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Flashback to the '90s: Cayman Airways in Business Class From Grand Cayman to New York

July 05, 2019
15 min read
Cayman Airways Business Class Review
Flashback to the '90s: Cayman Airways in Business Class From Grand Cayman to New York
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[tpg_rating tpg-rating-score="53" ground-experience="5" cabin-seat="11" amens-ife="2" food-bev="15" service="20" pros="A nice airport in Grand Cayman, plenty of space to spread out and relax onboard." cons="Very outdated aircraft, mediocre food and no amenities whatsoever." /]

Leaving a Caribbean vacation is never easy, but you'd expect flying in the front of the plane would make the journey home a little better, or at least more comfortable.

What you wouldn't expect is Cayman Airways' business class turning into a time machine that flies you straight back into the 1990s in the worst possible way. Sure, this was a great trip down memory lane for the AvGeek in me. But this was also an ancient plane ready for retirement — and a flight that I now hope to forget.


Cayman Airways has a loyalty program but no transfer partners. From the start, I knew this was going to be a cash trip. The nonstop flight schedule made that decision worthwhile.

I wish earning and burning miles on Cayman Airways were easier. But when you're the hometown airline, there's no need to partner with others, I guess. The upside is that I now have a Sir Turtle Rewards account with 4,375 miles in it. The downside is that I have nowhere to spend them until I return to the Cayman Islands.

This trip turned out to be a prime example of why it pays to be part of multiple points-and-miles programs. For instance, I could have used Chase Ultimate Rewards, American Express Membership Rewards, Capital One miles or Citi ThankYou Rewards points to book the flights. (Check out our full guide to using fixed-value points.)

The 7 Best Cards for Travel Purchases in 2019.

Since I paid cash for this round-trip ticket from New York-JFK to Grand Cayman's Owen Roberts International Airport (GCM) and back, one option was to earn 5x points on the Platinum Card® from American Express (when booked directly with airlines or through American Express Travel; on up to $500,000 on these purchases per calendar year). But in the end, I went with 3x points on Chase Sapphire Reserve to get the better travel insurance and delay protections, especially since we were flying during summer and its nasty thunderstorms as well as the start of the Caribbean hurricane season.

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My wife and I flew coach on Cayman Airways down to Grand Cayman. (You can read that full review to compare and contrast.) We took business class home. The total price, per person, was $987.81 -- an upcharge of about $600 for the one-way return in the front end of the plane.

[flight_stats ticket-class="first" review-stat-section="Ground Experience" tpg-rating="5" tpg-rating-max="10" tail="VP-CKZ" age="23" departure="18" departure-2="25" duration="3" duration-2="18" live-tv="0" tailcam="0" headphones="0" comp-alcohol="0" extra-pillows="0" turndown-service="0" /]

Getting a taxi to the airport was the hardest part of the trip, because it was a Sunday — a Sunday before a holiday honoring Queen Elizabeth II. When we finally got a cab, it was shared with another couple.

There was no traffic, and we were at the airport 20 minutes after leaving the amazing Kimpton Seafire.

Was the queen's holiday in this British overseas territory not enough royalty for you? A new terminal at GCM was opened on March 27, 2019, by Prince Charles and his wife, Camilla, and a plaque outside the building honors the royal couple.

(Photo by Scott Mayerowitz/The Points Guy)

The very modern terminal had wonderfully strong air conditioning. I can not emphasize how important that is following my visit earlier this year to Turks and Caicos.

(Photo by Scott Mayerowitz / The Points Guy)
(Photo by Scott Mayerowitz/The Points Guy)

There were few crowds inside the airport, and Cayman Airways had three lanes dedicated to New York passengers. But none, including the business-class one, were moving.

(Photo by Scott Mayerowitz/The Points Guy)

Maybe I’m just an impatient New Yorker. Maybe I didn't want to leave the island. Whatever the reason, I became frustrated by the lack of any rush. I had a plane to catch.

My wife held our spot while I walked back to the check-in kiosks. We weren’t checking bags but, in the interest of this review, I went see what the business-class counter service was like and discovered that the kiosks turned out to be easy to use, so we abandoned the counter service line. The couple waiting ahead of us to check bags ended up clearing security about 15 minutes after we did.

(Photo by Scott Mayerowitz/The Points Guy)

There was no wait for security. Our shoes stayed on, but the staff members were adamant about our liquids fitting in a quart-sized bag and swabbed my laptop for explosives.

(Photo by Scott Mayerowitz/The Points Guy)

Though the terminal is new, it still wasn't fully operational when we flew out in June, and there wasn't much in the way of amenities yet.

(Photo by Scott Mayerowitz / The Points Guy)

A Subway and an independent food stand called The Run Away Bar were open. The latter sold beer and liquor but lacked any seats, and I questioned calling it a bar.

(Photo by Scott Mayerowitz / The Points Guy)

There was a duty-free liquor spot selling Cuban rum, a cigar store, a small souvenir shop and a jewelry store. Coming soon, a sign promised, was a coffee and beer joint called Brew Hut. Another sign identified the future home of a Wendy’s.

(Photo by Scott Mayerowitz/The Points Guy)

There was no lounge of any sort, but a check-in agent spoke of plans for a future Sir Turtle lounge. Perhaps a place to spend my 4,375 Sir Turtle miles one day? (And why "miles"? Why not "shells"?)

There were plenty of seats in the terminal, but only one in every three rows had power outlets.

(Photo by Scott Mayerowitz/The Points Guy)

Boarding started 20 minutes before departure. There was a separate lane for business-class travelers, and it was an orderly process. All looked good.

(Photo by Scott Mayerowitz/The Points Guy)

Then we stepped outside.

