The Ultimate Grand Cayman Bucket List

The Ultimate Grand Cayman Bucket List

Grand Cayman, however small it may be, offers countless activities and adventures for visitors and locals alike. The best part? Most of these activities require very little planning and in many cases, minimal spending. These factors make this island a perfect setting to tick off a whole slew of bucket list items! Keep reading below to uncover the Ultimate Grand Cayman Bucket List and get started on your tropical adventures today.

Download the PDF version below of this bucket list below:

1. Kiss a stingray for 7 years of good luck: Stingray City is where you can go to feed, pet, and even kiss these gorgeous sea creatures. Hop on a boat party or book a group tour with Red Sail.

2. Enjoy a fish fry at Eastern Star: 30 minutes from central Georgetown, this beachside bar and restaurant offers a wide selection of locally caught fish, lobster, shrimp, and conch.

3. Visit the Parrot Sanctuary in East End: If kissing the stingray didn’t work, don’t you worry! Kissing a parrot is said to bring 10 years of good luck. The Parrot Sanctuary will bring you face to face with some of the island’s native plants and animal species. The stars of the show are of course, the Cayman Parrots! After your visit you can head across the road for a seaside lunch at Tukka.

4. Explore the Crystal Caves in Northside: Venture through three spectacular caves and the surrounding tropical forest on a 90-minute guided walking tour.

5. Dive or snorkel the Kittiwake shipwreck: Before moving to Cayman, I thought exploring sunken ships was only possible in the movies. This island makes these adventures so accessible with its plethora of shipwrecks and world-class diving culture.

6. Take a leisurely stroll through the Queen Elizabeth II Royal Botanic Park: Live like royalty for a few hours while wandering through these elegant gardens with their exotic floral display. This experience will leave you feeling peaceful and inspired!

7. Salsa dance a Tuesday night away at the Wharf: Can you name a more perfect backdrop for a night of Latin dancing? Arrive early to brush up on your steps as a dance instructor gives complimentary lessons. Entrance is free and water is provided!

8. Embark on a sunrise stingray cruise: Perfect for the early-birds, this tour gets you to the sand bar before the crowds. After Stingray City, you’ll head to the North Sound barrier reef for some snorkeling. A truly perfect start to the day!

9. Go horseback riding on the beach: Have the adventure of a lifetime by swimming bareback on your horse. Cayman’s crystalline waters create a dream-like setting for a truly unforgettable horse riding experience.

10. Take a Humane Society pup for a beach walk: This organization works so hard to care for homeless pups! Their shelter is often full and they greatly appreciate volunteer dog-walkers. No need to sign up or register, just stop in and they’ll give you the sweetest dog to take for a couple hours, the whole day, or even just 20 minutes.

11. Book a fitness class or sound healing on the Palm Heights rooftop: The view from atop this boutique hotel on Seven Mile Beach is absolutely breathtaking. Need relaxation? Clear your mind and soul with one of Janine Martins’ sound healing sessions. Want to sweat it out? Check out Jude Love’s Full Body Conditioning or Naturally Heated Pilates.

12. Star gaze at Barkers Beach on a clear night: This one is for the real adventurers wanting to go off the beaten trail. Away from the hustle and bustle of Seven Mile Beach, Barkers is a peaceful, remote setting for an evening of star gazing. Pack flash lights, bug spray, and refreshments of choice!

13. Snorkel with turtles at Spotts Beach: Another activity that rewards all the early risers out there! The best time to see turtles at Spotts Beach is from 7 am and onward. Swim around the seagrass area and you are sure to spot a few! Check out my Spotts Beach video here!

14. Swim in the natural topaz pool at Pedro St. James: Timing is everything with the swimming hole at Pedro St. James. Sometimes it is pristine and gorgeous, other times it simply an empty rock hole. If you are someone who understands tides, you may have a bit more luck with this! Wear durable shoes as you’ll have to traverse the Ironshore.

15. Go for a hike on the Mastic Trail: Immerse yourself in the island’s native plant species with this 7.4 km out and back trail near Bodden Town.

16. Kayak or snorkel the Bioluminescent Bay: Book with Cayman Kayaks for an unforgettable 2-hour bioluminescent kayak experience. Feeling brave? Other tours on island allow you to jump in and snorkel. Just beware of the jellyfish! Read about my failed DIY bioluminescent experience here!

17. Camp on the beach during the Easter Holiday: What a wonderful way to disconnect and enjoy the natural beauty of Cayman’s coastline! Hundreds of people turn out for this long-standing island tradition. If you’re unable to camp, take a walk on the beach to experience some of the fun first hand!

