Day 1 - Chora, the Portara and the west-coast beaches
Pick up the car at the port - we'll be waiting with your name on a sign, paperwork takes five minutes. Drive 5 km south on the main road to Agios Prokopios: wide white sand, organised beach bars, shallow entry ideal for kids. Lunch at one of the beachfront tavernas (Kavouri is a local favourite). Continue 3 km further south to Plaka - longer, less developed, peaceful naturist section at the south end. Return to Chora by late afternoon, park at the port car park (free, 5-minute walk to the old town) and watch the sun drop behind the Portara - the unfinished temple of Apollo, 2,500 years old, facing due west. It is the best free sunset on the Aegean.
Day 2 - The Tragea loop: Chalki, Filoti, Apeiranthos
The marquee Naxos drive - allow the full day. Leave Chora by 9:30 am and drive 16 km to Chalki through the Tragea olive plain, the largest in the Cyclades. Stop at Vallindras Distillery for a free kitron tasting - the Naxos citrus liqueur has been made here since 1896. Continue 9 km to Filoti, the largest mountain village: lunch under the plane trees in the main square (try the souvlaki at Babis, prices honest and portions huge). After lunch, 5 km further to Apeiranthos at 600 m altitude - marble-paved streets, Venetian towers, five small museums, and balcony tavernas with sweeping views over the eastern coast. Allow at least 2 hours here. Return via the same road or loop through Moni for a slightly different descent.
Day 3 - Mikri Vigla and Alyko (buggy day)
If you've pre-booked a buggy for today, this is the best day of the trip. If not, the car still gets you to the paved sections. Drive 17 km south to Mikri Vigla - two beaches separated by a rocky headland, one sheltered and calm, the other one of the world's premier kitesurf locations. Swim, watch the kiters, have coffee at the beach bar. Then push 6 km further south to Alyko: a cedar-scented forest tumbling down to three wild beaches. Walk through the woods to find the famous painted abandoned hotel - every surface an open-air mural, entirely unofficial and entirely breathtaking. Finish the day at Pyrgaki for one of the island's most private sunset spots. Reserve the buggy in advance - it books out fast.
Day 4 - Apollonas and the Kouros of the north
The most ambitious drive on the island - roughly an hour from Chora via Engares and Koronos, through villages so small the road narrows to the width of the car. The payoff: the Kouros of Apollonas, a 10.5-metre unfinished marble giant carved in the 7th century BC, lying in an ancient quarry above the village. It takes 10 minutes to visit and is one of the most quietly magnificent things in the Cyclades. Afterwards, seafood lunch at the small harbour of Apollonas - grilled octopus and fried squid, tables at the waterline. Return via Lionas if you want a quick, private swim on the east coast before heading back.
Day 5 - slow morning, return the car
One last swim at Agia Anna or Agios Prokopios. If you're catching an afternoon ferry, drop the car at the port - we'll take it from you dockside in under five minutes, so you can go straight to the departure hall. Flying out of JNX? Same service at the airport, no extra charge. We track your boat or flight and schedule the handover around your departure, not around our office hours. Send us your ferry or flight number on WhatsApp the evening before.