Five days is the ideal amount of time for Astypalaia. It is enough to see everything — every village, the best beaches, the boat trip, the castle at sunset — without rushing. It is also enough to do nothing at all on one of the days, which is, frankly, what Astypalaia is really for.
We wrote this itinerary based on 25 years of local knowledge. The restaurant recommendations, the timing, the warnings about dirt roads — all of it is real.
🚗 Vehicle recommendation for 5 days
- Days 1, 5: No vehicle needed — walk everywhere in Chora
- Day 2: No vehicle — boat trip
- Day 3: 4WD essential (Vatses, Kaminakia dirt roads)
- Day 4: Any car or scooter to Maltezana; 4WD if going to Vathy
- Best overall: Suzuki Jimny or Dacia Duster for the full 5 days — you'll be glad on Day 3
Morning: Arrival
Whether you arrive by ferry at Pera Gialos or by plane at Maltezana airport, your first view of Astypalaia will be the Chora — white houses cascading down a hillside, crowned by a 13th-century Venetian castle. It is one of the most dramatic first impressions in the entire Aegean.
Check into your accommodation. We recommend staying in Chora itself — the location is perfect, and the walks are everything. The best views are from the rooms overlooking the Kastro.
Afternoon: Walk through Chora
Chora is made for wandering. Start at the port area of Pera Gialos, walk through the narrow alleys past the bougainvillea and cats (Astypalaia has an enormous cat population — they are part of the island's identity), and climb up to the Venetian Castle of Querini. Built in the 15th century, the castle is free to enter and offers panoramic views over the entire butterfly-shaped island. Two whitewashed churches sit inside the castle walls: Panagia Kastrou and Agios Georgios.
On your way down, stop at the eight iconic windmills in the central square. They are the most photographed spot on the island. One houses a library; another is the tourist information centre.
Sunset: The golden hour
Be at the castle walls at sunset. The light on the white houses at golden hour is something you will not forget. The whole of Chora turns ochre and gold. Every local knows this is the moment of the day.
- Kafeneio Apanemia — traditional meze near the castle, try the pouggia (local cheese pastry)
- Ducato di Astypalaia — directly opposite the windmills, modern Greek with local ingredients
- Meltemi — all-day café in Chora, the local meeting point
Full day: The boat trip
Book your boat trip on Day 1 immediately — spaces fill up quickly in summer. The daily trip to Kounoupa and Koutsomitis (also called Koutsomyti) departs from Pera Gialos port at approximately 10-11am and returns by 6-7pm. This is a full day on the water.
The route typically includes: Koutsomitis beach (crystal waters, great snorkelling), the dramatic Red Rock (a red-hued cliff with an underwater tunnel leading to a secret rocky pool), and Kounoupa island — an uninhabited paradise with water so intensely turquoise it barely seems real.
Multiple guides and travellers describe this as the single best thing they did in Astypalaia. We agree. Do not skip it.
How to choose a tour
There are several operators. The larger boats take 30-40 people. The semi-private yacht options (Astypalaia VIP Yachting being the most recommended) take fewer than 15 people. The cost in 2024 was approximately €100-130 per person including lunch and drinks. The extra cost for fewer people is worth it.
- Antikastro (Pera Gialos) — the most consistently praised restaurant on the island. Views of the harbour, fresh fish, excellent service. Book ahead in summer.
- Akti (near the port) — elegant setting with private balconies, each with its own sea view. Best just before sunset.
This is the 4WD day
Today you need a proper 4WD — no exceptions. The Suzuki Jimny or Dacia Duster is what you want. The roads to Vatses and Kaminakia are rough dirt tracks that are genuinely impassable for regular cars and challenging even for smaller SUVs.
Morning: Vatses Beach
Leave early — ideally before 9am. Drive west from Chora, following the island road, then turn onto the dirt track for the last 4km to Vatses Beach. Take it slow on the rough section. Arriving early means you may have the entire beach to yourself. The cliffs, the colour of the water, the silence — this is Astypalaia at its most raw and beautiful.
There is a beach bar at Vatses. Order a coffee and sit with it. You earned the drive.
Midday: Drive to Kaminakia
From Vatses, continue south to Kaminakia Beach — another ~6km of dirt road. This one has the best taverna on the island. Taverna Kaminakia serves organic food, fresh seafood, natural juices. There are a few swings for children. The beach itself is pebbly but the water is extraordinary. Many visitors consider this the single best beach on the island.
Afternoon: Relax
Stay at Kaminakia for the afternoon. The drive back to Chora takes about 30 minutes on the main road (the return route avoids the worst of the dirt track).
Morning: Steno Beach
Drive east from Chora. Your first stop is Steno — the beach at the island's narrow isthmus, the "butterfly's body." From here you can see both sides of the island simultaneously. The canteen Kantina Steno serves excellent traditional food directly on the beach. Swim here and take your time.