18. Spend an afternoon boat partying: You will not escape this island without attending at least one boat party. Move to the rhythms of Soca music as you cruise about the dreamy turquoise waters of the Caribbean! Read my boat party tips here!

19. Steal the dancefloor at a Tillie’s theme brunch: A truly iconic experience, Tillie’s will wow you with their creative design, delicious food, and outrageously cool DJs. Read about my own Tillie’s brunch experience here!

20. Sip a Mudslide at Kaibo in Rum Point: This cocktail is as Cayman as it gets. Absolut Vodka, Kahlua, Bailey’s, and ice, finished with cinnamon, a cherry, and a shot of Kahlua down the straw!

21. Try a paddleboard yoga class with Vitamin Sea: There are few things more peaceful than a sunset savasana on the water. Surround yourself with the expansive beauty of Seven Mile Beach alongside a group of saltwater yogis. All levels are welcome!

22. Load up on fresh fruit from Tony the Mango Man: During the summer months in Grand Cayman, the sight of this man outside of Governor’s Beach will be enough to make your whole day. Bring cash to stock up on local produce and have a chat with the man behind the mangoes!

23. Participate in the Flowers Sea Swim: Hosted annually on Seven Mile Beach, this one-mile swim race attracts athletes from around the world. Grand Cayman is certainly an inspiring destination for such an exciting event!

24. Compete in (or spectate) the Cayman Islands Marathon: Runners from Cayman and around the world can compete in either the half or full marathon. Those who are not so inclined to long distance races can partake in the event by passing out water or simply cheering on the runners. Read about my own Cayman marathon experience here!

25. Spot a Nurse Shark at Eden Rock or Sunset House: Nurse sharks can be seen almost anywhere off Cayman’s shores. Eden Rock and Sunset House are highlighted because of their easy shore access. (And also because I have personally spotted nurse sharks at both of these sites). Go for an easy shore dive or a lengthy snorkel and you may just spot one yourself! Read about my very first shark sighting here!

26. Shop for amazing gifts at Pure Art in South Sound: A visit to this unique store guarantees a heartwarming shopping experience. With unique handmade gifts and island-inspired local artwork, you are sure to walk out with treasures for yourself and others. Not to mention, the store owners are incredibly kind and helpful!

27. Watch the sunset with a Paradise Pizza on the beach: This island is a paradise. Why waste time indoors? Paradise Pizza is located behind Tillie’s. Pick up a Neapolitan-style pizza and take a seat on Seven Mile Beach for unique sunset dinner experience.

28. Rise early for a sunrise Seven Mile beach walk: At this hour, you have the beach almost completely to yourself! Enjoy the cotton candy colored skies as you pad across the expansive stretch of beach. Afterwards, treat yourself to a pastry from Icoa or Marriott’s Anchor & Den — you earned it!

29. Try a local island dish at Vivines in East End: An authentic, West-Indian eatery, Vivines offers local favorites such as stew chicken, macaroni pie, oxtail, conch, and callaloo.

30. Coffee Crawl though Georgetown and Seven Mile: The “Coffee Crawl” is a caffeinated itinerary invented by yours truly! It is a guide to exploring the many coffee shops of Grand Cayman — a wonderful way to get to know the island and its businesses! Check out my guide here!

There you have it! The Ultimate Grand Cayman Bucket List is sure to inspire your future travels (if you’re a visitor) or weekend plans (if you’re a local). Of course, this is not an exhaustive list. Grand Cayman is always brimming with events, attractions, and activities (on land, at sea, and underwater). No matter what plans you end up making, this little island is going to wow you again and again — I can guarantee it!


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So you want to save money, practice sustainability, and build a wardrobe you’ll love? Don’t worry — you can do all three! Thrift shopping has been gaining popularity in the past few years as people begin to realize they can find high quality clothing at second hand stores. Don’t let those eerily specific Instagram ads trick you! You don’t have to purchase something online every other day to be “fashionable.” YOU create the fashion. And I am going to give you 10 tips to ensure you leave your next thrifty trip with clothing you love for a fraction of the original price. Oh, and don’t forget…all while saving the planet!

Step 1: Narrow Down The Best Thrift Stores In Your Area

I have visited enough thrift stores in my lifetime to tell you that not all of them are worth frequenting. Depending on where you live, there may be multiple options and you will want to narrow them down to one or two of your favorites to save time and avoid frustration. Some things to consider would be if the store is clean, organized, has enough inventory, and gives off an overall positive vibe. (I have been to some downright creepy thrift stores).

