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Travel Guide: Grand Cayman

When the winter blues hit, you start dreaming of stepping off a plane into warm air and beelining it for the beach. Is there really a better feeling than sitting down on the plane ready to jet off to paradise? There are endless places to go, but I keep returning to the same one: the Cayman Islands.

Call me crazy, but I can't relax when I know there are guards with machine guns that guard the entrance to your resort (this happens in an unnamed popular tourist destination), lounge chairs so close to yours that they are actually touching and you can hear your neighbor chewing their salad (this has happened to me), or when one of the pools turns into a foam party (thankfully I've never experienced this). We work hard and deserve to have a stress-free vacation that looks just like the ads you see on TV. The Cayman Islands are everything a getaway should be: jaw droppingly gorgeous, safe, full of activities, and amazing restaurants.

The Cayman Islands are a British Overseas Territory made up of three islands: Grand Cayman, Little Cayman, and Cayman Brac. Grand Cayman is the largest of the three and where you will find resorts and a cruise port and it's where I head on my trips.

Yes, I know what you're thinking. The Caymans are synonymous with luxury as many know them for yachts, bank accounts, and the jet set. Sure, all of this is there, but there is another side to these islands that make it accessible for most. Here I break down how to make the Caymans yours.

Getting there:

Unlike most island destinations, Grand Cayman has some pretty great air lift to/from major destinations. Airlines that fly in and out of Owen Roberts International Airport are Cayman Airways (which flies major routes like non-stop to JFK, Chicago, and Dallas to name a few), Air Canada, American Airlines, British Airways (direct from London), Delta, JetBlue, United, WestJet and Southwest.

Like other island destinations, Grand Cayman follows similar scheduling in the winter months wherein airlines only fly on certain days of the week like, Saturday and Sunday, in an effort to capture the week-long traveler, or perhaps entice you to stay longer. Fear not, however, as you can still get there during the week for a long weekend trip, it will just mean that you may have to layover somewhere like Charlotte, Atlanta, or Miami. Never let a layover deter you from getting some sun on your face!

where to stay:

There are so many options when it comes to accommodations, so the best thing to do is to decide on your budget first.

Wallet Friendly

Don't be afraid of exploring this option, because in Grand Cayman the term "wallet or budget friendly" is still nicer than 95% of resorts on other Caribbean islands. My pick for this category is undoubtedly Sunshine Suites.

Photo courtesy of Sunshine Suites

My family and I have been coming to this boutique hotel for years and years. What initially attracted us what was the room rate and it still does. During the peak of freezing cold weather in New Jersey (January & February) rates are typically below $300 which includes a continental breakfast. Despite the property being located across the main street from Seven Mile Beach, it is still one of my favorite places to stay. When I say the grounds are immaculate, I mean immaculate. I'm always in awe of it. They even have a hotel cat that roams around, lays in the grass, or lounges in the reception area. I'm not a cat person, but it definitely adds to the charm.

The rooms are clean and spacious and include a kitchenette which is a nice way to help bring down your expenses as well. We pay a visit to Foster's supermarket when we land, picking up things for breakfast and the days' happy hours (aka cheese and many bottles of champagne). The only time you will feel like you are not at a larger luxury resort is when you are carrying your luggage up the stairs because there are no elevators in the three-story buildings or even bellmen for that matter. In my opinion, you only have to deal with that twice: when you arrive and when you leave, so it's not that big of a deal to me. There are also no balconies in the guest rooms, however the aforementioned beautiful grounds offer comfortable adirondack chairs and hammocks that help you maximize your post-beach lounging.

