• April & Andy

Spontaneous Island-hopping in Greece

Updated: Aug 29, 2019

We had been planning a backpacking trip through Vietnam and Cambodia for months. These countries were pretty high on both of our lists. We'd booked a couple places to stay and one activity, but were mostly planning to wing it.

Standing in line for the REI garage sale early on the morning before, we checked the weather one last time and saw a solid forecast of thunderstorms--not exactly desirable on summer vacation, but also not uncommon for that part of the world. We joked about other places we'd love to go. Sunny places. Warm places. We were both dying to go back to Spain. I've always dreamed of Greece. Just for fun, we looked up prices.

Thanks to Andy's airline status (I'll have him write more on that later as it has saved our butts on numerous occasions), we were able to change our flights with no fees. We lost a bit of money on things we'd already booked in Vietnam, but thought it a fair trade for beautiful weather.

I threw a handful of bikinis in a bag and we were off to Athens!

When we boarded our first plane, all we knew was that we would arrive (after a few flights) in Athens and would need to make our way to the islands. Before boarding our first flight, Andy updated the Facebook world, and we were off. During our first layover, we learned some good friends were already in Santorini, so we decided to start our trip by meeting up with them and booked a cheep flight from Athens to Santorini (one of the few islands with an airport). We then used Booking.com to find an inexpensive hotel within a twenty-minute walk from the famous caldera.

While on Santorini, we strolled along the caldera's edge, ate delicious, fresh seafood, tasted local wines, relaxed on the beach, and took a sunset catamaran cruise. Once we'd had our fill, we consulted the Lonely Planet Greek Islands (Travel Guide) and used their suggestions to pick our next island. Again, we booked a last minute room on Booking.com and also booked a last minute ferry.

It's as if the islands are meant to be traveled this way -- hop to one, stay a few days, soak it in, and then try another.

We learned that the Greek islands have something for every whim and craving. After a few days on Santorini, we chose Amorgos for its small, peaceful fishing villages, hiking opportunities, and highly desirable lack of tourists.

We love flipping through these books to learn about a location before traveling and throwing them in our day pack to quickly find an activity or bite to eat while in a new place. Greece has 227 inhabited islands and reading about how different each one is makes us want to explore them all!

Thankfully, Amorgos did not disappoint. Our little fishing village had a few amazing restaurants and a couple of shops. We rented an ATV and drove across the entire island in a day. We hiked up to a beautiful monastery built into the cliffside and cooled off at an almost empty, picture-perfect beach. We spent an entire day reading books at a beachside bar and reached a level of relaxation I don't think either of us has ever known.

We fell in love with Amorgos.

Next, we chose Naxos. I don't fully remember why we chose Naxos, and it probably had no chance in our hearts following Amorgos. On this island, we found good food, but far too many tourists, especially ones toting kids. It felt like a family vacation that we didn't sign up for. Our favorite part of Naxos was our long trip to a small fishing village (we learned from Amorgos that tiny Greek fishing villages are our jam) where we found an expat's small, outdoor hippy bar with more books than booze behind the counter.

After relaxing there for a while, we asked for a dinner recommendation and he was glad to suggest one of the local spots, Niko's. On this night, we learned an important lesson that we won't soon forget: the Greeks take great pride in their cooking and not finishing your meal is a devastating blow. We also learned that there is a limit on how much we can actually eat in one night. While the food that we ordered was amazing, it was the largest portions we'd seen during our entire trip -- more like large American portions, which would have been fine if we hadn't ordered two appetizers, anticipating the light Greek-sized portions we'd become accustomed to. The appetizers filled us up before the entrees even came out, and the relaxed [read: slow] Greek-style service meant that it was starting to get late and dark, and we still needed to drive our ATV back to the other side of the island before our food comas set in. We struggled to make dents in our entrees in order to not offend. We were so full it hurt, but the sadness in the restaurant owners eyes at our apparent dislike of his food hurt more. We shoveled in more food. Eventually we were hurting so much we asked for to-go boxes (which doesn't seem to be a thing in Greece) and our check. Full beyond a point of satisfaction, we rode back in the darkness, carrying our to-go boxes of shame.

Lesson learned. Eat the food.

Sick of the tourists, we ended up leaving Naxos early. We headed to Antiparos, which sounded like more our style--more relaxed, less crowded. This was the last and smallest of the islands we visited.

Highlights included eating delicious octopus hanging up at every restaurant, exploring the Cave of Antiparos, and relaxing at the beach and by the pool at our beautiful hotel that was more like a resort, run by the nicest Greek family. This island was a bit pricier and more upscale than Amorgos and Naxos, but had an abundance of good restaurant and shopping options along its main street. We felt much more at peace and comfortable here than we had among Naxos' tourist families, and it was a successful end to our island hopping, for now.

*This post contains affiliate links, meaning if you happen to buy something from a site we’ve linked to, we earn a small commission which helps us save up for our next trip! It doesn’t cost you any more, and it helps keep this site alive!

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Hi! We're April and Andy -- a couple of world travelers always planning our next adventure. Join us as we explore it all!​


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