At 91 years old, Winnie McClennen made a decision that many people never do – at any age. After a year of profound change, she chose to begin again.
In the past twelve months, Winnie lost her husband unexpectedly after a fall. She sold her home. She moved. And somewhere between grief, exhaustion, and closing one chapter of life, she felt the pull to open another.
“I saw the cruise almost by accident,” she said. “I thought, if I’m going to do something like this, I better do it now. I can’t plan for a year or two from now – who knows?”
So she didn’t.
This week, Winnie flew to Fort Lauderdale and boarded the Viking Sky, beginning a 138-day around-the-world cruise with Viking Cruises, visiting 31 countries between December 2025 and May 2026. She’s traveling solo. She’ll turn 92 in January. And this blog will follow her journey – one week at a time.
A Journey Born From Change
As departure approached, Winnie felt what many travelers feel before a big trip: apprehension.
“I’m hoping I’m doing the right thing,” she shared. “I’ve had some big changes in my life. This feels like both a closure and an opening.”
Preparing for a journey of this scale was no small task. It took planning, stamina, and resolve. What she packed speaks volumes: photos of her family and her husband, her knitting, her Mahjong card. She’s bringing familiar touchstones into unfamiliar places.
“I’m taking a walker in case I have bad days,” she said. “But usually, I have pretty good days.”
Why This Story Matters
Winnie hopes her travels remind others that curiosity and adventure don’t have an expiration date.
“I hope people feel they don’t have to stop doing things as they get older,” she said. “There’s a world out there, and you can still go find out about it.”
That belief has long been central to Onward Travel. Our work is rooted in helping people mark transitions, reconnect across generations, and step into new chapters through travel. Onward Travel itself was born from Winnie’s legacy. Years ago, she founded The Cooking Cottage, where her love of food, teaching, and hospitality naturally evolved into traveling with her students. When The Cooking Cottage eventually closed, that spirit didn’t end. It was carried forward by her granddaughters, Molly and Kat, who planned trips for The Cooking Cottage and founded Onward Travel 12 years ago to continue what Winnie had started: using travel as a way to connect people, cultures, and generations. This journey may be different in scale, but it’s rooted in the same spirit that began it all.
In many ways, everything has come full circle. This time, Winnie is the traveler, supported by the same company her legacy helped inspire.
Winnie chose to book her world cruise through Onward Travel so she wouldn’t have to manage the details alone. Working in partnership with Viking, we helped coordinate the logistics, so she could focus on the journey itself.
What’s Ahead
In the months to come, Winnie will share reflections from life at sea, moments from ports around the world, and the small details that make long-term travel both challenging and rewarding. These posts won’t be travel guides but rather personal snapshots from Winnie—thoughtful, honest, and brave.
As Winnie put it simply: “I feel like I can do this now.”
We’re honored to share her story with you.
Next week: Winnie’s first days at sea and what it feels like to wake up knowing the world is quite literally ahead of you.
