Caribbean, North America

Grand Cayman: Warmer Latitudes, Positive Attitudes

The legendary Seven Mile Beach,  one of the most famous in the Caribbean

A direct flight from Detroit, Grand Cayman is an easy escape that delivers sandy beaches, crystal blue waters and no shortage of starfish. Stay on the west side, explore the east side and definitely don’t leave without checking out the north end and it’s beautifully perplexing bioluminescent bay.


JESSICA: So, why Grand Cayman? We were looking to kill a few days we had off over the holidays, but didn’t know where to go. We were looking for three simple, but elusive things: 1) a place warmer than Michigan in January, 2) a direct flight booked using Delta Skymiles, and 3) a Zika-free destination.

TREVOR: Enter…Grand Cayman, a 22-mile island shaped like a broken bottle opener located just south of Cuba. It’s flat as a pancake, but actually is a mountain peak atop an underwater mountain range.

J: Super touristy, but gorgeous beaches, great people-watching and comfortable resorts. Perfect destination to let your hair down after the holiday bustle.

T: Yeah. Sometimes, you’ve gotta go off the beaten path. But other times, you just need to follow it.

J: That was profound.

T: Thanks, I borrowed it from a bumper sticker.

Arriving to Grand Cayman and its crystal clear seas

J: Anyway, Grand Cayman has a time and a place. Like when you don’t want to worry about taking a crash course in a foreign language; and not spend 20 hours on a plane or in a terminal.

T: And, we clearly weren’t the only ones thinking like that. Booking only two weeks before we left was risky. We were very lucky to get two of the last available beachfront hotel rooms on the island. We probably should have booked in August.

J: So, what surprised you most about Grand Cayman?

T: Admittedly, I didn’t think this beachbum-inspired vacation would turn into a culinary adventure, but it did. The cuisine, a blend of English colonial hits (Indian, Filipino), Americana field-to-fork and Caribbean Jerk was outstanding. The desserts were good too. My favorite dish was Bouillabaisse. Mussels, scallop, lobster tail, calamari, prawns, salmon, fish and snow crab with coconut rice and lobster broth.

The photo really doesn’t do it justice, but you get the idea: amazing seafood


J: We arrived on a Saturday. Good timing – we now know – as the most cruise ships dock Tuesday through Friday.

Because we knew we’d be moving around the island quite a bit, we rented a compact car for a reasonable price (request an automatic transmission, if needed, because many of the vehicles are manuals), which was in a car rental plaza located just across the street from the airport.

T: You drive on the left side (or the Queen’s side) of the road in the Cayman Islands. This means that unless you’re coming from Great Britain, you’ll need a couple miles to get acclimated.

J: We were very clearly tourists, if it wasn’t obvious before our windshield wipers started rapidly flapping when you tried to hit the turn signal at every intersection.

T: She’s not wrong.

J: In terms of lodging, there are really only two options. The first is the west end of the island, near the capitol city of George Town. The west end is the most populated part of Grand Cayman. It’s home to the powdery white Seven Mile Beach.

Seven Mile Beach in its everyday element, bustling with activity

T: This is where most of the resorts are located. The vibe is buzzy; plenty of bars, restaurants and crowded beaches.

J: The second option is the east side of the island. Much more desolate and about an hour’s drive from the airport and west end. It’s far quieter with far less expansive beaches and two primary hotel options.

The east side of the island; gorgeous and rocky along the roadway

T: We ended up scoping out both sides purely based on hotel availability. Our first two nights were on the east end, and our last two nights on the west end. In hindsight, I’m glad we experienced both sides of Grand Cayman, mostly because they’re so drastically different. But, if I went back, I’d only stay on the west end.

J: And we can’t forget the north end of the island, specifically Rum Point and Starfish Point. the north end doesn’t have hotels, but there are a ton of larger homes available for rent for families, a couple great beach bars and restaurants (with live music and space for kids to play), and awesome spots to watch the sunset. The north end is about a 25-minute drive from the east end, and a 50-minute drive from the west end.

Starfish on natural display in the shallow waters of Starfish Point


T: Our flight arrived around 4 p.m., which gave us just enough time to get to our hotel  – the Wyndham Reef Resort – before sunset. It was a nice drive; most of it follows the ocean.

