While July and August are extremely busy, the beginning of May through the end of October comes with perfect weather for exploring the islands (think: warm, sunny days perfect for lounging on the beach and cooling off in the Aegean). And if you’re interested in visiting Athens, many locals said early spring or late fall is ideal. Restaurants serve regular bread, and many don’t even have pita on the menu. I asked a local guide about this and he told me that pita is typically served with meat (for example, when you order a gyro), but most restaurants typically serve bread with anything else. At first, I was a little disappointed, but turns out Greek bread is really delicious and an equally as satisfying way to sop up smoky eggplant dip and cucumber-laden tzatziki. Whenever I found myself talking to a Greek local, I made a point to ask about his or her favorite island. Everyone had a different response complete with a reason why. Every island seems to have such a different vibe and character, and now I just want to visit more of them. Turns out, there is tons of wine being produced all over Greece at just about every price point. I absolutely loved how most restaurants in Greece offered only Greek wines. I tried lots of grape varietals I’d never even heard of (Xinomavro and Assyrtiko were only the beginning). I also especially loved the delicious skin-contact (aka orange) wines that are prevalent in Greece. I arrived in Folegandros just in time to enjoy the breezy weather and take advantage of some great hiking trails, but I heard horror stories of ferries getting canceled and others getting stuck in the open, extremely choppy water for hours. Plus, on all of the islands, locals suggest visiting specific beaches depending on the wind conditions so that you’re sheltered from strong currents and breezes. If that sounds intimidating, it shouldn’t — because on every island I visited you could find plenty of boat tours to take you around the coast to the very best, hard-to-reach beaches. Some islands even provided boat shuttles running from one popular beach to another quieter one. Visiting these more remote beaches was some of my absolute favorite experiences in Greece. In Milos especially, I took a full-day boat tour around the entire island, which took me past caves, amazing rock formations, and some of the bluest water I’ve ever seen. Folegandros, by sharp contrast, is located just 40 minutes away from Santorini and was home to amazing, pristine, and quiet beaches where you could look around and see not one other tourist. Santorini was drop-dead gorgeous, but not a great beach destination. I did some things I would highly recommend: Sunset in Santorini was extremely chaotic, so I woke up to see the sunrise at the edge of Oia in peace and quiet. I found some restaurants away from all the crowds (Armeni and Metaxi Mas were two of my favorites), I walked a stretch from Fira to Oia, which really was breathtaking, and I took a boat tour to see Santorini from a totally different perspective. I would encourage you to go to Santorini for a brief visit and see it for yourself. Spend a day…maybe two, take in the beauty, and then make your way to the other islands. In Sifnos, I ate tons of mizithra, which is a soft cheese sort of like goat cheese. A big scoop of mizithra was often served on Dakos salad, a huge bowl of the ripest cherry tomatoes I’ve ever tasted, and crunchy rye rusks (sort of like Greek Panzanella). In Folegandros, the local cheese was sour, and it often replaced feta on Greek salads. I also had plenty of grilled Graviera drizzled with nuts and honey. In short, Greek cheese is spectacular and way more varied than your basic feta. Greece has a great ferry system that you can pretty much take anywhere. All of my ferries were direct and shorter than one hour. Everything was simple enough from booking to boarding. I used Ferryhopper, which has great customer service and was happy to assist me and answer my questions). Each arrived and departed pretty much exactly on time. All of my ferries were very smooth, but I’m glad that I packed some non-drowsy motion sickness medicine just in case. While I only spent about 24 hours in Athens this time around, it was a mistake. I can confidently say I am a member of the former party. As soon as I arrived in Athens I already wished I had more time there. I spent hours walking around and wanted to see more and more. The city reminded me a lot of Rome with its unique balance of ancient and new, complete with lots of charming alleyways, beautiful vistas, bustling cocktail bars, and tons of globally-inspired restaurants. One of my favorite parts of seeing a new place is just driving around and getting lost, then seeing what I find. I was surprised to find that taxis on all of the islands were sparse, and you always have to call ahead to arrange one so a car really makes things easier and more convenient. There are lots of scooters and ATVs available to rent as well if you’re comfortable with that. Not to mention many of the towns are very narrow in that distinctly European way where two-lane roads should really be just one lane. In Milos, driving was especially treacherous in places because of narrow streets and also unpaved, rocky, and often extremely vertical off-roading conditions. Rent a car, but you may want to consider a 4x4 and you’ll definitely want to drive very carefully. This was, without a doubt, the greatest stress of every day, but whatever we chose would be grilled and delivered to our table fully filleted and garnished with a mixture of olive oil and lemon. There is no other way to put it: Greek seafood is my personal heaven. I also loved exploring the vegetarian options — things like stuffed peppers and eggplant with couscous, chickpea fritters, and flaky savory pies stuffed with cheese and spinach.
