What is it: A Greek island in the Aegean Sea that suffers from split personality as it belongs to the Dodecanese bunch of islands (Rhodes, Symi, Patmos, Kos etc) , but resembles the Cyclades (Mykonos, Santorini, Paros, etc.)

Why go there: To experience a basic unspoiled beautiful island still frequented mainly by Greeks, with some of the most amazing beaches and water even by Greek island standards; fantastic food; unpretentious nightlife; affordable prices; and its very own Venetian castle on top of the hill.

How to get there: By ferry boat from Piraeus in Athens (approximately 8 hours, and make sure to rent a sleeping cabin as the price difference is minimal compared to the much more pleasant experience; or by plane (approx. 50 min).

What to do: Island vacations generally follow the same daily routine which is why they are so relaxing, yet offer just enough variety on the theme (different beaches to choose from, daily trips, different restaurants, etc) to keep them interesting. You definitely need to have your own mode of transport, depending on your preference (rental car, motorbike, quad, etc). It is not a good idea to skimp on that as not having a means of independent travel would totally diminish the quality of the stay. Below is a day-by-day program:

Day 1: You will most likely arrive late afternoon on the ferryboat from Athens after doing other stops. Your rental car will be waiting at the port. Pack your stuff and drive off to your apartment or hotel to settle in, before heading out to get your bearings. Astypalaia is all about stairs and steps and going up and down…either think of it as exercise, or take your car or bike. A good place to begin exploring is the old port, the “Limani”, in the shadow of the castle. En Plo is a great place for a sunset drink and to take it all in and relax. Then, it’s a short walk up the street to Akti, one of the best if not the best restaurant on the island in terms of location, food, and staff friendliness. This is an unmissable place, but better call ahead to reserve one of the cliff-side tables.

It’s been a long day getting here, so better skip the famous Castro Bar up by the castle and get a night cap on the platea (the main square by the windmills) before retiring for the night.

Day 2: After sleeping in and a lazy morning, it is time to hit the first beach. A good one to start at and get a grilled cheese sandwich and coffee (or beer or wine, depending on your definition of an appropriate alcohol start time) is Agios Konstantinos. It is a short drive from the chora (main island town), past the village of Livadi. Spend a couple of hours there either on the beach or in the beach bar. I learned while sipping an ice coffee that the Greeks call the whistling of the bush crickets (tzitzakis or something like that in Greek) the “sound of summer”. I liked that. There are apparently also the smells of summer, like the smell of fig trees.

Next, pack and head to Kaminaki, another beach in the general vicinity, but still requiring a good 20 to 30 minutes drive on a bumpy dirt road. But it’s a drive well worth taking to this most amazing beach with sparkling refreshing water- probably one of the best beaches not only on this island but on any of the islands. And when you’ve built up a good appetite, Linda is right next door with her famous tavern and home cooked food. She might have “boiled goat” on the menu when you’re there, an island specialty  but otherwise all else is much less adventurous and good.

You can also choose to come to Kaminaki by boat from the old port in the chora.

After heading back home around 8 PM for a shower and some rest, it’s time for the night activities. Going out around 10 PM is the standard island routine. You can begin this night with apperitifs with a great view at Archipelago, before hitting the amazing little bakery that became our best friend with its fresh handmade delicacies for some snacks (Pastry Sensations, just behind the supermarket on the platea). You can also go for a souvlaki on the main street, then walk over to the Butterfly Lounge and Bar nearby for night caps and Mastika on Ice, before calling it a night.

Day 3: The routine begins again with a late start, snacking on leftovers from the bakery goods and coffee, while agreeing on the plan for the day. Drive over to the other side of the island, to Analipsi and Maltazana beach. Just before reaching Analipsi, look out for a road sign to the Blue Port (Mple Limanaki). Go there for an hour or two in this little lovely cove and beach with its blue-green waters. Next, continue to the sandy Maltazana beach for the rest of the afternoon before trying around 7 PM Astifagia, one of the most famous restaurants on the island, a short walk over the hill. Enjoy great salads, appetizers, and fish (if you want lobster, better call ahead to reserve it) in a friendly tavern atmosphere, before heading back to get some rest.

Tonight is finally the night to walk up the steep narrow paths that go all the way to the top of the hill, to the Castle and the famous Castro Bar in its shadow. It is a tough walk but definitely venture in to the hauntingly dark castle (although brightly lit from the outside) for great views before charming your way into Castro for a table and some good drinks at the most happening place on the island.

Day 4: Today, it is Plakes Beach (on the same road towards Maltazana) for a few hours followed by a sunset late lunch at Korkodilos, a casual feet-in-the sand tavern in Livadi. You must stop in one of evenings to meet Stella, who teaches at the local high school, but volunteers in the evenings (until 11 PM) at the community library that is housed inside one of the windmills. It is hard to describe this character and her tone, looks, and manner, but be prepared to be mesmerized by her as we all were. It is something to be experienced.

Butterfly Lounge and Bar again or any of the several other bars around the main platea. Or if you feel inclined, walk up all the way again to the castle to Castro Bar!

Day 5: You cannot leave Astypalaia without a visit to the spectacular beach on the nearby island of Kounoupa. You can book a day or two before via one of the agents on the platea or the limani, and the boat will take you in the morning (11 AM or 1 PM departures) to the island, drop you off on this gorgeous beach, and return to pick you up in the afternoon. There is a small beach bar that serves a very good local salad and fresh minted lemonade, which will be good enough (along with some beer and wine) to carry you through until dinner time when back on the main island.

We found that ending this trip at Akti, where we started on the first night, was the most appropriate. We thoroughly enjoyed the lobster, oysters, and other great dishes, while drinking our wine and staring at the beautiful castle reflected in the water.

It was then back to the apartment or hotel to shower, pack, and catch some sleep before catching the 5 AM ferry back to Athens. Make sure to arrange transport to the ferry in advance if you’ve already dropped off your rental car, and again to book a sleeping cabin on the ferry boat.

And this concludes one of the most relaxing island vacation you can have with the most amazing waters you can swim in and best food anywhere in the world. And all still at relatively very affordable prices in comparison to the other more trendy but super noisy and crowded islands.

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