A Grand Return to Grand Cayman

Where we’re at: I’m recapping my two-country, three-island trip to the Caribbean in December 2023. It kicked off here, in Grand Cayman, Cayman Islands!

As I wandered wide-eyed through Newark Airport, it hit me — I hadn’t been on a plane since returning back from Burning Man in early September, and hadn’t left the country since I’d returned to Brooklyn in May. 

And now here I was, looking for my boarding gate to Georgetown, Grand Cayman. 

So what prompted my return to the world of international travel, albeit to a familiar destination? Well, it was kind of a crazy coincidental cocktail of love! Not only was Heather — yes, Alex in Wanderland OG world travel bestie Heather! — getting married, (pause for excited squeal), but three of my best friends from Tel Aviv were going the same week to visit a fourth friend of ours who had moved back to the island.

A very fitting occasion to head back through customs.

Yet my reunion with my passport was a comedy of errors that reminded me that travel too is a skill that starts to slip away without use. 

A friend and Wander Women Retreats regular Valerie had put in an upgrade for me — which didn’t clear — but with the newly renovated United Terminal I didn’t even miss the lounge. In fact, I wandered around wondering if I’d accidentally ingested psychedelics or it had just been a really long time since I was at an airport… the sun rising through the terminal was borderline overstimulatingly beautiful. 

Upon boarding the plane, I sobered up — guys I’m kidding, it was 6AM — when I realized I hadn’t charged my laptop, my seat had no outlets (I could have had them if I’d been in the Premium Plus seats I’m entitled to as a United Silver member, but I had moved into an open row in economy like a ding dong completely forgetting the outlet situation until I glanced them walking off the plane) and didn’t even have so much as a pen to write with. So instead I had an entire four hours to focus on self-loathing and my lack of productivity! Facepalm.

Upon landing, I realized my terrible travel day, due the fault of me and me exclusively, was continuing. As soon as we were deplaning and the trip was really dawning on me, I grappled with my choice to not rent a car. Regret was sinking in, but I just kind of followed the plan and took a cab to my accommodation — where I realized that I never let my hosts know my arrival time and had no idea how to get in. Facepalm part two! Luckily I called them and they very graciously scrambled to get me the keys. I stayed at the gorgeous Botanica Cayman, by the way — more on that in my next post!

It feels hilarious to kick off my first post in so long with this exhaustive account of how badly I botched a simple direct flight journey, but, it also feels quite apropos.

I immediately felt trapped without a car. Theres no Uber or Lyft on Cayman, cabs are pricey and a hassle to call and the bus system is in its infancy! I think I was just looking at the map with my New York eyes and thinking, these distances are not far. But Cayman is not a pedestrian-friendly place, and as a method of getting from Point A to Point B, it’s not really a bike friendly one, either. 

It was cheaper to rent the car for the day than hiring a one-time cab to my cottage — facepalm part three. Luckily, Heather was bringing some friends to her photography studio, Heather Holt Photo, and was driving right by me, so I got a tour of her cute studio and an airport drop off to boot, saving me at least having to pay a two-way ditz tax.

The downside of driving here is that Cayman drives on the left and some cars are left drive and some are right drive — to me though the stressful bit is the multi-lane roundabouts. I recommend reading up on those beforehand, because I had a few close calls and wasn’t sure if the other driver was unhinged or I didn’t understand the roundabout system. But honestly, after driving a rental car around Egypt, I kind of feel like I can make anything work.

Car secured, accommodation entered, devices charged — my trip could finally begin! 

I actually ended up flying in on a Tuesday, a day earlier than I’d originally planned, in order to fly with the Israeli crew; and I was glad I did — even relatively short-haul travel takes it out of me a bit more than it used to, and it was nice to have a full day to rest, recover from my ridiculous errs and get some remote work in before diving into weekend festivities.

It had been almost exactly two years since last time I was on Grand Cayman — long time Alex in Wanderland followers will remember I lived here for a summer in college in 2010, returned for Batabano in 2015, headed back when the borders opened post-pandemic in early 2022, and then found myself back again for Heather’s big day right then. I’ve seen Cayman change so much in that time, and of course as have I. 

One of the positive new developments? Cute cafés and plenty of healthy eats! Two of my absolute favorites this trip were Water & the Elephant, morning remote work fuel from the cutest little cafe, and Jessie’s Juice Bar — between work, wedding fun and friends here, workouts were not happening but I did make a valiant effort to eat one vegetable per day, and returned often to Jessie’s to make that happen.

After work and my dutiful daily nutrient consumption, I made my way to Silver Sands, HQ for the week’s wedding festivities, for champagne and pups on the paddle boards, which I did a terrible job documenting — I guess blogging is a skill I need to hone again, as well!

That night I met up with the Israelis for dinner at Peppers. Many of you will recognize Shai, my photographer from Wander Women Israel, Nim and Jannah, who’s New York and Tel Aviv weddings I attended, and Julia, a friend I met through all of them in Tel Aviv and immediately bonded with — especially over our love for Cayman, where we had both each lived previously.

