Underwater
A morning on the wall
Private boat to Bloody Bay before the day boats arrive. Two tanks with Captain Theo. Coffee and bun on the deck after.
02 — Tell us your plans
Start your trip three ways.
Book a ready-made vacation package, build your own with the Trip Composer, or hand it to a Caymanian concierge. Search below to get started.
03 — How it works
Three ways
to plan a trip.
Isla Cayman is a booking platform for the Cayman Islands — pick the level of help you want. Self-serve, build-your-own, or fully concierge.
01
Book a ready-made package
Curated vacation packages with flights, stays and experiences priced and ready. Pick one, customise as needed, and check out in minutes.
02
Build your own with Trip Composer
Drag flights, hotels, villas, dives and tours into a date grid. Live inventory across all three islands, one invoice at checkout.
03
Hand it to a Caymanian concierge
For complex multi-island trips, anniversaries, or large groups, our concierge team designs your trip and books it on your behalf — optional, never required.
04
Same platform, all three islands
Grand Cayman, Cayman Brac and Little Cayman covered from a single search. Inter-island flights, ground transfers and shore excursions roll into one booking.
06 — Curated experiences
The day we'd plan
if it were ours.
A small notebook of things we book for guests. Not everything makes sense for everyone — that's why we ask. Below: four we're currently in love with.
Culinary
Dinner at the chef's home
Chef Thomas Tennant cooks for six on his back porch in West Bay. Caymanian fish, Jamaican spice, his mother's bread pudding.
After dark
The bioluminescent kayak
Bio Bay, by paddle, on a moonless night. The water lights up under your hand. We bring rum.
On the water
A boat day, by sketch
Captain pulls a chart, you point. Stingray sandbar, Starfish Point, a quiet slip in Rum Point for lunch. Returns at sunset.
07 — Curated itineraries
Stories,
not packages.
Three of our most-requested journeys. Each is a starting point your advisor will pull at threads, swap chapters, adjust the pace. Use them to find the shape of the week you want.
7 nights · $8,400 pp
Grand Cayman → Brac → Little Cayman
The Three-Island Loop
A week for travelers who want the contrast: Camana Bay to a 12-mile island with no traffic light.
The chapters
- DAY 01Arrive · Seven Mile
- DAY 02Stingray Sandbar at dawn
- DAY 03Hop to Cayman Brac
- DAY 04The Bluff & Bat Cave
- DAY 05Float to Little Cayman
- DAY 06Bloody Bay Wall × 2
- DAY 07Slow morning, fly home
08½ — By place
A small map,
marked by hand.
The pins below are the places we send people most. Hover any to see what they’re known for — then ask your advisor about the ones that aren’t marked.
GRAND CAYMAN
CAYMAN BRAC
LITTLE CAYMAN
Caribbean Sea · 19°N 81°W10 marked
08 — Your advisor
You’ll work with
one of three.
Tell us your trip and we’ll match you with the advisor whose specialty fits — diving, romance, or family. They handle everything from there.
Maria Ebanks
11 years on islandSenior Advisor · Grand Cayman
Born in Bodden Town. Knows every villa owner from West Bay to East End by first name.
Multi-genVillasCulinary
Jonah Connolly
8 years on Little CaymanDiving & Sister Islands
PADI instructor turned advisor. Plans the dive trips. Has logged 2,000+ dives on Bloody Bay.
DivingBrac & LittleHoneymoons
Aisha Powell
6 yearsHoneymoons & Anniversaries
Came for a wedding, never left. Plans the quiet, romantic weeks — boat by Captain, dinner by chef.
RomanceBoutique staysPrivate dining
09 — Word of mouth
“We've used a half-dozen 'concierge' services. Maria is the only one who replied the same day, knew the villa owner personally, and somehow got us a table at Vivo. We've already booked next year.”
Sarah & Tom Whitfield
Anniversary trip · 7 nights · Rum Point
10 — When you're ready
The water is warm.
We're here when you are.
A trip starts with a search. Pick a ready-made package, build your own, or hand it to a Caymanian concierge — your trip, your way.