Hi! I’m Isy B. I’m a designer in the Cayman Islands and I love using our beautiful Islands as inspirations for my designs. One of my other favourite things to do is travel, and if you’re anything like me when I travel, you'll like to go beyond the usual tourist-curated fare and root out the more off-the-beaten-path experiences that will get you away from the tourist throngs.
I love little escapes on vacation which often become the real highlights because I get to meet new people, experience something different, and if only for a few hours, live as stylishly as the locals!
When it comes to traveling, I want to experience the best and most beautiful that every place I travel to has to offer. But isn’t that the same for everyone? So let me be your insider guide to the best non touristy things to do in the Cayman Islands when planning your vacation so you can experience our local spirit, and live the island's good life like us locals!
Welcome to my hometown, it’s fabulous here!
What to Not Miss in Grand Cayman
Of course there are the most popular tourist attractions in Grand Cayman such as Seven Mile Beach and Stingray City, but there are also many lesser-visited spots on the island that are definitely worth exploring. For the nature lovers the Mastic Reserve offers lush mangrove forests, and diverse flora and fauna, while the Pedro St. James National Historic Site boasts a beautifully restored Great House, history and stunning views of the Caribbean Sea. For the art enthusiasts, I can’t recommend enough the Cayman Islands National Gallery and the art galleries in George Town that offer an opportunity to discover unique works by our talented local artists. Foodies can embark on a culinary adventure by trying traditional Caymanian dishes or international fusion cuisine with a Caribbean twist, the Cayman Islands have the title of the culinary capital of the Caribbean for good reason!
Finally, those seeking a more peaceful beach experience can visit secluded coves or hidden beaches found in Rum Point, Starfish Point, Smith's Cove or Cemetery Beach.
The Best Non Touristy Things to Do in Grand Cayman
Grand Cayman is a magnificent small island boasting breathtaking natural beauty, clear waters, historic sites and delectable cuisine. It's also the largest of the three islands that make up the Cayman Islands. But not all your activities on the island need to be the typical tourist experiences. During your visit, you can partake in more curated activities, including indulging in a luxurious afternoon tea at the Ritz Carlton, practicing paddleboarding yoga, listening to live jazz at an authentic speakeasy, and chartering a sailboat for a day. Best of all, getting a taste of these activities offers a chance to support local businesses and immerse yourself in the unique local culture. So let’s dive in!
Experience Cayman’s British side with a stylish take on this English tradition with cakes and biscuits and teeny-weeny little English sandwiches, and of course a huge selection of teas worthy of royalty and served with all the charm and splendor of the Ritz Carlton. I also love the lobby bar here, so you can choose to skip the tea altogether and head straight for the champagne. Just saying…
Prepare to be dazzled by the natural light show that surrounds you as you swim or Kayak through the warm water in this beautiful nighttime adventure. Tip: Book this on a dark night when there is no full moon for the best underwater light show.
Let’s get you out of the studio and get into the sparkling, clear blue Cayman water. Your teacher; Paddleboard and Yoga expert Kirsten Cousins of the aptly named VitaminSea is so good at what she does that she has been featured in style magazines globally. She was also my amazing paddleboarding teacher back in the day.
May I also suggest that this is the perfect excuse to rock your signature Isy B. Rashguard!
GRAB YOUR PADDLEBOARDING YOGA RASHGUARD NOW
Prefer to keep your feet on terra firma? Join the free community beach yoga class on Sunday mornings at 8am at Governor’s beach, in front of the Governor’s House beside the Westin. A glorious way to start a Sunday with your toes in the sand and your down dog up in the air! And did I mention it’s free?!
After all that yoga, you surely deserve brunch. And brunch in Cayman is a big deal. We love to dress up for brunch in the Cayman Islands and there are so many options to choose from depending on your mood. Here’s a hotlist of where to go for brunch in the Cayman Islands, and what to wear.
