5 Days in Greece | Athens & Santorini

My sister and I watched My Big Fat Greek Wedding approximately 742 times when we were growing up, so it might be fair to say that sparked my love of all things Greek. Add in a viewing or two of Sisterhood of the Traveling Pants, and Greece was added to my travel bucket list. Mind you, this was in the early 2000’s, long before travel bloggers were a thing–I didn’t need the stunning Grecian views constantly popping up on my instagram feed to sell me on a trip, but believe me it only added to the drive that someday I would get there.

That someday finally, unbelievably, came on mine and my husband’s fifth anniversary European Holiday. I still find it hard to believe that trip even happened. The rainy NY weather has me daydreaming of bright blue skies, volcanic beaches, white-washed villages, and all the sweet, crunchy, gooey baklava I can fit in my face.

There is so much to do and see and experience in Greece; I know this measly blog post will barely scratch the surface. I only hope you’ll keep some of these nuggets in mind when planning your own trip.

Don’t have time (or care) for the full breakdown of our trip? Click here to skip to the good stuff and get my quick tips and recommendations for visiting Greece.

Day 1: Athens

We split our time in Greece into two nights in Athens, and three nights in Santorini. We landed in Athens at around 2 in the afternoon, after about 24 hours of travel, several delays, and missing luggage. Thus, most of our first day in Athens was lost to plush hotel robes and a great nap. Lesson learned: always plan on devoting your first day in a country many time zones removed from yours to rest and recovery. If you have the energy, you can certainly spend this day exploring Athens.

As for ourselves, we didn’t venture out until dinnertime. We stayed at the InterContinental in Athens, which was about a mile and a half walk to Plaka. In Plaka you’ll find narrow streets bustling with life, lined with shops and restaurants, and adorned with twinkling lights. Our first stop was to shop for an outfit or two to hold us over until we got our luggage back, and then it was time for the main event: our first meal in Greece. Of the many restaurants we could have stumbled into, I’m so glad it was Estia. I’ll confess, the food smelled irresistible as the waiter set it in front of us, and we were so ravenous that I didn’t get a picture of it. I had Pastitsio, which is like a Greek version of a lasagna made with béchamel sauce and a meat sauce with a hint of cinnamon.

Dinner at Estia on our first night in Athens

Day 2: Athens

Our second day in Athens was devoted to exploring as much of Ancient Athens as we could—starting with the Acropolis and its accompanying museum. (Well, it really started with discovering the pure delight of a Greek cappuccino freddo and flaky, feta-filled pastry). Before tackling the Acropolis itself, I definitely recommend starting with the museum. There is so much to learn and admire that will help steep you in the history of the ground you’re walking on. There’s also a nice cafe to stop in for a bite and a drink before heading outside to the main event.

When it comes to climbing the Acropolis I have three pieces of advice, bring water, cover up from the sun as best you can (a wide-brimmed hat is perfect here), and expect your white shoes to turn a lovely shade of beige by the time you’re done. In all seriousness, it may seem like a steep climb if you’re not used to doing much physical movement in your daily life, so take your time and stay comfortable. Being among the ruins of the Parthenon is surreal, and the view from the top of the Acropolis is incredible.

After our morning adventure, we stopped back at the hotel to freshen up and then headed to the Roman Forum and Hadrian’s Library. To be honest, both of these sites paled in comparison to the Acropolis and Parthenon so if you are pressed for time during your stay in Athens, I’d prioritize latter. We still had a great time wandering the sites, and there’s something about seeing a fat cat lounging on ancient ruins that really tickled me.

We walked more than ten miles this day! It was great after being cooped up on an airplane for so long, and we definitely were ready for an early dinner and bed.

Reaching the top of the Acropolis

Day 3: Journey to Santorini

If you are planning on taking a ferry from Athens to Santorini my advice is do not do that. We booked through Seajets, and our five-hour boat ride became eight hours. When the five and six hour marks came and went, someone finally asked a crew member what was up, and it turned out they had switched us to a slower boat without telling any of the passengers. I have to imagine the alternative, a 45-min flight, would have been worth it.

As soon as we arrived at our luxury villa, however, any bad feelings from that boat ride faded. We stayed at Santorini Sky in Pyrgos, which is located near the center of the island. Oia, at the northern tip of the island, is the more popular place to stay, but we really enjoyed being away from the hustle of the main tourist area. The village of Pyrgos is equal parts quaint and picturesque. It’s a short (but steep) walk from the hotel into the villa, and we found an amazing restaurant there for our first Santorini dinner.

