Greek Island Hopping Challenge

A 7-day Greek island sailing holiday itinerary. 

Best months: May–June or September for warm weather and fewer crowds.

Day 1 — Athens → Kea

Sailing: ~4 hours

Onshore activities

Wander the hilltop village of Ioulida

Visit the ancient Lion of Kea

Sunset drinks in the harbour at Vourkari

Swim at Otzias Beach

Evening vibe

Very relaxed and authentically Greek — a soft landing after arriving in Athens.

Day 2 — Kea → Kythnos

Sailing: ~3 hours

Onshore activities

Bathe in the natural thermal springs at Loutra

Hike to the double-beach at Kolona

Paddleboard or kayak around sheltered bays

Tavern dinner by the water

Kythnos is much quieter than Santorini/Mykonos and ideal for swimming days.

Day 3 — Kythnos → Syros

Sailing: ~4 hours

Onshore activities

Explore elegant Ermoupoli with its pastel mansions

Climb to Ano Syros for panoramic views

Try local loukoumi sweets

Optional winery visit

Syros is one of the most underrated islands in the Cyclades — cultural, stylish, and far less touristy.

Day 4 — Syros → Paros

Sailing: ~4–5 hours

Onshore activities

Explore Naoussa’s fishing harbour

Windsurfing or kitesurfing

Beach afternoon at Golden Beach

Cycladic cooking class

Sunset cocktails overlooking the marina

Paros gives you the classic Greek postcard experience without Mykonos prices or crowds.

Day 5 — Paros → Naxos

Sailing: Short hop (~2 hours)

Onshore activities

Hike mountain villages like Halki or Apeiranthos

Visit the Temple of Demeter

Try local cheeses and kitron liqueur

Windsurfing at Mikri Vigla

Sunset at the Portara ruins

Naxos is brilliant for food lovers and active travellers.

Day 6 — Naxos → Sounion

Longer sailing day: ~6 hours

Onshore activities

Swim beneath the cliffs

Visit the spectacular Temple of Poseidon

Watch sunset over the Aegean

One of the great sailing arrivals in Greece.

Day 7 — Sounion → Athens

Sailing: ~4 hours

Optional final activities

Acropolis visit

Rooftop dinner in Plaka

Athens food tour

National Archaeological Museum

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