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Tips For Planning a Vacation Many Months in Advance

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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, getting started as early as six months out affords you plenty of flexibility, and many opportunities to earn the points and miles you’ll need. Read on for his tips on maximizing the six months or so leading up to your award trip.

One of the most common travel questions I get is, “I really want to visit X next summer, but tickets are so expensive. What can I do to save money or get enough points to get a free flight?” Based on how often I hear this question, I wanted to share the advice I follow when planning a vacation that is still many pages away in the calendar. I realize not everyone is able plan trips far in advance, but it’s always smart to plan ahead when you can, and you should make the most of your time to construct the perfect itinerary.

Today, I’ll begin a series on planning vacations in the long-, mid- and short-term timeframes. First up, I’ll look at planning vacations with at least six months of lead time. I’ll lay out basic points- and miles-earning strategies, cover some important items to consider when planning your itinerary and discuss actions you can take now to avoid any surprises when it comes time to board your flight.


I’m a firm believer that points and miles are a bad long-term investment. That’s why planning this far in advance of your trip is wonderful! You can select your destination and plan a credit card strategy specifically tailored to get you the right number of points in the appropriate programs to score your award flights and free hotel nights. You’ll earn and burn your points and miles like a professional and have less to worry about in case any new devaluations should hit loyalty programs before your trip.

TPG contributors have shown great examples of credit card combinations to explore Europe, East Asia, Hawaii, Costa Rica, Puerto Rico and Paris. Today, let’s look at another example: three cards that can earn you a great introductory trip to Japan from the continental US during American Airlines’ off-peak season from Oct 1-April 30.

The Hyatt Regency Hakone is set in a volcanic area 1.5 hours outside of Tokyo. Photo courtesy Richard Kerr
The Hyatt Regency Hakone is set in a volcanic area 1.5 hours outside of Tokyo.


  • American Airlines and Oneworld partners round-trip economy from the US to Japan — 50,000 AAdvantage miles
  • Japan Airlines round-trip from Tokyo Haneda (HND) to Osaka Itami (ITM) — 9,000 British Airways Avios transferred from Chase Ultimate Rewards
  • Total points needed: 50,000 AAdvantage miles and 9,000 Chase Ultimate Rewards points


  • Three nights at the Hyatt Regency Tokyo — 36,000 Hyatt points transferred from Chase Ultimate Rewards
  • Two nights at the Hyatt Regency Osaka — 16,000 Hyatt points transferred from Chase Ultimate Rewards
  • Two nights at the Hyatt Regency Hakone — 50,000 Hyatt points transferred from Chase Ultimate Rewards
  • Points needed: 102,000 Chase Ultimate Rewards points

Credit Cards and Sign-Up Bonuses

  • Citi AAdvantage Platinum Select Mastercard – Earn 50,000 miles after spending $3,000 in the first three months of account opening.
  • Chase Sapphire Preferred Card — Earn 50,000 Chase Ultimate Rewards after spending $4,000 in the first three months. You also can receive another 5,000 Ultimate Rewards for adding an authorized user in the first three months.
  • Ink Plus Business Card — Earn 60,000 Ultimate Rewards after spending $5,000 in the first three months of account opening.
  • Total sign-up bonuses (after meeting requirements): 50,000 AAdvantage miles and 124,000 Chase Ultimate Rewards after completing $12,000 in spending and adding an authorized user.

I’d recommend flying Oneworld partner Japan Airlines to Tokyo from the states rather than American. With your flight, seven nights in Japan Hyatts and an intra-Japan round-trip flight from Tokyo to Osaka, you’ll still be left with 13,000 Chase Ultimate Rewards. That’s a heck of a trip from three credit card sign-up bonuses!

Visit Japan including Osaka and Hiroshima on 4 credit card sign-up bonuses. Photos courtesy Richard Kerr
Visit Japan, including Osaka and Hiroshima, on four credit card sign-up bonuses. Images courtesy of Richard Kerr.

As always, completing a round of applications for four cards requires you to have a plan to complete the minimum spending and the ability to pay off the cards in full each month. Make sure you understand what you’re going to attempt before halfheartedly jumping into four new credit cards.