Listen to Live Jazz at a Real Speakeasy
Offering everything from really good 5 piece jazz bands to sultry soloists and sensual burlesque, Next Door is just fabulous. This modern take on a vintage speakeasy is as intimate and sexy as they come. Also, the signature cocktails are to die for. Check out their website's weekly schedule for weekly happenings. Alternatively, the music scene is live and kicking, experience live music for free at beautiful venues like the Silver Palm Lounge at the Ritz Carlton, or the newly opened Library Bar at the Kimpton, and be blown away by local artists including Dan Ebanks, or Denys Carbo and his band.
Road Trip East for a Luxurious Picnic
First stop, The Tasting Room and Cellars for the yummiest picnic supplies; Italian cakes, cheeses, charcuterie, desserts, and wine, lots and lots of it! Owner Mario is super knowledgeable and will guide your selections. Or for something even more sumptuous have Graze Girl set up a picnic for you. Next, choose your perfect picnic spot from some of Cayman’s iconic historic and most beautiful sites including the lake by the Queen Elizabeth botanic park, the park at the wreck of the ten sails, or go North to Starfish Point (do visit with the starfish but don’t pick them up out of the water!)
Boat Taxi across to Rum Point/Kaibo
Want to feel like you’ve truly arrived?! Catch the boat taxi to the very glamorous Kaibo Beach Club for lunch or dinner. If you’re there for lunch; take your swimsuit and spend the afternoon lounging on one of their luxurious Ibiza-inspired beach daybeds listening to a DJ throwing down some live music. Alternatively, if you are lucky enough to bag a seat at one of their full moon dinners on the beach or their rare rum-tasting dinners, do it! This is an elevated Caribbean experience I doubt you’ll ever forget!
Charter a Sailboat For the Day
For the ultimate stylish VIP experience take a gorgeous private catamaran sail to explore the North Sound. Enjoy everything from champagne to gourmet platters on board. Visit the stingrays in style with your own private snorkeling guide. They might also take you to visit the 20ft nurse shark that lives at the coral reef nearby (I’ve seen her, she’s huge but I’m told she’s harmless…)
Planning a longer sail? Check out some of our suggestions for what to bring on a sailboat and download a packing checklist list for free!
Crystal caves and the Queen Elizabeth Botanic parks may be tourist attractions but they are one of our most picturesque areas of natural beauty on the island and so a must-visit. I get a lot of my inspiration for my Isy B. prints from the Queen Elizabeth Botanic Park. See if you can spot any of the influences!
The Crystal Caves are a spiritual and energetic wonder for me. It’s impossible not to feel the beautiful energy when you’re surrounded by crystals in their natural habitat.
Try a New Sport
For the more active vacationers (there’s only so much time I can sit on a beach personally). It’s easy to book golf, tennis, or even pickleball pro for a morning indulging in a sporting activity you may not have time for at home, or learning something new! Pickleball is apparently the fastest-growing sport in the world so why not get in on the game and learn to play pickleball in the Cayman Islands?
Immerse Yourself in Local Art
The National Gallery of the Cayman Island is a beautiful modern gallery set in its own gardens and filled with the works of Cayman artists of all disciplines. The exhibitions change regularly and the exhibitions themselves are always wide-ranging and give you a look behind the scenes into local island life from the turn of the century to date from the perspective of its artists. The gift shop is also a great place to pick up high-end stylish Island-inspired souvenirs, including your favorite Isy B. notebook journals and more!
Channel Your Inner Artist
Prefer to be more hands-on with your creativity? Try the ceramic painting or arts & crafts classes at 3 girls and a Kiln or local favorite, Art Nest Studio. With a changing weekly lineup of classes, it’s an opportunity to experience a new activity and potential future hobby!
