“Where the hell are you from?” said an old Caymanian guy in red horns and a sequin cape. The Cayman Islands is a sophisticated place, but we couldn’t resist a visit to its kitschiest attraction on Hell’s Highway. Inside the Devil’s Hangout, the owner Ivan Farrington chatted us up before his display of flame T-shirts, hot sauces, trinkets emblazoned with “Go to Hell,” and most of the original décor from its 1987 opening. When I told him I was from Los Angeles, it was if I sent him a care-package of comedic material. “City of Angels? They only sell one-way tickets from that place…make yourself comfortable!” Listening to pun after pun, fine-tuned from thirty years of chatting with tourists and still delivered with utmost pride, it was impossible not to fall in love with this man—a local celebrity and embodiment of Caymankind hospitality, as we begin road tripping Grand Cayman.
Missed our first post on the Cayman Islands? Read it here.
The Devil’s Garden in Hell
We sent a postcard from Hell, thanked our new friend Satan, and poked around the Devil’s Garden. The area is called Hell for its charred-black ironshore, a jagged and foreboding rockscape. It extends to the fringes of the island for an extra dramatic coastline, especially juxtaposed against Grand Cayman’s soft, white-sand coves.
Camana Bay Farmer’s Market
Heading east, our road trip continued past the famous Seven Mile Beach, to lesser-known and local gems of Grand Cayman, like the Camana Bay Farmer’s Market. Each Wednesday (12pm-7pm) this posh shopping boulevard is lined with stalls by Caymanian artisans, bakers, and farmers. We got chatting with a painter named Eugenio and sampled Teresa’s third-generation pepper jelly recipe.
Tip: For farm-to-table foodies, try Brasserie. This sustainable and delish restaurant raises their own chickens, has fisherman on staff, harvests honey, and even has vegetable beds in the dining room.
Pedro St. James Castle
We made our way to the town of Savannah and Pedro St. James, the Cayman Islands’ “birthplace of democracy.” We arrived just as they were closing, but the chief guide, said “It’s okay, I’ll show you around.” We walked the grounds of the 18th-century stone home (the oldest in the Cayman Islands), where the country’s Parliament was established, slavery was abolished, and the pioneering Eden family once lived. It wasn’t until the end of the tour that our guide, Stacey Eden Hurlston, said it was built by his great, great, great, great grandfather!
Road Tripping Grand Cayman: Lovers Wall
Cruising the Queens Highway (the Cayman Islands is a British Overseas Territory BTW), we reached “The Lovers Wall.” A hand-painted and heart-shaped highway sign need not justify itself to us, but it was curious we couldn’t find any information on its origins. One thing is for certain, whoever stops here must be in love.
The Blowholes
Grand Cayman’s ironshore comes to a head at the Blowholes on the North End, where waves rush under the eroded rock and erupt from the fissures. We watched this natural fountain show, spraying plumes of water fifty feet in the air, for the better part of an hour. Half the fun was trying to predict the biggest waves and see how close we could venture without getting drenched.
The Chill Northeast
The east half of the island is delightfully quiet, with mostly locals and scuba divers enjoying the beaches. While road tripping Grand Cayman, We pulled over to buy a coconut from a roadside stand and this little palapa captured the chill vibe.
Our Favorite Road
We approached Old Man Bay and the greatest street sign ever! If we could name a road, “Off the Beaten Path” would be it. Funny enough, the island didn’t have street names until a decade ago when the new ambulance system came in (I guess “take a left after the curvy palm tree” wasn’t precise enough). So the government called for submissions from locals, and clever and endearing entries like Uncle Bob Road, Sticky Toffee Lane, Lottery Road, and Snooze Lane all made the map.
Chef’s Counter at Avecita
We had dinner reservations back on the westside, so we took the cut-through at Old Man Bay (continue to Rum Point if you can and see ocean-view pics from Blog #1), and made it to the hot new Kimpton Seafire hotel and Avecita restaurant. We bellied up to their exclusive ten-seat chef’s counter for an awe-inspiring culinary performance. Chef Remy—French-born and trained in Spain—crafts a seven-course tasting menu that changes around his creative impulses and the freshest possible ingredients, like Turbot with grilled fennel and Emmental, and Lobster with beetroot and wild mushroom gazpacho. With the support of a sommelier, grill master, saucier, and pastry chef, each course shined with flavor and creativity. (Just look at that dessert?!)
Our Grand Cayman Getaway in Videos
Watch these videos for the full road-trip (left) and our Valentine’s Day escapades (right) chatting with the Devil, Epic diving the plunging North Wall, Hibiscus Spa couples massage, and more surprises from our Lonely Planet Snapchat Takeover.
