Ritz Carlton Grand Cayman

Ocean Tower Room w/Club Lounge

Dates: 3/1 to 3/6

Cash Rate: $13,725.42

Used 320,000 Marriott Rewards + $1,912.50

Point Value: 3.7 cents

Who’ll love it: Relaxers, Retirees, and Aspirational Travelers

Who won’t: Travelers looking for a vibrant party or club scene

I’ve dabbled in points and miles for about 18 months now – accumulating enough Chase Ultimate Rewards points to take a few United flights across the pond (in United’s acceptable, but subpar business class). Along the way, I accumulated a small hoard of Marriott points – thanks to brand loyalty during our hotel stays and strategic use of the Ritz Carlton Rewards card. So, when I decided to follow in the footsteps of some of my favorite bloggers like Gary Leff and Matthew Klint – I knew I needed to come out of the gate with a bang.

And, having just returned from Grand Cayman, I can safely say that we picked the right trip to kick off the blog. Aside from a spotty and downright frustrating Internet connection (more on that later), our five nights at the Ritz Carlton Grand Cayman were – hands down – the best nights we’ve ever experienced in a hotel.


We’re based in Raleigh, North Carolina – fairly convenient to the Caribbean in that three or four hours of flying time  gets us virtually anywhere and Grand Cayman is only 1,147 miles from home. For the last year we’ve been loyal to United, and they did have saver availability (from our United Mileage Plus Club card) for 50K roundtrip for two. BUT, all of their awards required an overnight layover in Fort Lauderdale – sapping a day of vacation and not really being an option. So, I turned to my small stash of Chase Ultimate Rewards Points – earned from the signup bonus on my Sapphire Reserve – and called Chase Travel. After 30 minutes on the phone with an extremely friendly travel agent, and some shenanigans on his end, I had two tickets on Southwest from Raleigh-Durham to Owen Roberts International for 46,352 UR points – the best value to be had for getting us from RDU to GCM. As an added bonus, because we “paid” through Chase Travel, we earned Rapid Reward miles for the flight.

The day of, we arrived at RDU after a 20 minute Uber ride from hell (long story short – the car was filthy and reeked so badly of pot that my fiancee was convinced we’d be alerted on by TSA dogs). After waiting in Southwest’s check-in line for another 25 minutes, we were through security in less than three thanks to TSA Pre✓ that came with our free Global Entry credit from her Ritz Carlton Rewards card and my Chase Sapphire Reserve. Boarding commenced on-time and we were delighted to get bulkhead seats in row one. We took off on time shortly after 6:40am and arrived in Florida well before our posted arrival time of 8:50.

Lester’s Diner – Great Breakfast for under $10.

Because we had three hours to kill before our next flight, we decided to go “off-campus” to grab a bite to eat. After consulting with nearby gate agents, they pointed us to Lester’s Diner – about a mile from the airport. And I’m so glad they did – this classic greasy spoon definitely hit the spot. I had three (large) pancakes, two eggs, sausage, and bacon for $8.99 – worth every penny.

With bellies full, getting back to our departure gate was a breeze, thanks again to Pre✓. Unfortunately, FLL is a bit of a dump at the moment (major parts were undergoing renovation) and has no lounges – Priority Pass or otherwise. So, we waited at the gate with about a hundred other leisure seekers. This flight too, boarded on time, and because it was nowhere close to full, we were on our way about 10 minutes early. Nobody complained. This was a short flight – the one highlight (before our destination came into view two minutes before landing) was when we overflew Cuba. I would have thought overflights wouldn’t be allowed – but they are, and apparently routine these days.


On Approach to Runway 08 at GCM

Once the door opened, from my vantage point in the first row, I could feel the warm Caribbean sunshine and see just how vibrant the visuals were. Owen Roberts International Airport is quite small, and all jets use portable stairs for passengers to deplane. As the first passenger off the plane, I was tempted to look around and wave like a foreign dignitary, but I was quickly taken by how bright the overhead sun and all the colors were. I’d also heard stories about how legendarily slow Grand Cayman immigration and customs can be, so we made a beeline for the luggage carousel to get our spot in line.

