Hello, Grand Cayman.

No 9-5er. No pets. No partner. No restraints.

It started off as somewhat of a joke, a mere suggestion to hear the response…until the fish bit.

A: “I’m going to Grand Cayman for a month to escape this city, work remotely in tropical paradise and reconnect with old friends.”

Me: “Maybe I should come with you.”

A: “Maybe you should…”

The prospect of taking a break from the hectic life I was building for myself in Vancouver was far too tempting to avoid. I had many reasons to stay, but many reasons to run: fresh wounds from a heart wrenching breakup, a workload that was overflowing, a fear of missing out (FOMO) with an overwhelming social schedule and thriving media life to back it up, plus a legitimate addiction to hiking, buying new gear and seeking out adrenaline rushes. I know none of this sounds terrible or unbearable, but it was enough for me to desire something “fresh” and jump ship. With only an iota of hesitation, I booked my flight…without even having a place to stay yet.

A month long working vacation in the Cayman Islands was on the horizon.

And now, here I am, almost a month into the trip and I’ve just changed my flight and extended it by another two weeks, with plans of staying with a friend whom I met on the first night in Grand Cayman. I’m contemplating getting my diving certification so that I can explore the reef and Kittiwake beyond the surface, and have made some contacts to enable and encourage that. I’ve explored a little, but have played the local card for the majority of the time so I have far more to discover.

What I’ve conquered thus far (in alphabetical order):