Sunshine Suites was recently acquired by the company that owns the Westin across the street and they have implemented a few changes, with the biggest being the addition of a resort fee. Personally, I'm not a fan of resort fees and would rather the fee be included in the room rate. Nobody wants to see all different kinds of fees broken down on their final bill. The bonus of paying this resort fee, however, is that guests are granted access to the Westin facilities on the beach, their fitness center, their spa, and, best of all, you can charge things directly to your room at Sunshine Suites while at the Westin. This is a vast improvement from the days when the only option would be to pick up a Tommy Bahama beach chair they provided, carry it across the street, and set it up in the area of sand between the Westin and the condos next door (although I secretly loved how quiet it was in that stretch of beach).

This is not photoshopped - the water is really that blue!

Sunshine Suites also offers a referral program and a repeat guest program. I've met many of the hotel guests who decided to stay for nearly a month as the hotel also offers a special rate for that. If you're flexible with your time, it's worth looking into.

And now, we've arrived at the best part, which I was saving for last: The Sunshine Grill. As the property's only restaurant, The Sunshine Grill serves up breakfast, lunch, and dinner. The included continental breakfast is held in another building, so this breakfast is for those who mean business and are looking to start their day with pancakes (award winning!), Cuban french toast, and omelettes galore. The real showstopper of this restaurant, however, makes an appearance at lunchtime. More on this later!

Middle of the Road

You guessed it! My pick for this category is the Westin. I love Westins and have fallen prey to their scheme. The scheme where they pump that white tea scent into their lobbies and use it in their products. I've even gone so far as to buy their white tea candle and was gifted their white tea air diffuser so that I was never without that scent in my nostrils. I even hoard their in-room products. It instantly makes me feel relaxed and like I'm on vacation. Well played, Westin, well played.

Photo courtesy of the Westin Grand Cayman

The rooms at this resort are very well appointed, each with a balcony to sit and relax on (some do have views of the parking lot, so be careful when booking). The public areas of the property are very comfortable and the staff is warm and welcoming. After a day or two on my last trip, one of the pool & beach staff members noticed where we like to set up our beach chairs and he had them all set up for us before we even came down one morning. This lasted the duration of our stay and this is service I can really get behind. Well done!

Ok, you caught me. This giant cup is filled with a mimosa.

The restaurants here are good and on my next visit I'd like to try their brunch at Ferdinand's because starting my day in a mimosa haze on vacation (see above) is always the goal. Tortuga Beach Grill & Bar is exactly what you'd expect for a bite on the beach and in the evenings the poolside bar has live music that creates the perfect atmosphere for watching the sun set over Seven Mile Beach. They also have a small cafe for grab and go items which I very much appreciate. Sit down breakfast can sometimes be too much, too time consuming, and too expensive. This creates a nice balance.

The spa is on the small side, but the treatment I had here was exactly what I was looking for. My massage therapist was so friendly (a given for anyone you will run into in the Caymans) that we ended up chatting throughout the whole massage. I didn't mind this a bit and as it turned out, she often visited friends in my home of small little Hoboken, NJ, so we ended up exchanging numbers so we could hit the town on her next visit! To me, the people you meet are one of the coolest parts of travel.


Photo courtesy of Ritz-Carlton Grand Cayman

If you're looking for that luxury experience, the Ritz-Carlton Grand Cayman is it. The property is huge with a structure on the beach and one across the main street, connected by an aerial bridge. You can seamlessly cross between the two properties and never notice that you've crossed the street as they did an amazing job in the transition. The bridge appears to be a hallway with local works of art lining the walls, distracting you from the fact that you are indeed in the air crossing the street. You'll make this trek regardless of which side of the resort your room is located on as the lobby is on the side that's across the street from the beach. If you're staying in Seven South, their 11-bedroom, 20,000 square foot suite (the largest suite in the Caribbean) you won't have to worry about this. In fact, you won't have to worry about much.