There were six planes lined up in front of the terminal and no signs or staff guiding you to the correct plane. We were told to turn left. Two of the six planes were that way, and I guessed that we weren’t on the turboprop but flying back on the same exact 737-300 that we'd flown down four days earlier, so we took our chances and hopped aboard.

(Photo by Scott Mayerowitz / The Points Guy)

The flight attendants at the door were checking to make sure passengers were heading to New York. We'd guessed right and made it onto the right plane instead of ending up in Havana.

[flight_stats ticket-class="first" review-stat-section="Cabin and Seat" tpg-rating="11" tpg-rating-max="25" configuration="2" configuration-2="2" lavs="1" live-tv="0" tailcam="0" headphones="0" comp-alcohol="0" extra-pillows="0" turndown-service="0" /]

There were no predeparture beverages offered in business class, although a bachelorette party in coach asked for drinks, forcing the flight attendants to huddle to decide whether the women in Row 12 needed to be cut off. There were no blankets or pillow, either.

The eight seats in business class on this aging 737-300 were similar to what you would find on most domestic first-class cabins, except older.

(Photo by Scott Mayerowitz/The Points Guy)

They had a foldout legrest. Mine, however, didn't fold out. The seat did recline, though, and the ancient levers amused me. If there'd been an ashtray built into the armrest, I wouldn't have been surprised.

(Photo by Scott Mayerowitz/The Points Guy)

At least there was room to spread out. Small victory, but not really worth the extra $600.

(Photo by Scott Mayerowitz/The Points Guy)

Business class had its own lavatory, which was clean, and the flight attendants really enforced reserving it for passengers in the front of the plane.

(Photo by Scott Mayerowitz/The Points Guy)

[flight_stats ticket-class="first" review-stat-section="Amenities and IFE" tpg-rating="2" tpg-rating-max="15" live-tv="No" tailcam="No" headphones="0" comp-alcohol="0" extra-pillows="0" turndown-service="0" /]

Just like in coach, there were no TVs or screens of any sort. There was no Wi-Fi on the plane. The only entertainment was my book and an amazing sunset during the first hour of flight.

(Photo by Scott Mayerowitz/The Points Guy)

Then I finished my book.

[flight_stats ticket-class="first" review-stat-section="Food and Beverage" tpg-rating="15" tpg-rating-max="25" live-tv="0" tailcam="0" headphones="0" meals="1" comp-alcohol="0" extra-pillows="0" turndown-service="0" /]

After takeoff, flight attendants served drinks in thick, plastic glasses. The business-class offerings were the same as in coach — just free, as opposed to $4 to $6 for everything but the complimentary rum punch.

(Photo by Scott Mayerowitz/The Points Guy)
(Photo by Scott Mayerowitz/The Points Guy)

Dinner was chicken fettuccine or beef stew. I was the third of eight passengers in business class to order and got the last chicken pasta. The other five passengers were stuck with beef stew. My wife passed on dinner in favor of a 6-inch Subway sandwich from the terminal.

Before the meal, we were offered hot towels to freshen up.

Cayman Airways offers free meals, even in coach. The options behind the curtain from me were pasta in marinara sauce or curry chicken over white rice with vegetables. One woman in business class successfully avoided the beef stew and was given a coach pasta instead.

The “tablecloths” were nothing more than a paper napkin unfolded, and the utensils were a shiny plastic that mimicked metal cutlery without being as useful.

Despite being doused in a cream sauce, the chicken was dry and chewy. The pasta was covered in pepper. The three plantains added to the dish were tasty — but confusing. Though a culturally important staple food served with many Caribbean dishes, what place did they have in my botched Italian dinner?

(Photo by Scott Mayerowitz / The Points Guy)

The salad was bland but the roll was fresh and the cheesecake enjoyable.

As the sun set to my left, I wondered how much more airport construction was necessary for the Wendy’s to open.

[flight_stats ticket-class="econ" review-stat-section="Service" tpg-rating="20" tpg-rating-max="25" live-tv="0" tailcam="0" headphones="0" comp-alcohol="0" extra-pillows="No" turndown-service="0" blurb="The flight crew wasn’t bad, but they weren’t attentive, either." /]

The meal service was prompt, but clearing off the tray took some time — time that I had hoped to use to work on my laptop. It turned out the flight attendant was busy writing up a report, something involving the woman in front of me passing drinks back to a friend in coach who then lied to the crew about receiving them.

Later on, an announcement reminded coach passengers to use their own two bathrooms in the back of the plane. The flight attendants really didn’t want anybody coming through the thick blue curtain that separated the cabins.

Most passengers tried to sleep but the crew never made another pass through the cabin asking us if we wanted an after-dinner drink. I had more beverage service on a two-hour flight in Delta Comfort+ to Orlando (MCO).

(Photo by Scott Mayerowitz / The Points Guy)

I forgave them in part because they had to deal with a particularly difficult crowd. After landing, rowdy passengers in coach needed to be reminded to sit down and keep their bags in the overhead bin. After a 15-minute wait for a gate, others took off their seatbelts and moved around, leading one flight attendant to almost lose it over the PA. Drunk passengers shouted back at her.

It had been a long day for all.

(Photo by Scott Mayerowitz/The Points Guy)

Overall Impression

Cayman Airways is getting new planes. The Boeing 737 MAX grounding has forced it to scramble, move flights around and keep its aging jets flying longer than anybody probably expected.

The new airport terminal is major step up from airports on other islands and will soon have more food options.

The cabin, food and liquor are not worth the extra price of flying business, especially since the airline has no miles transfer partners. But the eight-seat cabin was intimate and had plenty of room to spread out -- the same way a 737 flying from Detroit to Washington, DC, has extra room up front. Hopefully on that flight, passengers get pillow and blankets, though.

All photos by the author.

Featured image by (Photo by Scott Mayerowitz / The Points Guy)
Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.