See This, Skip That: Cayman Islands

How to enjoy your stay in the best way possible.

The laid-back allure of this island trio -– Grand Cayman, Little Cayman and Cayman Brac -– may well hinge on what locals call Caymankind. It’s an attitude of hospitality and inclusiveness that embraces the islands’ multi-faceted reality. Old and new converge here. Their reputation as an offshore financial hub is buoyed by their love for traditions. And the 100-plus nationalities that live here, including many American ex-pats, meld a colorful history (Columbus referred to the islands as “tortugas,” or turtles, when he dropped anchor here) with modern-day sophistication.

Here are a few of the neat things to do and see on the Cayman Islands:

Skip the Legacy Carrier, Fly Cayman

Don’t Just Dive, Dive with the Best

Diving buffs will tell you true relaxation here is found not on the beach, but rather 80 feet below the ocean’s surface. Diving to discover shipwrecks, reefs and a plethora of wildlife is a way of life here, and there are close to 400 diving sites to choose from. For recreational divers, or even novices, the best introduction to the sport may be the annual Legend & Lions. During an entire month – September 5th through October 3rd this year – visitors can book week-long packages that feature classes, equipment demos, special certifications and more. During the fete’s final week (September 26 through October 3rd), you get the added bonus of attending the International SCUBA Diving Hall of fame induction party as well as the chance to dive with one of the inductees themselves.

Skip Seven Mile Beach, Head to Rum Point

Congratulations to my colleague Matt Ring! A senior producer in Travelzoo’s New York City headquarters, he just tied the knot with his wife, Charleen, on Grand Cayman, and honeymooned there. Like many tourists, they spent time along Seven Mile Beach, whose coral sands and clear waters are home to many of the island’s luxury resorts. But when they needed some alone time, they drove about 45 minutes to Rum Point Beach. “It's a more chilled-out vibe, with hammocks and some casual restaurants, known for their signature mudslide cocktails,” he told me upon his return to reality. “It can get crowded when cruise ships are docked in Cayman, but weekends tend to see fewer ships.” Ring says locals also recommended nearby Kaibo Beach for its thinner crowds and its proximity to Starfish Point, where a large number of sea stars can be seen in shallow waters.

Skip the Stingray City Tour, Charter a Boat

The newlywed Rings also played tourist in Stingray City, easily one of Grand Cayman’s biggest attractions, allowing guests to pet dozens of stingrays wading in no more than three feet of water. But for a more personal experience, Mr. Ring suggests chartering your own boat. “If you are only a small family, buddy up with other people at your hotel,” he says. “We chartered our boat for less than $35 per person. Our guides were great and we visited Sting Ray City, Starfish Point and a reef for snorkeling. It was great because we could stay at each site on our own time and were not tied into a schedule. Our hotel concierge helped us set this up with a local charter company.”

Skip Stingray City, Hit the Park

For nature lovers and history buffs alike, the 65-acre Queen Elizabeth II Botanic Park is a wonderful alternative to the water. Located in Grand Cayman’s North Side district, it highlights Caymanian history and many native wonders. The Visitors Centre mirrors Colonial Caribbean architecture, with its wooden shutter windows, brick courtyard and colors of coral and green. The two-acre Heritage Garden features native plants and flowers, as well as a restored traditional zinc-roofed Caymanian wooden cottage. And a two-acre lake is dotted with islands that serve as a breeding ground for native birds. Check out the Blue Iguana Habitat; the male that stars in the park’s captive breeding program can be best spotted in mid-morning. Open every day, adult tickets are $16 and kids get in for $3, with free entry for kids under six. The park was named in honor of Her Majesty Queen Elizabeth II, who officially opened it in 1994.

Skip the SCUBA Gear, Ride a Sub

Among the guests at the Ring wedding was my pal Warren Chang, Vice President of Search at Travelzoo. He traveled 100 feet below the sea in a 48-passenger Atlantis sub from Cayman Islands Submarines. “You ride in an actual submarine, and it's battery-powered so it's environmentally friendly,” he tells me. “It's a neat experience for anyone who has never ridden an actual submarine before, and it's a great opportunity for people who do not snorkel or SCUBA dive – or otherwise do not like getting into the water – to see below the ocean’s surface!”

To Send a Postcard, Go to Hell

Chang also biked past Hell, a series of short, black limestone formations in Grand Cayman’s West Bay. It’s small, about the size of a soccer field, so it makes for a quick visit. “But what may be fun is that there is a post office there,” Chang says, “and so you can send people postcards from Hell.”

Skip the Beach, Take a Hike

Grand Cayman’s Mastic Reserve is significant for its rarity: it’s part of the largest contiguous area of untouched dry, subtropical forest remaining on the island. The 2.3-mile Mastic Trail is moderately rugged and peppered with wet sections, and it takes hikers through various ecosystems inhabited by native orchids, trees, parrots and reptiles. For a small fee, you can hire a guide through the National Trust who will highlight special areas and share interesting anecdotes about the area. The hike usually takes about three hours to complete and is not recommended for kids under 10 or the elderly. Bring your camera, water and bug spray.

Skip Grand Cayman, Visit Little Cayman

Truth is, Grand Cayman’s sister islands may be the best way to enjoy a more secluded and more off-the-beaten-path Cayman experience. Little Cayman is home to its own museum, which preserves the island’s heritage through collections of artifacts and documents; it’s open every day except Sunday. The Salt Rock Natural Trail is a footpath that dates back to the 1850s and leads hikers to myriad points of interest and past exotic plants and animals. At the Booby Pond Reserve, a high-powered telescope helps you spot the 20,000 boobies that live here, making this one of the largest colonies of this breed of sea birds in the Western Hemisphere. And for a truly secluded beach experience, visit the uninhabited islet known as Owen Island; kayak the 200 yards to get there and bring your snorkel gear. Little Cayman is also home to the Caribbean’s largest population of rock iguanas, and its South Hole Sound Lagoon is a popular spot for bonefishing. Divers who want an extended stay should check in to the Little Cayman Beach Resort, which offers all-inclusive stays, with all meals and several boat dives a day.

Skip Grand Cayman, Visit Cayman Brac

On Cayman Brac, a rugged 14-square-mile island named for its sweeping 140-foot bluff, R&R is the name of the game. There’s plenty of wildlife here, too, which you can discover through free customizable tours offered through Nature Tourism Guides. Brac Parrot Reserve is a hiker’s heaven, with myriad paths that traverse varying types of terrain – from mango orchards and thickets to old forests and farmland; there are native trees here that are breeding ground for various birds and are not found on Cayman Brac’s sister islands. Culture and history are alive and well, too; you’ll find the oldest museum in the Cayman Islands here, and the Heritage House, a pretty replica of an old traditional Caymanian home, hosts cultural events throughout the year. For SCUBA buffs seeking an escape, the Brac Reef Beach Resort offers all-inclusive dive vacations that also include fishing trips and rock climbing excursions.

Gabe Saglie is senior editor for Travelzoo, which features exclusive deals to and in the Cayman Islands at