The property has so much to offer in terms of activities. Multiple pools, a nine-hole golf course, and their Ambassadors of the Environment program (nature and cultural activities developed by Jean-Michel Cousteau) will keep you busy. Their facilities on Seven Mile Beach are the best on the island as are their dining offerings. Each year, they host the Cayman Cookout which gathers some of the most influential and talented people in the culinary industry. They feature demonstrations and tastings from the likes of Anthony Bourdain (Tony if you're reading this, call me!), José Andrés, and Emeril Legasse. The whole event is hosted by Eric Ripert (owner of NYC's Le Bernadin which is consistently voted the best restaurant in the city) who houses one of his restaurants, Blue, at the Ritz-Carlton.

The service is exactly what you'd expect from a Ritz-Carlton which a very good thing. On my stay, I was there for business which required me to work some really long days. My housekeeper took note of this and I returned one evening to find a bubble bath drawn for me and the below note left next to the tub. I stood there reading it with my feet aching and nearly cried tears of joy.

Grand Cayman is also home to many many condos available for weekly rentals. The majority of these are oceanfront which makes it a really nice option. If you can't find a hotel that fits your needs, a condo just might!

where to eat:

Ok, back to the tasty stuff. Sunshine Suites' fish tacos are renown with visitors from every inch of the island trekking here for a bite. Go for an early or late lunch to avoid having to wait for a table. Two or three (your choice) perfect tacos come on a plate and are served with coleslaw, but I recommend substituting with the Sunshine Scramble which is a mixture of fried onions, jalapeños, mushrooms, and fries. They make their own hot sauce which is readily available on all tables and is a mix of a spicy and a vinegar-y punch.

In the evenings, the restaurant offers a delicious dinner menu which includes things like wahoo, mahi, and my favorite, the Havana chicken. All dishes come with so many sides that the plate is nearly overflowing. For Cayman standards, all of their menu items are at a very affordable price point. Also, shoutout to their yummy cocktails!

This is my absolute favorite dinner restaurant on the island. We love it so much that we always save it for our last night of the trip so we can end on a high note. Situated in the West End, you'll be driving down small roads wondering where you're going. You'll hit a dead end and Calypso Grill will be right in front of you on the water. When you enter the restaurant, you're immediately hit with a cozy and an eclectic atmosphere. While the terrace outside is the prime place to sit, the inside is wonderful as well. We once had dinner inside at a cozy little table amidst a torrential rain storm outside and it was the best. Their menu features so much fresh seafood and they have nightly blackboard specials.

The Brasserie was one of those places that I randomly started following on Facebook with the intent of trying it on my next trip and that's exactly what I did. Driving up we felt a little unsure as it was in what seemed like a corporate office building, but I'm so glad we didn't turn around. They pride themselves on growing their own produce and catching their own fish and you can really taste the difference. I had the best ceviche (it was wahoo - the fish, but it made me "wahoooo!" as well) of my life here. I still follow them on Facebook and can't wait to go back on my next trip.

While Camana Bay itself is not a restaurant, it offers many fun places to dine. As a master planned community complete with it's own school and movie theater, there are shops and restaurants all set along the waterfront. I love the atmosphere here and each time we visit, we try a new restaurant. Some have come and gone and others have been there for years like Karoo and Abacus. Many of them have great happy hours where you'll likely mingle with a lot of residents who work in the financial center at Camana Bay out for some drinks after work.

what to do:

Stingray City

This is the obvious answer when you ask anyone what there is to do in the Caymans. It's a large sandbar located within the barrier reef that surrounds the island. Wild stingrays come here to feed and hangout which apparently someone thought was the perfect opportunity to let tourist swim up close. It's something that I think you should try once and then you won't need to do it again. It can get a bit crowded when some of the larger boats roll in, so I recommend heading out with Captain Dexter on his catamaran.

Our trip with Dexter was hilarious and unexpected all at the same time. He picked us up in his little van and made a pitstop at the supermarket where he ran in to get provisions for the trip, leaving us in the running van in the parking lot. We had that moment where we were wondering what we'd gotten ourselves into. After the quick stop, we boarded his catamaran and headed out. There were only about six of us on the boat which allowed for us to comfortably lounge on the front trampoline (the netting that allows you to lounge and see the ocean underneath) and on the back of the boat.

