A guide to Greece for first-timers
Greece has been at the top of my to-go list for ages (those beaches! those ruins! those gyros!), but somehow, money/time/other travel plans always conspired to push it to the “next time” list. We *finally* booked our flights, found some dream Airbnbs and planned our island-hopping itinerary for June 2020 and…you know how that goes. All of that to say that our recent trip to Greece was a LONG time in the making with a ton of anticipation–and somehow, it still managed to exceed expectations.
I optimistically rebooked the trip in early 2021, cancelled when Covid cases spiked in the country in spring, and then once David and I were both fully vaccinated AND Greece announced it was welcoming vaccinated tourists…we decided to go for it. And I’m so glad we did! Although I was pleased to see as many travelers as we did in a country heavily reliant on foreign tourism, it never felt too crowded or impossible to book things on short notice. The islands were insanely beautiful, the food was delicious, the people were friendly: what’s not to love?!
We were originally supposed to start our trip in Athens, but we had to reshuffle some plans due to bad weather and a missed connection in New York City. We ended up flying directly to Santorini a few hours after we landed in Athens, and then took ferries from Santorini to Sifnos, to Milos and then back to Athens. Overall: ferries were a super easy and affordable way to get around the islands (I booked everything on Ferryhopper and had mobile tickets on my phone), but don’t be surprised if things run a little late.
Santorini
Santorini was not in our original 2020 travel plans. Although I was dying to see those iconic white houses next to the blue Aegean Sea, I’d heard tales of the island being extremely over-touristed in recent years–especially by Instagram influencers. But when we realized we’d be traveling during a uncommonly quiet time, we decided to sneak it in.
Although it was just as gorgeous IRL as it is in the photos and we enjoyed our time here, it wasn’t my favorite island. There are more than 200 Greek islands in the Aegean Sea, so although I think Santorini is a delight: I’d definitely recommend looking beyond it, especially if you are hoping for any deals or a more laid-back experience.
That said, we had plenty of fun while we were here! We especially loved the day we spent on the water with Santorini Yachting Club: I’m a big fan of any type of day-long boat tour, and this one was a fun way to experience the water surrounding Santorini (there are high cliffs, and not a ton of easily accessible beaches).
Santorini is also known within Greece for its vineyards and its signature local wines. One of my favorite evenings was at Anhydrous Cellar Door: we popped over for a menu that paired several small dishes with local wines. Every single dish was delicious and so full of flavor! The one thing I’ll say is that the portions are generous: we both did the food-and-wine tasting (which cost about 40 Euros each), and I think we probably could have split one tasting menu and just added on one wine tasting (and maybe thrown in one extra dish or appetizer) since we weren’t absolutely starved. That said, the courtyard is lovely and the service was wonderful. One of our best sit-down (aka non hole-in-the-wall perfect gyro) meals by far! (Although if you are looking for a hole-in-the-wall gyro, Lucky’s Souvlaki is not to be missed.)
We also loved our leisurely lunch at Pelican Kipos. We had some time to spare between checking out of our Airbnb and going to the ferry, so we ducked into this shady, plant-filled courtyard with our suitcases. The staff could not have been more accommodating: after we ate our lunches and (slooooowly) sipped our drinks, they surprised us with a bonus dessert, sliced watermelon and a digestif on our way out. The food wasn’t anything too spectacular, but it was very solid–and the greenhouse vibe is a very nice change from all of the sea-front views.
There are SO many accommodation options on Santorini: you can really pick and choose whatever vibe you want, but it likely won’t be cheap. We absolutely loved our Airbnb: the host (a Greek man who was raised on Santorini, and then spent 25 years living in London before moving back) gave us so many great recommendations. The “cave home” is beautifully updated and has all of the little luxuries you could hope for, including a rooftop plunge pool and a daily housekeeping–with the bonus of having a little kitchen, where we kept some Greek yogurts, fruit and honey to make breakfast at home. It *is* a two-bedroom, which would be perfect for two couples (we were hoping that David’s best friend Chris would be able to pop over and join us from the UK, but the Covid travel gods did not deem it so!).
Sifnos
I was especially excited to visit Sifnos: it’s quietly recommended as an alternative to Santorini for its beautiful white houses and picturesque main cobblestone street, but with the added bonus of being an excellent foodie destination (it’s especially popular with French tourists!). Our visit was a bit dampered by rain: I am someone who *loves* blue skies and sunshine every single day of every trip (and every day of my life), so I will admit that a rainy day is something that can really mess with my overall mood and vibe for the day.
But the rainy day also affected our one full day in Sifnos: in a place known for its restaurants, and with plenty of sprawling al fresco courtyards, eating well normally wouldn’t be an issue. But with indoor dining closed due to Covid regulations during our stay in Greece, and outdoor tables washed out: we weren’t able to indulge in delicious meals quite as much as we would have liked!
That said: I can’t overstate how incredible every single meal was at our hotel, Gerofinikas Boutique Hotel. Our resident breadman David bonded with the chef over the Tartine cookbook on display: turns out the (extremely talented and personable!) young chef ordered starter from Tartine (in San Francisco) and makes a fresh loaf of sourdough every day. We thoroughly enjoyed breakfast at the hotel every morning: in addition to freshly baked bread, there was also a truly perfect Greek scrambled eggs dish, thick Greek yogurt with fresh fruit, dried fruit and nuts, and a variety of other homemade baked goods. Bonus: thick Greek coffee and freshly squeezed orange juice! We also had dinner on the property after we arrived on a late ferry our first night, and every single thing was exquisite–especially while overlooking the infinity pool and Aegean Sea.
