Planning the Perfect Cayman Road Trip

Rightfully so, most people would not put the words “Cayman” and “road trip” in the same sentence! Given that the island is only 22 miles long, you can never get too far. That doesn’t mean that there aren’t a multitude of sights to see and experiences to have on our small island paradise. It helps that Plantana is the perfect place to start! Follow us along as we describe the perfect Cayman road trip for your next stay.

Turning out of Plantana’s exit, head towards George Town on West Bay Road. Stop at Foster’s in the Strand (soon to be relocated to Camana Bay!) to pick up some snacks and refreshments before you truly hit the road! Continue on West Bay Road through to George Town – the view can’t be beat! Can you believe the Burger King is ocean front?! Be sure to park at Bayshore Mall and walk around George Town to find a few souvenirs to take back home to your loved ones.

As you continue driving, you will begin to enter South Sound, sprinkled with gorgeous ocean front properties and developments. Dart Family Park is right across from Pure Art Gallery – both a must do! Keep the kids entertained, then go across the street to pick up some gorgeous local art.

When you reach Shamrock Road, stop at the Cayman Islands Brewery for a fun brewery tour through our island’s only microbrewery. Continue on Shamrock Road instead of the East-West Arterial for a never-ending view of roadside beach! Spotts Beach is a great place for a pitstop to relax, stretch your feet, and take a dip! This beach is known for being able to snorkel with wild turtles (making GoPro pictures even more fun). Continue on until you see Wendy’s and make a right down Pedro Castle Road to find one of the most historic places on our island. Previously a plantation house and known as the birthplace of democracy in the Cayman Islands, Pedro Castle holds so much history and incredible landscape views.

Follow along through Bodden Town, Cayman’s first capital, and experience a calmer, quieter way of life. Stop into Beach Bubbles to enjoy local handmade soaps. The next stop is Lover’s Wall! The perfect photo opportunity with your loved ones or on your own, it’s sure to create lasting memories of your “road trip!” Just down the road are The Blowholes – known for their explosive waves crashing up through the iron shore. Try taking a Boomerang video of this cool natural phenomenon!

Now it’s lunch time and Big Tree BBQ is a MUST for local food. If there’s only one place you eat in Grand Cayman, make sure it’s Big Tree BBQ. You won’t be able to miss it – once you see the big tree and the bigger smiles of the owners, you’ll feel right at home. Your belly and taste buds will thank you!

As you hit the furthest end of the island, you’ll begin to turn up onto the Queen’s Highway. Yes, that’s really what it’s called! Keep your eyes peeled on the right hand side of the road for an obscure sign labeled “Barefoot Beach.” Shoes aren’t necessary, but being prepared for ultimate fun and relaxation is. Enjoy before you get back onto the road! Drive for a little longer and… you’ve hit the tip of the island! Your choice between Rum Point or Kaibo, both boasting incredible mudslides and delicious afternoon snacks to share. Tip: if you’re heading to Rum Point, ask for the “Atlee’s Mudslide” and if you choose Kaibo, make sure to order the conch fritters or a flatbread to share.

On the way back down, follow the same route, taking the short cut at Frank Sound, all the way back to your beach home away from home! Be sure to stop at the jerk stand next to the Prospect Playhouse for some of the most mouth-watering jerk you’ve ever had – dinner is served!

We hope you enjoyed your fun adventure! Did we miss any of your favorite stops?