When we got to Stingray City. Dexter expertly anchored us away from all the other boats. This allowed us to have what felt like a completely private experience. He jumped off the boat and pulled out some food which brought the stingrays right to us. They practically laid in his arms, allowing us to come over and pet/hold them ourselves. You'll notice I have no photos of this experience. That's because I jumped off the catamaran, dove down to pick up a conch shell, and when I surfaced, six stingrays gracefully swam over to me. They then proceeded to circle me over and over again. I'm no wildlife expert. but I thought to myself that this had to be some sort of ritual before they go in for their prey. I could not have swam to the boat fast enough and unable to hoist myself back up from that angle, I clung to the side of the boat as tight as I could. While everyone got QUITE the laugh out of this, I was convinced that I outsmarted the rays. The truth is, they are extraordinarily friendly and there is no need to act like a lunatic. Oops!

Dexter dove down and collected some conch shells which he brought aboard. He craftily extracted the conch from the shell and whipped up some ceviche right on the spot. When we went to leave, the boat got stuck on the sandbar and off Dexter went again, diving down into the clear blue water. He maneuvered the boat so well and we were off the sandbar in no time. We later found out that Dexter was retired from something like the local police force which made perfect sense and made him even more endearing to us.

Located on the quiet north side of the island lies Rum Point and Rum Point Club. Accessible by either car or boat, the club offers lounge chairs, a bar/restaurant, and shopping. From Rum Point looking south, you can see back to West Bay. It makes for a nice little day trip away from Seven Mile Beach.

George Town

As the capital of the Cayman Islands, George Town is a financial hub and the port for cruise ships. This means that there is a lot of shopping here in terms of jewelry stores and souvenir shops. It's good for a morning stroll, but make sure to check which days the cruise ships are pulling in. It's crowded, but some of the stores will only open on these days.

The Blowholes

Many islands have blowholes and Grand Cayman is no exception. This is when the ocean rushes in through sea caves that have grown upwards, creating an opening where the water blows out of when a wave rolls in. The rocks along the area are riddled with fossils which is pretty interesting to see. It's a neat little stop and on my last visit there was a gentleman (who has an uncanny resemblance to Obama and will do an impersonation if you ask him to) there who is the unofficial guide of the Blowholes (he's a local teacher by day). He took us around and pointed out things that we would not have otherwise noticed. We tipped him a few bucks for his efforts and continued back on our way north with a quick stop in Hell. You read that right, there is a small town named Hell where you can stop off and mail some postcards at the Post Office and play a fun little trick on your friends back home.

If you've traveled to the Caribbean, you know very well how bad the stray dog issue is. Cayman is not immune to this, however it is much more under control than other islands all thanks to places like the Cayman Islands Humane Society. I'm a believer in leaving a place in better shape than when you arrived. For me, this meant paying a visit to the Humane Society with bags of food, a donation, and my time. We offered to take any dog, not just limited to puppies (because everyone wants to play with puppies), but they gave us two pups who had just had a bath and were heading to an animal rescue group in Long Island that afternoon! They were the cutest and spunkiest little beings, so I was glad we could make their day and help to drain some of their energy. It broke my heart to later hear from the staffers that they just do not have enough volunteers during the week to give every dog a walk each day because of regular jobs. Many of the older dogs sit in their kennels THE ENTIRE WEEK and only get their walks on the weekend (cue the waterworks). While the Humane Society is doing a world of good, they need more help because no animal deserves to live like that. Please consider popping over during the week on your trip to take out a dog. You'll both appreciate the exercise!

I have only touched upon the many activities on the island. There's everything from butterfly farms to botanical gardens and countless museums. All of this is my favorite thing about Grand Cayman. You aren't restricted to your hotel and when you do venture out, you feel extremely safe. With so much to do, you can try something new on every visit because there is no doubt that after your first trip, you'll be planning your second.

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