We were helped by a friendly porter who grabbed our bags, walked us to the front of the immigration line, and escorted us through customs. In all, the experience took about 10 minutes. This was a tremendous relief, as I heard from other travelers they’ve been stuck for up to 3 hours (all flights tend to arrive around the same time in early afternoon, and Caymanians are notoriously laid back, so I could see this being the case). Praise for small airports: Less than 20 minutes after deplaning, we were in the back of our cab for the drive up West Bay Drive to our home for the next six days and five nights.


3.7 Cents Per Point. Amazing.

Since we booked the room with points, we should have been relegated to the Resort Tower (bay-side and much less desirable than Ocean Tower). However, a few days before our arrival, I received a welcome email from the hotel’s guest relations manager Ailene asking for more information about us, and what we’d like to do during our stay. I took a few minutes to reply, and was delighted to find at check-in that she had upgraded us to an Ocean Tower Penthouse room in celebration of our engagement (we’re getting married at the Ritz Carlton Naples, so I think some information sharing was definitely afoot!). Factoring in a very heavy resort fee (in this case, not a bad deal since it includes snorkeling, sailing, kayaking, paddleboarding, and all non-powered watersports), the total for our stay would have been $375. BUT. We were offered an upgrade to the Club Level for $250 per night, and I happily accepted the offer since it meant we’d never have to leave the property for breakfast or lunch, and could have all the drinks we liked throughout the day. The new total came to $1912.50 – an absolute bargain compared to the $13,725.42 the room would have cost in cash and representing 3.7 cents per point.


We were given room 822 – on the penthouse level of the Ocean Tower. It’s listed on the website as 480 square feet, which from past experience is more than enough space for us to relax (and work as needed). Although we requested a King bed, we were given a room with two Queens – most likely because we arrived a few hours early. Sleeping in separate beds isn’t a problem for us, so we happily accepted. Walking in, our room was immaculate, and huge. There was a good four feet of space between everything in the room – giving it a wide open feel. Opening the sheer curtains revealed a stunning panorama of the beach side portion of the property. I could get very, very used to this.

Beautiful Room 822 – No complaints with two Queen beds instead of one King.

Amanda may or may not have done an Evita Peron impression the first time she stepped out on the balcony


Not sure if this is an everyday occurrence, or just an isolated issue during our stay, but the Wifi was awful. For most of the visit, it was spotty and slow. On our third day there, it gave up altogether and wasn’t working for the better part of 12 hours. Thankfully, there wasn’t a lot of work to do, but it was a still a major inconvenience. The way in which the hotel handled the issue, though, was amazing. One of the call center managers for the property kept me informed of status updates (though I hadn’t asked for them) and extended a $100 credit for the inconvenience (again without asking). It’s little issues like this that remind my why our loyalty to the Ritz Carlton brand is well placed.


One of my favorite aspects of the Ritz Carlton chain is the Club Lounge. Since we have the Ritz Carlton Rewards card, we’re gifted three club level stays of up to seven nights each year (though this can’t be used on award stays) and make frequent use of the benefit. I’ve always enjoyed the food and drinks, as well as the conversation and personal attention from Club concierges who are far less busy than their front lobby counterparts – so when we were offered a paid upgrade to Club level, I was happy to accept.

Grand Cayman Club Lounge. Clean, well stocked with delicious food and beverages, and manned by wonderful concierges

We ate breakfast in the lounge every day and lunch most days (except when we skipped it altogether) – the food was great with plenty of choices. Breakfast was the same spread every day, but the lunch menu changed daily – with pulled pork, fish tacos, mini Italian club sandwiches, and sliders headlining the meals we had.

Fresh Fruit Portion of the Breakfast Spread. As a devout carnivore I was able to resist the temptation.

The Club Bar (good stuff hidden away behind the white louvered doors)

During our stay, there were four different concierges on staff, and we got to know them all. They took an interest in our vacation, surprised us with their service, made excellent recommendations, fulfilled every single request we had (even the unusual ones like a Ziploc baggie), and felt like friends by the time we left.