What a trip! We were super impressed with Grand Cayman’s gourmet restaurant scene, scuba diving (no one else has wall dives like this), and the local characters we met in our island wanderings. Unlike many tropical isles, where it’s recommended to stay at an all-inclusive resort, explore with a guide, and only drink bottled water, Grand Cayman is carefree. Safe, clean, straight-forward, and exquisite, it’s the perfect place for those who want an easy foray into Caribbean exploration and just get away from it all.
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A big thank you to the Cayman Islands Department of Tourism for sponsoring this Grand Cayman Road Trip post.
I have friends who moved to the Caymans recently. They really love it. They say it’s like a small town that just happens to be an island. Can’t wait to visit someday.
Everyone is really friendly and it does have a small town feel…but with amazing resorts and restaurants 🙂
There are some beautiful spots here! I can’t get over that place that is called Hell, it looks like what I’d imagine “Hell” to look like haha
Even Hell is good-looking, right? This dramatic, craggy ironshore is all over the island making for some really cool landscapes.
I love this recap of your roadtrip to the Grand Caymans. I pinned this instantly. I want to come here so I can take my significant other to the Lovers Wall area and take a pic!
Thanks so much, Kiwi! Lovers Wall is the cutest little sign…begs for a photo opp with your honey.
That looks like a fun time, I have never thought about visiting there but I have had friends go. I am not really a far away travel type person just because there are so many things I haven’t seen in America yet so I feel like I should take those short trips first. Although the clear waters and scenery make me want to just head out there!
Melissa, you should consider it. Nowhere in America has water this color!
Love this!! The Grand Canyon is on the top of my list for places we must visit. We hope to plan a family road trip so this is perfect to help me do just that!
Oh wow! That is so beautiful! I would love to road trip Grand Cayman. I think it would be a much more unique experience than just staying at a resort.
Yea, we liked the Westin didn’t feel penned in. Also, for a really hot new spot, try Kimpton Seafire or get remote in the East End. Can’t lose!
I’m all about really discovering a place with a road trip. We did that in Alaska! That said, now my husband wants a trip with warmth and beach so maybe we should head there! I love the street signs and the dessert photo!
OMGeee that water is SO BLUE! I want to go!! Hell looks pretty amazing to me from here!
Wow! There’s a lot of amazing spots! I would truly love to road trip on Grand Cayman, that is extreme and unique. Can’t wait to go there!
This sounds like it was such an interesting road trip indeed. I would love to go to the Cayman Islands some day. It sounds beautiful and looks like there is quite a bit to see for sure. In Hell Satan sounded like so much fun to just talk too. Thanks for sharing your amazing experiences.
It is stunning with tons to do, you are absolutely right. Definitely say hi to Ivan the Devil when you go!
OMG! That is so beautiful. Grand Cayman has a lot of spots. I would love to visit there soon!
Beautiful photos. What a fun and interesting road trip.I should add this to my bucket list.
Oh my goodness! This place looks gorgeous. I haven’t seen much about Grand Cayman but it is now on my bucket list.
I would love to go on a road trip like this. I’ve never been there before. Looks like a beautiful place to see too.
It’s so close to the States too. Great for a long weekend even!
All of these photos are so beautiful!! It looks like an amazing trip!
Grand Cayman was one of my favorite stops on our cruise. The water was so different compared to the beaches here in the states. We walked around the shops. I wish that we had more time there.
Omg looks like y’all had a blast!!!! I’ve only been to Grand Cayman once and it was on a cruise. Would love to go back and explore
What a fabulous road trip! We may need to book a trip to the Cayman islands one day soon. We have never been.
You should…try to do Grand Cayman and Brac!
I couldn’t help but laugh at the older man you met. He sounds like he was a lot of fun to chat with. I would love to visit that area.
Oh wow, this is absolutely beautiful. I need to totally add these trips onto my bucket list. I would love to visit!
I have heard amazing things about cayman islands. It looks so gorgeous and fun!
What great photos!! I would love to travel to the Grand Cayman one day!!
It’s such a photogenic place, we hope you go!
This sounds like a blast! I am now putting it on our family bucket list!
These places look amazing! I would love to visit someday! The grand cayman is on my bucket list.
Grand Cayman is bucket list worthy–especially for divers and foodies. We want to add Cayman Brac to our list now.
It looks like you all had a great time. The Farmer’s market looks lively. – yolonda
This place seems like definitely worth visiting! Loved your pictures, Anne and Mike!
Hi, where is this charming little lighthouse ?
These places look amazing! I would love to visit someday! The grand cayman is on my bucket list.
Great post! I saved it all to my list of places to visit!
What was your best experience?
Thanks! We really loved road tripping to the northeast along Queens Highway; it showed the local side of the island and cool natural features like The blowholes–such a hoot!