  • Alfresco: A popular restaurant in West Bay that offers great ambiance right by the ocean. With only a small seating area outside, you’re best off making a reservation. Popular choice is the pizza. I ordered the (fatty) steak sandwich…and it definitely wasn’t the best on the island.
  • Al La Kebab: The place to go for your after hours snack, or after a long night of drinking. Choose your protein, your vegetables, your sauce (last time I had peanut satay) and whole wheat or white pita. [MENU]
  • Attic: A very young crowd here for the most part. This should’ve been obvious by the MLB style Beer Pong poster hanging from the balcony. The pool table set-up is good though and you can play for 12 CI an hour. Plus, O Bar is conveniently right next-door.
  • Bacardi Gras: March 4th, our first day on the island, and we wound up at a Mardi Gras party. Slightly jet lag and definitely sleep-deprived, it ended up being a pretty entertaining evening. Beads were doled out, but most guests kept their clothes on, shots were had, and plenty of Bacardi was consumed.
  • Billy Bones: Our convenient swim-up bar at Treasure Island. There are often a bunch of children nearby during the day, but in the late afternoon the older “kids” come out to play…and drink…a lot… If GM, Jesse, is working ask for an Oreo Mudslide, you won’t be disappointed. Jesse also owns Melting Hearts sunglasses, which you’ll see showcased in the seating area. Naturally, I had to snag a pair while down there; they taunted me every time that I was sipping on a bevy in the bar!
  • Café Icoa: The closest coffee shop to our apartment. Overpriced coffee and average pastries, but lovely service and tasty menu items. Eggs benny was a bit too tangy, but beautifully presented and chock-full of vegetables. Apparently the omelet is also loaded with vegetables and is quite delicious. I liked the egg salad smoked salmon croissant because it was an unusual combination.
  • Café del Sol: There are three of these cafes on the island, and I’ve been to two of them. They offer made-to-order sandwiches, salads, “rumified” cakes, real fruit smoothies, pastries and of, course, coffee. The sandwiches are decent and are served with plantain chips, but be warned that the Turkey Mango salad is turkey and mango blended with mayo, rather than slices of turkey and chunks of mango. Not so healthy anymore. The cake was dense and delicious, and the fruit smoothie was refreshing, but very sweet.
  • Calico Jack’s: Busy during the day with locals and cruise shippers, and very popular in the evening with locals. It seems to be the place that everyone ends up at over the course of the night, whether the beginning, middle or end. Read about the history behind the name. 
  • Camana Bay: The “posh” part of town. Through strategic design, there is a constant breeze through the area, allowing for a longer stay. Hang out in a hammock, do a little shopping (expensive) and grab a bite to eat at one of the many eateries. Feeling antisocial? Head into the cinema, it has six screens and is the only theatre on the island. http://www.camanabay.com
  • Chicken!Chicken!: SOOO tasty! Lunch special for 8.50 CI includes jerk chicken (spicy!), two sides and corn bread. You won’t leave here hungry. Extremely busy lunch rush. http://www.chicken2.com
  • Cimboco: Same owners as Chicken!Chicken!. They offer a 5 CI breakfast special Monday to Friday that includes toast, eggs, bacon/ham and hashbrowns. Coffee with unlimited refills is only .99 CI.
  • Coconut Joe’s: Service was great; food was average. For breakfast, they offer a decent fruit salad instead of hashbrowns for no extra charge, which is unusual for the island. I ordered the eggs benny and was pleasantly surprised by the thick chunks of ham and the hollandaise sauce that was balanced with enough acidity and creaminess. They have daily drink specials, such as two (specific) cocktails for 12 CI. Expect to see a lot of tourists here; they even have a t-shirt shop.
  • Craft: I’m a craft beer lover so was delighted to hear about this newly opened brewpub. They have a plethora of craft brew to choose from so I recommend telling the bartender what you like and letting them choose one for you. Even if you don’t like beer, check this place out as everything about the design is incredible. They hired a Japanese designer who laid it all out beautifully, with “crafty” light fixtures, funky shelving holding antiques and unique furniture and art. The owners also own Fidel’s and Mizu. http://craftcayman.com
  • Fidel Murphy’s: Every Island needs an Irish pub! Classic Irish pints on tap, as well as the local brew. Carvery lunches are a great deal at 13 CI. They also play all of the football games your heart could desire.
  • Grand Cayman Saint Patrick’s Day: At the aforementioned Irish pub. I drank from 10AM until closing. Surprisingly, the Caymans and expats go all out for Saint Paddy’s. Nearly everyone was wearing green, everyone was drinking and the party extended from one day to four days.
  • Grocery shopping: Always an interesting experience to be a tourist shopping in a grocery store. Foster’s is cheaper than Kirk’s but, for most, it is about accessibility. At Kirk’s, if you save your receipts you’ll get money off your next bill (when purchased Mon-Wed) if over a certain denomination.
  • Guy Harvey’s: Touristy. Overpriced. One should not pay nearly 18 CI for a quesadilla; I don’t care if it’s delicious (it was). Service was great, and it had a nice patio atop of the busy Georgetown marina area where the cruise ships dock. Expect hoards of tourists during the weekdays.
  • “HELL”: A tourist trap, but a unique sight. If only it had a better story behind it (hint: 1930’s, commissioner). I couldn’t resist buying the “Hotter than Hell” hot sauce. Cheesy shirts and a cheesy man dressed as the “devil”, but lovely staff. Be sure to pop in to see Ms. Mabel in the next shop. Oh, and don’t forget to get your passport stamped and send a postcard from “Hell”! Expect to spend very little time there as you’ll be bored quickly, so plan a trip to the Turtle Farm as well since it isn’t far away.
  • Karma: Chaos on a Friday evening with DJ’s rocking the house. Popular, pricey, confused identity (disco balls, a waterfall and Asian décor?). They have good specials during the week, including a three-course lunch for 18 CI or 22 CI with a glass of house wine. http://www.karma.ky
  • Kittiwake: In 2011, $3 million was invested in shipping the USS Kittiwake to act as a diving site. I only saw it snorkeling from above (so far) but was with friends who dove inside. Pretty impressive.
  • Local brew: Ironshore Boch, Caybrew, White Tip. Everyone has their local flavour. I opted for Ironshore because it has more character (in my opinion) than the others. They’re pretty much served at every bar on the island and often on tap for 4-6 CI. Or you can purchase them at the liquor store in a six-pack for roughly 10 CI. Also available during my visit was the limited edition, seasonal Twisted Citrus.
  • Lonestar: It’s a happening place on Thursday’s with tourists and locals, as the place fills up for six rounds of Rock & Roll Bingo. It’s often standing room only if you get there after 7:30 (it starts at 7:45 and ends at 10:45). Two (sometimes three) bartenders tend to the whole crowd so be patient, be brazen in the ordering stage, and be generous in tips – they’re working their butts off.
  • Macabuca: This restaurant is coined as the “premier ocean front tiki bar”, so draws in tourists and locals alike. We went in the afternoon, just missing Monday’s BBQ buffet that is a great deal and includes seafood, meat, salads and sides. I had a tasty steak panini with a side salad, switching the Swiss cheese for Brie. Now I just have to go the brother restaurant, Cracked Conch. http://www.crackedconch.com.ky/macabuca.php
  • Mizu: Sit inside for a more elegant experience, even if it is a tad crammed. Pricey, but good quality, which was evident in the sashimi.Popular rolls are the Mafia (delicious) and the Stuffed (though some find it too big). The restaurant menu boasts a slew of other items for those who don’t like sushi, as well as a special teppanyaki dinner for 49 CI.
  • O Bar: Seemingly the main bar on the island, though DREAM is new and brings in a lot of “spring-breakers”. Shabby compared to big city clubs, but a happening place on the island that draws a decent sized line on the weekend.
  • Paperman’s: Love this coffee shop! They use Intelligentsia coffee and make great sandwiches. Items are fairly priced and I haven’t tasted anything that I don’t like yet, from the ham and cheese croissant and the chicken bacon sandwich, to the oatmeal raisin cookie and the iced coffee. [Facebook Page]
  • Private Charter: It’s not cheap to rent a private boat, but it was a lovely experience. Being able to drink beer and make plans on the fly were novelties that made a world of a difference. Our hosts, Pirate Divers, where informative and amiable.
  • Public buses: A fun experience. There doesn’t seem to be a set schedule or set route, but there is a set amount: $2.50 USD or 2 CI. They will cram as many people in as they can, and if you’re lucky they’ll have the windows open. Be sure that you let them know where you’re getting off when you get in…and it doesn’t hurt to give a reminder when near your destination.
  • Rackam’s: This is a great place to have dinner as the restaurant’s seating area is on the water, taking the term “waterfront dining” to another level. Be sure to stay for the tarpon feeding at 7:30PM. And hit up happy hour from 5-7PM to save 1 CI off beer and wine. Word to the wise: don’t drink the Cayman Chi Chi (shown below).