Midday: Maltezana (Analipsi)
Maltezana is the island's second village, 9km east of Chora. It has a small harbour, fishing boats, a laid-back atmosphere, and excellent tavernas. Stop at Almyra restaurant in the quiet port — the tuna tartare is extraordinary, and many visitors rate it as the best meal of their trip. Walk along the waterfront afterwards.
Near Maltezana, explore the archaeological site of the ancient Roman baths (Talaras Baths) — mosaics dating back to the 2nd-4th century AD, remarkably well preserved and freely accessible.
Afternoon: Blue Harbour & Vathy (optional)
Just before Maltezana on the narrow peninsula hides Blue Harbour (Ble Limanaki) — a collection of tiny, private coves with extraordinary water. Perfect for an afternoon swim away from everyone.
If you have a 4WD, continue east to Vathy — the most remote village on the island, at the end of a rough dirt road. The turquoise lagoon at Vathy looks impossible. The Galini taverna, run entirely by Mrs. Maria herself, serves the freshest fish on the island with local ouzo. No menu — you eat what was caught that morning.
- Almyra (Maltezana) — the tuna tartare is exceptional
- Galini (Vathy) — legendary local taverna, self-service, run by Mrs. Maria alone
- Marinos (Maltezana) — beautiful café, excellent cakes and coffee
Morning: Chora one more time
Your last day. Walk up to the castle early, before the heat and the other visitors. The morning light on Chora is different from the sunset — cooler, bluer, quieter. Have a coffee at Kafeneio o Mouggos, a traditional kafeneion that doubles as a small local culture museum. The owner speaks with history and nostalgia in equal measure.
Walk through the alleys one more time. Buy local honey — Astypalaia honey is exceptional, produced from the wild herbs that cover the hillsides.
Afternoon: Agios Konstantinos
For your last swim, go to Agios Konstantinos Beach — 7km south of Chora, accessible on any road. Sandy, calm, beautiful. The white chapel on the hillside to the right. The natural underwater springs that create a jacuzzi effect on the left. A taverna and sunbeds. The perfect last day beach.
On the way back, stop at Livadi if you haven't seen it — the most popular beach village on the island, 2km from Chora, with several excellent tavernas and bars right on the waterfront.
- Agoni Grammi — great traditional taverna by the windmills, consistently excellent
- Castro Bar — right under the castle walls, best sunset cocktails on the island
- Archipelago — local sweets and views of Chora at sunset
Best restaurants — the complete list
Based on consistent recommendations across multiple independent sources and our own 25 years on the island:
- Antikastro (Pera Gialos) — the best overall. Fresh fish, harbour views, lovely staff. Book ahead.
- Almyra (Maltezana) — best tuna tartare on the island. Quiet port setting.
- Galini (Vathy) — most authentic experience. Mrs. Maria, no menu, what was caught today.
- Taverna Kaminakia (Kaminakia beach) — organic food at the island's best beach.
- Akti (Pera Gialos) — most elegant setting, private balcony tables over the water.
- Kafeneio Apanemia (Chora) — best meze and local specialties near the castle.
- Ducato di Astypalaia (Chora) — modern Greek opposite the windmills.
- Kafeneio o Mouggos / Oi Myloi (Chora) — traditional all-day kafeneion, local atmosphere.
- Agoni Grammi (Chora) — reliable, good value, traditional Greek food.
- Castro Bar (Chora, near castle) — the only place for a sunset cocktail.
What to order: marinated octopus, zucchini balls (kolokythokeftedes), shrimps saganaki, local feta with sesame and honey, grilled lamb or chicken on the spit, stuffed aubergine, fresh fish of the day. Almost everything served in Astypalaia is local and organic — the honey, the vegetables, the olive oil.
Practical information
- Best time to visit: Late May-June or September. Fewer people, same great weather, lower prices. July-August is peak season — more crowded (relatively speaking), higher prices, book everything far in advance.
- Getting around: Hire a vehicle. The island has a small electric bus (AstyBus, on-demand via app), but it won't get you to the best beaches. A 4WD for 2-3 of the 5 days is ideal.
- Cash: Bring cash. Not all tavernas (especially remote ones) accept cards.
- Weather: Average 20-25°C in summer. Wind can be strong (Meltemi from the north). Sea temperature 23-28°C from June to October.
- Population: Around 1,300 permanent residents. In August this can rise to 5,000-6,000. Outside August, the island is remarkably quiet.
Planning your 5 days?Start with the vehicle.
For this itinerary, we recommend the Suzuki Jimny or Dacia Duster. Free delivery to your hotel, airport or port. Secure booking needed.