Cayman Islands

Cruising the Cayman Islands

What to Do in the Cayman Islands

A Cayman Islands cruise is the ultimate getaway for relaxation and adventure. As you explore this unique group of Caribbean islands, you’ll find a high standard of living combined with all the flavors of tropical allure. Foodies flock to the Caymans to tickle their senses at world-class restaurants. Adventurers prepare to dive into pure wildlife-abundant waters. Beach lovers anticipate lazing in the sun on palm-fringed shores. If you want to travel to a Caribbean destination that’s both elegant and laid-back and has all the features of tropical splendor, wait no longer to explore the Cayman Islands.

In This Article

About the Cayman Islands

The Cayman Islands is a British Overseas Territory situated in the Caribbean Sea. The Islands sit atop an underwater mountain range that stretches from Belize to Cuba. The group includes Cayman Brac, Little Cayman and Grand Cayman. Grand Cayman is the largest of the islands and the most populated, and it’s where you’ll find the capital city of George Town along with luxe resorts and top attractions. Little Cayman and Cayman Brac are the less-visited islands that boast some of the best diving opportunities in all of the Caribbean.

Christopher Columbus spotted the islands in 1503. The Spaniards originally called the islands Las Tortugas after the many turtles found in its nearby waters. The Treaty of Madrid in 1670 surrendered the islands to Great Britain, and afterward, the first settlement was established there.

Today, the Cayman Islands is known as one of the world’s largest financial centers, but it still maintains its island charm. The islands draw millions of visitors to their pristine beaches, renowned diving sites and top-rated restaurants

Why Cruise to the Cayman Islands?

As cruise travelers know, the Caribbean Sea holds many island jewels worth visiting. What differentiates the Cayman Islands is how easy it is to enjoy. First, English is the official language there, so you’ll have no trouble communicating with locals. Secondly, U.S. dollars and credit cards are widely accepted, so it’s no big deal if you’re short on the Cayman Islands dollar. It’s also safe and easy to get around, so you can feel comfortable exploring at your own pace. Combined with immaculate beaches, lush mangrove forests, and world-famous dives sites, it’s easy to see why travelers love the Cayman Islands. Here are more reasons to pack your sunscreen and head there on your next cruise.

Legendary Cuisine

Many sources refer to the Cayman Islands as the “culinary capital of the Caribbean.” Just about everywhere you turn, you’ll find foodie-worthy eateries, from modern but casual waterfront restaurants offering as-fresh-as-it-gets seafood to beachside huts selling Caribbean-style fried fish. Many of the restaurants emphasize local ingredients such as plantains, coconuts and mangoes. Make sure to sample local classics like conch stew, jerk chicken and deep-fried Johnny cakes.

Euphoric Beaches

If tropical beaches float your boat, the Cayman Islands will not disappoint you. Seven Mile Beach on Grand Cayman, for example, is regarded as one of the Caribbean’s best beaches and one of the most breathtaking places in the world. It’s silky white sand, unbelievably clear water and gentle waves make it a fun spot for snorkeling, swimming and soaking in the sun.

And that’s just the beginning — there are many other beaches worth checking out. For example, Smith Cove is loved for its striking rock formations and sea grape trees. Beachgoers in search of tranquility can kayak to Owen Island, a tiny uninhabited haven and the perfect place for a low-key picnic.

Rare Adventure

The Cayman Islands is a bucket-list destination for those who crave unparalleled adventure. For example, the Cayman Islands is recognized around the world as a scuba diver’s dream and is home to over 200 known dive sites. The area has exceptional visibility, so scuba divers can clearly see the coral reefs, colorful sea life, shipwrecks, and other submerged treasures. All ages and abilities will have no problem finding qualified instructors to help them start a scuba diving excursion. If you’re not into scuba diving, you’ll find many other watersports to enjoy in the Cayman Islands, such as snorkeling, kayaking, sailing, and paddleboarding.

If you’re more of an inland adventurer, there’s plenty to keep you busy. From nature reserves to scenic bluff trails, curious explorers will feel satiated in the Cayman Islands.

