North Side, Grand Cayman: Perfect Afternoon Itinerary

North Side, Grand Cayman: Perfect Afternoon Itinerary

Tired of the Seven Mile scene? Ready to add some flavor to your standard weekend plans? This itinerary for North Side, Grand Cayman is simple, easy, and a perfect way to spend an afternoon! I have kept this list to 3 essential stops so that you may complete the tour in 3 hours or less with maximum enjoyment and minimal exhaustion! Read on to uncover the perfect North Side itinerary and begin planning your next Cayman adventure!

Setting Out

I am a firm believer that a good road trip is never complete without a preliminary coffee stop! If you are meeting up with others, a great place to start the journey is at Jessie’s Juice in Camana Bay. Grab some caffeinated encouragement for the road and go over your afternoon game plan with the group.

Stop #1 Over the Edge Café

312 North Side Road KY1-1601, Old Man Bay

If departing from the Seven Mile area, the drive to Over the Edge will take roughly 40 minutes. (Might as well be a 3 hour road trip for Cayman standards.) Roll the windows down, turn on 98.9, and enjoy endless Caribbean vibes while cruising through Savannah and Bodden Town.

Over the Edge is a no-nonsense, oceanfront bar and restaurant located in Old Man Bay. Serving delicious Caymanian cuisine in a casual setting, this is the place to go if you want a seaside meal at a very reasonable price. I myself ordered the Mahi Mahi (pictured below) with plantain, rice and beans, and sautéed vegetables. They also brought complimentary Cayman fried bread to our table upon arrival. We sat as close to the water as possible and enjoyed a soft breeze and sweeping views of the glittering turquoise waters. Over the Edge is sure to leave you feeling relaxed and satisfied, ready for a Barefoot Beach adventure!

RECOMMENDED READ: East End Girls Trip Itinerary

Stop #2 Barefoot Beach

Queens Highway

After lunch, it’s time to make your way to the beach for some exploring! A 6 minute drive east from Over the Edge, Barefoot Beach is a secluded area offering stunning vistas and a bohemian feel. It is best known for its picturesque seaside steps and jagged cliffs. (Cliffs in Grand Cayman?? Yes, it’s true!) Wear good shoes and do some exploring along the rocky paths. Although the ocean entry is a bit rocky, I managed to swim around and wade through the light waves. It was very refreshing! All of this sounding a bit too adventurous for your liking? Simply pack a cooler of drinks and enjoy the gorgeous surroundings!

Above Photo Credit: The Cayman Expats

RECOMMENDED READ: The Ultimate Grand Cayman Bucket List

Stop #3 Willie’s Fresh Fruit & Juice Stand

Corner of Bodden Town Rd & Frank Sound Rd

After an hour or two at the beach, you definitely won’t say no to a fresh mango or guava juice. I certainly didn’t! While driving back to the Seven Mile area, be sure to stop at the Willie’s fruit stand located at the corner of Bodden Town & Frank Sound Rd. You wouldn’t believe the joy we experienced when we came across it. Our group stocked up on juices for the road as well as freshly baked bread and a native Cayman fruit we had never seen before. We were told it was an apple but I beg to differ! At any rate, it was fun to try something new. With fresh island goodies for reinforcement, it’s now time to make the trip back west. So roll down your windows, turn up the soca, and cruise with your sun-kissed skin and mango-stained lips all the way back to home base.

RECOMMENDED READ: 7 Best Healthy Restaurants in Grand Cayman

This island is beautiful, but living in the Seven Mile area with prices as high as its condos can start to feel a bit like an artificial paradise. I love going out to the North Side of Grand Cayman because it has a nitty-gritty island feel that reminds me I am, IN FACT, living in the Caribbean! Crazy, I know. Anyone who has driven out this way understands the shift in mindset that occurs once you’ve passed through Savannah. I recommend these three stops to anyone who may be looking to add flavor to their weekend plans. It will give you a beautiful and authentic taste of Cayman. Happy adventuring!

Recommended Read: 10 Tips for Your First Trip to Rum Point


Cayman Islands Travel & Lifestyle

MEET KATE

 Hi, I’m Kate! I’m a Wisconsin native who traded her snow boots for flip-flops in May of 2020 when I packed my whole life into two suitcases and moved to the Cayman Islands with my partner, Bryan.  I created Island Diaries as a way to document my island adventures and share about the Cayman lifestyle. A Midwest girl at heart, I bring a fresh perspective to Caribbean life, serving as a guide for locals and tourists alike on all things Cayman Islands. Whether you are local to Cayman, planning to visit, or just curious about island life, I invite you to explore Island Diaries and let this site guide you on your next island adventure!

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Cayman Islands East End Girls Trip Itinerary

Cayman Islands East End Girls Trip Itinerary

Are you looking for a unique day trip to shake up your girlfriend plans in Cayman? Look no further! Below you will find a unique East End itinerary featuring food, art, and drinks! While our outing did not include any beach stops due to overcast skies, I will offer some suggestions for additional or alternative activities to customize your very own girls day out! 