J: On the east end, there are two hotel options, the Wyndham and Morritt’s resort owned by the same parent company. Both are similar in look and feel, with the most notable exception being that all Wyndham rooms are ocean facing (yay!). We booked a studio guest room because IT WAS LITERALLY THE LAST HOTEL ROOM LEFT ON THE ISLAND on our arrival day.

And before I share room details, I want to hit pause for just a second to add that once we checked in and were sipping on complimentary rum punch cocktails (another yay!), it was requested that we touch base with the concierge. She was a vibrant, funny lady, but she did lay down the hard sell for us to attend a timeshare presentation in exchange for her covering one of our excursion fees. We weren’t interested, but she persisted, which may not have felt offensive if we weren’t fresh off a plane and hour-long drive.

Okay, I’ve vented. In short, be prepared for that tactic if you visit the Wyndham and please don’t pretend to be polite if you’re a grumpy traveler like I was. Just be frank.


T: Since the sun had set while we were being sold on a timeshare presentation, we dropped off our bags in our room (a pretty basic, no-frills setup: king bed, small bathroom, kitchenette with refrigerator and microwave) before heading out to grab dinner.

One of the folks at the front desk had recommended a restaurant called Southcoast Bar & Grill for a lively vibe. Cayman Elvis performs here on Karaoke nights. But, Elvis must’ve left the building before we arrived because the vibe was…mehhh. We ended up heading up the road to the more promising-looking Tukka restaurant.

J: I loved Tukka! So much so that we went twice during our stay.

T: The food and service were excellent. Prime location on the water. Plenty of outdoor seating. A rare rum bar, including a choose-your-own flight selection. Perfect way to settle into our first night on vacation.

J: When we woke up in the morning to a perfectly sunny day and slid open our patio doorwall, we were bummed to see that the beaches were covered in seaweed. I’m not sure if it was a seasonal issue (I imagine it is), but there was enough of it to make the water un-swimmable.

T: Thankfully, Sunday morning brunches are a thing in Grand Cayman, so we made a reservation at the Ritz-Carlton Grand Cayman. Farewell, seaweed beach!

Champs, anyone?
Living our best life and drinking ALL of the champagne at the Ritz-Carlton

J: The brunch, which happens to be a champagne brunch – ahem – was lovely. During the island’s tourism season, it takes place every Sunday at the Ritz-Carlton’s Seven restaurant and not only does it include limitless champs, the food was amazing.

And green iguanas (peaceful, dinosaur-like lizards) hung out in the garden nearby. The champagne helped take the edge off whenever they crept a little too close.

Didn’t anyone tell you that staring is rude? 

T: I need more brunches in my life. Think charcuterie and cheese boards, sushi, fresh oysters, lobster claws, prawns. And, of course, all the classics you’d expect … eggs, bacon, ham, pastries. It was pricey, but Jess has always got to sneak in at least one bougie experience. Afterward – three hours after we sat down – we hit the beach to let our buzz wear off.

J: Then, we went sunset chasing. We made it to Starfish Point on the north side of the island just in time to watch the sun drop while ogling a handful of starfish that had taken up residence in the shallow waters of the bay.

A stunning sunset at Starfish Point

T: We learned starfish are carnivores that eat clams and mussels. They move using hundreds of tube feet. They don’t have a brain, and can grow up to 40 arms. Also, never take them out of the water, it hurts them. I got yelled at.

J: By the time we left Starfish Point, the sun was setting and we somehow found ourselves hungry again, so we stopped into the only restaurant that seemed to be open on a Sunday in that area, Kaibo.

T: Kaibo was freaking great. Right on the bay, picnic tables spread across the sand and live music.

J: The food was good, but the ambiance was great. Definitely recommend!


J: The next morning, we checked out of the Wyndham and headed to west end. We had booked a room at The Westin on Seven Mile Beach, one of a few resort properties spread along the beach. The Westin offers central location and all the amenities you’d need. In short, we loved it. Very different than the more sterile, business traveller-oriented Westin Hotels that come to mind for many folks. We had a partial ocean view with a balcony, which was where I posted up with breakfast each morning.

