A First-Time Caribbean Cruise: A 7-day Sail in the Western Caribbean

Caribbean Cruise Travel | Seven days spent cruising the Western Caribbean to Grand Cayman, Jamaica, and Cozumel. Notes from the journey.

“I thought I would sail about a little and see the watery part of the world.”

Herman Melville

Caribbean cruise travel theroadtakento


We basically spent the day swapping one room for another. Goodbye corner suite at the JW Marriott Marquis Miami; hello quiet balcony room in the ship’s aft. Lying on the bed you can feel yourself slightly rocking as the waves churn beneath.

Standing on the upper deck, we watched crowded Miami fade, feeling the welcome coolness of open water just as we passed the rocky barrier of the bay. 

The best part about a cruise, as cliche and commercialized as they can sometimes be, is the physical (and forced technological) disconnect that comes with your own traveling island.

After dinner that night, we hit the casino to soothe our itch for maritime blackjack and poker. They have continuous shuffle machines on board, which we don’t like because we typically lose, but the stakes were low and the drinks continuous, so who were we to complain?

The evening ended back in the room, drinking…something…on the balcony and re-reading Walt Whitman’s Leaves of Grass. I realize Whitman isn’t exactly everyone’s typical “beach” read but to each his own.

Miami beach florida


I came in 3rd place in the Blackjack Tournament, and I have the t-shirt to prove it.

Seriously. I sleep in it whenever I’m on a gambling trip.

So here’s a question: are premonitions real? Or do we have them all the time and only notice and call them “premonitions” when they come true? Which would mean it’s just a coincidence, right? 

I say all this because we showed up late to an art auction, quickly signed up for the raffle, and when the painting was brought out, we both had a premonition we would win it.

And, we did.

It was a painting we liked too–bonus.

Dressed in a blue mermaid-style gown that evening, we stopped for pre-dinner scotch at the piano bar because—why not? 

We filled the night with more casino action, late-night comedy club, and the best part—midnight pizza in evening wear.

Swift wind! Space! My Soul! Now I know it is true what I guessed at; What I guessed when I loafed on the grass, What I guessed while I lay alone in my bed….and again as I walked the beach under the paling stars of the morning. My ties and ballasts leave me….I travel….I sail….my elbows rest in the sea-gaps.
—Whitman, Leaves of Grass


Jamaica. From my balcony, I see green mountains through the bright haziness of the morning and a half-sunken boat.

It’s quiet. Other than a mysterious clanking.

Supposedly Ian Fleming’s Goldeneye is just around the bend—the birthplace of Bond, James Bond.

Now I’m craving a dry martini…at 8:00 in the morning…

With no excursions planned, and being in the (somewhat seedy) Montego Bay port, we decided to spend our day on the boat sans the crowds. 

After breakfast we lounged on the deck under a red umbrella, watching tourist after tourist pile into a relatively small catamaran while the noisy vendors hawked their trinkets. All in all, I was happy with our choice to stay on board. 

Island dreamer catamaran


A day in Grand Cayman intrigued us, so we arranged room service for an early breakfast on our balcony and took a ferry across the clear emerald water to Las Tortugas, the name Columbus bestowed on the island in honor of the massive and numerous sea turtles, which is a heck of a lot better than Los Logartos—alligator island or land of the large lizards.

A walk through Georgetown was pleasant but not too exciting. Unless you count the chicken brazenly hanging out in the Burger King parking lot.

After some major confusion over getting a cab to take us to West Point Beach for our lunch reservations at The Cracked Conch and a whole lot of walking back and forth, we found a cabbie who regaled us with his story about how he met and married his wife while we drove along 7 Mile Beach.

7 mile beach grand cayman
I hear and behold God in every object, yet I understand God not in the least
-Whitman, Leaves of Grass

The restaurant wasn’t open yet, so we walked out over the volcanic rock and admired the view then sampled rum and rum cakes in the rum shop next door.

Our lunch at the Cracked Conch was the best meal we had the entire trip–johnny bread with onion butter, conch soup, watermelon salad, and mahi paired with a perfect view of the clear blue waters stretching out into the distance.

Getting back to the cruise port was an adventure unto itself.

According to the hostess, the best way to get around the island was a bus transportation system that stopped every 15 minutes or so. Well, “stopped” is a loose term. It only stopped if you were daring enough to walk out in the road while waving your arms wildly to get the driver to stop.

The seats were so packed that at first, I wasn’t even sure why he bothered to stop, but apparently, there was room for two to squeeze onto the back seat.

The Nightbus in Harry Potter is tame in comparison.

We, literally, careened our way through the island. I had a death grip on the corner of the seat in front of me. 

I was so focused on hanging on that it wasn’t until we were halfway back that I noticed there were finger hole rips in the seat where other terrified people had hung on before. Who needs to overspend on a “thrilling” excursion when you have these crazy buses tearing up and down the island?

We unwound that night in the casino until around midnight. Pizza and drinks in hand, we strolled to the front of the boat where we looked down into the dark, rough waters, then up into the millions of twinkling stars–then sleep, deep sleep.


Cozumel has the most tangibly blue water and is home to the Mesoamerican Reef (the largest reef in the western hemisphere) which explains why it’s one of the top diving locales in the world. We’ve been to the island several times, so we decided to stay on board the ship and continue our extreme laziness.

After breakfast, I found a few solitary, cushioned deck chairs, ordered a martini with a wedge of lemon and watched two sailboats race. The spectacle reminded me of our own America’s Cup sailing adventure in St Maarten less than a year ago. So seemingly quiet and effortless—at least from this distance.

Five days.

We had done everything in our power to slow down this Caribbean Cruise—stayed up late, stayed on board, let ourselves get bored—and yet here we were. Time still has a way of flying past you.

Jamaica caribbean boat
Not I, not any one else can travel that road for you, You must travel it for yourself. It is not far….it is within reach, Perhaps you have been on it since you were born, and did not know, Perhaps it is everywhere on water and on land.
—Whitman, Leaves of Grass


Our last day at sea and the ocean is choppy.

My first thought is to hope it slows us down.

On the bright side, the casino opened early. Although we had to pack up, we managed to make the most of the day. I’ve almost finished Leaves of Grass.


Back in Miami, other than losing a luggage wheel, the disembarkation went smoothly. Since we were staying one more night, we had made reservations at Turnberry Isle

Our room wasn’t ready, so we explored the sprawling grounds and villa-esque hotel, finally collapsing on the bronze and silver velvet sofa in the pale blue lobby lounge.

That evening, after a long nap in our room, we drove to the nearest casino and redeemed most of our losses at the blackjack tables, this time playing at a table with a real shoe. 45 minutes later, we were out of there.

Our last evening closed with the two of us lounging on the balcony, watching a lightning storm web itself across the sky.

Caribbean sunset
If you want me again look for me under your boot soles.
You will hardly know who I am or what I mean,
But I shall be good health to you nevertheless,
And filter and fibre your blood.
Failing to fetch me at first keep encouraged,
Missing me one place search another,
I stop some where waiting for you
—Walt Whitman, Leaves of Grass

Things to do in the caribbean

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