Stop #1 Jessie’s Juice

Jessie’s is a great rendezvous point to kick off your girls day out. Here you and your girlfriends can meet up and equip yourselves with caffeine for the exciting journey ahead! After all, what’s a road trip without a coffee companion?


Stop #2  Charles Long Art Studio

114 West Ln, Savannah

This East End itinerary features two very distinct art studios; the first of which is located in Savannah along a pebbled residential road beside the artist’s private home. Arriving at the Charles Long studio felt like total submersion into the local Cayman culture as Charles himself came out to greet us and shake our hands one by one. The studio is open and airy with natural light streaming through the domed ceiling. A visit to the gallery must be reserved in advance via Instagram or by calling directly. The pure island vibes and familiar spirit of this gallery make it an excellent detour off the beaten tourist trail. 

Instagram: @ckglong

Phone: +1 345-917-5741



Suggested Stop: Pedro St. James

Pedro Castle Road, Savannah

Charles Long’s studio is very close to Pedro St. James, a natural historic site situated alongside the sea. While I have yet to tour the 18th century Great House, I have enjoyed a drink and appetizers at the distillery that overlooks the water. There is also a stunning swimming hole that sometimes fills completely with water. Wear sturdy walking shoes and venture down the Ironshore to take a dip in the natural topaz pool.

Stop #3:  White Dog Art

Bodden Town Road

As you continue further east toward Bodden Town, you will near the second stop on our girls trip itinerary. White Dog Art is a simple modern house that greets visitors with a stunningly vibrant mural painted by the artist herself. Similar to our experience at Charles Long studio, the artist, Ren Seffer, came out to greet us with a warm and welcome smile. She invited us into her bright studio space where we felt right at home amongst her cheerful canvas paintings. It was so fun to see the contrast between the artwork of Charles and that of Ren. While both artists showcase a sea of bright, happy colors, their styles are utterly distinct and cannot be compared. (A visit to White Dog Art studio can be arranged through their website)

Instagram: @whitedogartcayman

Our group posing in front of the studio’s mural with Ren on the far right

Although I did not walk away with any pieces, I enjoyed getting to know more about the culture and history of Cayman through the art itself as many of the paintings featured emblematic places and people of the island. A few of the girls in our group gathered information from both artists to have a piece commissioned. This is also something to look into if you are searching for the perfect art for your home or as a gift.



Suggested Stop: Fruit Stand

Just up the road at the corner of Bodden Town Rd and Frank Sound Rd there is a fruit stand where you can pick up some local produce (cash only). This is a nice stop to restock your refreshments as you continue on your East End ramble!

Stop #4: Tukka

898, Austin Conolly Dr, Gun Bay

At this point in your girls trip, you have most likely worked up quite an appetite. No worries, delicious island fare is right around the corner! East End offers several excellent options for waterfront dining. For this itinerary in particular we selected Tukka, an Aussie-owned restaurant with a Caribbean twist. Their menu is quite large and diverse featuring local favorites as well as many international & Australian dishes. Being that our trip took place on a Sunday, they were offering a brunch deal for $CI 34. I myself ordered a la carte, selecting a lionfish taco and coconut prawns. While I am typically a cocktail girl, I was feeling rather rustic and decided to order a local bottle — Caybrew light. The highlight of lunch was sitting on their patio overlooking the water with a lovely ocean breeze!



Suggested Stop: Barefoot Beach

Queen Highway, East End

Unfortunately, the day we went on our East End trip it was a bit cloudy and cool (for Cayman standards) so we decided to skip the beach. However, I would recommend a stop at Barefoot Beach either before or after lunch. Even if you do not plan to swim, it is a beautiful spot to relax, take photos, and enjoy some drinks and snacks from the cooler. 

Barefoot Beach

Stop #5: Czech Inn

Bodden Town Rd

Circling back from East End en route to George Town, the Czech Inn is the perfect place to finish an East End outing on a high note. Arriving at the Czech Inn is a visual overload as this bohemian, outdoor bar and grill is decked out head to toe with unexpected decorations like surfboards for tables. While it is definitely not known for its scenery, the vibe of this place is one of a kind and 100% worth a visit. Although our group did not order food, the place has excellent menu reviews making it a perfect casual, roadside lunch spot. 



My thoughts on the day:

This itinerary provides a well-rounded cultural taste of East End that includes food, art, and nature. It is a perfect day trip for you and your girlfriends but could be enjoyed by anyone for any occasion! I am by no means an art enthusiast but I really appreciated the unique perspective these galleries provided me. I was able to see the island through the eyes of local artists — a truly special experience! I will definitely be back to Tukka soon for some more lionfish tacos and coconut prawns! Happy trails on your next journey out east!

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