How to use points to plan a backup vacation in case your first plan falls apart

Sep 15, 2021

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These days, vacation plans are extremely unpredictable.

Entry restrictions for different destinations are frequently changing, and when or where the next COVID-19 surge will happen is a gamble. It’s almost impossible to know if your anticipated vacation will truly happen — especially if it’s a trip that involves flights and/or passports.

That’s why having a backup plan — or even multiple backup plans — is important. Fortunately, with points and miles, it’s possible to have many vacations scheduled, all at the same time, without having to front very much cash.

I currently have not one but four travel plans in place for winter break. I was able to lock in some great vacations using points and miles and I won’t lose a dime if I have to cancel. Here’s how — and why — this backup plan strategy might back sense for you.

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Plan A: Hawaii

Nine months out, I planned an amazing vacation for my family that would include two Hawaiian islands over this upcoming winter holiday break. Knowing that there was only a 50-50 chance that this vacation would actually happen, I made sure that all flights and hotels were fully refundable. At the time I booked, Hawaii’s COVID-19 numbers were low, there were strict entry requirements in place and tourism wasn’t out of control.

Related: Delta variant is on the rise — here’s what to do if you need to cancel your trip

Now, many months and a new variant later, Hawaii is not looking nearly as promising. If I were a bettor, I’d now put only a 20% chance on this trip actually happening as planned.

The governor in Hawaii is requesting tourists to hold off on visiting as their hospitals are overwhelmed and COVID-19 cases are at an all-time high. While I know we would be extremely respectful visitors, I am not sure I’d feel comfortable visiting a place that is asking us to push back our vacation to another time.

We are also an extremely COVID-19-conscious family, and 12-hour flights in packed planes going to a destination with surging numbers doesn’t necessarily sound like the best plan anyway.

Related: 6 beach destinations to consider if you are canceling your trip to Hawaii

Fortunately, our airfare doesn’t have to be canceled until the last minute — we booked using Alaska Airlines miles and the miles will just go back into our account with no fee if we cancel. Our hotel reservations have a seven-day cancellation policy. This means we can make a penalty-free decision up until one week out.

In Florida on our last family trip in February 2020. (Photo by Jennifer Yellin/DealsWeLike)

But while the odds we go to Hawaii have dropped, I am dead set on going somewhere during our winter break. My family hasn’t gone on a real vacation since February 2020. While I know this is a first-world problem, my family’s core is traveling, and the lack is really starting to hit us.

Living in the Boston suburbs, in 2020 we had strict quarantine restrictions if we went out of state and we always felt a little uneasy traveling to a destination that we deemed less safe than the Northeast.

But with two weeks off of school for winter break this year, I am making as many plans as possible to increase our chances that we will be able to experience a true vacation.

Plan B: Grand Cayman

If Hawaii ends up not happening, my first backup plan is a trip to Grand Cayman.

While this is a great plan since COVID-19 numbers on the island are extremely low — more aligned with my comfort level — and we’ll only have a four-hour nonstop flight, the island is being incredibly safe and has a phased approach to opening its borders to tourists. As of now, vaccinated parents with children under 12 (who are not yet eligible to be vaccinated) will not be able to enter until Nov. 18. If that date gets pushed back again — which is very feasible — that could jeopardize our vacation plans.

So with the uncertainty, I was able to book round-trip flights on American Airlines for just 25,000 miles per person.

The best part of using American Airlines miles — aside from the fact that I got an amazing value — is that flights can be canceled with no fee. If I need to cancel, the miles will be redeposited back to my American Airlines account, with no redeposit fee, and the taxes paid will go back to the credit card I used.

Related: Airline coronavirus change and cancellation policies: A complete list of major carriers

The Westin Grand Cayman Seven Mile Beach Resort. (Photo courtesy of Westin)

I then used my Marriott Bonvoy points to book the last award room available at the Westin Grand Cayman Seven Mile Beach Resort & Spa. And with Marriott’s fifth-night-free policy on award bookings, I only had to pay for six of the seven nights of our stay. The only roadblock is that there’s a 21-day cancellation policy, so I’ll have to make a decision about this trip prior to potentially canceling the Hawaii vacation.

Related: Where to use hotel points in Grand Cayman

Fortunately, I had enough points to book the room right away, but if you are short on points, Marriott allows you to book using their points advance feature. This allows all Bonvoy members to reserve a room and earn enough points to cover the cost within 60 days of making the reservation.

While this is a short turnaround for some, if you were planning on applying for a Marriott credit card to earn the points, meeting the minimum spending requirement quickly should earn you the points in time. You’ll want to be wary though — with points advance reservations, you are not locking in the price, just the reservation. If the number of points increases due to peak and off-peak pricing, then you could be on the hook for additional points.

Related: 17 ways to earn lots of Marriott Bonvoy points

Plan C: Costa Rica

Costa Rica has been high on my list for a family trip for quite some time. Although rules are always changing, as of now, my family is able to enter since my husband and I are fully vaccinated (even though the kids aren’t due to their ages).

Truthfully, this is a great backup backup plan, but there’s a part of me that is still nervous about taking a trip with a long layover flight and multiple hotels in the country. Not to mention that the mu variant is already prevalent in South America, which is not too far away from Costa Rica. There’s also the requirement of having to test before returning to the U.S (which I fully support) but it can be nerve-wracking if there is a positive — or false positive — result. This testing concern also applies to Grand Cayman but increases the more complex the trip becomes.

