Greece is an incredibly popular summer destination for tourists from Europe and around the world. The incredible weather, fun nightlife and unique landscapes make it hot spot June – September. The major islands — Mykonos, Rhodes & Santorini — are absolutely packed all summer long, so you should expect big crowds. I was actually shocked by the crowds during my 2 weeks there, and I was grateful that we had our own private sailing vessel to retreat to.
If you’re looking for a more off-the-beaten path experience, it can definitely be found; you just have to hunt a little further. But once we found them, they turned out to be some of my favorite islands! The smaller crowds give you a deeper experience and understanding of the unique differences between all the different islands.
Below are my 5 favorite off-the-beaten path Greek Islands that I would recommend visiting!
Our first stop on the Greek Island tour is Kos. The third largest of Dodcanese island chain, Kos has a lot of landscapes and viewpoints to offer. We ported just outside of the main city, Kos Town. We only planned on spending the night here, but strong Maltemi winds from the north “stranded” us onshore for an extra day. And honestly, I’m thankful it did! We explored the town on the first day and were slightly disappointed by the touristy shops and loud bars.
But on the second day, we opted to take out some ATV’s (four wheelers) to explore other parts of the island. Rented from Escape Tours, 8 of us departed out of Kos town up the island’s main mountain, Dikeos. On the way up, you will notice the change in vegetation as the altitude increases. At the bottom, there are palm trees and more tropical vegetation, while up at the top you feel like you’re in Colorado, surrounded by tall coniferous pines. We didn’t make it to the summit, but did make it to a small village called Zia with absolutely stunning views. The Greek islands in this area are quite close together so we could see several of the islands from the mountain.
Recommended to us by a local, we stopped at Taverna Dikeos for lunch. Now as many of you may know, the Greeks know how to eat. We ordered a family style meal where we all shared a bunch of different dishes, including Gyros, Mussaka (eggplant casserole), Saganaki (fried cheese), Pork chops, calamari, fried eggplant, and my personal favorite, Stifado (veal and onion bake). This restaurant was, at least to me, the epitome of what I picture a Greek restaurant. It had an adorable trellised patio with plaid table cloths and vintage decor on the walls. With the Greek flag flying at the entrance, this was the perfect stop to fuel up for the rest of our ride.
I highly recommend taking an open air vehicle to explore some of the islands, whether it be moped, go-kart or ATV. It allows you so much more visability and freedom. Plus you can work on your tan! Sam drove our vehicle and I was simply the passenger. But I had so much fun letting the wind blow through my hair! They can get going pretty fast, so even if the island is big like Kos, it’s still easy to see lots of different areas. After lunch in Zia, we made it all the way down the island to Paradise beach. Living up to its name, this popular spot was packed with chairs, umbrellas and floating toys. It’s tucked delightfully in a small bay, so the water is calm and warm and ready for a swim! We made our way back after a few fru-fru drinks at the beach along the main road. We essentially went the entire navigable length of the island in about 6 hours on the ATVs. Such a fun day!!!
A sleepy fishing island, Kalymnos is north of Kos still in the Dodcanese island chain. After a morning of sailing and playing in the water, we arrived in the late afternoon to Kalymnos and ported in the city of Pothia. Ideal for a day stop, this town honestly doesn’t have a ton of activities to offer but is scenic and quiet. It’s a nice contrast from the busier islands!
Kalymnos is a largely barren island that had a booming sea sponge industry in the early 1900s. But now, it just feels like a fishing city, and there are few sights to see. Although if you are into adventure sports or rock climbing, Kalymnos has lots of rope laid out for climbers and North Face actually hosts an annual invitational for climbers here.
For us, we spent the afternoon wandering around Pothia only to find closed storefronts and private churches. If you make the way up the hill in town, you will be greeted by lovely views of the town. And we got a great view of the Dolce Mare (our sailing vessel) which quite literally TOWERED over all the other boats in the harbor. It’s dual masts could be seen from just about anywhere in town.
A quaint and authentic island, Astypalea has been my favorite island thus far. One of the largest in landmass, this island has two large mountains on either end, with deep valleys and towns in between. Getting here was a bit of a hike, involving 8 hours of boating today through heavy winds. I’m not prone to seasickness but even today, I was suffering from a bit of a headache. But once we arrived on settled our stomachs a bit, we really got to enjoy Astypalea.