Step 2: Carve Out Some Time

If you think shopping at a run-of-the-mill retail store is time consuming, just wait until you give it a go at thrift shopping. The key to finding amazing items is time and unwavering patience. You are going to sift through 20 duds before you find something worth a second glance. It is not a glamorous job, but the hard work pays off! 

Step 3: Have In Mind What You Are Looking For

In a store where each and every item of clothing is unique in color, size, and style, it can be easy to become distracted. That is why I always walk in with a few ideas that narrow my search and help me to concentrate. For example, I may be hoping to find a new pair of shorts, a beach bag, and a casual dress. If after hitting those targeted areas in the thrift stores I still feel like browsing, I will branch out to other sections.

Step 4: Narrowing The Search – COLOR

Some thrift stores, such as Goodwill, organize their racks by color making it incredibly convenient for shopping. However, most leave their racks a haphazard mess of rainbow clothing and let the shoppers fend for themselves. Whatever the case, it is helpful to know what colors you favor when shopping secondhand. This streamlines the experience and helps you identify clothing that you are more likely to wear. If you hate the color yellow don’t buy a yellow shirt just because it cost $1. Focus on colors that match your style and are more likely to combine with the rest of your wardrobe.

YES. You are seeing this correctly. Lululemon leggings and tank top from the thrift store. Original price roughly $140 in total but I snagged these two for $15 only!

Step 5: Narrowing the Search – MATERIAL

Yet another way to focus your shopping is to pay attention to the material. A common misconception surrounding second hand clothing is that it lacks the quality of new garments but this is not always the case. Just by eyeing or feeling the fabric you immediately have a sense of its quality. If you are not looking for a cheap cotton t-shirt then simply skip over any and all cotton t-shirts. Set your sights on your preferred fabrics. For example, these days I have been searching for linen tops so I scan the racks with laser focus on linen items almost exclusively.

Step 6: Scanning the Item: SIZE

Okay, so you have found an item you are mildly interested in. Before you even pull it off the rack, take a quick peek at the size. This is the quickest elimination method as less than a quarter of the clothing on the rack will actually fit you. 

Step 7: Scanning the Item: IMPERFECTIONS

This is another very quick elimination strategy. Yes, you are willing to buy used clothing but not when there is clear evidence of it having been used! Some stores do a good job of filtering out dingy items but I have been to many that just throw everything on the racks and leave you to do the dirty work. If you pull out an article of clothing that is heavily used or damaged, next it! Please do not buy a yellow-stained blouse just because the brand is nice.

Step 8: Scanning the Item: BRAND & PRICE

This is the final check before you go into the dressing room. For some, clothing brand is inconsequential and not a factor in the purchase. However, it can be useful when considering the price of the clothing and if it is actually worth it. Use your previous shopping experience to determine the overall value of the product and if its price is fair. For example, I once went into a second hand store with many designer brands. However, I randomly found an H&M top priced at nearly $20 (basically the same or more than you’d buy it new from an H&M store). That was an obvious mismatch for price and value. If you see something like this, don’t even waste your time trying it on. If the whole store is like this, find a new thrift store!

Step 9: Time to Try On!

Don’t be afraid to try on an insane amount of clothing. It is not everyday you get lucky at the thrift store, so when you hit the jackpot you have to take advantage! If you keep finding clothing that passes all of your tests, then simply add it to the pile! Remember, you carved out plenty of time for this 🙂 But when trying on clothing, use the same standards as if you were paying the big bucks. If it doesn’t fit or doesn’t look good, don’t buy it just because it is unbelievably cheap. If you’re not going to wear it, leave it for someone else who it could be perfect for. 

Step 10: Wash & Sanitize

Woohoo! You found some winners and are walking out of the store with new threads that you love and that cost less than your dinner last night. Now what? Well, there is one last important step and that is of course to wash the clothes and yourself. Immediately throw your “new” purchase in the washer and take a shower. Actually, you should do this even if you are buying brand new clothing from the mall. In 2021, this is now self-explanatory.

Havana Club Bag: Originally priced at $30, I got it for $5 James Perse Dress: Originally priced at $85, I got it for $6.

Bonus Tip: FLAUNT IT

Get ready to brag to all your friends and family about the amazing deal you just got at the local thrift store. Oh, these Lululemon leggings? Just $6. This Columbia rain jacket… only $4. You will watch them shake their heads in disbelief and you will feel like an economically-wise, sustainable bad ass. Who says millennials have no life skills?