This place is more old school Cayman with casual outdoor vibes, BBQ eats, and soca music blasting.

Official wedding festivities kicked off on Thursday, when the entire guest list was generously treated to a catamaran trip to Stingray City! This was super nostalgic for me as Heather and I spent so much time here together the summer we met.

Back then, Heather was my boss and mentor at Heather Holt Photo, and she taught me underwater videography right here on this sandbar, where I filmed tourists all day to sell them little DVDs of their trips! (Side note: I reread my posts from that summer in preparation for writing this and… no one can convince me my brain was fully developed, despite my being halfway through college. At least my writing got better with time!)

When we weren’t on the water, we were busting our dive booties to market her new topside photography business; getting her flyers in hotels and condos, logo-wrapping her car, and getting her online presence going. Along the way we became the best of friends and travel buddies, going on to visit Hawaii, Belgium, Greece, Thailand, Indonesia, Philippines, Brazil, and Mexico together — not to mention the USA.

I look back and see that summer was one of those big breaks that helped me to build the life of my dreams, and I’m so proud of little Baby Alex for hustling so hard to make that summer in paradise work! I went to Cayman chasing a relationship that eventually left a lot of scars, but I made so many incredible friends and learned so many indelible skills that caused a massive positive ripple effect on my life.

One thing has stayed steady through it all — my heart is so happy in the sea.

That love was tested on this day by just about the roughtest waters any of us had ever seen at Stingray City, which typically features glass-like conditions.

But, after a few laughs and shrugs, we all braved the waves anyway. I’d arrived with several underwater cameras in tow, unsure which I wanted to play with. Last trip, when I was also in Cayman with Jannah and Nim, we did a pretty magical sunrise trip, and I got some of my favorite images ever from it.

This time, I brought that same classic underwater setup — my Canon G7X and underwater housing, which yielded the black and white images here and the above-water people shots — but also brought a new toy! I’ve never had better luck with myGoPro and GoPro Dome than I did here. I always hesitate to pack it due to the bulk and the quite niche use, but wow. These were my favorite photos I’ve ever taken on it, which are the wide-underwater shots here. I’m in love!

As always, one of my favorite parts of a wedding is getting to know all my loved ones’ loved ones! Of course, some of Heather’s circle I already knew; having met along the years in Cayman or around the world with Heather. Others were names I’d heard for years and years.

And there’s no better way to bond than over a beverage! As I mentioned, Cayman has changed enormously since my first summer here. One of the worst ways? All the amazing Caribbean dive bars that were the setting for so many hot, hazy summer nights got razed to make way for big resorts, which has taken a lot of the fun out of the once-decently-raucous Cayman nightlife. Yes, there’s still plenty of places to get an expensive cocktail and watch the sunset — which, clearly no shade; I love doing! — but far fewer places to boogie and drink a cheap beer in jean shorts.

While it is located, regrettably, in a strip mall, Bird is at least a tribute to the good ol’ days, with the old Calico Jack’s sign hanging up, and a few of us made our way there that night as a dedicated tribute to a different era.

Friday was kind of a “free day” in terms of wedding festivities, so I used it to treat Heather to her first ever gel manicure and pedicure that I successfully and proudly bullied her into getting. Lately I have this habit of treating the bride to something outlandish as my wedding gifts, which is so much fun… sorry grooms!

Once our nails were looking fresh, Heather headed off for bride duty, and I shuffled over to the Israelis for super brief beach time and Beyoncé (more on her later!)

Speaking of the Cayman old days, we of course had to bring Shai, our Caribbean first-timer, to Heritage Kitchen! While they generally serve up only fish — which is not on my personal menu — they also served up plenty of photogenic backgrounds that satisfied me just as much.

Add this to your place for sure if you’re looking for classic Cayman charm!

But… back to Beyoncé.

It just so happened that our trip coincided with the Cayman release of Renaissance, Beyoncé’s self-directed and produced movie about her tour of the same name. And lucky me, I got to watch it with some of her biggest fans! While I haven’t followed Beyoncé’s career very closely, I’ve always loved her music, and I left the movie super inspired by her artistry, determination and focus shown in the creation of this tour! It made me wish I saw it live. I love seeing a woman so at home in each of her many roles as business woman, artist, sexual being, mother, daughter, etc. And honestly, I love going to the movies any time, including yes, when I’m traveling!

Shai, Beyoncé-ing

Finally, the big day had arrived. 

I couldn’t help but smile thinking of how many weddings Heather and I had photographed together on this island… and now she was the one about to walk down a sandy aisle!

The wedding too was at Silver Sands, where Heather’s parents bought a condo when she was a girl; setting in motion decades of family ties to this island, including their oldest daughter building her business, and starting her marriage here.

