14 days in Cayman Islands Itinerary

14 days in Cayman Islands Itinerary

Created using Inspirock Cayman Islands trip planner

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Route & dates

14 days in Cayman Islands Itinerary

Start: Anchorage
Drive + Fly:  20​h 15​min
George Town, Grand Cayman
— 6 nights
Fly + taxi:  1​h
Little Cayman
— 3 nights
taxi + Fly + taxi:  45​min
Cayman Brac
— 3 nights
Fly + Drive:  21​h 45​min
End: Anchorage

George Town, Grand Cayman

George Town ©
George Town is a city situated on Grand Cayman island of the Cayman Islands. Get some historical perspective at Pedro St. James National Historic Site and Mission House. Get a sense of the local culture at Cayman Islands National Museum and Davinoff's Concrete Sculpture Garden. There's lots more to do: cool off at Cayman Turtle Centre: Island Wildlife Encounter, explore the striking landscape at Hell, enjoy the sand and surf at Starfish Point, and see some colorful creatures with a scuba or snorkeling tour.

For more things to do, maps, and more tourist information, read our George Town online trip planner .

Anchorage, USA to George Town is an approximately 20.5-hour flight. The time zone changes from Alaska Standard Time (AKST) to Eastern Standard Time (EST), which is usually a 4 hour difference. Prepare for much hotter weather when traveling from Anchorage in July: high temperatures in George Town hover around 90°F and lows are around 79°F. Finish your sightseeing early on the 28th (Sun) so you can travel to Little Cayman.

Things to do in George Town

Parks Outdoors Wildlife

Side Trips

Grand Cayman, West Bay, Seven Mile Beach, Mission House, Davinoff's Concrete Sculpture Garden
Find places to stay Jul 22 — 28:
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Stingray City Grand Cayman ©
Stingray City Grand Cayman
Seven Mile Beach ©
Seven Mile Beach
Scuba & Snorkeling

Little Cayman

Little Cayman ©
The smallest and undeniably quietest of the Cayman Islands, Little Cayman is truly little in terms of its population, with fewer than 200 permanent residents, almost all of whom work in the tourism industry.
Your cultural itinerary includes sights like Little Cayman Baptist Church and Little Cayman Museum. Visiting Bloody Bay Wall and Point of Sand will get you outdoors. And it doesn't end there: step off the mainland to explore Owen Island, explore the gorgeous colors at Marilyn's Cut, explore the fascinating underground world of Cumber's Caves, and explore the activities along Randy's Gazebo.

To find traveler tips, ratings, other places to visit, and more tourist information, use the Little Cayman day trip planning website .

Getting from George Town to Little Cayman by combination of flight and taxi takes about an hour. Expect a daytime high around 89°F in July, and nighttime lows around 82°F. Finish your sightseeing early on the 31st (Wed) so you can travel to Cayman Brac.

Things to do in Little Cayman

Parks Wildlife Nature
Find places to stay Jul 28 — 31:
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Bloody Bay Wall ©
Bloody Bay Wall
Little Cayman Museum ©
Little Cayman Museum

Cayman Brac

Cayman Brac ©
At just 36 sq km (14 sq mi), Cayman Brac is a small but hugely rewarding eco-tourist's paradise, offering countless chances to spot birds, scuba dive, fish, spelunk, hike, and rock climb.
On the 1st (Thu), see some colorful creatures with a scuba or snorkeling tour, then contemplate the long history of MV Captain Keith Tibbetts, and then make a trip to Kissime Wreck. Here are some ideas for day two: explore the gorgeous colors at Elkhorn Forest, then contemplate the waterfront views at Wilderness Wall, and then explore the fascinating underground world of The Bluff.

To see reviews and other tourist information, read our Cayman Brac trip maker app .

Traveling by combination of taxi and flight from Little Cayman to Cayman Brac takes an hour. In July, daily temperatures in Cayman Brac can reach 89°F, while at night they dip to 82°F. Wrap up your sightseeing on the 3rd (Sat) early enough to travel back home.

Things to do in Cayman Brac

Wildlife Nature Parks
Find places to stay Jul 31 — Aug 3:
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The Bluff ©
The Bluff