Go to the Movies
But not just any movies! Rent the Cayman VIP Movie theater for 2 and up to 25 people for a private screening of your favorite movie on the big screen in plush VIP armchair seating, surrounded by your favorite people for your very own private red carpet Cayman Islands experience. Alternatively, why not catch a movie on the beach? The Westin Hotel screens different themed movies on its beach. You can enjoy a movie with a delicious dinner from the casual beach-front restaurant with sand between your toes and a beautiful beach sunset backdrop.
Ok, so, I know that shopping on the Islands is one of the most touristy things to do, but at the same time it is something that locals love doing too! Head to George Town or Camana Bay for some of the best shopping. You’ll find Isy B. in Camana Bay at TABS Cayman, along with the freshest lineup of local and Caribbean designers, also find Sand Angels, Ame, and NKY for the best mainstream shopping options. If you want to dive deeper into the Cayman Islands luxury shopping culture we've got you covered with the ultimate guide for 2023!
We also recommend checking out the hotel boutiques as they carry the widest range of local and international brands at surprisingly good pricing. Check out La Boutique at the Ritz Carlton, The Mercantile at the Marriott hotel, and the spa boutique at the Kimpton Seafire. Best of all, you can grab a cocktail at the fabulous hotel bars as a reward for an afternoon of shopping!
Want to experience Cayman Islands shopping from home? Shop online Isy B.’s Storyteller Collection, inspired by whimsical Island folktales.
This is a pleasant way to spend an adult afternoon or evening for wine lovers. You can have fun “tasting” as many wines as you like for a flat rate while searching for the one you really love. We know you may need to sample half a dozen to find your wine soul-mate. The setting is a lovely courtyard on the Paseo at Camana Bay, also great for people-watching in all their fabulous island glory with a glass of vino in hand.
We have one of the best gelato shops that it’s been my privilege to visit anywhere in the world, even in Italy. And Yes, the owner Marcella is Italian. Stop here, grab a gelato, and then lounge on one of the waterfront rocking chairs or hammocks in Camana Bay or keep yourself cool as you wander around the stores in George Town at their other location. Perfect.
Day Trip or Overnight Break to the Sister Islands
Cayman Brac and Little Cayman give a taste of what life would have been like on the island before the tourists arrived. Both are much smaller than Grand Cayman with a fraction of the number of inhabitants of the big island, so definitely have a Robinson Crusoe/Lost vibe. Imagine wandering along the powder-white beaches of Point of Sand with no one else in sight, or exploring Owen Island, a tiny island you can swim or kayak to from the shore in less than 10 minutes, or rock climbing the towering bluff cliffs of Cayman Brac.
On Cayman Brac, stay or have lunch at the fabulous Soleil D’Or Hotel, a farm-to-table boutique hotel tucked into the cliffs below its own private farm where they'll hand-pick the vegetables for your lunch.
Dance Your Heart Out
Try Salsa lessons and salsa night at The Wharf restaurant on Tuesdays or take a private lesson with the teachers at Fuego Latin Dance to prepare yourself.
Look out for Boogie Nights at the Sand Bar on the last Friday of every month. It's a 1970s and 80s music-fueled night of gloriously infectious dancing madness. I dare you not to do the “YMCA” while singing at the top of your lungs along with 300 to 400 other people of all ages. Don’t be shy. It feels somehow like a bonding experience.
For something more elegant try your hand at jazz, pole and aerial dance classes with Quintessential Movement on Seven Mile Beach.
Cook Up A Storm
Meet your fellow cooking enthusiasts and gourmands at Bon Vivant’s show kitchen for a private cooking class with some of the most talented chefs on the island. The best part? Eating everything you’ve made of course!
Shop Vintage Books and Lounge on the Beach at Tillies
With its now iconic yellow striped umbrellas, 1940s vintage style pool, and mid-century modern styling to match, Palm Heights hotel has become the Caribbean media darling for its hip, chic offerings since its opening just a few years ago. Loved by the jetset (the Hadid sisters have been spotted here a few times), it's been featured in publications such as Vogue, WWD, CN Traveler, and Travel & Leisure magazine among others, and rightly so. Its beachfront restaurant Tillies serves up delicious food inspired by the Antilles and has a weekly roster of fun events. I love going to lunch in my one piece swimsuit and taking a dip in the sea in between courses. So very indulgent! They also have a fabulous vintage bookshop that I drool over every time I visit. The book covers look like works of art in themselves.
