Some trips begin with a destination. Others begin with a celebration.
Big birthdays, anniversaries, career breaks, retirement, honeymoons and family reunions: they each mark a new chapter and provide a reason to gather the people who matter most in a place none of you will forget.
Milestone travel is not about going further for the sake of it but choosing a trip that fits the celebration. These are just a few ideas from our Specialists.
Big birthdays
Japan
Mark your birthday with a journey that balances the iconic with the unexpected. After Tokyo’s backstreets and Kyoto’s temples, travel to Shikoku, one of Japan’s lesser-visited islands. Here, days unfold slowly: hot springs, hiking trails, rafting, farming communities and quiet villages. For an even lesser-visited part of the country, the Seto Inland Sea Islands feel far removed from the main tourist circuit. Perfect for a birthday shaped by food, scenery, culture and discovery.
Holiday to Japan including Tokyo, Kyoto and Shikoku
Botswana
For a milestone that deserves more than the dinner table, Botswana is an amazing destination for a multi-generational family celebration. From the Chobe River to the Okavango Delta, the Makgadikgadi Pans to the Kalahari desert, there’s something for everyone. One of our favourite experiences is quad biking across the vast, open expanse of the salt pans, where the horizon seems to stretch forever. End with a night under immense skies, surrounded by space, silence and stars before waking to the salt pans on your birthday morning.
Svalbard
Nothing quite compares to the feeling of seeing a polar bear in the wild, especially if it happens on your birthday. Sail through the Svalbard Archipelago in search of polar bears, walruses, arctic foxes, reindeer, belugas and seabirds. It’s a trip for embracing the elements and expecting the unexpected; with your days governed by the ice, the weather and the wildlife, there’s always something to surprise you on the horizon. This is a birthday marked not by candles, but by the sudden thrill of the Arctic.
Landmark anniversaries
India
For an anniversary that brings you back to India, or if you’re looking for a trip beyond the classic routes, the Deccan Plateau offers you the chance to delve deeper. Cycle or walk through Karnataka’s ancient landscapes, explore the rock-hewn caves of Ajanta and spend time in Hyderabad with Jonty, our resident expert, for a personal introduction to the city
Hampi and the Treasures of the Deccan Plateau
Italy
What better way to celebrate your anniversary than with an olive oil farm tour, followed by mozzarella-making and a long lunch in the sun? This journey spans the Baroque-influenced architecture of Lecce, Ostuni, Gallipoli and Galatina, before continuing on to Matera, Fasano and the whitewashed towns of Itria Valley. Spend time on the coast, where long beaches and clear waters bring an easy romance to the journey. A slower, more intimate side of Italy, made for marking years well spent together.
Puglia’s Cathedrals and Coastlines
South Africa and Mozambique
South Africa is a destination that always delivers. Whether you’re returning with fresh eyes, or looking for a quieter side of the country for your anniversary, KwaZulu-Natal brings together private wildlife concessions, the Drakensberg Mountains and wild beaches in one beautifully varied journey. It’s one of the few places where you can spend the morning tracking rhino, cheetah and rich birdlife, then spend the afternoon kayaking, diving or unwinding beside the Indian Ocean. To make an already special journey feel even more complete, continue into Mozambique for some of the finest beaches in the region.
KwaZulu-Natal Wildlife, Coast and Battlefields
Career breaks and sabbaticals
El Salvador, Nicaragua and Costa Rica
Overland through Central America, embracing the true scale of the region now that you have the time. As you make your way from El Salvador through Nicaragua and Costa Rica, the golden thread becomes clear: volcanoes, wildlife, communities, colonial cities and the Pacific coast. This is a journey that rewards the time you give it.
El Salvador, Nicaragua & Costa Rica
New Zealand
Let the landscape lead and take the time to explore New Zealand properly. There are few better ways to explore than through a self-drive across the North and South Islands. Your adventure includes wildlife tours, Maori life, scenic flights, glacier adventures, overnight cruises and so much more. A journey for those with the time to slow down.
Ultimate New Zealand Self-Drive
China
Your route travels from Kunming to Dali, Lijiang and Shangri-La, moving through Yunnan by road and train rather than rushing between China’s great cities. This is one of the country’s most beautiful and naturally diverse provinces, with terrain ranging from tropical rainforests to snow-capped mountains. A journey for those who want their break to feel expansive, thoughtful and far from the expected.
