06/14/2026
“A client asked me a great question this week…”
‘Why should I book my winter trip now instead of waiting for Black Friday?’
It’s a fair question , especially when it’s hot outside and March feels far away.
But here’s the reality I’m seeing every day as I quote winter packages:
• Prices have already increased, even in the last few weeks
• With Cuba closed this winter, demand is shifting fast to Mexico, DR, and Jamaica
• Inventory is tightening earlier than usual
• Black Friday doesn’t bring back sold‑out rooms or ideal flight times
• And many winter packages can’t be repriced later without losing your deposit
Could prices go down in a sale? Sure, it can happen.
But right now, the trend is the opposite, and waiting often means paying more or settling for what’s left.
Booking early isn’t about chasing a deal.
It’s about locking in the resort, room, and flights you actually want before everyone else starts thinking about winter.
If you’re dreaming of palm trees next March… now’s the time.