Grand Cayman Vacation

We went to Grand Cayman for Michelle’s birthday, and boy, was she in for a surprise! Grand Cayman is a very special place to me as I had the luxury of first visiting in the 1990’s thanks to a friend’s father investing in some condos on 7 Mile Beach.  I’ve been back many times since then, but with this being Michelle’s maiden voyage, I was excited to show her around.

How to Get to Grand Cayman From Miami

Getting to Grand Cayman from Miami is very easy.  There are currently two direct flights from MIA thanks to American Airlines.

There is also a Cayman Airways flight, but being in Miami and using MIA and FLL as home base airports, we’re partial to keeping the loyalty and points to American Airlines.  While they aren’t my favorite airline, I’m always using them and have Executive Platinum Status so I get a lot of upgrades.

The flight from Miami is quoted around an hour and forty minutes, but it rarely takes more than an hour once you leave the tarmac and touch down in Georgetown, Grand Cayman.  An easy walk off the plane finds paradise waiting, and you’ll hear the steel drums playing from the first step you take off the plane.

Customs and immigration is a cinch in Grand Cayman, you literally breeze right through.  If you don’t have any bags checked, you can walk right outside and grab a cab.  From the airport to 7 mile beach it’s about 12 minutes, give or take with traffic.  We got there on a Thursday afternoon after a slight delay on the way out and hit “Cayman Rush Hour” but it wasn’t bad, it was maybe 17 minutes to the Ritz Carlton.

Our Itinerary in Grand Cayman June 2023

As mentioned, we chose the Ritz Carlton for our stay. I’ve stayed there a few times in the past, and the service is first class. It’s very well respected in Cayman and largely known as the best hotel in Grand Cayman.

—> Check Out the Ritz Carlton

It does come with a steep price tag, (check rates here) but Grand Cayman is expensive no matter how you slice it up or where you stay, but I find it to be something worth splurging on whenever I’m on the island.

Other places you can check out that are similar, but not quite as expensive, include:

  • The Kimpton Seafire
  • The Westin Grand Cayman

There is also a Marriott property, but it’s a little older, yet it’s totally serviceable.  You’ll also find a lot of boutique properties like the Caribbean Club that offer a lot different experiences including three bedroom oceanfront rentals.

Overall, we were once again very happy with the Ritz Carlton.  There have been a few changes since my last visit with my son in 2019, including the re-design of “Bar Jack,” which now has a new name but it still located by the pool, and much to my liking, an addition of pickleball courts!  (I’m a fanatic and play just about every day in Florida.)

Other than that, you still have the various restaurants on property, the sprawling pool, amazing beach front chairs and sunning area where you are waited on hand and foot by their amazing staff, and of course, all the activities you want to do in the water, including snorkeling, stand up paddle boarding, and other water sports.

Dining in Grand Cayman

Our first night’s meal was at “The Wharf,” which is located at 43 West Bay Road, right on the water.  The entire experience was very enjoyable, and it’s a place we’d go back to in a heartbeat.  If you have ever heard of “Barefoot Man,” an entertainer who has graced the Cayman Islands for many years, he usually shows up here on Saturday nights to play. Unfortunately we didn’t get to see him this time around.

The Wharf Grand Cayman
That is a plant behind me! Thats not my hair!
the wharf grand cayman
Huge drink list. Huge cigar list. What more could a man ask for?

Friday night’s meal was at Morgans, located in the Cayman Yacht Club.  This restaurant blew us away so much that we went back on Saturday for lunch!  The staff was absolutely incredible and the menu was very expansive, featuring not only a deep seafood menu but also steaks, pasta, and other specials.  You can choose to sit inside in the covered area or on the outdoor patio. Both are elegant and the atmosphere is very inviting, friendly, and upscale, but not stuffy or pretentious, if that makes sense.

Lobster at the Wharf Grand Cayman
Lobster @ the Wharf.

As mentioned, we went back on Saturday afternoon for lunch since we went on a boat excursion from the Yacht Club, and Morgan’s is in the same vicinity within walking distance. (More on the excursion further down in this trip report.)  

Saturday night featured a meal at Taikun, which is inside the Ritz Carlton property so we didn’t have to go very far.  We found it to have a small, but very tasty menu.  We had sushi and ramen, as well as some sake that our Kenyan server, who was amazing, recommended.  In fact, it’s worth pointing out that most of the staff all over the Ritz Carlton was an assortment of folks from around the globe, and each had been expertly trained in Customer Service and had stories and advice for anyone desiring to learn more.  I can’t speak enough about the quality of the staff at the Ritz!

Following dinner at Taikun, we had drinks at the Ritz Carlton lobby bar, which has long been a place to meet people and have some laughs.  We did this nightly and made friends, per usual.

Sunday night was the highlight dinner for me, as a huge fan of Italian food, we went to the incredibly hyped up Luca, which is inside the Carribbean Club just blocks from our hotel.

Luca did NOT disappoint.  The wine room is very impressive, the craft cocktails even more surreal, and the food was to die for.  I wish I came with more of an appetite because I would have tried more.  This was a very good meal that I’ll be repeating in the future.

Morning meals were spent at the Ritz Carlton Restaurant “Seven,” which offers a buffet.  Since I booked through American Express Travel we were given two free brunches each morning, which was a $50 value, so that was very hard to pass up all things considered.  Booking through Amex also offered $100 food and beverage credit for our stay which was also appreciated.  The only downside is all that spend didn’t get to go on the Marriott Bonvoy Credit Card which would have earned 6x points.  Oh well, the $400 + in savings offset the points any day.