When to Cruise the Cayman Islands

You can enjoy the Cayman Islands any time of the year, as the region boasts warm tropical temperatures regardless of the season. However, you may want to consider the crowds and weather when choosing a time to cruise. Here’s what you can expect during the high and low seasons.

High Season

The high season runs from mid-December to mid-April. It’s when the weather is dry, warm and laced with a cooling breeze. If the weather is your priority, April is the best month to visit. In April, you can expect comfortable weather and enjoy the beach before the summer heat rolls in. You may have to deal with more crowds during high season, but if swimming, snorkeling, and lounging on the beach area at the top of your to-do list, it may be worth it.


Generally, the off-season runs from mid-April to mid-December. You can expect fewer crowds during this time, and some restaurants and facilities will be closed. Rainy season falls within this timeframe, or from mid-May through October. However, even during the rainy season, it doesn’t rain every day, and showers are usually short and intense and followed by clear skies and sunshine.

How to Spend Your Time at the Cayman Islands

Imagine floating above friendly stingrays in water as clear as glass, or watching the sunset from a hammock, frothy cocktail in hand. Once you arrive at the Cayman Islands, you’ll soon realize it takes minimal effort to enjoy your time there. Nevertheless, here are some ideas to help you enjoy your voyage even more. 

How to Spend Your Time at the Cayman Islands

1. Walk the Mastic Trail

Nature lovers won’t want to miss a chance to walk the Mastic Trail. The Mastic Trail is a centuries-old gravel path that meanders through a mangrove swamp and ancient woodlands. You’ll experience the island’s various ecosystems during your journey and have the chance to spot or hear wildlife like parrots and bananaquits. The trail is a little over 2 miles long one way, so plan to spend a few hours exploring.

2. Hang With Stingrays

Would you love to hand-feed wild stingrays in shallow, crystal-clear water? If so, make sure to add an excursion to Stingray City to your itinerary. Although Stingray City is the top attraction of all the Cayman Islands, travelers and locals still say it’s a must. Stingray City is the name given to a sandbar where wild stingrays flock in the hope of getting fed. You can take a trip to Stingray City by booking a tour with a local company and then exploring the site by snorkeling, scuba diving or cruising on a glass-bottom boat.

3. Decompress at Rum Point

If you want to immerse yourself in island vibes, consider spending the day at Rum Point, located at the northernmost tip of Grand Cayman. Here you can snorkel, swim or relax on the powdery beach. You’ll also find colorful picnic tables and places to grab a bite or fruity drink as you take in the scenery. Make sure to stop by the Wreck Bar for the legendary Rum Point Mudslide – a creamy, boozy concoction. No matter how you spend your time at Rum Point, you may find it hard to leave.

4. Visit Iguanas at a Botanical Park

The Queen Elizabeth II Botanic Park invites you to connect with nature, delve into local history and stroll through tranquil gardens brimming with endemic plant and animal life. Visit the Heritage Garden to view a traditional sand garden, fruit trees and restored cottage. Walk the Orchids Boardwalk to witness the beauty of rare orchids found nowhere else in the world. Make sure to stop at the Blue Iguana Habitat along the Woodland Trail for a chance to spot this ground-dwelling endangered species.

5. Scuba Dive Near a Wall of Coral

The Bloody Bay Marine Park is the prime diving spot in Little Cayman and is where beginners and seasoned divers can enjoy exploring the park’s main site — the Bloody Bay Wall. The Bloody Bay Wall consists of colorful coral that drops deep into the sea, astonishingly close to the shore. You can also expect high visibility here, making it easy to see the turtles, fish and stingrays swimming around you.

6. Experience History at a Former Plantation

History buffs may want to head to Pedro St. James to explore Grand Cayman’s past. Here you’ll visit a former plantation home called the Great House. The Great House was built in the 18th century, and over time had been used in a range of ways, including as a jail and a restaurant. After surviving fires, hurricanes and vandalism, this three-story stone structure still stands and welcomes guests to explore. You’ll also have a chance to experience an immersive presentation in the Pedro Theater, view rare Caymanian stamps and sample rum.

