Quick verdict: Greece needs island-hopping planning + ferry coordination. Santorini sells out fast. Refined across 3 personal Greece trips.
8-step planning checklist
1Decide islands + duration
Classic: Athens + 2-3 islands (Santorini + Naxos + Mykonos or Milos). 10-14 days for full circuit.
2Book flights 2-4 months ahead
From US: $700-1300. From Europe: EUR 100-400. Athens ATH or Santorini JTR. Aegean Airlines internal.
3Book Santorini hotels 6-9 months ahead
Premium caldera hotels (Canaves, Mystique) book 6-12 months ahead. Mid-range 4-6 months. Sells out fast.
4Book Greek island ferries 1-2 months ahead
Use Ferryscanner or DirectFerries. Sea Jets + Blue Star reliable. Window seat preferred.
5Reserve Santorini sunset dinner 4-8 weeks ahead
La Maison + Pelekanos + Lauda all need ahead-booking in season. Iconic experience.
6Book Milos boat tour to Kleftiko
Boats limited + book 1-2 weeks ahead. Adamantas boat operators. Most-iconic Milos experience.
7Apply for visa (if needed)
Schengen visa-free 90 days. EU ETIAS launching 2026.
8Get travel insurance + Greek phrases
Travel insurance covers ferry delays. Greek phrases basic. ATM-friendly bank for cash.
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Updated 2026. Some links on Packzup are affiliate links.
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Written by
John Morrison is the founder and lead travel writer at Packzup. Over the past decade he has explored destinations across Africa, the Americas, Asia, Europe, the Middle East, and Oceania — always self-funded, never on a press trip.