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Ultra Luxury Cayman Islands Holidays 2024
Plan your dream Cayman Islands holiday with the help of our expert Personal Travel Managers. Holidays
Plan your dream Cayman Islands holiday with the help of our expert Personal Travel Managers. Holidays
Plan your dream Cayman Islands holiday with the help of our expert Personal Travel Managers. Holidays
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Map Come and discover the Cayman Islands where a carefree way of life, friendly locals, paradise beaches and amazing activities will have you returning year after year.
This wonderous destination is made up of three islands, each boasting different personalities and have unique reasons you would want to visit. Whilst luxury resorts and barefoot elegancy seeps through Grand Cayman, a visit to Cayman Brac will have adventure-seekers filled with excitement. And those seeking a secluded stay should head to Little Cayman, a 10-mile remote island full of empty beaches postcard seascapes and impressive wildlife.
There really is something for everyone in the Cayman Islands. History buffs will love the traditional architecture and fantastic National Museum; bird-watchers can enjoy spotting endangered parrots, brown boobies and peregrine falcons; and those looking for something a little more luxurious can book themselves into a sublime resort and head to George Town where you can shop ‘til you drop, duty free, for some of the world’s best designer brands.
WINGED BOOTS WISDOM
Explore the Bloody Bay Wall Marine Park, a renowned dive spot that is a submerged mountain range with an outstanding 5,000ft drop off. This phenomenal backdrop is a diver’s paradise where exotic marine life, sharks, turtles and stingrays can be spotted.
This wonderous destination is made up of three islands, each boasting different personalities and have unique reasons you would want to visit. Whilst luxury resorts and barefoot elegancy seeps through Grand Cayman, a visit to Cayman Brac will have adventure-seekers filled with excitement. And those seeking a secluded stay should head to Little Cayman, a 10-mile remote island full of empty beaches postcard seascapes and impressive wildlife.
There really is something for everyone in the Cayman Islands. History buffs will love the traditional architecture and fantastic National Museum; bird-watchers can enjoy spotting endangered parrots, brown boobies and peregrine falcons; and those looking for something a little more luxurious can book themselves into a sublime resort and head to George Town where you can shop ‘til you drop, duty free, for some of the world’s best designer brands.
WINGED BOOTS WISDOM
Explore the Bloody Bay Wall Marine Park, a renowned dive spot that is a submerged mountain range with an outstanding 5,000ft drop off. This phenomenal backdrop is a diver’s paradise where exotic marine life, sharks, turtles and stingrays can be spotted.
Come and discover the Cayman Islands where a carefree way of life, friendly locals, paradise beaches and amazing activities will have you returning year after year.
This wonderous destination is made up of three islands, each boasting different personalities and have unique reasons you would want to visit. Whilst luxury resorts and barefoot elegancy seeps through Grand Cayman, a visit to Cayman Brac will have adventure-seekers filled with excitement. And those seeking a secluded stay should head to Little Cayman, a 10-mile remote island full of empty beaches postcard seascapes and impressive wildlife.
There really is something for everyone in the Cayman Islands. History buffs will love the traditional architecture and fantastic National Museum; bird-watchers can enjoy spotting endangered parrots, brown boobies and peregrine falcons; and those looking for something a little more luxurious can book themselves into a sublime resort and head to George Town where you can shop ‘til you drop, duty free, for some of the world’s best designer brands.
WINGED BOOTS WISDOM
Explore the Bloody Bay Wall Marine Park, a renowned dive spot that is a submerged mountain range with an outstanding 5,000ft drop off. This phenomenal backdrop is a diver’s paradise where exotic marine life, sharks, turtles and stingrays can be spotted.
This wonderous destination is made up of three islands, each boasting different personalities and have unique reasons you would want to visit. Whilst luxury resorts and barefoot elegancy seeps through Grand Cayman, a visit to Cayman Brac will have adventure-seekers filled with excitement. And those seeking a secluded stay should head to Little Cayman, a 10-mile remote island full of empty beaches postcard seascapes and impressive wildlife.
There really is something for everyone in the Cayman Islands. History buffs will love the traditional architecture and fantastic National Museum; bird-watchers can enjoy spotting endangered parrots, brown boobies and peregrine falcons; and those looking for something a little more luxurious can book themselves into a sublime resort and head to George Town where you can shop ‘til you drop, duty free, for some of the world’s best designer brands.
WINGED BOOTS WISDOM
Explore the Bloody Bay Wall Marine Park, a renowned dive spot that is a submerged mountain range with an outstanding 5,000ft drop off. This phenomenal backdrop is a diver’s paradise where exotic marine life, sharks, turtles and stingrays can be spotted.
Come and discover the Cayman Islands where a carefree way of life, friendly locals, paradise beaches and amazing activities will have you returning year after year.
This wonderous destination is made up of three islands, each boasting different personalities and have unique reasons you would want to visit. Whilst luxury resorts and barefoot elegancy seeps through Grand Cayman, a visit to Cayman Brac will have adventure-seekers filled with excitement. And those seeking a secluded stay should head to Little Cayman, a 10-mile remote island full of empty beaches postcard seascapes and impressive wildlife.
