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Tips for Planning a Vacation 1-6 Months Out

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Planning a perfect trip requires putting in some time to research your best options, from flights to hotels and local activities. As TPG Contributor Richard Kerr explains, the earlier you start the more flexibility you have and the more opportunities to earn the points and miles you’ll need. Keep reading for his tips on making the most of those 1-6 months before you trip.

Planning a vacation is an exciting endeavor for some, while for others it results in a good deal of stress. In any case, the effort pays off once you arrive at your destination by award flight and start enjoying the hotel stay you redeemed with points. Today, I’ll continue from looking at long-term vacation planning and discuss the topics you should think about in the mid-range timeframe — or between one and six months from your intended departure date.

Of course, not everyone’s life is conducive to planning vacations far in the future, nor is everyone able to plan last-second. Regardless of whether you can plan six months or one month out, here’s what you should think about as the months count down:

Six Months Out

Depending on your personal situation, there are lots of details to iron out at this stage. If you aren’t a long-term planner and haven’t decided on the specifics of your trip, take care of the mundane yet necessary tasks associated with leaving town. If you have kids, the school calendar is always something to consider. Think about a parental consent form if both parents aren’t traveling with the child. If family or friends are watching the kids, consider a in loco parentis. Six months away from your travel date is the time to look at everything from house sitters to pet sitters.

Regardless of when you can plan your vacation, there are specific steps to take. Photo courtesy of Shutterstock.
Regardless of when you can plan your vacation, there are specific steps to take. Image courtesy of Shutterstock.

Five Months Out

If you’re able to plan your trip at five months out, you likely have an idea of where you’re going and how you’re going to get there. Once the basics are decided, I spend my time around the five-month mark on arranging the specifics of my accommodations. With five months to plan your hotel, Airbnb or rental, there’s so much you can do:

  1. Attempt a status challenge or apply for a status match.
  2. Try and Best Rate Guarantee your intended hotel stay.
  3. Apply for a Barclay Arrival Plus World Elite MasterCard and redeem Arrival points for free Airbnb stays or vacation property rentals if they code as travel purchases.

In addition to offering you plenty of opportunities to maximize or otherwise enhance your accommodations, planning hotel stays five months out lets you take advantage of the lucrative nights and air mile packages many hotel chains are now offering. Starwood’s Nights and Flights package is one of the best uses of Starpoints, and the same goes for using Marriott points with Marriott’s Hotel + Air package. I look at these packages five months out for both award availability of the property and my availability, as I’ll generally be missing five to seven days of work.

Four Months Out

If you’ve reached the four-month mark and haven’t decided specifically where you’re going and how you’re going to get there, this is an important month. In fact, four months out from an intended departure date is really a special timeframe in the points and miles world. Why? That’s how long you have for points and miles to post if you complete your minimum spending for a credit card bonus. With most cards offering three months from account opening to completing the minimum spend threshold, this means your points or miles will usually post at the closing of that statement or at the beginning of the fourth month, unless you meet the minimum spending more quickly.

I've had the Alaska Airlines Visa bonus post before I received the card.
I had the Alaska Airlines Visa bonus post before I received the card.

If you’re short on points and know you’ll need another big push to reach your goal (and are fairly confident availability will be there) then four months out is really the longest I would wait to sign up for a credit card. Not all cards are created equal when it comes to bonuses posting. I’ve had my Alaska bonus post from my Bank of American Alaska Airlines Card before I even received the card in the mail. Just this past week I completed the minimum spending of my United MileagePlus Explorer Card and the bonus miles posted four days later. On the other hand, it took two months for the bonus to post with my Platinum Card from American Express.

Bottom line: If you’re planning an award trip and don’t yet have the miles, be wary of the four month mark!

Three Months Out

It’s time to decide what to do with your points and miles. If you’ve had a long-term strategy to earn points and have been watching availability, it’s time to jump on the best option you’ve found. If you’re still teetering on the edge of possibilities, get both feet wet and make a decision.

I’ve found the three-month point to be a sweet spot when it comes to award nights and flights. If you’ve been searching for award tickets or hotel nights for several months, by this time you’ll have a good idea of a program’s patterns of availability, and the results you see now are what you’re going to see in the future for the new award searchers. The exceptions to this award availability pattern are flights like Lufthansa first class, which only becomes available to Star Alliance partners 14 days before departure.

The three month point is the drop dead time to decide the specifics of your trip. Photo courtesy Shutterstock.
The three month point is the drop dead time to decide the specifics of your trip. Image courtesy Shutterstock.

Three months is the time to sit down with your travel companion, lay out your options and make a decision. If you have the ability to plan this far in advance but are wavering, know that it’s (generally) not going to get any better the closer you get to your departure date.

One to Two Months Out

Award travel aside, let’s talk about buying revenue tickets in this timeframe. Statistics suggest that roughly 60 days out is the cheapest time to buy plane tickets. If you’re looking for revenue fares, I generally see promotions appear within this timeframe. Buy too early, and the airlines aren’t yet motivated to offer lower prices; buy too late, and your carrier can charge what they want since seats are filling up.

Statistics aside, I believe airline revenue algorithms and managers have become so sophisticated that searching specific days of the week and at certain times, among other tricks, no longer unearth cheaper airfare. I stick to 60 days out and haven’t regretted my decision. What you need to know is where and how to search for your tickets. A few suggestions for one to two months out:

  • Learn to use ITA Matrix (it’s still extremely useful).
  • Know that Spirit Airlines, Southwest, Frontier, Virgin America and smaller airlines like Silver Airways are not shown on all online travel agencies. If you simply search Expedia for the best fare, you could be missing opportunities.
  • My favorite site for airfare searching is It categorizes search results with a unique “Agony” feature. Agony factors in painfully long layovers, the number of stops and price to really give you a legitimate best option.

When you find yourself near the one-month mark, your plans and reservations should be solidified and good to go. Plane tickets — either award or revenue — should be booked. You should know where you’re staying and have the best rate available booked (with Best Rate Guarantee policy hopefully tested) or your free award night booked.

I booked a suite at the Park Hyatt Dubai off of a Points + Cash rate and Diamond Suite upgrade at the 5 month point. Photo courtesy Richard Kerr.
I booked a suite at the Park Hyatt Dubai off of a Points + Cash rate and Diamond Suite upgrade at the five-month point. Image courtesy Richard Kerr.

How Much Does Time Frame Matter?

I laid out all the different actions to take and why, starting at six months and counting down to one. Is this a perfect matrix for what to plan and when? Maybe not — it depends on your situation — but it should remind you of all the logistics involved in planning a fantastic time away.

Regardless of what your lifestyle lends itself to, planning in the one- to six-month range should give you the time to find the best revenue deals, acquire the right points and find the best award availability for flights and hotels.

What do you consider when planning a vacation in less than six months?

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