Trip Ideas for 7 Life Milestones

Words by Aislinn Corbet

Life is all about moments and milestones. Falling in love. New friendships starting. Old ones ending. The annual family getaway. Getting the job of your dreams. Or your best friend’s wedding weekend.

Some moments will be fleeting and some you will never forget, but either way, these are moments and milestones worth celebrating  – ideally in a beautiful place with the ones you love.

These are the places that will make the big life milestones extra special…

21st birthday

This is the birthday that introduces you to independence  – celebrate it by going on an epic backpacking trip or travelling somewhere you’ve always dreamed of going to.


If you want to make it last all night, head to New York, the city that never sleeps and where there is always something to do. Or head to Rio de Janeiro, the heart of Brazil, where life is all about Caipirinhas, beautiful people, lazy beach days, and nights spent samba dancing down at the real Copacabana. Or go on a solo backpacking trip around Thailand. Get lost in the chaos and wild energy of Bangkok or head straight for the bustling streets and beautiful beaches of Koh Samui.

Getting a promotion

Making progress in your career is a big deal. Your hard work and ambition paid off and you are taking the next step in your career. Treat yourself to a break between careers in a faraway place.


Sicily is all Mediterranean beaches, world-famous food, and winding cobbled alleyways – the perfect island oasis for enjoying the finer things in life before you go off and achieve great things in your career. But if you want a bit more adventure, a wild camping trip in Norway is a beautiful way to take a break from reality, connect with nature, and treat yourself to some rest and relaxation before you start the next big thing. Or head for Buenos Aires in Argentina –- a stylish city known for grand Art Nouveau buildings, art museums, sidewalk cafés, wine bars, and tango clubs.

Mending a broken heart

Heartbreaks are one of those things that eventually happen. It’s a difficult experience to go through, but often it helps us grow in some way. The best way to get through it is to get away for a while.


Replace the heartbreak with hot nights and beautiful mornings in India. Check yourself into a beach cabin in Goa and grieve on Arabian beaches, in spice plantations, and at legendary parties. To really get away, Bali is still one of the best places to detox and comfort yourself with a retreat. But if any place is perfect for mending a broken heart, it is Lisbon – or pretty much anywhere else in Portugal. Somewhere between gazing up in awe at the magnificent Baroque architecture, wandering along the old narrow streets, and eating custard tarts, you will forget all about being heartbroken.

Getting engaged

Why would you not celebrate your engagement with going somewhere romantic and secluded so you can revel in your affection and love for each other? Consider it a pre-honeymoon.


Forget Paris, the most romantic places in France are the small towns and villages. The best ones are in the wine regions of Alsace, Burgundy, and Provence. Spend mornings having breakfast in cute corner bistros and afternoons taking cooking classes. Or celebrate the next step in your relationship by learning something new, like scuba diving in Belize or how to make real Italian pasta and olive oil from scratch in the valleys of Tuscany in central Italy.

Your kid’s first big holiday

The first holiday with your kid is a special one for you and them. It’s great bonding time as you watch them experience more of the world and it will be a special memory for them.


Riviera Maya is one of the best places in Mexico for a family holiday. All-inclusive resorts on the beach and the outdoor adventure parks make it a hit with young travellers. But the real winner on this particular family holiday is Mauritius. Family-friendly resorts, short travel time, and visa-free travel make it a great option for your kid’s first big trip.

Honouring a 10-year friendship

You’ve gone through the good, the bad, and the ugly together and are still there for each other. Friendships this strong deserve a special trip. Go to that place you’ve always talked about going to.


Perhaps the plan involved riding a Vespa along the coast of Spain, renting a caravan and going on a road trip across the United States right down to Key West, or getting lost in the ancient sites and aromatic scents of Turkey. If you need a reason to splurge on that holiday, this is that reason.

A special wedding anniversary

Much like the 10-year milestone in a friendship, milestones in marriages are also important and worth celebrating. Whether it is your 10 or 30th anniversary, plan a trip or go back to a special place.


Maybe you met and fell in love while working in London, went on a trip together to Tokyo while you were dating, or spent your honeymoon in Tahiti  – relive those moments from your life together by recreating them. Or go somewhere you have never been and make completely new memories.

The big 50th

There’s no such thing as too old to travel. And when you’ve been around for half a decade and you’re still going strong, celebrate your health and well-lived life by doing something amazing.


Trek the Inca Trail to Machu Picchu, watch the sunrise over Angkor Wat in Cambodia or leap out of a plane over the island of Oahu in Hawaii. This is the big one so something unforgettable!

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