Unique Things to Do in Grand Cayman
Grand Cayman offers many unique and exciting experiences beyond the usual tourist attractions. Visitors can explore the island's lush forests by hiking, biking, or even rock climbing, take a horseback ride along the beach, or discover local art at the National Gallery or ask them and make it even more unique by visiting the working studio of a local artist. Other unique activities include meeting a 20ft nurse shark, practicing yoga on a paddleboard while watching the sea life beneath you, or taking a culinary tour to taste traditional Caymanian cuisine. Each of these unique experiences offers a chance to delve deeper into the island's culture and natural beauty.
Secret Things to Do in Grand Cayman
For those seeking off-the-beaten-path adventures, Grand Cayman offers several hidden gems that are worth checking out. Visiting the endangered blue iguana sanctuary at the botanic park, exploring the Crystal Caves, a stunning natural wonder with crystal-clear pools and unbelievable rock formations, or wandering along Starfish Point, a quiet beach where visitors can see starfish in their natural habitat.
Want to experience the luxurious side of the Islands while staying away from the crowds? Book a private catamaran sail to explore the North Sound, or rent a VIP movie theater for a private screening of your favorite movie and have your own secret red carpet party.
Is Grand Cayman Worth Visiting?
Grand Cayman is absolutely worth visiting, not just for its beautiful beaches and clear waters, but also for its unique culture, delicious cuisine, and welcoming locals - Caymankind is taken very seriously here. You can enjoy everything from water sports and island tours to shopping, dining, and nightlife. The island also offers a range of accommodation options, from luxury resorts to budget-friendly guesthouses and condo rentals, making it accessible to a variety of travelers.
When to Travel to Cayman Islands
When planning a trip to the Cayman Islands, it's important to consider the best time to visit based on your preferences and interests, and of course budget. The peak tourism season in Grand Cayman runs from December to April, when the weather is typically dry and temperatures are comfortable around 80 degrees Fahrenheit. This time of year is also great because the cooler weather makes it easier to explore further afield but it can also mean higher prices and larger crowds. If you're on a budget and want to skip the hustle of the big crowds, consider visiting during the off-season from June to November. While the weather may be slightly hotter and more humid and there may be the odd risk of a rainstorms, this time of year can offer lower prices and a more laid-back vibe. Additionally, you might also want to consider the fall months of September to November if you enjoy diving, as the water is often clearer and there are fewer crowds. If you’ve just started planning your trip the official Visit Cayman Islands website is the one of the most useful online resources for general information about the Cayman and the low down on the biggest events that are happening.
In conclusion, the cosmopolitan nature of the Cayman Islands means that it can offer more than just the typical tourist attractions. Get adventurous and immerse yourself in the non-touristy side of the island, you can discover unique experiences and find hidden gems that will make your trip truly unforgettable. Whether you're a first-time visitor or a seasoned return visitor to our Islands, I encourage you to step outside of your comfort zone and discover the lesser-known side of Grand Cayman. Join us in living the island life for a spell.
For me, travel is about enjoying the good life, and when you visit my hometown, I'd love you to experience the best of the Cayman Islands and feel welcome here, just like a local. And don't forget to drop us a line at Isy B. to say hello when you're on the Islands!
You can now shop the designer’s exclusive limited-edition luxury resort wear collection on the Islands at The Mercantile at Marriott Grand Cayman, La Boutique at Ritz Carlton Grand Cayman, the Spa at Kimpton Seafire Resort and Spa, and TABS.
Also, find all pieces in Isy B.’s website with a free delivery within the Cayman Islands, or to the USA for orders over $250.
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