Kelly Marion, Rackams

  • Royal Palms: Popular on “Sunday Fundays” and DJ nights, this place has plenty of seating and an adult only pool. Margaritas had there were killer…containing mostly tequila with a dash of fresh lime juice and salt.
  • Rum Point: A tourist attraction, though it is great for snorkeling and lounging. The supposed “must-have” is a mudslide at Kaibo as they are said to be the best on the island due to their “special ingredients”.  I opted for the Rare Rum Mojito instead. The day we were there the service was horrendously slow.
  • Rum Punch: In the Caribbean one must drink rum. And they’re pretty damn good in the Caymans…for the most part. Hello, free pour. 
  • Sea dooing: I rented from Red Sails because the friend who I was riding with had a personal connection with the company. For 30 minutes, ($38 at the local rate) we were restricted to a certain area but could fly around as fast as we wanted. Because I was with a local we were lucky enough to be given the “chaser”, which meant that when I hit full throttle when I took the reins and he became passenger, we probably hit 80 miles per hour! Thankfully, I didn’t hit a wave and flip us.
  • Smoothie Factory: If you’re looking for something healthier, opt for a smoothie! This place is chock-full of nutritional supplements that they also add to a handful of their smoothies. Not sure what you feel like having? The staff is helpful and will customize your smoothie if you don’t like certain ingredients. I’ve tried the Factory Original, Tropical Squeeze and the Peanut Butter Powerhouse. http://www.smoothiefactory.ky
  • Snorkelling: Grand Cayman is a mecca of underwater adventures with pockets of reefs to explore and fish to see, not to mention a shipwreck (Kittiwake). Eden Point, Beach Bay, Cemetery Reef, to name a few…

Snorkel Selfie

  • Stingray City: A very unique experience. I’ve swum with stingray before but they’ve always been contained. These are wild stingray (so perfectly humane) that have the choice to come and go as they please. But why would they leave when they get squid hand-fed to them multiple times a day? Like feeding a horse, hold your hand flat and let them vacuum it up. If you’re adventurous, get your guide to show you how to hold one in your arms. The females are the big ones, and the males are the small ones.

Stingray City

  • Sunday Funday: An unfaltering “tradition” on the Island. Expect to hop from venue to venue from early afternoon (or maybe morning) to late in the evening. Bring your ‘A Game’, and be sure to eat along the way (we learned that the hard way).
  • Sunrise run: Hit up the beach before the hoards of people get to them, or explore the area by running the streets before it gets too hot. I found that I had to cross the streets many times to stay on a sidewalk, but that’s because I veered off of the main roads and ran some of the quieter, local streets.
  • Tarpon feeding: Tarpon feeding is popular at a few restaurants (namely The Wharf and Rackam’s) and gets tourists riled up and elated.Since I’m more of a doer than a watcher, I asked for some gloves from the kitchen at Rackam’s and helped chuck scraps to the monstrous fish.
  • Treasure Island (and its horrendous gym): Cheapest place to stay…particularly when looking to rent an “apartment” for a month. And it’s not even that cheap considering it’s more of a hotel room with no cleaning service and rusty cutlery. The gym isn’t air-conditioned, and most of the equipment is also rusting. Indeed, no frills, but a decent pool with a swim-up bar and a small, private beach protected from the bigger waves when they strike. At night, depending on where you are, expect to hear either the lobby bar or pool bar music and crowd.

What’s left on my agenda (ever growing): Cayman Brac or Little Cayman, Turtle Farm, Botanical Garden, Parasailing, Botanical Gardens, North Shore, Mastic Trail, Conch Fritters, Cracked Conch Restaurant, Westin Brunch, Margaritaville…

Have any suggestions for what I should see or do? Leave me a comment and I’ll add it!

Check out more photos here, I’ll be updating it periodically.

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3 thoughts on “Hello, Grand Cayman.

  1. Pingback: #60Days in Paradise: Tobago’s Island Connoisseur | Marionate Overnight

  2. Pingback: Home sweet home… | Marionate Overnight

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