Our 20th Anniversary Holiday Collection

To book your consultation to discuss the incredible holidays in our 20th Anniversary Collection, please call 01342 612341 9am to 5pm Monday to Saturday.

We are proud to be celebrating our 20th anniversary – marking two decades of helping our customers create incredible memories. To mark this milestone, we are thrilled to introduce our exclusive 20th Anniversary Holiday Collection – a handpicked series of extraordinary journeys across seven continents.

Each of these 20 one-of-a-kind itineraries has been specially created by our team of travel experts across Tropical Sky and our six brands. You won’t find these tours anywhere else – they’ve been thoughtfully designed to include once-in-a-lifetime experiences, hidden gems, and iconic landmarks, all brought together in unforgettable ways.

From immersive cultural encounters and meeting sporting legends and royals, to breathtaking natural wonders and VIP access to world-renowned attractions, these holidays go far beyond the ordinary – they celebrate everything we love about travel, and everything that’s made the past 20 years so special.

Explore our 20 exclusive anniversary itineraries and discover your next unforgettable adventure:

1    Endangered Species of Africa Safari and Trekking Adventure
2    Luxury Southern African Rail and Safari Adventure
3    Paradise Found: A Maldivian Twin-Centre
4    Ultimate Sri Lankan Safari & Tea Trail
5    Private Invitation to Taj, Tigers and Tea in India
6    Asian Discovery Vespa Road Trip in Vietnam & Cambodia
7    Exclusive Trip of a Lifetime Down Under
8    Kiwis, Vineyards and Glaciers
9    Cruise to the End of the World
10  West Coast Maritime Dual-Nation Vacation
11  Unrivalled Rockies Rail Adventure in Canada
12  A Tailormade Discovery of Grizzly Bears and Polar Bears in Churchill
13  VIP Sounds of the South by Rail in the USA
14  Defying Gravity with Astronauts and Coasters
15  The Essence of St Lucia, from Chocolate to Celestial Experiences
16  Antigua & Barbuda in Style with Sir Richie Richardson Golfing Experience
17  Shaken not Stirred in Jamaica
18  Golfing Glory with Sir Gordon Greenidge and a Day at the Races in Barbados
19  Beyond the Beaten Path of Costa Rica
20  Volcano Extravaganza and Culinary Indulgence in Italy

1. Endangered Species of Africa Safari and Trekking Adventure

Explore three Kenyan game parks with private vehicles, trek mountain gorillas in Uganda, and track lions alongside expert researchers. Only with Tropical Sky, enjoy private talks with Born Free conservationists, KWT Mara predator specialists, and an eco-lunch with Dr. Mohanjeet Brar - Director of Game Watchers Safaris. Stay mostly in authentic conservancies that support wildlife sustainability and local communities, for a uniquely immersive and unforgettable safari experience beyond the typical tourist trail.

Enjoy exclusive access to Africa

2. Luxury Southern African Rail and Safari Adventure

Thoughtfully designed by our Africa Director, using personal experience and insider knowledge to bring Africa to life, this 21-night luxury itinerary combines Southern Africa’s most iconic highlights into one seamless journey. Enjoy private safaris, Rovos Rail journeys, Victoria Falls, a private yacht charter, VIP helicopter transfers, scenic landings, and Cape Town’s vibrant foodie scene. This perfectly designed itinerary - crafted with insider access and meticulous detail - is available only through Tropical Sky.

 Private safaris and journeys await

3. Paradise Found

Only available to book through Tropical Sky, this 10-night Maldivian twin-centre escape is the pinnacle of luxury and exclusivity. Enjoy VIP lounge access, private transfers, and stunning overwater villas with pools. Indulge in a couples massage, private whale submarine tour, island-hopping by catamaran, sandbank dining, a hands-on cooking class, and a private Boduberu drumming session - all hand-selected for an unforgettable, immersive experience you won’t find anywhere else.

Discover private paradise in the Maldives

4. Ultimate Sri Lankan Safari & Tea Trail

Curated exclusively by our Sri Lanka experts at Tropical Sky, this 17-night itinerary features extraordinary experiences you won’t find anywhere else. Enjoy private safaris in Yala, behind-the-scenes access to closed tea estates, and a sunrise hot air balloon ride over Sigiriya. Arrive on the southern coast by helicopter, enjoy a private island picnic, and stay in Sri Lanka’s most characterful properties - an unforgettable itinerary crafted with insider knowledge and personal connections.