A partial ocean view room at the Westin Seven Mile Beach

T: Also, there’s constant activity on Seven Mile Beach. It felt like a tropical version of Broadway.

J: Outside, they had a large pool and swim-up bar with a good amount of lounge chairs and cabanas near the pool and on the beach. Staff was always available to provide towels, help you find open beach chairs and take drink and food orders.

Not surprisingly, walking Seven Mile Beach is a fabulous way to people watch

T: After asking a few staffers and considering purchasing pricey New Year’s Eve tickets to a resort party, we ended up taking the locals advice and bought tickets to the Royal Palm Beach Club, about a mile down the beach, which turned out to be far more lively than any of the resort parties we walked by en route.

J: It was club-ish, but it was New Year’s Eve! Turn up that bass and drop a bad beat!

T: Ha. Never change.

J: We bought a bottle of champagne to share and took it down near the water, where the DJ was set up, and ended up clinking in the New Year with our feet in the Atlantic.

T: I wouldn’t have done it any other way.

Clinking our plastic wine cups as we walked down to Royal Palms Beach Club

J: New Year’s Day was our last full day on the island. A casual lunch at Coccoloba (best beachfront restaurant on Seven Mile Beach in Trevor’s opinion), and a drink or two at the swim-up bar were our only plans before our singular activity for the day, a glass-bottom kayak tour of the bio-luminescent bay.

T: This was the one group “excursion” we’d booked during our trip and it was a bit of a risk because the reviews online were all over the place. Some people loved it and some people thought it was a total waste. But most confusingly, there were no photos to help you judge who was right and who was wrong because the bioluminescence can’t be photographed.

That said, we ended up loving it.

Walking the plank at Starfish Point

J: After a mile and a half of kayaking in the dark ocean, our tour guide directed our group of 10 or so in toward the bay. We listened as he spoke about jelly fish, constellations and how Mark Cuban had been on the same tour yesterday … all the while wondering why we were in the bay but didn’t see any bioluminescence.

T: Until we did! As we paddled deeper into the bay, through the glass bottom of our kayaks, you could see these tiny bioluminescent organisms sparking as we slid over the water. Like microscopic neon blue fireflies.

Even with the threat of jelly fish, it was intriguing enough for me to jump in. It was incredible. My skin lit up as I swam.

J: It was well worth the $59 per person we paid. If only it’d been Instagrammable! Regardless, the perfect end cap to our little holiday vacation.

Sunset on Seven Mile Beach


Day One

  • Arrive in Grand Cayman and pick up a rental car
  • Hit up a grocery store for snack foods and drinks en route to hotel
  • Check into a Seven Mile Beach hotel like the Westin Grand Cayman
  • Enjoy a leisurely dinner at the resort

Day Two

  • Start your morning right with reservations for Seven’s Champagne Brunch (Sunday only)
  • Spend the rest of your day enjoying Seven Mile Beach

Day Three

  • Head out on a relaxed road trip to the east and south ends of the island
  • Enjoy the smaller, remote beaches and consider hiking the island’s main trail, the Mastic Trail
  • Stop for lunch or dinner at Tukka

Day Four

  • Morning and early afternoon spent on the beach
  • Drive out to Starfish Point to enjoy an hour or so of starfish gazing
  • Meet your White Sands tour group at Starfish Point for the Bioluminscent Bay tour
  • Dinner at Kaibo on the north side of the island
Live music beside the beach bar at the Westin Seven Mile Beach


  • Grand Cayman is known for its snorkeling, but if you’re not a big fan, don’t let that scare you off! We never ended up snorkeling, and still found plenty to do during our short stay.
  • When researching accommodations, focus on those located directly on Seven Mile Beach, the most gorgeous and expansive beach on the island.
  • Car rentals are relatively inexpensive (and neither hotel we stayed at charged for parking). Cars allow you access to the full island for exploration. Request an automatic transmission if you’d prefer one over a manual, and be sure to remember that you’ll be driving on the left side of the road.
  • Note that grocery and liquor stores are closed all day on Sunday. If you want to stop by one, plan to do so beforehand.

NOTE: All items and resources are up to date as of January 2019, when this travel occurred. 

That Tukka rum flight though …

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