Honeymoons
Sri Lanka
A Sri Lankan honeymoon provides variety without you needing to cover vast distances. Hand-in-hand, journey through the ancient sites of the Cultural Triangle, search for wildlife in Wilpattu and travel into tea country by train and on foot. End on the coast at Galle, where UNESCO-listed streets, cafe culture, beach time and marine life bring a softer rhythm to the final days. A honeymoon for couples who want more than one kind of escape.
Argentina
For couples who want good food, good wine and a little drama from their landscapes, Argentina delivers. Begin married life with time in Buenos Aires before retreating to Mendoza’s wine country, where days can be shaped around vineyard stays, long lunches and blending your own bottle together. Journey south on a self-drive adventure through the Argentinian Lake District, with time for kayaking, sailing or windsurfing beneath snow-capped peaks. This is a trip defined by both sophistication and adventure.
Self-Drive Mendoza & the Lake District
Southeast Asia
Join local communities on your newlywed journey throughout Vietnam, Cambodia and Thailand for the privilege of experiencing their own country from their perspective. Each leg of the route reveals something new: Hanoi’s markets and temples, the shores of the Mekong, the temple complex of Angkor and the energy of Bangkok. Add a stop in Singapore on your return journey and retreat to Bawah Reserve, where clear waters, quiet beaches and slow days make a beautiful final chapter. A honeymoon for couples who want discovery first, then time to simply be.
South East Asia – Through Local Eyes
Retirement
Chile
When your diary finally opens up, take to the road on one of the world’s greatest self-drive adventures. The Carretera Austral is for those who’d be happy to go days without seeing another soul. With the space to stop, look and listen, your adventure takes you to marble caves, stilt houses, Patagonia Park – and, if you’re lucky: pumas.
Australia
Spanning outback ranges and island wildlife, rail travel and the Indian Ocean, it’s easy to see why Australia is such a good fit for that first holiday post-retirement. Travel through South Australia and Western Australia, meeting the people who know these landscapes best. Highlights include 4×4 excursions, Aboriginal rock art, kangaroo sightings and the vineyards of Margaret River. Shaped by open space, wild coastlines and wildlife far beyond the expected, now is the time to travel further and slower.
Australian Safari – Outback to Ocean
Central Asia
With time and curiosity to spare, the Five Stans offer the newly retired one of the world’s greatest overland journeys. Travel through Kyrgyzstan, Kazakhstan, Tajikistan, Uzbekistan and Turkmenistan, crossing deserts, mountains and grasslands in five distinct countries. Each shaped by nomadic traditions, Silk Road history and its own sense of identity, this is the perfect adventure for those who want to use their newfound time not just to travel further, but to understand more.
Journey through Central Asia – The Five Stans
Family reunions and multi-generational holidays
Kenya
When different ages need different kinds of adventure, Kenya is hard to beat. Stay in Lewa Wildlife Conservancy, where expert guides lead game drives and bush walks in search of rhino, elephant, lion, leopard and cheetah, before ending on the Kenyan Coast at Diani for snorkelling, diving and kayaking. Something for every generation to remember.
Family Safari – Kenya Chronicles
Indonesia
When time together is rare, chartering a boat through Indonesia’s volcanic islands is hard to match. Days are spent snorkelling, kayaking, paddleboarding and swimming in waters home to manta rays, sea turtles and whale sharks. Between adventures, the boat becomes your private world: slow mornings, shared meals, games, books, dolphins at the bow and the kind of uninterrupted time that busy families rarely find at home.
Canada
Time together needs to work for everyone. Western Canada provides the right balance for families who want wilderness without sacrificing comfort. Start in the mountains for guided hiking, canoeing and wildlife, fly over dramatic canyon waterfalls accessible only by air, then retreat to a coastal lodge for surfing, hiking, kayaking or time simply spent together by the shore for a slower end to your adventure.
Canadian Contrasts – A Family Adventure
Plan a journey around the occasion
Milestone travel is not a category as much as a way of planning. The occasion comes first. The destination, pace, season, guiding and accommodation follow.
Whether you’re celebrating a birthday, marking an anniversary, taking a sabbatical, planning a honeymoon, beginning retirement or gathering the family, our Specialists can tailor a bespoke holiday to you.
Speak to them today about planning a holiday built around some of life’s most meaningful occasions.