Honeymoon in the Cayman Islands: Orlando to Grand Cayman

Honeymoon in the Cayman Islands: Orlando to Grand Cayman


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Image courtesy: Chalky Lives

Trip Information

Reader Lauren is getting married in May! She’s looking to travel on an awesome honeymoon with her husband-to-be but lacks the budget to get it done on her own. The couple’s sights are set on Grand Cayman for the trip.

Current Program Status

Though not a program we’ve covered previously, Lauren has a healthy points balance with Citi’s ThankYou points program. With roughly 85,000 Thank You Points to work with, we’ll see how to put these to use soon.

Redeeming ThankYou Points

ThankYou points can be redeemed for a wide variety of things, from concert tickets to gift cards to restaurants and movie theaters, statement credits and – yes – travel expenses.

Unlike programs like Ultimate Rewards or Membership Rewards, ThankYou points can’t be transferred to partner programs. Instead, travel must be booked through ThankYou.com.

Points are worth 1¢ each when used toward travel expenses, meaning Lauren has roughly $850 of travel credit to work with just from her ThankYou points.

As I’m not a member of the ThankYou rewards program, I was unable to run price comparisons in the program to see if the rates quoted for flights and hotels via ThankYou are competitive with rates found on other travel sites. Chase and Amex both offer pay-with-points options in their programs and offer generally fair rates compared to what you’d find on a cash booking travel site like Orbitz or Hotels.com.

Hopefully the same is true of ThankYou’s booking engine, but it would behoove Lauren to compare any bookings she’s thinking of making with points with the cash cost found elsewhere so she can determine exactly how much value she’s getting per point.

Using ThankYou Points Effectively

Without knowing how consistent ThankYou’s price in points for any given flight or hotel stay is with the cash prices seen elsewhere, this requires a bit of speculation on our part. The cheapest cash flight from Orlando to Grand Cayman on the day Lauren’s looking to travel is on American Airlines through Miami for $438 roundtrip per person:

If ThankYou brings up the same flight, it would require roughly 43,800 points per person. Yikes! Despite her sizable points balance, Lauren wouldn’t even have enough points to cover both roundtrips. Though in theory she’d be getting her money’s worth, with a redemption no better or worse than is possible on other travel expenses using ThankYou points, there’s a better program for handling this specific flight itinerary that would preserve these ThankYou points for use later on.

It’s time to say hello to our old friend, Ultimate Rewards.

Ultimate Rewards to the Rescue!

We’ve spoken about Ultimate Rewards at length in the past, showing the best ways to earn Ultimate Rewards points and the best ways to redeem them.

It should be no surprise that Ultimate Rewards points can come in handy here given how versatile the program is, with its 1:1 transfers to a variety of travel programs. In this case, we’re most interested in the ability to transfer to British Airways’ Avios program.

Another long-time favorite of PointsAway, the power of Avios is in its distance-based award flights on partners including American. While most airline programs charge a flat rate depending on what region or country you’re in and where you’re traveling, the number of Avios needed depends on the length of the flight. That means long-distance redemptions can often be a poor value, but short, expensive flights can offer tremendous value.

The same American Airlines itinerary from Orlando to Miami to Grand Cayman listed at $438 per person roundtrip above can be had for 18,000 points each via Avios. Avios redemptions are calculated per segment, so each connection or transfer requires more points, even though they can often be booked like one award. That means it’s 4,500 Avios for the short flight from Orlando to Miami and 4,500 more for the short flight from Miami to Grand Cayman, and then the same amounts for each segment home.

Since Ultimate Rewards points can convert into Avios at a 1:1 ratio, we’re looking for a way to earn at least 36,000 Ultimate Rewards points. Thankfully, there’s a straightforward solution. The Chase Sapphire Preferred offers a sign-up bonus of 40,000 Ultimate Rewards Points after $3,000 in spending in the first 3 months.

Between the points Lauren can earn on the bonus and the points she’ll earn on spending – 2x on dining and travel and 1x on other expenses – she’ll have at least 43,000 points to work with upon meeting the minimum spend. Happily, the card’s annual fee is waived for the first year, so Lauren could knock the price of these $438 flights down to only the $2.50 mandatory security fee for both her and her husband-to-be, saving some serious cash without touching her ThankYou points.

