This is a basis for a driving tour of Grand Cayman I posted on Trip Advisor. Others are invited to add with their recommendations, pictures and advice via post or comment.
Please be advised Cayman follows the British Rules of the Road and driving is done on the left hand side of the road. Posted speed limits are in Miles Per Hour and the police do stop and ticket speeders, so be mindful.
A suggested island tour or rainy/off-weather day trip (but sunny conditions really do the scenery justice) that basically circumvents 3/4 of the island, originating from the Seven Mile Beach area and heading East would be:
Head East from Seven Mile Beach along West Bay Rd. As you enter town, the Island Glass Blowing Studio offers up a chance to see one of a kind glass creations being made.
Proceed into George Town along Church Street and try not to run over any cruise ship visitors. If the weather is not the best and you are killing time or if parking is readily available, the Cayman Islands National Museum is a hidden in plain sight gem.
Next, stop at Pure Art just down the road if you like handmade local art and crafts.
Just a few hundred yards down the road is Smith Cove Bacadere. A picturesque little swimming hole, you’ll probably want to return to later on during your stay. Water is usually calm and there is some OK snorkeling around the Elkhorn coral in the left center of the cove. If you didn’t happen to yet see one of the many Cayman Blue Iguana statues around the island yet, here is a chance.
Just past town is the Black Coral Clinic where the “unique” Doc Carey will be glad to display his creations and collections.
Back on the road through South Sound you can admire the “nice” homes of this well-to-do neighborhood. There are a few small community beaches all along this tour that you can stop off at (most are nothing special, but nice to check out regardless. Just look for the green and white community beach access signs).
Once you reach Red Bay, look for the Flip Flop Tree photo op just past the docks on the right. It even has its own Facebook page!
At the end of South Sound Rd., merge onto Shamrock Rd, follow signs towards the Eastern Districts. If you like beer or are just curious as to how it’s brewed, stop off at the Cayman Islands Brewery. The tour is less than 30 minutes or you can just say “hi” and get samples of the days production and shoot the breeze with the brew-master.
If fresh fruits (mangoes, papaya, limes etc..) are in season keep an eye out for the roadside stands anywhere along this entire route.
Continuing along Shamrock Road you will reach the town of Savannah. A nice stop here is the Pedro St. James ”castle”; a restored mansion with well regarded tours describing the history of the island.
Just off the parking lot are impressive cliffs that make a dramatic photo op when framed by the sea.
Back on Shamrock Rd (becomes Bodden Town Rd.) traveling towards Bodden Town you will come across the Market at the Grounds, the agricultural heart of Cayman, where a Saturday morning farmers and craft market is held (not a suggested stop unless you happen to be passing before 10:00 on a Saturday).
Back on Bodden Town Rd., you will soon be entering Cayman’s first capital, Bodden Town. On your right will be Rankins Jerk Pit (as called on Trip Advisor), the first of a few jerk and fish fry establishments for those craving some “local fare”. This section of the island was hit hard from Hurricane Ivan and is just now (2011) beginning to get fully restored to it former conditions. Coe Wood Beach is restored public area with some basic facilities and the Grape Tree Cafe fish fry if you need to make a stop.
The Mission House is another spot for history buffs to explore.
Towards the center of town are a few attractions that may be of interest: Beach Bubbles is a small store in the strip center next door to the post office that carries a collection of locally handmade soaps and lotions and other giftables, the Bodden Town Pirate Caves is a stop for only the youngest or most obsessed pirate lovers in the group and a local art and gift store in the Bodden Town Art Shop. Some good snorkeling exists off of the Govenor Russell Public Beach adjacent to the Bodden Town Cemetery.
There is some good snorkeling off the beach from the Turtle Nest Inn and Governor Russell Public Beach for those needing to commune with the fishes.
Opposite the cemetery is Anton Bodden Drive where the Look Out Convenience Store is located a few hundred yards on the left. This is a nice place to stop and sample some of their fresh squeezed local juices post snorkeling. A sign is usually posted along Bodden Town Rd. with the juices available that day.
Continuing on the way out of town you’ll pass Chester’s Fish Fry home to one of the most famous signs in Cayman “Buy one jerk, get one free” and Woods’ Jerk Stand.
In a few minutes the wide expanse of Pease Bay’s scenic water vistas will unfold. On a sunny day the blue water can glow electric and make another great photo op.