Go behind-the-scenes in Sri Lanka

5. Private Invitation to Taj, Tigers and Tea

Only available with Tropical Sky, this 13-night private tour of Rajasthan is filled with immersive, unforgettable moments. Enjoy VIP Taj Mahal access before opening hours, a private boat ride on Lake Pichola, exclusive high tea at a Maharaja’s palace, and a conservationist-led insight into tiger protection at Ranthambore. Stay in intimate homestays and boutique hotels, with your own driver and guide - discovering Rajasthan in a deeply personal and culturally rich way.

Enjoy VIP access to India's attractions

6. Asian Discovery Vespa Road Trip

Curated exclusively by Tropical Sky, this 13-night private tour of Vietnam and Cambodia goes far beyond the ordinary. Journey through Bai Tu Long Bay - a serene alternative to Halong hardly visited by tourists - and enjoy three immersive Vespa tours that reveal each destination’s vibrant soul. With private guides for each excursion, including the Marble Mountains and Ba Na Hills, this is a stylish, deeply personal adventure you won’t find anywhere else.

Get ready for a vespa trip of a lifetime

7. Exclusive Trip of a Lifetime Down Under

Meticulously crafted by our Australia experts, this 18-night self-drive adventure blends luxury, freedom, and hidden gems. Enjoy an exclusive scenic seaplane flight over Sydney Harbour with lunch at Cottage Point Inn, koala spotting at a secret location, and a new-to-UK market breakfast watching wild kangaroos in the Blue Mountains. Cap it off with a private Uluru Kata Tjuta sunset flight, offering panoramic desert views just for two.

Discover Australia your way

8. Kiwis, Vineyards and Glaciers

This exclusive 20-night self-drive itinerary is only available through New Zealand Sky, including a unique opportunity to sponsor and name your own Kiwi chick - a memorable way to connect with New Zealand’s wildlife. Enjoy VIP upgrades throughout: premium ferry and TranzAlpine train cabins, complimentary car upgrades (including a double upgrade in the Coromandel), room upgrades, and a private Franz Josef Glacier helicopter flight with guided hike. A luxurious adventure like no other.

Sponsor and name your own Kiwi chick

9. Cruise to the End of the World

Far beyond the ordinary cruise, this 13-night Antarctic adventure is one you can only book with Tropical Sky. Designed for those seeking true wilderness and once-in-a-lifetime experiences, you'll travel aboard a small expedition ship to remote corners normally unreachable by larger vessels. Camp overnight on the ice, kayak through crystal-clear channels, and take to the skies on a thrilling helicopter flight - all part of this rare and unforgettable journey south.

Explore our luxury expedition

10. West Coast Maritime Dual-Nation Vacation

Exclusively available through Canadian Sky and American Sky, this 10-night itinerary celebrates World Maritime Day with a luxury journey through Vancouver, Victoria, and Seattle. Travel by catamarans, clippers, and floatplane, enjoy a private jet ski tour of Howe Sound, and savour VIP foodie experiences like afternoon tea at the Empress, a Vancouver dinner cruise, and private food tours in each city. With curated wildlife encounters and exclusive access, this is coastal North America like you’ve never seen it.

Maritime adventure awaits

11. Unrivalled Rockies Rail Adventure

This is a Canadian Rockies rail journey you’ve never seen before. Available to book with Canadian Sky only, stay in luxurious Fairmont hotels and experience a unique rail journey aboard the renowned Rocky Mountaineer. This 10-night holiday includes VIP excursions in Calgary, an exclusive meeting with the train driver of the Rocky Mountaineer, and travelling the breathtaking Icefields Parkway in a private vehicle.

Experience the Rockies in style

12. A Tailormade Discovery of Grizzly Bears and Polar Bears

Embark on a truly exceptional 15-night journey through Canada's most remote and wildlife-rich regions, designed by Canadian Sky for those seeking unparalleled experiences. Witness majestic grizzly bears in their natural habitat on Vancouver Island, where you will also spend one-on-one time with astronaut Dr. Dave Williams. Book with Canadian Sky and venture north to Churchill for an exclusive polar bear safari, immersing yourself in the awe-inspiring Arctic landscape while observing these magnificent creatures up close. 