I couldn’t think of a more perfect place!

While Heather may have to be bribed into a nail salon, we share a deep love of a spa moment. And so I was super honored when she asked me to join the bridal spa morning at the Kimpton Seafire Resort + Spa. Modern and bright, this is one of my favorite of the big beautiful beachside resorts that’s opened since my first Cayman summer (hey, I said they replaced the beach bars, I didn’t say they didn’t replace them with something nice!)

In addition to massages, we also enjoyed the sauna, steam room, gorgeous spa pool, and the relaxation room with an iPad full of meditations and soothing sounds. I loved this spa!

I had heavily debated what to wear for the festivities, and settled on a dress I’d tried on months and months before and hadn’t been able to get out of my head, from my beloved brand Farm Rio. It was especially apropos as I first discovered Farm Rio on my big trip to Brazil… with Heather!

Having spent many a lazy afternoon at Silver Sands over the years, I was delighted to arrive and find the space so thoroughly transformed!

Of course, Heather and Morgan’s beloved dogs had to be involved somehow…

As were Heather’s plants! Heather has been running plant sales as fundraisers for the island’s animal organizations for years, which gave special meaning to this eco-friendly table decor. We used to volunteer at the humane society together, in fact, and I was on the island when she adopted little baby Sabai!

And how thoughtful are these framed photos as place cards! Remember where this photo is from?

Also in true Heather and Morgan fashion there was lots of champagne, lots of reminiscing about good times around the globe, lots of ooh-ing and aah-ing over the sunset, and lots of laughs with loved ones.

After dinner and speeches, we all hit the dance-floor! Perhaps my favorite moment of the night was the bride and groom, and the bride’s lovely parents, who I’ve known for so long, dancing side-by-side under the pavilion.

Have I mentioned that I love to cry at a wedding?

Congratulations to my dear friend on finding love and building a life with someone!

Heather and I have always kind of done things in our own way, on our own schedule, and Heather and I have supported each other through many relationship highs and lows, and many years of being unpartnered women in a society that isn’t always very warm to that.

I loved this wedding for reminding me there’s no timeline for finding your person or your path. 

…or throwing a rocking party! 

A party that good is apt to spill into the next day.

After Katie of The Traveling Spud’s wedding — one I hope to blog someday, too! — I will never again make the mistake of trying to depart a wedding weekend the day after the big event past the age of twenty-nine.

Especially when there’s an epic post-wedding brunch to attend! Heather, forever one of the most inspiring of party animals in my life, truly broke me, and I made it to Macabuca for the post-wedding brunch in body and eventually in spirit, thanks to a mimosa and what felt like seventy-seven Diet Cokes.

This place is one of my old-school Cayman favorites! I’d never been up in the proper restaurant before, but done many a shore dive and had many a sunset drink and bite from their cliff-side bar, The Cracked Conch.

Post-brunch, we headed back to Silver Sands for a day of splashing around in the sea. As you can see, my rental car really did come in handy for escorting the bride and her sister back safely from brunch!

We floated around Silver Sands until sunset, when I headed back to Botanica to freshen up. That night, I picked up Shai and Jannah for one last goodbye over the original Girl Dinner™ — carbs and gossip.

Paradise Pizza, a part of Palm Heights resort, is so cute and an absolute fresh must for me in Cayman. Heather has brought me to other restaurants in the resort previously on my last trip, though Paradise Pizza is perfect for a more casual late-night dinner if you’re not fussed with being on the sea.

Like The Kimpton, Palm Heights would definitely be on my Alex-approved list of Cayman resorts!

My flight out of Cayman was an evening one, so I was able to squeeze in one last lunch with Jannah after dropping Shai off at the airport. On last year’s trip to Cayman (which I never blogged, I know!), Heather introduced me to Mrs. Piper’s Kitchen + Garden — one of my favorite Cayman gems for lunch!

We dined inside, but it also has a super cute pool if you want a break from salt water and have a desire to linger for the afternoon. 

I can say with absolute certainty that I burned the candle at all ends on this trip! I was definitely struggling with feeling unwell due to all the travel, coordinating between the wedding and my Israeli crew, and the work I was doing behind the scenes — while I was in Cayman we actually launched Wander Women Maldives, which sold out in days. (Go team!)

But, sometimes, when life blesses you with so many opportunities all at once… you just have to embrace all of them. Even if you’re enjoying easing into a slightly slower pace of life, sometimes it is worth it to speed back up for a bit to soak up all the joy and celebration.

I’m grateful to Cayman for continuing to call me back after all these years, and giving me the opportunity to reflect on so many different chapters of my life. What an absolutely wild ride the last fourteen years have! How grateful I am, to have it all here to look back on.

And to all of you, for allowing me to share my life with you, even if I do so a bit more sporadically these days. Here’s to love.

Stay tuned for my new go-to accommodation in Cayman! And let me know if you’d like to go back and blog last year’s trip…