Onwards towards Breakers, at the other end of the bay, is the the landmark Lighthouse Restaurant and the neighboring down home Cayman style South Coast Bar and Grill.
A mile or so past the Lighthouse is the turn for Frank Sound Rd. and the short-cut to North Side. If you want to visit either the Queen Elizabeth II Botanic Park and Blue Iguana Sanctuary or the Mastic Trail, turn there. If not, continue along the coast towards East End. You can also visit either attraction on the return as well.
Entering the East End District, (the road name changes to Seaview Rd. and then Austin Connolly Drive) you will begin to get a glimpse of the Cayman of olde. No hi-rise condos or fancy hotels here. Other than the solitude and and stunning views, the biggest attraction in this area are the Blow Holes. Fun for kids and adults alike, especially if the there are some swells crashing ashore.
Along East End there are some quick stops like the East End Light House Park (inland side) and Wreck of the Ten Sails (look for the giant ship’s propeller). Keep a look out for the “old folks” crossing sign near the rest home.
In this area, some folks like to eat at Vivine’s Kitchen for a truly Caymanian culinary experience or at Tukka’s for a taste of Down Under meets Caribbean. Both have great water views.
You’ll soon come upon the East End Public Beach at Colliers. There are restrooms here and the cabanas and piers make for nice photo backdrop. Another Iguana for those keeping track.
Just past the beach, keep your eye’s peeled for the East End’s Flip Flop Tree in the undeveloped area just before Morritt’s Tortuga Club & Resort and the Reef Resort.
A nice stretch of beach fronts the neighboring resorts and feel free to stop at either for a look-see, to grab a drink or bite to eat at one of their bars, or check out the good snorkeling grounds.
After the Reef Resort you can stop off at the hidden Barefoot Beach and climb the stairs off to the right for another dramatic photo op. It can be hard to spot the hidden turn-off, but a great find for those who manage to. Refer to the link above for instructions on where to find it.
Back on the road towards Rum Point (now called Queen’s Highway) you’ll pass the town of Old Man Bay, just after the intersection with the ball fields. If you happen to be driving by on a Friday or Saturday there may be some local food for sale roadside.
Over the Edge restaurant and bar makes another nice spot to grab some lunch for fresh fish lovers and take in a great view.
Continuing towards Rum Point, you’ll enter Cayman Kai, another spot to check out some “nice” snowbird homes and try and make sense of their mostly whimsical names.
As you get to the end of Rum Point Drive (now the name of the road), stop at the Rum Point Club beach and see if it is crowded or not. You will notice the rum barrels spelling out the destination at the parking lot entrance. If not, spend some at the beach (free to use amenities like chairs and restrooms), imbibe one of the Wreck Bar & Grill's famous Mudslides, walk to the end of the pier or just chill in a hammock (taking in the amazing shades of blue). Yes, that is yet another Blue Iguana statue you just tripped over.
If you have packed a lunch or have you own food and drink (neither of which are permitted at the Rum Point Beach Club), there is a public beach section at the far western end of the Rum Point Club’s parking lot. Look for the public beach access sign and park along the street. Just follow the white fenced bordered path to the beach. Same great beach, just no lounge chairs and some fallen trees.
If you happen to arrive with a hoard of cruise ship visitors still enjoying their excursions or on a Sunday afternoon when the locals have descended for a weekend get-away, head towards Kaibo Restuarant and Star Fish Point (as it is termed on Trip Advisor). The turn onto Water Cay Rd. is just before the rum barrels and there should be a sign for Kaibo.
This is a great little spot where Cushion starfish usually congregate in the sandy shallows off the point. Refer to the linked guide for Starfish Beach on how to get there.
The cruise ship crowds have usually vacated by 2:00 PM, so it if the timing has worked out you can now head to the Rum Point Club.
You have now covered most of the island east of Seven Mile Beach, so it is probably late in the day and time to head back. When returning, take the Frank Sound Rd. “short-cut” at the intersection by the ball fields. Stick to the “highways” and you’ll make the return trip in 45-60 minutes.
Map featuring many of the points of interest contained in the travel guide (be sure to look at page 2 on the map as well):
(Driving Tour Map)
(Download Driving Tour Here)
Safe travels and happy motoring.