How Far in Advance Should You Start Planning a Luxury Trip?

Honeymoons and Milestone Trips: 9–12 Months in Advance

If you’re planning a honeymoon, anniversary trip, or major birthday celebration, give yourself plenty of lead time. These trips are often once-in-a-lifetime — and you don’t want to be choosing from what’s left.

Many couples are surprised to learn that premium resort categories (like overwater villas or beachfront suites) can book up a full year in advance, especially in popular destinations like Bora Bora, the Maldives, or the Caribbean.

Best time to start: As soon as you’ve set a date or window. Even 12–14 months out isn’t too early if you’re eyeing a top-tier property.

Holiday Travel: 10–12 Months in Advance

Thanksgiving, Christmas, New Year’s, and Spring Break are some of the most in-demand times of the year. Families travel together, school breaks align, and many of the world’s best resorts fill up — fast.

If you want your first choice of destination and room category, holiday travel is something to book nearly a year ahead. Pricing tends to increase significantly as availability shrinks.

Best time to start: The earlier the better — January or February for that year’s December holidays is ideal.

Destination Weddings: 12–18 Months in Advance

If you’re planning a wedding abroad, you’ll want to begin the process even earlier. Between coordinating group travel, securing a venue, and working through legal logistics, there’s a lot to line up. I guide couples through this process from the very beginning — from choosing the destination to handling RSVPs and room blocks.

Best time to start: As soon as you're engaged or have a season in mind.

Multi-Generational or Group Trips: 8–12 Months in Advance

When you're coordinating multiple households — especially with different travel needs, ages, and preferences — time is your best friend. The earlier we start, the more likely we are to find a property that fits everyone comfortably. Early planning also gives guests time to budget, request time off, and prepare.

Best time to start: 9 months out (minimum), earlier if traveling during a school break or holiday.

Bucket-List Trips and Cruises: 12–18 Months in Advance

Think: African safaris, Arctic expeditions, around-the-world cruises, or in-demand luxury rail journeys like the Venice Simplon‑Orient‑Express. These are trips that operate on limited departure schedules and tend to sell out well in advance.

Best time to start: A year or more ahead — and yes, you’ll thank yourself later.

Last-Minute Trips: 1–3 Months in Advance (But Let’s Be Honest…)

Yes, last-minute luxury travel is possible. But it’s a different experience.

You might have to compromise on room type, exact location, or travel dates. You’ll need to be more flexible, and pricing may reflect higher demand. That said, I’ve helped clients pull off gorgeous, short-notice escapes when timing worked out just right — but it’s always a little more puzzle-piece planning.

Best time to start: Now. Because availability changes by the day.

Why Planning Early Makes All the Difference

When you plan ahead, you get:

• First pick of resorts, suites, and experiences

• Better airfare options and more reasonable pricing

• Time to coordinate upgrades, perks, and special touches

• Less stress and more time to actually enjoy the planning process

My role is to take that lead time and use it to your advantage — securing the details that make your trip unforgettable.

Let’s Talk Timing

If you’ve been thinking about your next big trip, don’t wait for things to “settle down” or for a better time to appear. The best time to start is now — even if we’re just getting the conversation started.

Want help creating a timeline or talking through ideas? I’d love to walk through it with you.

One of the most common questions I get is, “How far in advance should we start planning our trip?” And the honest answer is: it depends.

Some destinations and travel styles book up months — or even a year — in advance. Others leave a little more flexibility. But when it comes to luxury travel, early planning isn’t just helpful. It’s what allows you to access the best rooms, flights, experiences, and perks without compromising.

Here’s a breakdown of what I recommend based on the type of trip you’re planning, and why sooner really is better in the world of elevated travel.