautiful towns and architecture, the island of Zakynthos does this purely with its stunning natural landscapes. The dramatic cliffs are sheer 600ft drops into some of the bluest water I’ve ever seen in my life, anywhere. The color in these photos are true to nature. Shipwreck beach (also called Navagio Beach) lies in a cove on the Northern corner, and is accessible only by boat. It is the home of an actual shipwreck, and was definitely the highlight, and I was lucky enough to see it from the cliffs above, from the eyes of my drone, and also from the sea.

My favorite part though, was that the shipwreck beach boat ride, along the cave-lined cliffs of Zakynthos, included a swim in the famous blue caves. This was an amazing experience. Our boat was small enough to go through the series of rock arch caves that are near the blue cave, and then we got to jump ship and swim in the blue cave itself. It’s accessed by a narrow looking crevasse in the cliff wall, and when you swim in, the water is electric blue, and the cave is more open than you’d expect. It was pretty wicked, for lack of a better word.

Other highlights of Zakynthos were the dramatic Keri Cliffs and mermaid-blue waters below. Make sure you stop at the Keri Cliffs restaurant for a drink or bite, and to view the cliffs from the 200 meter high gangplank that juts out above the aqua sea below.

We also drove to the little island called Cameo, on the Southern coast of Zakynthos. Attached to the mainland by a 1/4 mile wood-plank bridge, this beautiful island is a nice little side-excursion that can be combined with other activities that day. We walked across to check it out, and crashed a wedding that was about to start. Fortunately, no one was the wiser that we didn’t belong there, and we got to take some awesome photos of the totally secluded little beach (where they were setting up), where there would normally have been lots of people. I also flew my drone over the island to get some perspective from above.

I seriously keep thinking the trip couldn’t get better, but Greece kept knocking me off my rocker! We left the beautiful Island of Zakynthos, flew back to Athens, rented a car, and then headed to the crazy magical next location….

Meteora will humble you in a way nothing else ever has.

About 1000 years ago, Monks, seeking total isolation and peace, and in an attempt to be closer to God, scaled these 1000-1800 foot cliffs, hermit-ing themselves for years in caves all the way up the stone pinnacles. They eventually rock-climbed their way to the tops, and began to build what became the unbelievable monasteries that you see today.

Meteora is located about 220 miles from Athens, and immediately upon entering the area, you can see why it is a UNESCO World Heritage site. It’s landscape alone, is jaw-dropping. You can take the train from Athens to Kalambaka (5 hours), or drive (3-4 hours, depending on your personal speed), or take a day-trip tour with a bus and guide, however, to get the full experience of Meteora, I would most definitely recommend going more than one day!

At one point, hundreds & hundreds of years ago, there were over 25 monasteries atop the cliffs. Today, there are 6 fully functional ones that still exist, and are open to the public. We spent three full nights in Meteora, and visited all six monasteries, strolled the town of Kalambaka, and enjoyed the many amazing panoramas that are everywhere.

I wrote a full post about Meteora, here. You can read all about the various monasteries, surrounding area, and things to do/see, and why you should NOT leave Meteora off your list when visiting Greece!

My next Greece destination was really quite difficult to truly capture in images. Where Santorini & Zakynthos were picture-perfect, and easy to photograph, and Meteora was a photographer and droner’s dream, Athens was a whole different creature! It’s more difficult to properly explain or depict through photos, because its beauty is in its constant energy and eclectics. I loved this city!! It’s both grungy and historically rich & beautiful at the same time. Its little streets are jam-packed with shops, restaurants, and bars, side by side with age-old ruins, and grafitti-decorated trains. The combination of the people, the smells, and the sights, are what make up this Ancient city’s awesome vibe.

I had four days in Athens, and wanted to make sure that I had as much time to meander aimlessly around the little charming streets, as I had to visit the famous World Heritage ancient ruins, like the Acropolis. I wanted a central location, close enough to everything, where I could just step outside the hotel and be in easy walking distance of all the main attractions. I could’ve easily stayed a whole other week, and still not seen all the areas I wanted to.

The cute, clean, comfortable, and affordable Lotus Inn, in the middle of the city, was the perfect place to hang my sandals each night, and has a beautiful, light & airy restaurant with views of the Acropolis, where you can get a nice breakfast every morning. It is located a few blocks from the Acropolis, just steps away from the famous Monasteraki market area and the train station, (should you want to hop on the metro to visit other areas.) It is also just a few blocks from the Plaka, which was my favorite neighborhood for amazing little shops & restaurants. Strolling this area was a highlight of each day. It’s also not far at all from Syntagma Square & Greek Parliament, where you can watch the changing of the guard. If you go to see this, make sure you time it perfectly, as they only do it once an hour, and you don’t want to stand in the sweltering heat, with zero shade, waiting for them to do their synchronized steps. (Trust me- I almost passed out!) Another tip: Go to see the Acropolis as early as you can, as early as it opens. It can get extremely crowded by about 10:00am already, and they then have to herd you out through single file lines, that, when in the thick of the afternoon heat, can again, feel stifling & uncomfortable, and having you waiting an hour, just to exit! If you go earlier, you will enjoy the experience much more. Don’t forget to wear a hat, sunscreen, & bring water!

The history of Greece, the birthplace of modern Democracy, is fascinating, and the shopping is colorful, and crafty, and beautiful, but….. did I mention the big fat street Gyros?!?!? I loved the food in Athens- Greek Salads with monumental chunks of fresh feta, creamy tzatziki (in which to dip thick golden french fries), and fresh seafood everywhere. But the street gyros- Wow! Don’t leave without getting one. (Or six!)

Other mentionable places for tastiness: Couleur Locale – this swanky-casual rooftop bar serves up incredible views of the Acropolis, along with delicious Cocktails! It’s right across the street from the Lotus Inn. And Cafe Chocolat Royal, is an awesome place to get dinner or just dessert at night after strolling the charming Apostolou Pavlou Street, that runs along the side of the Acropolis. It has great food and amazing views of the Acropolis. You definitely need to make a reservation though!

In Greek mythology, Poseidon, brother of Zeus, was the God of the Sea, so it’s no wonder that he was highly worshipped in a country with over 8,500 miles of coastline, and has a temple, surrounded on three sides by the sea, named after him.

The temple was built in 444 BC of marble (the same time the Parthenon was built), and is home to the legend of Aegeus. According to legend, Aegeus, king of Athens, waited at the cape to watch for his son to return from battle. Mistakenly thinking that his son, Theseus, did not survive his symbolic encounter with the Minotaur in Crete, King Aegeus jumped to his death off the cliff, in despair, thus giving his name to the Aegean Sea. Sad story. Magical Place. Epic Sunsets.

I absolutely cannot wait to go to Greece again! There are sooo many more amazing islands to discover, not to mention other Mainland sites too. As I shelter in place now, I’ll choose to fantasize about that future trip….

Until next time…… Aloha, Greece!

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