Someone recommended a cooking class at Narlis Farm, but (unsurprisingly) we weren’t the only people interested in an indoor activity on a rainy day. (There were strict participation limits due to Covid while we were there). We opted for an afternoon pottery class at Narlis Farm instead: David took some pottery classes as a kid, and his grandmother had a wheel and kiln, so he was excited to get back on the wheel! It’s definitely good for beginners (aka me!), but it was a really fun way to learn a bit more about the signature pottery of Sifnos and realize just how challenging it is. We also bought a few gorgeous bowls to bring home: even if you don’t do a class, swing by Narlis Farm just to browse and potentially pick up a beautiful handmade piece.
And although the weather wasn’t entirely cooperative, we also loved strolling through the extremely picturesque streets of Apollonia and Artemonas. However, we especially enjoyed the little seaside collection of buildings of Kavos: it was a short walk down the hill from Gerofinikas, and home to the incredibly scenic Chapel of the Seven Martyrs. Another bonus was Kavos Sunrise, an unassuming mojito bar overlooking the water (you’ll know it by the piles of Havana Club rum), and Leonidas Restaurant, owned by an extremely friendly multilingual Greek.
Milos
Milos was, without a doubt, our favorite island: the beaches were absolutely STUNNING, and the whole vibe felt very laid-back.
We had the best time cliff jumping on the crazy white rock formations at Sarakiniko Beach: you can jump off the edge into the crystal clear water, and then swim through a cenote to easily climb back up onto the rocks. Once you get here, it’s worth walking around and exploring a bit: we almost stopped right at the gorgeous little inlet of shallow turquiose water, but David walked around to the other side of the rocks and discovered some very cool places to jump and swim.
Tsigrado Beach is insanely beautiful, but tricky to reach: you have to climb down (and back up!) through a slim canyon. After enjoying the view, we popped over to Fyriplaka Beach: it’s less than a five-minute drive away, and it’s an “organized beach” (aka a lovely European beach where you can pay for a chaise lounge and umbrella, and order any drinks you’d like). The water is just as clear, but it’s a sandy, shallow beach. We spent our last day on the islands just hanging out here before our late afternoon ferry, and it was an extremely relaxing delight!
We did end up having to cut our time in Milos a day short so that we were able to explore Athens (see: reshuffling due to a missed flight above!). The big bummer about this was that we weren’t able to do a boat tour around the island in the time we had: some of the most beautiful beaches and caves on the island are only accessible by boat.
The most unique part of our stay in Milos was our Airbnb: it was a tiny fisherman’s cottage right on the water in the tiny “town” of Skinopi. I loved falling asleep to the sound of the water and having our own little private swimming cove, but the remoteness was also a downside. We ended up having to upgrade our rental car when we arrived so that we could drive over bumpy dirt roads (we have bad luck with rental cars and flat tires), and we both were in a state of high anxiety every time we had to drive down the single-lane dirt road (with a steep drop on one side!).
It was worth driving through the tiny roads of Trypiti to get to lunch at OKTO, which had delicious food (the shakshuka!) paired with expansive sea views. Another delightful outing was to Klima, a colorful and picturesque fisherman’s village.
Athens
I wasn’t sure what to expect out of Athens: some people hate it, but we also heard quite a few people say it exceeded their expectations. We definitely fell into the second group! I’m also really glad that we ended up in Athens after a stint in the islands: it was really refreshing and fun to be back in a city. Although we didn’t originally plan it this way, I’m so glad that we ended the trip in Athens when we weren’t jetlagged and were ready to totally enjoy it!
The main thing we wanted to see in Athens: the Acropolis! The ruins you just can’t miss. After so many history/philosophy/art classes focusing on Greek civilization, it was surreal to see it in real life. Although it was definitely one of the most “touristy” things we did in Greece, it’s worth experiencing. We went in the late morning (in the late June heat), and my only regret is that we didn’t opt to go in the late afternoon instead: I think it would have been much more pleasant temperature- AND crowd-wise.
After the Acropolis, we walked to Kostas for truly the most perfect meal of our trip. A little hole-in-the-wall souvlaki place had truly the most delicious gyro that we’ve ever eaten: it was so good that David got back in line for a second. I wish that I had gotten a second as well!
Right around the corner is a very fun and fancy grocery store, Ergon House. We wanted to buy EVERYTHING. A wonderful place to pick up some souvenirs to bring home! Afterwards, we took a stroll through the National Garden, which was a sprawling and lovely green space–and then popped into The Clumsies for a fun cocktail in a hip and well-designed space.
We stayed at Fresh Hotel, which was a super convenient location: about a 20-minute walk to the Acropolis and right by the hip neighborhood of Psyri. The tree-lined streets along Ag. Anargiron are full of bars with al fresco seating: perfect to set up with a drink and people watch.
Overall, Greece was just as fantastic as we could have hoped: I could easily go back to all of the places we visited, and there are so many other islands I’d love to explore. I’d also go back for the Greek salads (with giant blocks of feta on top!) and gyros alone: without a doubt, Greece is going on my short list of favorite food destinations. Fingers crossed we’ll make it back again one day!
Have you been to Greece? Anything worth checking on a next trip or any questions on traveling there in 2021?