Planning a churn like this six months in advance allows plenty of time for the sign-up bonuses to hit your account, and with this timeframe you shouldn’t have much trouble finding award availability. That said, I wouldn’t recommend trying this technique in a shorter period of time, as it could be more difficult to find the necessary award flights and there may be delays in the sign-up bonuses posting to your accounts.


You have the time to make sure your itinerary is as perfect as possible, so take advantage. Here are some items I consider when planning my itinerary far in advance:

1. Denied boarding ruins your trip before it starts — Your itinerary will be wrecked from the start if you haven’t done your homework on country entry requirements. Most countries require a passport to be good for six months after arrival, so check your expiration date. Check for the latest country entry and visa requirements (and great country-specific information). Planning your trip far in advance means you have plenty of time to get your passport renewed or tackle complicated visa issues.

2. Avoid national holidays — It can be a huge bummer when you arrive to a destination only to find museums and attractions closed, roads unbelievably crowded and hotel prices triple the usual rate. I find this Wikipedia page helpful in making sure my host country won’t be shut down, crowded or extra expensive on my intended travel dates.

3. Vaccinations — These provide another hurdle that can cause itinerary headaches and even prevent you from being allowed entry to a country. Particularly, pay attention to having proof you received the yellow fever vaccine when visiting many parts of Africa and the Indian Ocean.

4. Check minimum connection times, and count on schedule changes — You can prevent either missing a connection or having your luggage lost by allowing for plenty of time between connection flights. Plus, one of the many great things about booking more than six months out is the high probability of an airline changing your flight times. You can usually invoke the schedule change rule and select the more convenient flights that were more expensive or had no award availability at the time of booking.

Choosing the wrong dates for your travel could have you stuck in huge crowds. Photo courtesy of Shutterstock.
Choosing the wrong dates for your travel could have you stuck in huge crowds. Image courtesy of Shutterstock.


1. Are the seasons the same? — I’ve chuckled a few times at seeing some friends arrive in New Zealand planning to ski over our Christmas break and forgetting that it’s summer in the Southern Hemisphere. It happens more than you think.

2. Ask the informed questions — Regardless of whether your destination is Florida or Spain, coming to the conversation with basic destination knowledge will yield you more results when asking for advice. For example, instead of asking, “Which Disney park should I visit?” ask, “Would the Magic Kingdom or Animal Kingdom be better for my family of 5?” People want to help you, but you have to put your effort into the equation initially to get all the expertise people can offer.

3. Will your hotel be undergoing renovation/construction? — Last week, I followed a Twitter user’s updates as she arrived to her destination wedding in Aruba only to find her hotel and wedding venue under heavy construction with an empty pool and plywood sidewalks. If I see a hotel is announcing a construction completion date, I usually add a month to the end of it to make sure I’ll miss the ugliness.

4. How are the labor relations for your airline? — Lufthansa has proven the importance of asking this question — at least every time you fly with this carrier in particular. A simple search of Google news should reveal when the next contract negotiations will happen for the airlines you are deciding between. If they fall within your travel window, do whatever you can now to avoid the airline in question.

5. Have you budgeted? — While your flights and hotels can be covered by points, you still have to plan for expenses. Food, entertainment, taxes and fees on your award flights, etc. can quickly balloon. Begin contributing to a vacation fund now to alleviate any financial stress when it’s time for the trip. Once you’ve saved, plan how you’re going to spend the money so you don’t come back in the hole.

Planning for the Maldives was tough, but because of the effort I put into it well in advance, we had an incredible trip. Photo courtesy Richard Kerr
Planning for the Maldives was tough, but because of the effort I put into it well in advance of our departure, we had an incredible trip. Image courtesy Richard Kerr.


Plan your churn, execute your minimum spend, find award availability, complete itinerary research and ask the right questions. Making the most of your six months can really lead to a fantastic vacation you probably thought was out of financial reach. The time you put in now will directly correlate to how smooth your trip goes, and can make a huge difference in how much you enjoy your vacation.

What tips do you have when planning a vacation that’s more than six months away?

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  • Earn 5,000 bonus points after you add the first authorized user and make a purchase in the first 3 months from account opening
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