But for now, I have flights on Southwest Airlines to Liberia Airport (LIR) in Costa Rica. I booked the flights the moment Southwest opened up their booking calendar for the holiday time and fortunately I was able to score reasonably priced flights using my Rapid Rewards points.

And since I have the Southwest Companion Pass, I only had to use points on three tickets and then add my daughter as my companion — for only the cost of taxes and fees.

Related: 13 lessons from 13 years’ worth of Southwest Companion Passes

When using Southwest points, you can cancel your flight — for free — up until 10 minutes prior to departure. Typically, this allows me to have many speculative bookings at a time in case my plans are not yet 100% confirmed. The taxes and fees paid also go straight back to the credit card.

Andaz Costa Rica. (Summer Hull/The Points Guy)

For hotels, I actually only have half of the trip planned out. I currently have the Andaz Costa Rica Resort at Peninsula Papagayo booked for five nights. At just 20,000 World of Hyatt points per night, it’s a great deal since room rates are well over $700 per night — and the 24-hour cancellation policy will give me a ton of leeway to figure out which vacation to take.

Related: The most award-friendly hotel program: Everything you need to know about World of Hyatt

Also, at the time of booking the hotel, I didn’t have enough points in my account, but those with Globalist status (which I am), can make a points-advance booking. These reservations cannot be made online, but with Hyatt directly.

Pro tip: I find contacting them via direct message on Twitter to be the easiest communication method. The only requirement is that you must have the points in your account at least a week before your arrival date. If you don’t have the points to cover the cost seven days before your stay, the reservation will change to a paid stay, which could end up being a lot of money last minute.

Even though I am not staying at Hyatts often these days to increase my account balance, I can easily transfer points from my Chase Ultimate Rewards account if we end up staying at this property.

Or, if you have a friend with status, you can ask them to book a stay for you using the Guest of Honor benefits.

Related: Is the Sapphire Preferred now the premier Chase card to get?

Plan D: Local ski trip

If all else fails, my family will be driving up to Stowe, Vermont, for an extended ski trip.

This isn’t unique for us since we ski most of the winter, but typically it’s just for a weekend and we don’t normally get the pleasure of a weeklong ski trip due to the kids being in school. But with our Epic ski passes in hand, we’ll only have to worry about the cost of a hotel.

Fortunately, there’s a Fairfield Inn & Suites by Marriott just 25 minutes away from the mountain in Waterbury, Vermont. While this might be farther from the mountain than we’d like, it’s very close to many other activities, such as the Ben & Jerry’s factory and even the town of Stowe.

Ski trip to Stowe in 2020. (Photo by Jennifer Yellin/DealsWeLike)

Even better, it’s a Marriot Category 5 property and although our plans would be to go during peak Christmas season, it’s charging only standard pricing when using points.

This means 35,000 points per night, which is the perfect price point for using the Marriott Bonvoy award certificates that come with the Marriott Bonvoy Boundless Credit Card and Marriott Bonvoy Business™ American Express® Card. Between my husband and me, we have seven of these certificates in our accounts.

Related: How to plan your ski trip with points and miles

And with the cancellation policy just requiring two days’ notice, I truly can make this a last-minute decision. If all other plans fall through, we still have a quality option within driving distance.

The only disadvantage of waiting until the last minute is that those Marriott certificates scheduled to expire right after the new year might go unused. In the past, pre-COVID-19, Marriott was pretty good about extending expiring certificates another six months or a year, especially for those with status, but I am not sure if they will continue to be as lenient with these ones since the extension has already surpassed the one-year mark. There’s also the chance that these certificates will ultimately be extended — again — for all members.

Tips for booking a backup plan

While I truly don’t know which vacation will end up happening for my family (fingers crossed for plans A, B or C), here are some tips to help you plan one — or more — backup plans.

Don’t book your backup trip with the same airline

You generally can’t have multiple flights booked on the same airline for the same date and time. Most airlines will automatically cancel your flight if you have multiple bookings for the same time. So if you are using miles with the same airline to book some backup-plan flights, make sure to stagger your flights.

But airline systems don’t speak, so you can have flights booked on the same date and time among different airlines. For example, my flight to Costa Rica on Southwest and my flight to Hawaii on Alaska Airlines overlap and there’s no problem there since they are with different carriers.

Fortunately though, on the hotel front, you can use points from the same loyalty account in multiple destinations at the same time. This allows you to truly maximize your backup plan potential. For example, in my Marriott account, I have a reservation in Hawaii, Grand Cayman and Stowe during the same time frame.

Keep track of cancellation policies

When booking multiple trips, make sure to jot down when you need to cancel for all of your hotels. Juggling multiple reservations can be challenging and the last thing you want to happen is to be on the hook — with points or money — for a hotel reservation you ultimately aren’t going to use. You’ll also want to keep track of your airfare bookings.

And lastly, if you are traveling outside of the country, or even to Hawaii, make sure to tune in to travel restrictions. Even though a country might allow you in today, that doesn’t mean the border or testing policies are going to be the same a few months down the road.

Testing, vaccination and travel insurance requirements are also evolving daily, so make sure that your original or backup plan works with your particular situation.

Featured photo by Clint Henderson/The Points Guy.

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