One of the most common travel questions we hear is, “How far in advance should I book?”
And unfortunately, there isn’t one magic number.
A quick weekend trip to Florida requires a very different timeline than an Antarctica cruise, a summer trip to Europe, or a Christmas vacation. In our experience, the best time to book depends on where you’re going, when you’re traveling, and how important it is to get exactly what you want.
In our experience, booking early usually gives you the best combination of pricing, availability, and choice. That doesn’t mean you need to book every trip the second it crosses your mind, but if you know where and when you want to travel, there’s usually very little benefit to waiting just for the sake of waiting.
And if you’re planning to use points and miles? We’re even bigger advocates of booking early. Award availability is limited, and some of the best redemptions disappear quickly.
Here’s how we approach it!
Start With Your Dates
Before worrying about flights or hotels, ask yourself one question: How flexible is this trip?
If you can travel almost anytime in October and don’t care whether you leave on a Tuesday or Thursday, you have room to wait and compare prices.
If you’re traveling for spring break, Christmas, a honeymoon, or a specific event, that changes everything.
We recommend booking earlier when:
- Your dates cannot change
- You’re traveling during a holiday
- You need multiple hotel rooms
- You want a specific resort or room category
- You’re traveling with a larger group
- You’re visiting during peak season
This is especially important for milestone trips. If you’ve dreamed about a specific overwater bungalow in Bora Bora for your honeymoon, we would not wait until three months before departure and hope it’s available.
The more specific your wish list, the earlier we’d start planning.
Flights
There’s a common misconception that airfare is always cheapest the moment the schedule opens. That isn’t necessarily true.
For a normal domestic trip, we generally start watching flights a few months before departure. For international trips, we start looking much earlier.
Airfare changes constantly, so we prefer to start tracking prices rather than blindly booking on a specific day!
Google Flights is one of our favorite tools for this. Set a price alert for your route, and you can watch the fare without searching every morning.
And remember to compare the total trip, not just the cheapest ticket. We’d rather pay a little more for a reasonable nonstop flight than save $75 and add two connections and eight hours to our travel day!
Using Points for Flights?
This is where our advice changes significantly.
If we’re booking a flight with points or miles, we usually want to start looking as soon as the airline’s award calendar opens, which is often around 11–13 months before departure.
Unlike cash airfare, where prices can rise and fall over time, award availability is limited. There may only be a handful of seats available at the lowest redemption rate, especially in business or first class. Once those seats are booked, you could end up paying significantly more points or losing the option altogether.
This is especially important if you’re:
- Traveling during peak season or a holiday
- Booking multiple award seats
- Trying to fly business or first class
- Looking for a specific nonstop route
- Using airline transfer partners to maximize your points
Can great award availability pop up closer to departure? Absolutely. We’ve seen some incredible last-minute options. But we consider that a bonus, not a strategy.
If we know we want to take a specific trip and use points to get there, our preference is almost always to book as soon as good award availability opens!
Hotels and Resorts
Hotels are where waiting can really hurt you, especially if the property itself is an important part of your vacation.
For a normal city trip with dozens of good hotel choices, booking several months ahead is often fine.
Luxury resorts are different.
If you want a specific resort, suite, view, or room configuration, we recommend booking much earlier. This is especially true for destinations like the Caribbean, Hawaii, Bora Bora, and popular European resort areas.
As a general rule, we’re comfortable booking hotels as soon as our travel plans are firm, especially when the rate has flexible cancellation. Booking early gives us access to more room categories and rates, and if we’re able to cancel or modify the reservation, we can always keep an eye on pricing afterward.
And just like flights, we recommend booking especially early when using hotel points. The lowest award rates, standard rooms that can be booked with points, and highly sought-after properties can disappear months in advance.
Many major hotel programs open their calendars roughly 12–13 months ahead, and for a bucket-list property or peak travel dates, we’ll often start looking as soon as that calendar opens!
Cruises
Cruising is one area where we tend to recommend planning farther ahead.
Cruise lines release itineraries well in advance, and booking early can give you access to better cabin selection and sometimes stronger pricing or promotions.
For most cruises, we’d start looking at least 12 months ahead – maybe even earlier!
Think:
- Alaska during peak summer
- Mediterranean cruises in summer
- Christmas market river cruises
- Antarctica expeditions
- Small ship and luxury cruises
- Holiday sailings
If you’re particular about your cabin, this matters even more.
Maybe you want a specific suite category, connecting rooms for a family, or a balcony in a particular location. There may only be a handful of those cabins on the entire ship.
This is especially noticeable on smaller luxury and expedition ships. A vessel carrying a few hundred guests simply doesn’t have thousands of cabins to choose from.
For a major cruise, starting 12 to 18 months ahead is not unreasonable at all.
Big Trips
Some vacations are simply more complicated than others.
If you’re planning a two week trip through Europe with four hotels, train tickets, restaurant reservations, tours, and several flights, we’d much rather have nine months to plan than nine weeks.
We’d also start early for destinations or experiences with limited availability.
Examples include:
- Antarctica
- African safaris
- Bora Bora
- Galápagos
- European Christmas markets
- Major sporting events
- Popular national parks during peak season
You may be able to plan some of these trips at the last minute, but your choices become much more limited.
For bucket list trips, we generally recommend beginning the planning process 12 to 18 months in advance.
That doesn’t mean every single restaurant reservation needs to be made a year ahead. It means getting the major pieces in place early, then filling in the details as the trip gets closer.
When Waiting Makes Sense
We generally prefer booking early, but there are situations where waiting can pay off — especially if you’re extremely flexible!
Maybe you don’t care where you go and an incredible flight deal pops up to Portugal. Maybe a cruise line releases a last-minute offer and you can travel with very little notice. Maybe you find an unexpectedly good resort rate in the Caribbean.
That’s when flexibility becomes your advantage.
But we wouldn’t intentionally wait on a trip we already know we want to take just because a better deal might appear later.
And we’re especially cautious about this strategy when using points. Great last-minute award availability does occasionally appear, but we wouldn’t count on it. If you find a great redemption for a trip you know you want to take, booking it early is usually our preference.
Our Booking Rule
So, how far in advance should you book a trip?
Our general rule is pretty simple: if you know you want to take the trip, start planning early.
We’ve found that booking ahead usually gives us the best combination of pricing, availability, and choice. For a simple domestic getaway, you may only need a few months. But for international trips, cruises, luxury resorts, peak-season travel, and bucket-list vacations, we’re very comfortable planning a year or more in advance.
For award flights and hotels (those booked with points & miles), we’ll often begin searching as soon as the booking calendar opens — typically around 12–13 months out. The best award availability can disappear quickly, so waiting can mean spending significantly more points or settling for less convenient options.
Our biggest advice is not to confuse booking early with paying early. Depending on what you’re booking and the cancellation terms, you may be able to reserve parts of your trip well ahead of time without making everything fully nonrefundable from day one.
That’s why we’d rather secure the flight, hotel, cruise cabin, or award redemption we want and continue monitoring our options than wait and hope something better comes along.
Because planning ahead gives us something we value just as much as a great price: choices.
Better flight times. Better hotel rooms. Better cruise cabins. Better award availability. Better tours. And far less stress trying to piece together whatever is left.
