10:00

Chora and the medieval quarter

Set aside about two hours to explore the alleys of Chora on foot, among whitewashed houses, stairways, and views over the harbor: shoes with good grip are useful because the route can be steep and uneven. Start from the center of the village and make your way slowly toward the upper part, stopping to take in the compact layout of the quarter and the details of the houses. The village visit is a self-guided walk; allow around 8–18 € per person for a simple lunch nearby and check the available options on site.

After the walk, plan on a lunch break and some rest before heading up to the castle.

14:30

Querini Castle

Reach Querini Castle on foot from Chora: the short climb usually takes about 5–15 minutes, but it can be more demanding in the heat or on the steps. Set aside about an hour for the visit and the viewpoints, looking down from above at the village rooftops and the coastal landscape; respect any boundaries and be careful on uneven surfaces. Do not assume access or an entrance fee: check the latest information on official local channels; as a cautious reference, allow 0–5 € for any paid admission.

Bring water and check access conditions before climbing; the rest of the afternoon can be devoted to a break in the village.

10:00

Windmills

Spend about 60–90 minutes at the windmills and the surrounding alleys: admire the white buildings, their alignment, and the views over Chora and the sea. From the center or from the port area of Pera Gialos, you can get there on foot, keeping in mind an uphill climb; wear shoes with sturdy soles. The outdoor walk usually does not require an entrance ticket; allow around 0–5 € for a drink during the stop.

The surfaces may be exposed to the sun: bring water and sunscreen.

14:00

Panagia Portaitissa

Reach the church on foot from the windmills in about 10–15 minutes, following the lanes of Chora, and allow 45–60 minutes to visit respectfully and take in the architecture and decorations. Before entering, check for any local guidance and the latest information on access and visits on the official website or at tourist offices: opening times and conditions may vary. Budget 0–5 € for a possible offering or personal expense; for lunch nearby, allow about 15–30 € per person.

It is a place of worship: dress respectfully and ask before photographing the interior.

10:00

Archaeological Museum of Astypalaia

Spend about an hour with the collection, which helps tell the island’s long history through finds from the area and its necropolises. Take a close look at the pottery and everyday objects, useful for imagining life in ancient Astypalaia. Admission may be free or have an indicative cost of 0–5 EUR; check the official website or local authorities for opening hours, availability, and tickets.

To reach the museum, consider a walk from Pera Gialos harbor; if you are coming from Chora, allow about 10–15 minutes on foot, downhill.

12:00

Pera Gialos

From the museum, reach the seafront with a walk of just a few minutes and take your time exploring the harbor, watching the boats and the houses climbing up toward Chora. You can stop for a fish or meze lunch in a taverna, with an estimated cost of 15–30 EUR per person, then enjoy a stroll along the coast and a coffee break, about 3–7 EUR. Leave the afternoon free to relax on the waterfront and head back toward the harbor for dinner: expect roughly 20–40 EUR per person, depending on the venue and the dishes you choose.

The route between the two stops is short, but the paving can be uneven; comfortable shoes and sun protection are useful.

10:00

Livadi Beach

Spend the morning at Livadi: pick a comfortable spot on the beach, take a swim, and set aside time to relax while taking in the coastline and the view toward the town. Allow about 3–4 hours in total; beach access is usually free, while any food, drinks, or services are paid separately, typically 3–10 €.

Bring water, a hat, and sunscreen; check on site for the availability of shade and facilities.

16:30

Agios Konstantinos Beach

After a lunch break and some rest, head to Agios Konstantinos by car or taxi: allow roughly 10–20 minutes for the transfer, depending on the road and your departure point. Spend the afternoon here alternating between a swim and some time by the shore, keeping in mind that accessibility and facilities may vary; beach access is generally free, while a taxi ride may cost around 8–18 € each way.

Before leaving, check road conditions and arrange your return if you are relying on a taxi; bring water and everything you need for your stop.

10:00

Steno Beach

Reach the beach by car or taxi: from Chora the trip is short, but the actual time depends on the road and your starting point; check in advance for any bus services as well. Set aside about three hours for swimming and relaxing, taking in the shape of the channel and the coastline; bring water, sun protection, and something for shade, as facilities and shelter can vary. Beach access is usually free, while an umbrella or sunbed may cost around 10–25 € for a pair.

If you are using public transport, check the updated schedules and plan your return before settling in at the beach.

14:00

Maltezana (Analipsi)

Head to Maltezana by car or taxi, taking only a few minutes; allow a little extra time for parking and local traffic. Spend about an hour walking along the seafront and the small harbor, then stop for lunch or a coffee: a simple meal may cost around 12–25 € per person, depending on your choice and the venue. In the late afternoon you can relax along the waterfront and stay for dinner, budgeting about 20–40 € per person; check the official website or the operators’ updated channels for any service hours and seasonal availability.

Bring cash as an alternative to card payments, and ask for prices before ordering, especially for fish and dishes sold by weight.

10:00

Talara Baths

Reach the Maltezana area by car or taxi and set aside about 45–60 minutes for the Roman bath ruins, known for their floor mosaics: take a close look at the figurative and decorative patterns without crossing the marked areas. Then stop for lunch in Maltezana or along the way; as a rough guide, expect 15–30 € for a simple meal, and check accessibility, any entrance fee, and official information on the website before your visit.

The island’s roads can be narrow: allow extra time for transfers and do not rely on unverified schedules.

14:00

Vathy Bay

From Maltezana, reach Vathy by car or taxi, allowing roughly 30–45 minutes depending on the route and road conditions. Spend the afternoon on a leisurely walk along the bay and a stop to admire the inlet; for a drink or snack, expect around 4–10 €, while a meal may cost roughly 15–30 €. Head back while there is still enough daylight, and arrange the taxi in advance if you are not driving.

Bring water and shoes suitable for uneven surfaces; services and availability may vary by season.

10:00

Dragon Caves (Dracos)

Board at Pera Gialos and reach the cave by sea, allowing about 45–60 minutes of sailing depending on the boat and route. Spend about an hour visiting from the sea and, if conditions allow, enjoying a swim nearby; do not enter caverns or passages without the crew’s guidance. For a private trip or combined excursion, expect roughly €25–60 per person, to be confirmed with the operator.

Agree before departure that the cave is included on the route to the islets, and ask whether mask and snorkel are provided.

12:00

Boat trip to Koutsomitis and Kounoupa

Continue on to the islets, allowing around 5–6 hours for sailing and stops: the program may include swimming, snorkeling, and a break for lunch as a packed meal or on board. Bring water, sun protection, and suitable shoes for any rocky sections; follow the crew’s instructions and the sea conditions. Return to Pera Gialos is expected roughly between 18:00 and 19:00; a shared excursion may cost about €35–70 per person, while drinks and meals may be extra.

Route, duration, stops, and departure vary: check availability, price, and details directly with the operator before planning your day.