I can see why people would spend $15,000 for a week here. In a word, the resort’s entire setup is flawless. Plenty of beach chairs with built in sun shades, an ample amount of pool chairs with nearby umbrellas, cabanas to rent (next time!), a watersports hut 30 yards down the beach, and a small army of attendants and servers ready to cater to your every need. One of them even pretended to get offended when I tried raising the shade on my beach chair – admonishing me with “you aren’t allowed to lift a finger. You’re on vacation.” Ok, I give in.

Pool and beach at sunset – a magical time

View from my beach chair – no effort involved, I swear!

Breathtaking sunset on our first night in Grand Cayman

I sampled a variety of the “free” watersports included with the $75 per day resort fee. I snorkeled, kayaked, paddleboarded, and even learned how to sail (you can call me ‘Captain Al’ now). About the only thing I didn’t do was take out one of the aqua tricycles after some other guests warned “it’s a lot of work and not a lot of fun”.

We also took a 3 hour tour (alas not on the SS Minnow) with Sapphire Motorsports to hang with the stingrays at Stingray City, snorkel amongst the reefs at Rum Point, and see the starfish at Starfish Point (which is so named because there USED to be starfish there… now, not so much). We had a blast with Danny and Liam – thanks guys.

Captain Danny and First Mate Liam – an exceptional crew

One drawback to the beach – and the resort as a whole: The second the sun goes down, everything stops. It’s not a lively scene to begin with, but becomes a ghost town in the span of about 20 minutes.


There’s not a whole lot to say about the epicurean aspect of our trip – which is a bit unusual since we’re wannabe foodies. Because the whole purpose of this trip was to lay around in the sun and do nothing, that’s what we tended to do. We did go off campus the first night to Coconut Joe’s – which turned out to be an excellent use of our time. Clearly designed with a beach shack vibe – it was a good mix of locals and tourists enjoying traditional Caribbean fare. As a bonus, Amanda was particularly delighted by an obnoxious child at the next table doing his King Curtis impersonation.

Coconut Joe’s Fish Tacos – Delightfully Kitschy Ambiance, Delicious Food, and Fairly Priced

For the next three nights, we stayed in, eating at a combination of Seven, Barjack, and the Club Lounge. The food was good, but value was definitely in short supply for the first two establishments, as evidenced by this $40 plate of nachos we got at Barjack.

Barjacks annoy and steal from other fish. We know how those other fish feel after paying $40 for this

On the last night, we went to Peppers on the recommendation of more than one staff member at the hotel – mostly to cleanse our palette after the nacho experience. It had a similar vibe to Coconut Joes, and we really enjoyed it – excellent food and service. Especially when the owner came out and hung out with us while we waited for our taxi after dinner – giving us a history lesson on the last 20 years on the island.


If you couldn’t tell already, we absolutely loved our stay at the Ritz Carlton Grand Cayman and feel it was well worth the 18 months of saving points to make this happen. The only things we would improve would be a balky toilet, our awareness of the the sometimes outrageous food prices, and the crappy WiFi connection.  We’re already looking forward to our next trip sometime in 2019 and can’t wait to hang out with the Ladies and Gentlemen again.



This was a VERY aspirational trip for us, and as a result, we saved points for approximately 18 months to make it happen (sticking to our philosophy of not increasing spend to speed up accumulation). Here’s the full breakdown of how we did it:

  • 25,000 Starwood Points from signup bonus for SPG Business Amex (Converted to 75,000 Marriott Rewards Points)
  • 12,000 Starwood Points from Everyday Business Spend (Converted to 36,000 Marriott Rewards Points)
  • 101,935 Marriott Rewards Points from stays at Ritz Carlton, Marriott, and Renaissance properties
  • 10,625 Marriott Rewards Points from social media promotions – including NFL Sunday Trivia
  • 63,858 Marriott Rewards Points from Ritz Carlton Rewards purchases (varying from 1x for everyday, 3x for travel/dining, and 5x for Marriott purchases)
  • 10,000 Marriott Rewards Points from Ritz Carlton Rewards card for adding an authorized user
  • 5,582 Marriott Rewards Points from Ritz Carlton Rewards card annual bonus
  • 2,000 Marriott Rewards Points for MegaBonus stay
  • 15,000 Marriott Rewards Points from Tysons Corner Ritz Carlton as an apology after an unpleasant stay