The last place we literally stumbled into was a Mexican restaurant that had only been open for six months.  Don’t let that fool you, this place knocked our socks off!  Taco Cantina is located in Buckingham Square directly across from 7 Mile Beach and offers ice cold beers, a massive tequila selection, and more importantly for June, air conditioning!

We had cold beers, queso fundido, and a quesadilla to get out of the heat and found this to be a great low key spot for that exact purpose. The staff was super friendly and it seemed to have a few locals in there enjoying lunch at the time we were there.

One place we missed out on going to was Peppers.  It’s an authentic taste of Grand Cayman, and it’s on our list for next time.  We heard great things about it but just didn’t have time to fit it into our itinerary.

What Did We Do in Grand Cayman?

Thursday’s flight delay had us arrive right around happy hour in Grand Cayman.  We arrived, checked in, got settled, and I showed Michelle around the property before making our way to dinner.

Friday was our first full day in Grand Cayman and following a niche breakfast at Seven, we spent the majority of the day enjoying the views of 7 Mile Beach from our beach-side chairs.  We cooled off many times in the gorgeous water, sipped cocktails brought to us by the world class service at the Ritz, and just took it all in.  It was an incredible day that had hours upon hours of sun and cocktails.

We spent some time walking the entire length of 7 Mile Beach, starting from the Ritz and heading to the Kimpton, stopping at the Westin along the way for a drink.  The sand and views are simply second to none.

With a few hours to spare before dinner, we headed to downtown Georgetown.

Downtown is where the cruise ships arrive so naturally, it’s where the shopping takes place.  If you are looking for jewelry, this is the place you want to be.

TIP:  You are able to negotiate in Grand Cayman at MOST venues.  Always ask for a discount and never pay sticker price.  You can save a lot of money buying in the duty free zone of Georgetown.

We had eaten lunch already and didn’t want to spoil our appetite for Morgan’s, so we mostly went browsing and purchased a few souvenirs.  You don’t really need to spend a ton of time in Georgetown unless you are price shopping for jewelry as there isn’t much else to do there.

I did find a great cigar shop called “La Casa del Habano” where I picked up one of my favorites, a Montecristo #2 Cuban Cigar.

la casa del habano grand cayman

After this amazing find, we returned to the hotel to prepare for dinner.

Saturday was our big day, as I’d booked a boat charter from Crystal Charters Cayman.  I’ve done boating in the Cayman’s a few time and have a perfect four hour itinerary (half day rental) if anyone wants to copy it.  You’ll see just about everything you need to see in plenty of time.

  • Start at Stingray City.  This is a bucket list item if you haven’t been to Grand Cayman.
  • Snorkel in the Coral Reef.  You’ll see fish you only dream of seeing.  So many colors and species are here in the crystal clear waters.
  • Starfish Point.  You can see where the starfish gather and take pictures.  Do not take them out of the water, as they will stop breathing!

Pics of these events are all below.

Starfish Point

Finally, we end-capped the boat charter with a trip to the famous Rum Point.  Rum Point claims to invent the mudslide, which is iconic as it’s a globally-recognized drink.  There is a very long dock leading you to a bar and beach area and a souvenir shop selling largely Rum Point merchandise you can take home and enjoy.  However, on our trip in June 2023, it was under renovation.

This really irked me because I was planning on proposing there! 

Luckily for us, plan B opened up and we headed to the adjacent beach bar and grill, Kaibo.

kaibo rum point
Kaibo will forever be magical for us.

It was at this point where I proposed and it made Grand Cayman an even more magical place for us.

Upon sealing the deal and grabbing a bottle of champagne for the boat ride back in, we let Tyrell, our captain, know of what transpired.  He was very happy for us and told us he’d take his time getting us back to shore.  He gave us about an extra 1-2 hours of cruising as he didn’t have another charter that day, so I made sure to really take care of him after that day.

Engagement Rum Point
She said “YES!”

An unforgettable day at sea swimming with stingrays, snorkeling in a reef, playing with starfish, and having beach side cocktails that ended in an engagement – what’s better than that?

The boat day had us cover a ton of ground, and it was the highlight of the trip.

Upon getting back to land, we were pleasantly surprised that Morgan’s was open for lunch (we were starving) so we got to try items we didn’t get to try the night before.  The staff welcomed us back and upon hearing of our engagement, gave us a bottle of champagne.  Extremely nice of them!

As mentioned, Saturday night was spent at Taikun eating sushi and ramen before making our way to the always bustling Ritz Carlton Lobby bar.  We had made a few friends there who were all excited for our engagement.  We celebrated with a lot of drinks.

Ferry is one of the best bartenders on the planet and a true gentleman if you are there.

Sunday was spent on the beach again before making it to Taco Cantina for drinks and Luca for dinner.  I can’t stress enough how impressive Luca was.  Their wine cellar is STOCKED, so if wine is your thing, you will love this place.

We would have loved to play the 9-hole golf course at the Ritz Carlton or engage in some pickleball, but we truly relaxed and decided it wasn’t in the cards as we prioritized lounging vs. being our usual, active selves.

Monday was the end of our trip, and it was tough to leave Grand Cayman, but now that it’s a special place for us both, we know we’ll be back soon!

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Tim Schmidt is a 20+ year Entrepreneur and Digital Marketer. A Fort Lauderdale-based "Digital Nomad," he enjoys traveling as much as possible with family and friends. AllWorld is his escape to document all of his adventures, including being a hardcore "foodie." He has property in Costa Rica and visits several times each year and is happy to offer his expert advice for planning your trip.

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