It's the second week of October, and my phone has started ringing with the same question: "Where should we go for the holidays?"
Here's the honest answer I give every client: December is the most rewarding month to travel well — and the most punishing month to plan late. The best rooms, the best villas, the best guides get claimed early. If you're still deciding, this is your moment. Here's my shortlist.
The Maldives: Barefoot Luxury at Its Peak
December sits squarely in the Maldives' dry season — calm seas, clear skies, visibility that makes divers weep. This is the month the overwater villa earns its reputation: breakfast delivered by boat, afternoons that dissolve into turquoise, and service so intuitive it feels like mind-reading.
I've placed clients at a dozen Maldivian properties — the right island match matters more than the star rating.
European Christmas Markets: Vienna and Prague
If warmth isn't the goal, magic is. Vienna's Christkindlmarkt in front of the Rathaus is the most beautiful Christmas market in Europe — full stop. Glühwein, roasted chestnuts, hand-blown ornaments, and a backdrop that looks like a film set.
Pair it with Prague for a two-city festive run, or fold it into a Danube river cruise sailing — the Christmas market cruises are among the most requested trips I plan each year, and the best cabins sell out by early fall. If this is calling to you for 2026, we need to move fast; if it's for 2027, you're right on time.
Safari Season: Tanzania and Kenya
December is the start of the short rains' end and the calving season's approach — green landscapes, dramatic skies, and far fewer vehicles than the summer migration crush. The Serengeti and the Maasai Mara in December feel private in a way July never does.
This is also one of the best-value luxury safari windows of the year: several top lodges run seasonal rates before the peak festive fortnight. My safari desk works with the finest operators on the continent — private vehicles, expert guides, camps positioned for the wildlife, not the crowds.
A Private Caribbean Villa: St. Barths and Anguilla
For the "we just want our own space" holiday, nothing beats a fully staffed private villa. St. Barths for the scene, Anguilla for the beaches — both deliver the kind of Christmas where the biggest decision is pool versus ocean.
Villas with full staff (chef, housekeeper, concierge) for the Dec 20–Jan 3 window are typically committed by October. There are still gems available, but the selection narrows every week.
Why Now, Not November
Luxury holiday travel rewards the decisive. The properties worth staying at don't discount for the holidays — they sell out. Every year I watch clients get their first choice in October and their third choice in November.
If any of these sparked something, let's talk this week. Tell me who's traveling and what the holidays should feel like — I'll build the rest around you.
Ready to plan your holiday escape? Let's start the conversation —