Cava Alta was our first real taste of Greek hospitality. The waiter was so friendly, and as soon as we sat down he brought us shots of tsipouro (the Greek equivalent of grappa) on the house, he also brought out free dessert wine at the end of hte meal. The atmosphere, the view, and the food itself were all incredible. We had a delicious three-course meal with a bottle of wine for about 80 euro—a meal like that back home would cost at least twice as much and tasted half as good. I think the Greeks have really mastered the art of cooking food that leaves you satisfied and refreshed rather than full and heavy, even in the heat of summer.

Dinner at Cava Alta in Pyrgos

Day 4: Santorini

There are a lot of exciting, adventurous things to do in Santorini—catamaran rides, jet ski volcano tours, snorkeling—we did none of it. On our first full day in Santorini we slept until the sun woke us up, then donned our robes and slippers and padded out to our back porch to enjoy the breakfast that had been waiting at our door. We had a private hot tub and pool in our villa, and other than wandering into the village to find treats, that’s where we spent most of our time.

We took an Uber into Oia to explore a bit and have dinner at a restaurant called Roka. I had hand-made Greek pasta, and as I should have come to expect by then, the food was out of this world. We didn’t stay in Oia long because it was quite crowded, and we made it back to our villa in time to catch our private view of the most incredible sunset I’d ever seen.

Sunset view from our private villa

Day 5: Santorini

After another slow morning and deliciously curated breakfast, we checked out of our villa and headed to our next hotel, Golden Sunrise Suites. We had a very early flight ahead of us the next morning (the kind you wake up at 3am for), and decided staying near the airport would be worth it (it was). Our hotel was great and Cristina, the host, was so sweet. It was everything we needed for one night. We walked 30 minutes to Kamari Beach where we lounged in the sand for a bit then did some shopping and bakery visiting. After walking back to the hotel and freshening up, we headed to Gaia Winery, which turned out to be a highlight of the trip (as the half dozen bottles of wine in my cellar with their name on it can attest to). A wine and cheese tasting overlooking the Mediterranean Sea? It was one of those pinch-me moments. The wines themselves were fantastic and the sommeliers were so knowledgeable in explaining how the unique volcanic soil on Santorini affects the wine.

We had a quick, early dinner, and our time in Greece ended the next morning during a bleary-eyed 3am taxi ride to the airport.

Wine tasting at Gaia Wines

Quick Tips & Recommendations

Here is the TL;DR section of my European Holiday posts—skip the play-by-play and get (what I think) are the most important things to know.

Where to Stay?
  • In Athens: Plaka is the place to be. Find a hotel or Airbnb in that area and you’re in the heart of it all. We stayed at the Intercontinental, which is beautiful but a bit of a hike into town. It was fine for us, but not fine if you’re not a fan of walking.
  • In Santorini: Pyrgos is a hidden gem! I cannot recommend the Santorini Sky resort highly enough. Luxury, private resort experience at a fraction of the price of staying in Oia.
Where to Eat?

Honestly, anywhere. I truly think you cannot have a bad meal in Greece. But, here are some of my recs!

  • In Athens: Bread Factory for breakfast, sweets, or something carb-y to keep in your bag. Estia for dinner!
  • In Santorini: The Bakery of Pyrgos for daytime snacks. Cava Alta or Roka for dinner. Gaia Wines for a wine and cheese tasting on the beach
What foods should I not miss?
  • Baklava for breakfast, second breakfast, lunch, and dinner. Moussaka. Pastitsio. Gyros. Street souvlaki. Put feta on everything.
How to get around?
  • Expect to do LOTS of walking. If visiting a Greek island, prepare ahead of time by working out on the StairMaster (I’m only half joking)
  • In Santorini: Ask your hotel or resort about booking private transfers to/from the sea port or airport. The most reliable way to get somewhere on time
  • Uber (expect to pay $$)
Is it okay that I don’t speak Greek?
  • Yes! Greek people are so understanding—they know their language is a difficult one to master, and they are kind enough to speak English for tourists.
  • Learning a few common phrases and greetings will go a long way to show respect for another culture. Good Morning, Yes, No, Thank You, Please are great places to start.
What essentials should I pack?
  • A wide-brimmed hat
  • Sunscreen
  • Comfortable walking shoes that you don’t mind getting dirty
  • Loose, airy clothing (think linen pants)

Greece is heaven on earth. Having time to unwind in paradise was the perfect way for us to start our three-week European adventure. We were truly blown away by Greek hospitality. Even more so than the beauty of the country, the kindness of its people is one of our fondest takeaways from our time in Greece. Please add it to your bucket list if you haven’t already.


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