4 Fabulous Bucket-List Trips To Take In Your 50s

There's no time like now to go on an adventure.

By

Terry Ward

 
Published December 19, 2025
Women sail on a tall-masted schooner and spend carefree day among the islands of Maine!
Courtesy Maine Windjammer Cruises

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Midlife is full of surprises, some more welcome than others. Among the more pleasant ones I’ve found of late, anyway, is that turning the big 5-0 doesn’t have me burdened with nearly the age-dread I had when launching into my 40s a decade ago.

Could it be because I finally feel like I (mostly) have my ish together? Or is it this perimenopausal state of mind that has me selectively narrowing my bandwidth for BS to focus more on what really matters in life?

Whatever it is, I feel ready — and more importantly, really excited — to celebrate 50 with my college friends this year. We’re feeling healthy and happy to launch a new decade together with an adventurous spirit we might not have believed we’d still have if you’d told us so back in our daring 20s.

Originally, my friends and I had tossed around the idea of a long weekend of city strolls and fine dining in Quebec City, which sounded like a perfectly fine plan. That is, until it occurred to us that we could easily save that foray for our 60th (or why not 70th) birthdays and embark on something a little more adventurous to mark our 50th birthdays while our bodies are still totally willing and able.

So we’re celebrating this winter with an extreme sledding trip to Switzerland, hurling ourselves (like the kids we still are at heart) down slick toboggan runs into a winter wonderland — and no doubt feeding our gumption with copious amounts of fondue and Glühwein.

The way I see it, these years are still the ones to go big (then go home, of course, to our busy sandwich generation lives).

Read on for suggestions for awesome adventures to consider having in your fabulous 50s.

Woman in a snowy mountain scene beside her bike sled velogemel
Terry Ward with her Grindelwald velogemel in the Swiss Alps
Courtesy Terry Ward

Go sledding in the Swiss Alps.

More accessible and generally less expensive than skiing, sledding is a national pastime come wintertime in Switzerland. According to Switzerland Tourism, the country has more than 370 miles of sledding runs to explore (just find the local sports shop wherever you land in the mountains to rent a wooden toboggan, and you’ll fit right in with the sporty locals). And be prepared. This is hardly the tame driveway variety of backyard sledding you might have grown up with. You can ride the longest sled run in Europe, Big Pintenfritz, which descends for just over 9 miles, near the beautiful alpine village of Grindelwald (accessible via a three-hour train ride from the convenient railway station at Zurich’s international airport). Then soak off the soreness from any spills in the rooftop hot tub at the charming Hotel Fiescherblick, walkable to everything in town. For something extra fun, plan your visit during February’s annual Velogemel World Championships, when you don’t even need to be a local to register to try racing downhill atop the region’s unique bike-style sled (the Velogemel).

Snorkel with humpback whales in Niue during their annual migration.   

There are only a few places in the world where you can snorkel with humpback whales — an experience as awe-inspiring for the animals’ sheer size as it is for the thundering acoustics their singing shoots through your chest as you snorkel and observe them. The only way to get to the South Pacific island of Niue, where humpbacks come extremely close to shore during their annual migration north from Antarctica from July through September, is via a three-hour flight north from Auckland, New Zealand (why not tack on a few days in that beautiful country to try fly fishing at the North Island’s legendary Huka Lodge in the lakeside resort town of Taupō).

In Niue, PADI Eco Center Niue Blue leads guided daily snorkeling tours that put you in the water with the gentle behemoths (and quite often their curious calves, too). There’s only one hotel on the island, Scenic Matavai Resort Niue, with an oceanfront tiki bar and pool and a “whale bell” to announce sightings that rings all day long during the season as humpbacks fluke and tail slap right in front of the clifftop property.

Woman and man with long beard smiling beside a motorcycle
Terry Ward with biker, Papa Bear, in Cape Town South Africa beside the Harley Davidson
Courtesy Terry Ward

Ride pillion on a Harley-Davidson around Cape Town in South Africa.

Much ink has been spilled about the glorious cable car ride up Table Mountain in South Africa’s most beautiful city (and it’s no doubt a thrill). But for something different, why not explore Cape Town on two wheels in the saddle behind an experienced driver (a.k.a riding pillion) aboard a Harley-Davidson motorcycle during a chauffeured ride along the Western Cape with West Coast Motorcycles (licensed drivers can rent their own bike to explore). Full-day peninsula tours take you to Boulders Beach to see the penguin colony and along the famed Chapman’s Peak Drive, with 114 curves and ocean views all the way. Make your Cape Town base the art-filled Relais & Châteaux property, Ellerman House, a luxury boutique hotel with just 13 rooms and sweeping views of the Atlantic Ocean. Forays into Cape Town’s close-in wine country are within easy reach at spots like Buitenverwachting in Constantia and the stunning Delaire Graff Estate in Stellenbosch. You can always jet north to Johannesburg, too, to finish your trip on safari in a big-five hotspot like Madwike Game Reserve.

Learn to sail aboard a tall ship along the Maine Coast.

You’ve got plenty of years left to go on a cruise. So why not push yourself to actually learn the ropes of sailing during multi-night adventures along Maine’s spectacular coastline with The Maine Windjammer Association? Join a group (or round up some friends for a private charter) aboard one of the fleet’s traditional tall ships, complete with a captain and chef. A typical day onboard might see you pulling the halyards to raise the sails and maybe even taking the helm before anchoring in a pristine cove for a (no doubt refreshing) swim or settling in at a quiet beach for a sunset lobster bake. Come nightfall, there’s nothing quite like lying on the wooden ship’s wide deck and gazing up at the canopy of the Milky Way to make you grateful you’re still adventuring in this great wide world.

What's the biggest adventure you've ever been on? Let us know in the comments below.

Florida-based travel writer and freelance journalist Terry Ward is a mother of two who travels frequently with her young children while reporting for publications like CNN, National Geographic, Conde Nast Traveler, Travel+Leisure and Scuba Diving Magazine.