Great Places Wrong Season
Everything here is worth going to. None of it is worth going to in December or January — and the reasons are written down so they can be challenged.
Not “bad places” Reasons given Argue one back in
Not "bad places"
Everything here is worth going to. None of it is worth going to in December or January. If we ever do this trip in summer instead, this list becomes the itinerary.
🇬🇷 The Greek islands
Santorini, Mykonos, and the Cyclades
The islands run on a summer season. Outside it, ferry schedules thin out dramatically, and a large share of hotels, restaurants, and tour operators simply close for the winter. Weather is windy and wet, and swimming is out of the question.
The deeper problem: a cancelled winter ferry can strand you for a day or more, which is a genuine risk on a fixed two-week schedule.
Crete
Large enough to stay open year-round, and Chania and Heraklion are real cities rather than seasonal resorts. Ruled out anyway on geography: it is an extra flight or a long overnight ferry from Athens, for a place whose main draws — beaches, gorge hiking, coastal driving — are all warm-weather activities.
🇮🇹 Coastal and northern Italy
Cinque Terre
The same seasonal shutdown as the Greek islands, in a smaller space. Many restaurants and guesthouses close, the coastal walking paths are frequently shut for winter weather and landslide risk, and the villages are cold and quiet. The appeal is warm-weather village-hopping and swimming.
Amalfi Coast and Capri
Sorrento stays partly open, but Positano and Capri largely close down, and the boat connections that make the coast work are reduced or suspended. Naples and Pompeii cover the same region far better in winter.
🇬🇷 Mainland Greece beyond Athens
Delphi and Nafplio
Both lovely, both wrong for this trip. Delphi is an outdoor mountain site — spectacular in clear weather, miserable in cold rain, and a long day trip from Athens either way. Nafplio is a charming seaside town that is very quiet in winter.
The real reason: with two weeks and teenagers, these are the weakest cards in the deck. Athens carries Greece on its own.
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