9 days in Cayman Islands Itinerary

9 days in Cayman Islands Itinerary

Created using Inspirock Cayman Islands Trip Planner

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Route & dates

9 days in Cayman Islands Itinerary

Start: Lexington
Fly:  15 h 30 min
Cayman Brac
— 2 nights
Taxi + Fly + Taxi:  45 min
Little Cayman
— 1 night
Taxi + Fly:  1 h
George Town, Grand Cayman
— 5 nights
Fly:  12 h 15 min
End: Lexington

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.
Kick off your visit on the 27th (Wed): take some stellar pictures from West End Point Outlook, Head underground at Rebecca's Cave, then explore the fascinating underground world of The Bluff, and finally contemplate the long history of MV Captain Keith Tibbetts.

For reviews, other places to visit, where to stay, and tourist information, read our Cayman Brac vacation builder.

Lexington, USA to Cayman Brac is an approximately 15.5-hour flight. Expect a bit warmer weather when traveling from Lexington in September: highs in Cayman Brac hover around 89°F, while lows dip to 81°F. Wrap up your sightseeing on the 28th (Thu) early enough to travel to Little Cayman.

Things to do in Cayman Brac

Parks Nature Historic Sites
Find places to stay Sep 26 — 28:
Highlights from your plan
The Bluff ©
The Bluff

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.
Start off your visit on the 28th (Thu): contemplate in the serene atmosphere at Little Cayman Baptist Church, then enjoy the sand and surf at Point of Sand, and then see the vivid underwater world at Bloody Bay Wall.

To see where to stay, more things to do, maps, and other tourist information, read our Little Cayman travel itinerary planner.

Traveling by combination of car and flight from Cayman Brac to Little Cayman takes an hour. In September, plan for daily highs up to 89°F, and evening lows to 81°F. Cap off your sightseeing on the 29th (Fri) early enough to travel to George Town.

Things to do in Little Cayman

Parks Wildlife Outdoors
Find places to stay Sep 28 — 29:
Highlights from your plan
Bloody Bay Wall ©
Bloody Bay Wall

George Town, Grand Cayman

George Town ©
George Town is a city situated on Grand Cayman island of the Cayman Islands. George Town is known for adventure, breweries, shopping, sightseeing, and fun & games. Your plan includes some of its best attractions: look for all kinds of wild species at Stingray City, sample the fine beverages at Cayman Spirits Co. Distillery, Head underground at Devil's Grotto, and explore the striking landscape at Hell.

To find other places to visit, where to stay, traveler tips, and tourist information, refer to the George Town itinerary builder.

Traveling by combination of car and flight from Little Cayman to George Town takes an hour. In September, daily temperatures in George Town can reach 89°F, while at night they dip to 78°F. On the 4th (Wed), you're off tohome.

Things to do in George Town

Parks Wildlife Outdoors

Side Trips

Grand Cayman, Seven Mile Beach, Cayman Turtle Centre: Island Wildlife Encounter
Find places to stay Sep 29 — Oct 4:
Highlights from your plan
Stingray City Grand Cayman ©
Stingray City Grand Cayman
Seven Mile Beach ©
Seven Mile Beach