The most important thing to keep in mind is Avios can only be redeemed toward flights on American when Saver Economy award flights are available to passengers in American’s own AAdvantage program.

Thankfully, flights from Orlando to Grand Cayman look wide open:

As do flights returning home:

On Friday, we’ll be showing how easy it is to book flights like this on the British Airways website, so stay tuned!

Back to ThankYou

Having found a better solution for our honeymooners’ flights, we still have roughly $850 worth of points that can be used toward accommodations. That’s a good thing because there’s no easy answer using points to stay on Grand Cayman.

For a week’s stay on the island, Marriott’s property would require an eye watering 240,000 points, which is actually a discount from the normal daily rate because travelers receive a 5th night free when booking 4 award nights with Marriott.

Image courtesy: Marriott

The Ritz-Carlton would require an even more astonishing 360,000 points for the week.

Though both of these hotels are also transfer partners with Ultimate Rewards, there’s simply no way to accrue this type of points balance quickly and the redemption would offer fairly abysmal value per point, at least compared to the great deal we found on flights above.

The Holiday Inn Resort Grand Cayman offers a more compelling points+cash option – requiring 20,000 points and $40 per night.

Image courtesy: IHG

The IHG card listed on our sign-up links page offers a bonus of 80,000 points after $1,000 in spending, but it’s difficult to recommend going this route given the property isn’t fabulous and we have so many ThankYou points to use.

The simple, if not particularly clever, solution is to simply find the best deal through ThankYou.com and to apply as many points as possible to help pay it down. Assuming the program’s booking engine includes most of the Grand Cayman properties found elsewhere, they could easily book a room at the very same Marriott we mentioned above: its cash price starts at only $197 per night during their travel window. That means Lauren could easily book four free nights using her ThankYou points!

Wrapping Up

By throwing Sapphire Preferred and the Ultimate Rewards program into the mix, we find an elegant way to save nearly $900 on airfare. Just as importantly, this preserves the ThankYou points so they can be used where points transfers to hotel partners fails to be a reasonable option.

Even if Lauren had hundreds of thousands of Ultimate Rewards points, I wouldn’t recommend using them toward a Marriott stay given the relatively affordable nightly rates available. Our mainstay for high value hotel redemptions – Hyatt – doesn’t have a property on island, so this is a time when pay-with-points points like ThankYou offer a better value than the Marriott or IHG options.

This is not, however, an endorsement of the ThankYou program. In the future, I’d still recommend Lauren consider moving more of her spending to an Ultimate Rewards-earning card.

Ultimate Rewards not only has the versatility of 1:1 transfers to many other programs, often providing very high value per point, but also offers the same pay-with-points option as ThankYou, but at a more advantageous rate since it offers 20% off all travel bookings. That equates to 1.2¢ per point in value for these kinds of redemptions using Ultimate Rewards, compared to the 1¢ per point offered by ThankYou.

With plenty of wedding expenses surely coming down the pike, now’s a great time to make sure Lauren’s earning the most – and best – points possible for their next vacation after the honeymoon!

Trip Component Cash Price Points + Cash Savings
Avios Award Flights: Orlando to Grand Cayman Roundtrip on American • Economy, 2 Passengers $428 per passenger on American 18,000 Avios + $2.50 Taxes per Passenger $851
7 Nights at Grand Cayman Marriott Beach Resort $2,255.26 Including Taxes/Resort Fees $850 in ThankYou Points + $1,405.26 in Cash $850
Total: $3,111.26 36,000 Avios (via Ultimate Rewards) + 85,000 ThankYou Points + $1,410.26 Cash $1,701 (55% Off)

Happy travels!

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About PointsAway
Casey Ayers is a consultant and entrepreneur with a passion for travel. After amassing enough miles and points to travel anywhere in the world for almost free in less than six months, he developed PointsAway as a way to help others make travel dreams big and small come true.
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