Cayman Islands: Hot Spots and Highlights for First-Timers

5 days of luxuriating on Grand Cayman

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Is this your first visit to the Cayman Islands? If so, Grand Cayman probably offers the biggest bang for your buck of the three islands, with more than enough for Cayman Islands first-timers to fill five days of fun. This itinerary takes the hassle out of researching the endless options by including all the big-hitter tourist attractions, as well as some less touristy areas where you can soak up the island’s more authentic side. All the favorites are here, above and below water, including sublime Seven Mile Beach, Stingray City and a few off-the-beaten track activities. Note that you’ll need to rent a car for this itinerary, so you can explore some of the less crowded areas of this beautiful island.

Cayman Islands for First-Timers: Day 1

Stay at the Kimpton Seafire Resort + Spa, Seven Mile Beach Grand Cayman


Stumble out of your ultra stylish guest room and slide your toes into the silky-soft sands of Seven Mile Beach, one of the Caribbean’s best beaches. Swim around in the turquoise sea for the morning. Stroll along the shore, and if you’re feeling energetic, you can try stand up paddleboarding or kayaking on the translucent waters.

Lunch: Feast on Mexican street taco fare at beachfront Coccoloba, Kimpton Seafire Resort + Spa

George Town

Now that you’re refreshed, summon the energy to glide into George Town with your after-sun glow.

Cayman Hot Spots and Highlights: Day 2


Sign up for a Stingray City and Snorkel/Dive Tour with lunch. If you have a fear of stingrays, this is the day you can conquer that phobia. Many tours also include a stop at two other snorkel spots and lunch at the Kaibo Yacht Club.


After your tour, head to Camana Bay for a gelato and browse the upscale shops. You can also scend the observation tower and enjoy 360-degree views across Seven Mile Beach, George Town, and the North Sound.

Cayman Islands for First-Timers
Photo by Katie Thebeau

Grand Cayman: Day 3


Head to Cayman Turtle Centre: Island Wildlife Encounter, about 20 minutes north of George Town, for close-up critter encounters.

After exploring the turtle center, stroll over to Dolphin Discovery Grand Cayman and sign up for a dolphin experience. Note that photographs cost extra.

Lunch at Macabuca Bar & Grill. Soak up the salty sea air on the outdoor deck and watch the divers come and go at the adjacent dock.


Drive three minutes inland to the town of Hell for a must-do photo op.

Cayman Islands for First-Timers
Photo by Katherine Thebeau

Grand Cayman: Day 4


Take an 11am guided hike through the Queen Elizabeth II Botanic Park and keep an eye out for the islands’ elusive blue iguanas, as well as other tropical flora and fauna.

Lunch: From the botanic park, drive through the interior of the island to Kurt’s Corner, a local’s favorite serving authentic Caymanian cuisine, like conch and whelk fritters and coconut shrimp.


From Kurt’s Corner, head to the nearby Cayman Crystal Caves for a 90-minute tour of these beautiful stalactite and stalagmite encrusted caverns.

Afterwards, drive nine minutes west to Rum Point, where you can kick back in a hammock with a Cayman Colada before you drive home.

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Grand Cayman: Day 5


Drive about 10 minutes east of George Town to soak up some island history at the Pedro St. James National Historic Site.


Stop off at Spotts Beach on the way home to swim and snorkel with sea turtles.

Spend the rest of the afternoon basking on Seven Mile Beach where you began your five days of bliss.

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