Winter Sun

The shortlist

Estimated cost is a week for two — flights from a mid-US hub, mid-range stay, food. It's a planning number, not a quote. Verify before you book.

Destination	Best window	Typical high	Est. week for two	The honest note
Puerto Vallarta, MX	Nov–Apr	82°F / 28°C	$1,300	Dry season starts Nov. Best value-per-degree in North America.
Oaxaca coast, MX	Nov–Mar	85°F / 29°C	$1,150	Cheaper and quieter than Vallarta. Harder to reach.
Aruba	Year-round	84°F / 29°C	$2,200	Outside the hurricane belt. Reliably dry, reliably windy.
Curaçao	Year-round	84°F / 29°C	$1,900	Same weather as Aruba, fewer resorts, better food.
Canary Islands, ES	Nov–Mar	72°F / 22°C	$1,400	Europe’s winter sun. Warm, not hot. Long flight from the US.
Phoenix / Scottsdale, AZ	Nov–Apr	72°F / 22°C	$900	No passport, no jet lag. The snowbird default for a reason.
Puerto Rico	Dec–Apr	83°F / 28°C	$1,500	No passport needed. Peak-season pricing bites in Feb.
Belize	Dec–Apr	82°F / 28°C	$1,800	Dry season is genuinely dry. English-speaking.

Weather figures are typical seasonal highs, not forecasts. Costs are researched estimates and move constantly — treat them as a starting point for your own pricing.

When to actually book

The single most expensive mistake in winter sun is booking in December for December. Peak-season Caribbean and Mexico inventory prices on scarcity, and the scarcity is real.

Aug–Sep: best window for December and January travel. Airlines haven't loaded holiday premiums on every route yet.

Oct: still fine for February and March. The sweet spot for shoulder-season value.

Nov–Dec: you are now buying at peak. Go somewhere less obvious instead of paying the premium — Curaçao over Aruba, Oaxaca over Vallarta.

Jan: genuinely good last-minute deals appear for late April and May, once demand craters.

The shortlist

When to actually book

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