Planning a Grand Cayman Itinerary

For a “little something different” in the Caribbean, Grand Cayman is the place to be. The island is unique, whether it’s the accommodations, restaurants or attractions and activities.

Cotton Tree Resort

During my recent visit to Grand Cayman, I stayed at the only true boutique resort there, Cotton Tree. Almond was my cottage, one of the four in the property which officially opened a couple of years ago. Almond is tucked away to the back of the resort, just about 20 feet from the resort’s main swimming pool. It boasts a living room, full kitchen, a washer and dryer, a guest room with twin beds, and, of course, a master bedroom with a king-size bed, flat-screen TV and a bathroom that has a tub and open-wall shower. The guest room also has a bathroom with a shower.


Agent Advice

“Grand Cayman offers so much for anyone from honeymooning couples – it’s great for destination weddings too – to families,” says Sandra Weaver of All-Travel, an agency based in Los Angeles. The latter in particular would be drawn to “my favorite, the Cayman Turtle Farm where they breed turtles, and Atlantis Adventures, which offers submarine rides, located right in Georgetown.”


There are speakers throughout the room, including two each in the ceilings of the living area, the bedroom and guest room. The entertainment system placed under the living room TV features an iPod docking station and a Nintendo Wii.

The top category, however, is the Thatch cottage. It is the only cottage that has ocean views and can sleep up to six people. All other cottages sleep four people.

The grounds are lush and well maintained. While there is an outdoor area for massages, clients can also request in-room treatments. The beach is just 10 feet from the resort, but it is only good for sunbathing; a rocky floor makes swimming unsafe.

While Cotton Tree does not have the space for large wedding receptions, it can accommodate up to 30 people for these functions. If you have clients looking to tie the knot here, I suggest booking the entire resort. Property takeovers are allowed for a maximum of three nights and limousine transfers can be had upon request.

For couples looking for a true Caribbean boutique, this resort gets our vote. We also think it is a great pitch for small families. For spa arrangements, restaurant reservations and other requests, agents should contact owner Heather Lockington (345-943-0700, [email protected]).

Culinary Options in Grand Cayman

Cotton Tree does not have a restaurant on property but within walking distance is one of Grand Cayman’s best, Ristorante Pappagallo, which has entered into an agreement with the hotel to offer clients room service upon request. However, if they want to venture off the property, tell guests it is worth checking out Ristorante Pappagallo in person since the ambiance is one of a kind in Grand Cayman. Most tables face the window, offering stunning views of the water. But tell clients to dine here when there is still some daylight so they can appreciate the views. Recommend the New Zealand lamb chops with a cold, local Caybrew beer.



Stingray City
Stingray City is Grand Cayman’s most popular visitor attraction.


Another extremely popular restaurant in Grand Cayman is the Calypso Grill. Whereas Ristorante Pappagallo is quieter, Calypso Grill’s outdoor deck area lends itself to more vibrancy. The food here was on par with Ristorante Pappagallo, serving up all the local seafood dishes you would expect from the Caribbean. Like Ristorante Pappagallo, it’s a bit expensive, so tell clients to expect to spend at least $60-$70 if they are going to go the whole hog and get appetizers, entrees, a glass of wine and dessert. I recommend crab cakes for the appetizer, “Lobster and Shrimp Champagne” for the entrée along with a glass of Pinot Grigio and crème brûlée for the dessert. The atmosphere and the food make this a great dining option for couples looking to splurge for a great meal and some great views of the water.

For a more casual atmosphere, suggest Morgans Harbour Seafood Restaurant, which also has an outdoor deck area facing the water. This is a docking station for many charter boats. This place was a bit more affordable than the other two options I mentioned. I suggest the shrimp stir fry; the cheese, potato and bacon soup; and the homemade bread pudding for dessert. All of that and a few adult beverages will probably run your clients about $35-$40.

Island Activities

Clients looking to explore the island should check out Sting Ray City, which is considered Grand Cayman’s most popular attraction. Here, clients can feed and touch stingrays of different sizes and swim with them. We suggest booking a three-hour tour, which includes snorkeling at the Stingray City Sandbar; the Barrier Reef, where clients can snorkel among a wide variety of coral formations and beautiful tropical fish; and the Coral Gardens, where they are treated to some more beautiful marine life. Tickets for adults are $44.44 and those for children ages 4-11 are $27.50; it’s free for children 3 years and younger.

Another great option for families is the Cayman Turtle Farm, which opened in 1968. Tickets for the farm, home to turtles and their little ones, are $30 for adults (12 and older) and $20 for children (4-12 years old).


Cotton Tree
Almond is one of four cottages that comprise Cotton Tree, the island’s only true boutique hotel.