7. Explore a Sunken Submarine

The Kittiwake Shipwreck, located off of Seven Mile Beach, is yet another popular dive site, and it’s easy to see why. The water is so clear, even those who prefer to snorkel can see the wreck. The USS Kittiwake was once part of the U.S. Navy as a rescue submarine, but was decommissioned in 1994 and is now used as an artificial reef. Divers can explore the mess hall, crew quarters and main deck. They might also spot sea creatures like eels, turtles and barracudas during their adventure.

8. Swim With Sea Turtles

At the Cayman Turtle Center, you’ll encounter a variety of animals and have opportunities to interact with them. Watch an American saltwater crocodile named Smiley at feeding time, meet birds such as the Cayman parrot and the scarlet ibis at the Caribbean Aviary, snorkel with green sea turtles at the Turtle Lagoon, or stroll past native trees on the Blue Hole Nature Trail.

9. Go Shopping in Georgetown

If you’re wondering what to do in Grand Cayman on a cruise, look no further. If one of your favorite activities to take part in at home is shopping, why not go on a shopping spree during your vacation in the Cayman Islands? Georgetown is the capital of the Cayman Islands and home to its primary commercial district. If you love art galleries and high-end shopping, you won’t want to miss out on the vibes circulating down at the southwest part of the island.

10. Relax on Seven Mile Beach

Seven Mile Beach is a well-known hangout spot on the Cayman Islands. It’s 7 miles of white, sandy beach, which you’ll be able to catch a glimpse of as your cruise is docking. If you’re on a trip to the Caribbean, you’re probably already looking forward to lounging around with the ocean only a few feet away.

Still, if you’re not a traditional beach-goer, you can discover something fun while you’re there. Whether you’re a busy body or you’re looking to relax, Seven Mile Beach has numerous ways to keep you busy. So, grab a towel and get ready to lay out in the sun, or fire up your water sports gear and get moving! Find water sports equipment rental shops on the beach’s northern end to get started.

Enjoy your time on one of the beautiful beaches of the Cayman Islands.

11. Try Your Hand at Fishing

There’s no better place to fish than on an island, especially when you’ve never gone ocean fishing. If you’re interested in fishing on the Cayman Islands and don’t have any experience, you can hire a fishing crew to help you discover the beautiful marine life in the depths of the Caribbean Sea.

12. Say Hello to Ghost Mountain

Ghost Mountain, found in Grand Cayman, is a freshwater dive site that’s certainly worth a visit. Schedule a charter with other experienced divers to get in on the action. Whether you’re an advanced diver or a beginner, you’ll enjoy your time here.

If you’re an advanced diver, you can start by swimming off the sloping wall and to a 60-foot detached pinnacle, which you’ll find covered in sponge and gorgonian. If you want to go on a treasure hunt of sorts, you can also see whether you can spot any black coral, coral shrimp or scorpionfish. Those who have never dived before can go with a guide, which is a wonderful learning experience. 

Say Hello to Ghost Mountain

13. Take the West Island Tour

If you want to take the West Island Tour, you’ll start out by hopping aboard your own three-wheeled scooter. Using a GPS, the scooter will navigate you to several attractions on the Island. As you drive, you’ll be able to see the beautiful sights and the GPS app will provide you with interesting historical facts on the Cayman Islands. During the tour, you will also have time to stop at the beach or any other attraction sight you may find interesting.

14. Have a Jeep Adventure

Why not take a 4×4 Jeep adventure on the Cayman Islands? First, you’ll start by getting to stop at Morgan’s Harbor, where you’ll see the magnificence of the North Sound. The next stop will be Barkers National Park, where you can view blue iguanas in their natural habitat, the mangroves.

After you delve deep into nature, you’ll take a turn through the West Bay District, which houses the Cayman Turtle Farm. Next, you’ll make a pit stop in a small village called Hell. This village got its name because of the rock formation adjacent to it, which glows orange at dusk. You’ll even get a chance to mail postcards off at the post office, which will read “Mailed from Hell.”

Are you ready to head to the Tortuga Rum Cake Factory, an iconic bakery on the Cayman Islands? After you sample some rum cake, you’ll take a drive to Seven Mile Beach, where you’ll turn in your vehicle and get the chance to spend two free hours doing whatever you please on the beach.