Discover Canada's wildlife

13. VIP Sounds of the South by Rail

Discover the rhythm of the American South on this 10-night rail holiday expertly crafted by our USA Director. From Chicago’s iconic Chess Records and a private boat tour of the city to Graceland’s VIP “Presley for a Day” tour and New Orleans’ International Jazz Day celebrations, immerse yourself in blues, jazz, rock and soul. Scenic train rides, private tours and an unforgettable jazz brunch create a truly exceptional journey - this itinerary can only be booked with American Sky.

Uncover the soundtrack of the South

14. Defying Gravity with Astronauts and Coasters

Dive into the magic of Florida with this incredible 14-night itinerary. We’ve handpicked unforgettable experiences the whole family will enjoy - from early park access and Express Passes at Universal Orlando Resort to meeting an astronaut at Kennedy Space Centre. Drive a classic Mustang to Miami, tour the city in a vintage convertible, and unwind on a private sunset cruise. Florida has never felt this special.

Step into Florida's magic

15. The Essence of St Lucia, from Chocolate to Celestial Experiences

More than a holiday, this 12-night St Lucian escape is a celebration of chocolate, rum, iconic landscapes and world-class luxury. Stay at iconic resorts such as Rabot by Hotel Chocolat, Cap Maison and Jade Mountain, with experiences ranging from chocolate-making and rum tastings to private catamaran sailing and a private starlit dining experience on Jade Mountain's Celestial Terrace.

Experience the spirit of St Lucia

16. Antigua & Barbuda in Style with Sir Richie Richardson Golfing Experience

Immerse yourself in the tropical paradise of Antigua, where you will stay at the elegant Galley Bay Resort & Spa. Book with Tropical Sky and you can play golf with West Indies cricket legend Sir Richie Richardson, take a helicopter trip to the island of Barbuda for lunch at Nobu and indulge in an exceptional dining experience with a private chef. Every detail is designed to ensure a truly unforgettable Caribbean escape.

Discover tropical paradise

17. Shaken not Stirred in Jamaica

Venture into the world of James Bond with this one-of-a-kind 10-night itinerary at the legendary Jamaica Inn in Ocho Rios, where you will be personally welcomed by the Morrow Family - owners of this iconic hotel. Book with Tropical Sky so you can participate in an exclusive Vesper Martini masterclass at the birthplace of the "shaken, not stirred" line, gain exclusive early access to Dunn's River Falls before it opens and relive Bond's legacy with a moonlit beachside screening.

For your eyes only: find out more

18. Golfing Glory with Sir Gordon Greenidge and a Day at the Races

Escape to the sun-drenched shores of Barbados on a 10-night itinerary filled with iconic moments and exclusive encounters for those who book with Tropical Sky. Play golf with West Indies cricket legend Sir Gordon Greenidge, enjoy a VIP day at the races from a private box and sail aboard a luxury catamaran. Savour the island's world-class dining with afternoon tea at the legendary Sandy Lane, lunch at The Cliff and an exquisite seafood dinner at Tides.

Golf with a cricketing legend

19. Beyond the Beaten Path of Costa Rica

You can only book this extraordinary 13-night Costa Rica adventure with us at Tropical Sky. From white-water rafting to your jungle lodge in Pacuare to a scenic helicopter flight and horse riding through breathtaking landscapes, every moment is unforgettable. Enjoy private experiences like snorkelling with a beach picnic, kayaking through mangroves, and birdwatching tours - all thoughtfully crafted to connect you with Costa Rica’s stunning natural beauty.

Your Costa Rican adventure awaits

20. Volcano Extravaganza and Culinary Indulgence

Experience southern Italy in style on this 11-night holiday in Sicily, Vulcano and Sorrento, meticulously created by our Europe Director. Stay in exquisite resorts, enjoy a spectacular helicopter transfer between Sicily and Vulcano and and embark on a private boat trip and tour of Capri. Along the way, exceptional experiences await including a guided hike up Mount Etna and a hands-on Sicilian cooking class - all tailored for an unforgettable Mediterranean escape.

Experience Southern Italy

To book your consultation to discuss the incredible holidays in our 20th Anniversary Collection, please call 01342 612341 9am to 5pm Monday to Saturday.