Although there are 12 of us on the boat, usually once we hit port we split up into smaller groups to explore the towns. It’s easier for the shop owners that way, plus everyone gets to do what they want. We ported in Skala, which had a simply adorable town. Astypalea is largely an island that is visited by Greek travelers and some European travelers. It’s a little off the beaten path and not on the normal Greek island circuit. And it feels that way in the town. There are not tourist souvenir shops on every corner or the cheap chain restaurants. Everything feels more…. real. Like real people own these business, and eat at these restaurants and shop at these stores. I love that! It feels very authentic.
Sam and I just wandered around for an hour, getting lost in the little side streets. Since the islands are very mountainous, the town streets are built into the hills, ie steep. The streets wind around these narrow little corners and sidewalks don’t exist. You will find long flights of curling stairways going up to what seems like nowhere. The houses are built terrace style, where the roof of one home is the floor of the next one. And in typical Greek island fashion, everything is white washed with blue accents. It is very picturesque!
We made it up to the top of the hill and were greeted by the ruins of an old castle. Situated on the corner in between two bays, the view from this castle was to die for. And obviously a very strategic location during warring times. You could see more islands in the distance as well as a look over the port and town. Again, our boat was towering over the next ship in the bay and it was awesome to see it from above. But we managed to get there just as the sun was peaking behind the hills, making the sunset light a nice glowing color. As we made our back down the hills through the streets, we stopped at a view shops and petted a view of the stray kitties. They’re just too cute to resist!
Pronounced “Ee-Os”, this small Greek island is known for its lively nightlife and teenage hordes of tourists. As the avid partier that I am, I was hardly excited for this little stop. We ported in the main town, but were on the water, which is a little more seculded from the party people. Most of the day drinking takes place on the beach and the night drinking occurs up the hill from the port. I wandered around the port and checked out the beach. Honestly, nothing to write home about. I took this opportunity to catch up on some free Wifi at Buon Giorno (which had a variety of delicious baked treats I took the liberty of sampling), soak in some extra rays on the front of the boat and nap. This is what a relaxing vacation on the Mediterranean all about, right?
The largest of the islands in the Cyclades chain, Naxos has a beautiful skyline with its towering volcanic mountains and fertile slopes. It is also one of the view islands that can support its economy without tourism. It exports large amounts of potatoes, olives, grapes and lemons to bolster its people. However, tourism has grown recently increasing the amount of visitors.
We ported right in the center of the main town, Naxos town. When you come into the port, you are greeted right away by the ancient ruins of the Gate of Apollo. Standing formidably on the wind swept corner of the island, these impressive pillars were once intended to be the entrance to a great temple for the Greek god Apollo. However, construction was never completed on the site and what remains is on the entrance. Hordes of people come for the sunset, as you can get a lovely picture of the sun in between the arches, but its worth a visit during the day to. With free admission, there’s no point in not checking it out!
Also when you arrive, you will see a fortified castle on the top of the hill overlooking the town. On the other end of the main drag from the gate of Apollo, there is both an archaeological museum and castle tour you can opt for. I did neither, choosing to just wander my way up to the castle. And this was the best experience of all, because the old town market and new town market surround the slopes of the castle. The alleys and streets wind around and you stumble upon little art galleries, fabric stores, jewelry shops and clothing boutiques.
I was particularly enamored with this town at night. I walked through the same market track as I did during the day, but it looked completely different! All of these little restaurants had opened up, putting tables out in the streets and these secret patios I hadn’t noticed before were now packed with talkative and hungry guests. As with most Greek islands, night time is when the cities really come alive. People of all ages were out walking around, shopping, eating dinner, snacking on ice cream cones and simply enjoying their time. These narrow alleyways were now vibrant and well-lit, with all the merchandise hanging out in the street for you to see. It was really quite charming, and would definitely entice me to come back here.
Another large island in the Cyclades chain, Paros is a nearby neighbor of Naxos. After 2 weeks touring the Greek islands, the islands and towns are starting to blur together. We stopped for a beach afternoon in Alika, and then ported in Parikia for the night. Alika was a tiny spot, good for the beach but not much else. But the sand bottom beach and gold Mythos beer were a nice diversion from the windy afternoon. They we scooted around the other side of the island for the night.
There aren’t any major tourist sites in Parikia, but it does have a lively restaurant street and shopping area (much like the rest of the islands). We had a lovely pizza dinner on the water front watching the sunset. With 12 people barreling into town off the tender, it was quite a site to see.