15. Take a Segway Tour

If you want to tour the Cayman Islands in a unique way, look no further than a segway tour. These are mobility devices that are easy to learn how to use and fun to drive. Using the segway, you can explore numerous locations, such as Seven Mile Beach and the bay nearby. This is an activity you may not get to so easily try at home, so take advantage of it here!

16. Go Kayaking

Picture yourself drifting through calm, expansive waters on a kayak. Then, picture getting to enjoy all of Grand Cayman’s majestic scenery from that kayak. While you’re kayaking, you might even see some wildlife playing in the mangroves. Exercise your body while relaxing your mind in the Cayman Islands.

17. Explore Hidden Caves

There are several interconnected caves on the Cayman Islands. What awaits you inside the caves? Hopefully, you’ll catch a glimpse of wildlife, such as bats and iguanas, and various crystal and stone formations.

If you go on the Cayman Crystal Caves Adventure, you’ll first arrive at a magnificent tropical forest. After your guide lets you in on the history of the caves, which includes a bit of pirate trivia, you’ll head down inside the first cave. Once inside the cave, you’ll have plenty of chances to take spectacular photos of stalagmites and stalactites.

Cruising the Cayman Islands With Windstar Cruises

On a Caribbean cruise with Windstar, you can expect to stop at popular ports like George Town as well as lesser-known gems like Cayman Brac. At every port, you’ll have a chance to explore the area as you wish, whether you prefer to stay closer to the ship or take an excursion a bit farther away.

For example, after docking in George Town, you’re free to explore the city’s colorful streets and its many restaurants, shops and bars. From there, you might hop on a bus, catch a taxi or rent a car to visit your site of choice, keeping your itinerary in mind. If you have a full day ahead, you can take an excursion that involves more time and may require travel to and from the dock. If you’ll have less than 8 hours at a destination, consider your preferred pace and make sure to leave time for taking breaks, enjoying local cuisine or picking up a souvenir before booking an excursion. Here are a few more tips to help you prepare for a memorable Cayman Island experience:

  • Try local fare: You won’t want to go to the Cayman Islands without sampling regional cuisine. For example, the conch season generally runs from November until April in the Cayman Islands. If you travel during this time, make sure to try conch stew or conch fritters. Other must-try dishes include Johnny cakes, jerk chicken and rum cake. If none of the regional specialties appeal to you, consider filling up on fresh seafood.
  • Find unique souvenirs: Want to shop for treasures to take home or send to loved ones? You’ll have your pick at the Cayman Islands. Keep your eyes open for authentic jewelry made from caymanite, a gemstone only found in the Cayman Islands. You can also treat friends and family to a famous rum cake or comb the beaches for lovely seashells to take with you.
  • Drive on the left: If you plan to rent a car during your visit, make sure to follow other drivers and drive on the left.
  • Prepare for sunshine: No matter where you go in the Caribbean, you’ll want to prepare for heat and sun. Wear sunglasses, apply sunscreen habitually and stay hydrated. If the sunny weather makes you want to rest in the shade, go ahead and take it easy. There’s nothing wrong with kicking back with a refreshing drink and enjoying the scenery.
  • Prepare for bugs: You might encounter insects like mosquitoes and gnats when traveling through the Cayman Islands, but you can protect yourself from itchy bites. Bring some insect repellent, wear light-colored clothing and avoid wearing perfume to help deter bugs.

Browse Windstar’s Caribbean Cruises

Windstar Cruises knows the Cayman Islands. At Windstar Cruises, we can give you an entirely new experience. Whether you’ve been on several cruises before or you’re ready to book your first one, we’re here to make the process as easy and memorable as possible.

To see the Cayman Islands in a whole new light, sail with Windstar Cruises on a smaller ship, which will allow for more unique, immersive travel adventures. The smaller numbers on our ships allow us to provide you with more personalized experiences, such as intimate guided tours, wine tasting and other one-of-a-kind excursions. There’s simply nothing like getting to see the area’s stunning scenery up close and personal on a small ship.

The Cayman Islands beckons you to slow down, take a deep breath of coconut-scented air and celebrate being alive. At Windstar Cruises, we’re ready to sail you to the Cayman Islands and other tropical gems aboard our small, elegant ships. Browse our Caribbean cruises today or contact a Vacation Planner to learn more.

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