There really is something for everyone in the Cayman Islands. History buffs will love the traditional architecture and fantastic National Museum; bird-watchers can enjoy spotting endangered parrots, brown boobies and peregrine falcons; and those looking for something a little more luxurious can book themselves into a sublime resort and head to George Town where you can shop ‘til you drop, duty free, for some of the world’s best designer brands.
WINGED BOOTS WISDOM
Explore the Bloody Bay Wall Marine Park, a renowned dive spot that is a submerged mountain range with an outstanding 5,000ft drop off. This phenomenal backdrop is a diver’s paradise where exotic marine life, sharks, turtles and stingrays can be spotted.
This wonderous destination is made up of three islands, each boasting different personalities and have unique reasons you would want to visit. Whilst luxury resorts and barefoot elegancy seeps through Grand Cayman, a visit to Cayman Brac will have adventure-seekers filled with excitement. And those seeking a secluded stay should head to Little Cayman, a 10-mile remote island full of empty beaches postcard seascapes and impressive wildlife.
There really is something for everyone in the Cayman Islands. History buffs will love the traditional architecture and fantastic National Museum; bird-watchers can enjoy spotting endangered parrots, brown boobies and peregrine falcons; and those looking for something a little more luxurious can book themselves into a sublime resort and head to George Town where you can shop ‘til you drop, duty free, for some of the world’s best designer brands.
WINGED BOOTS WISDOM
Explore the Bloody Bay Wall Marine Park, a renowned dive spot that is a submerged mountain range with an outstanding 5,000ft drop off. This phenomenal backdrop is a diver’s paradise where exotic marine life, sharks, turtles and stingrays can be spotted.
Best Luxury Hotels
Best luxury
hotels in Cayman Islands
- We've found 1 hotels in Cayman Islands for you
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- Six exquisite bars and restaurants with extensive menus
- An on-site luxury Swiss spa
- Family friendly programme to educate guests on local culture
- Six exquisite bars and restaurants with extensive menus
- An on-site luxury Swiss spa
- Family friendly programme to educate guests on local culture
Call us on 0203 816 0985
to start planning your holiday
to start planning your holiday
Extra Mile Guarantee
Our Extra Mile Guarantee
Our Extra Mile Guarantee
We appreciate every Winged Boots customer and to prove this we want you all to receive a very high standard of customer service when booking with us. Our Extra Mile Guarantee is just that. A promise that no matter the destination, whether it is your first or your hundredth time using Winged Boots, you will be treated like a VIP from enquiry through to departure and even when you return home.
David Ox, managing director- Dedicated personal travel managers
Each with a minimum of 10-years’ experience
- Complimentary event invitations
Meet the team at our annual shoot day, O2 London, a private dinner and more
- Transparent price
No hidden fees, quotation costs or admin charges
- The human touch
Just honest conversations with real people
- Out of hours contact
Via email, direct dial and even on Whats’App
- Concierge service
Celebrating? Let us know and we may surprise you
- Your holiday is protected
We're licensed by ATOL & ABTA
- We make it happen
Wherever, whenever, however and every time
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Adventure awaits:
- As well as fantastic land-based activities, many adventures can be had beneath the waves with some of the most incredible snorkelling and dive spots in the world. From submerged mountain ranges to murky shipwrecks or calmer coral reefs close to shore, expert divers and nautical novices will have the experience of a lifetime.
- With such a thriving sea life, its unsurprising one of the most popular places for people to visit is Stingray City where you can wade through crystal clear waters as these impressive creature’s swim around you. Also be sure to take a trip to The Turtle Centre where you can have one-on-one encounters and give back to the island’s marine life.
- The Cayman Islands are home to some of the most beautiful beaches in the Caribbean, one of which is the award-winning Seven Mile Beach. Powdery white sands, cerulean oceans and swaying palm trees are what you can expect, with only the most opulent hotels and resorts positioned along it.
- Located on the north side of Grand Cayman you will find the Bioluminescent Bay. Take a tour to go and visit this natural phenomenon, where high concentrations of bioluminescent phytoplankton can be found. When disturbed, they let off a light which reacts causing an electric blue light to shine, making you feel like you are floating through pixie dust.
- The Cayman Islands are known as the foodie capital of the Caribbean where dining is its own activity. As well as fresh seafood and Caymanian cafés serving local cuisine, also expect to enjoy a fantastic variety of other gastronomic delights such as French, Italian Japanese and even Australian delicacies.
- Head to The Wreck Bar at Rum Point where it claims to have invented the Mudslide cocktail. The story goes that a customer asked for a White Russian (vodka, Kahlua and cream) but the barman had never made this before. He didn’t have any fresh cream and so decided to substitute for Irish Cream – therefore making the now known Mudslide.
Good to know
- TimeDifference: GMT-5
- Currency: Cayman Islands Dollar
Best time to travel
Average Temperatures
Jan: 25°c  | Feb: 25°c | Mar: 26°c | |||
| Apr: 26°c | May: 27°c | Jun: 28°c | |||
| Jul: 29°c | Aug: 30°c  | Sep: 29°c | |||
| Oct: 28°c | Nov: 27°c | Dec: 26°c |
Location map
Get in touch with our team of personal travel managers to start planning your trip
- The human touch
- Complete concierge service
- 24/7 out of hours contact
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