2025 In Travels - Where These Heels Went - And What I Learned
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2025 In Travels – Where These Heels Went – And What I Learned

I rang in 2025 bundled up with my friend and her young family at Disneyland Tokyo! What a fun way to kick off the year. As someone that didnโ€™t grow up watching a lot of TV or Disney movies, I entered the year declaring that I would play more, and choose wonder! 

Right now, Iโ€™m in Sydney, Australia, where it is warm and sunny. Iโ€™m alone, and Iโ€™m here to ring in the new year in Sydney, something Iโ€™ve dreamed of doing for a very long time – choosing wonder! 

Between these two New Yearโ€™s Eves, so much has happened. Iโ€™m a different person standing in Australia than I was in Tokyo twelve months ago. Hereโ€™s what the journey between these two countdowns looked like.

Dee, a travel blogger, reflects on her journeys of 2025 and how they impacted her life.

On Flexibility 

A much awaited trip to Kenya to reunite with my Jordan girlies had to be cancelled/postponed, because life happens and scheduling things as an adult is an extreme sport. It was disappointing, but I chose to find joy in plan B – Hawaii! This was my third time in Hawaii, and my second time in Maui, and my first time seeing the sunrise on Haleakala, a spectacular sight. My friend L came along and she wins the award for meeting up on 3 continents  (North America, Asia, and Africa) in 2025.

Dee reflects on meeting her friend, L, in Maui Hawaii in one of her many trips.

The Work Trips 

This year, work took me to the USA and London in March, then Hong Kong in September.The jetlag from Japan to the US (14+hours) and UK (8 hours) always has me fighting for my life. I’d typically arrive the night before, then have to be sharp and ready for C-suite conversations by morning, which feels like 2am on my body clock. It gets tough, and the long hours of travel (thankfully in business class) does a number on my body. I love that I get the opportunity to travel internationally for work and yet, it can be tough. 

Dee a travel blogger reflects on her journeys in 2025, meeting friends from across the world.

The silver lining? In the US, I got to meet my friend’s new baby in Minneapolis. In London, I caught up with old colleagues and friends over dinner. 

A travel blogger celebrates meeting her friend in London o a work trip, among several other international travels.

September was particularly brutal. My Hong Kong visa came through at the last possible minute, and then I spent the entire two days of meetings terribly sick and miserable. Too late to cancel.

On Connection

Travel doesn’t just take you places, it brings people to you. This year, Tokyo became a gathering place for friends from different chapters of my life, proof that all those passport stamps over the years were building something bigger than just memories.

Dee meeting up with a college friend in Tokyo on one of many travels in 2025.

I had the pleasure of hosting friends throughout 2025, with January, June, October, and November being particularly full. I’m blessed that some of my besties from different stages of my life made the journey to Tokyo. Beyond those I hosted, I caught up with other friends passing through the city (including 3 people I met through this blog – Hi A, T, and S). The most surprising reunions? Meeting up with old schoolmates I hadn’t seen in 14 and 16 years, respectively.

My friends visiting for New Year’s set the tone for the whole year. While most of Japan heads to their hometowns for the holiday, we made our own celebration in Tokyoโ€”my first time ringing in the new year here. We went to Tokyo Disneyland and celebrated my friend’s daughter’s birthday at DisneySea, indulging our inner children and choosing wonder from day one.

I also made it to the USA in August to celebrate my 40th birthday with family and friends, more on that later.

Life is generous, and travel taught me that the connections you make along the way have a beautiful habit of coming back to you.

On Returning To Places Iโ€™ve Loved –

This year taught me that some places deserve a second (or third) visit. Except for Taiwan and Australia, every other country was a repeat visit in my stamp collection. 

Both Thailand and the Philippines created such an impression on me the first time that I had to return. Getting the visa to Thailand was hectic as I had to send my fingerprints to the FBI in order to be cleared for visa approval (told the story here), but spending my new year retreat on Koh Samui relaxing, sipping fresh coconuts, taking a cooking class, snorkeling and exploring the coast was absolutely worth it. 11 years later, the food, and people of Thailand remain top tier!

A Nigerian American woman shares her challenges in obtaining a Thailand visa for her 2025 travels.

In the Philippines, I chose to close out some unfinished business from 2016 by going to Cebu as I didnโ€™t have enough time back then. In Cebu and nearby Bohol, I swam with turtles, saw a sardine run, and stood by the majestic chocolate hills. It definitely is more fun in the Philippines.

Visiting Chocolate Hills, Philippines, in 2025 was a memorable moment for Dee from Well Worn Heels.

On Being Present Where I am Planted

This is my final year in Japan, and I made a list of 52 experiences to savor every moment. I know I’m actively living in the ‘good old days.โ€™ This year I went skiing for the first time, tasted caviar for the first time, attended my first Japanese wedding, visited a museum on a random public holiday, and got into Japanese fashion a bit.

Dee shares her first skiing experience in Gala Yuzawa, Japan as a memorable moment in 2025.

I explored Hiroshima with my Japanese teacher, experienced a head spa, hopped on a 3-hour train ride to see autumn leaves, saw Mount Fuji, and even ate KFC for Christmas.

Just this month, it finally hit me that I don’t just like living in Japan, I LOVE it. I was shocked! I canโ€™t quite tell you when that shift happened. I was walking home from trying a new restaurant, using an umbrella given to me by the host (it was raining and I didn’t have one with me), as I walked home on a quiet street (a frequent occurrence) in the most populated metro area/city in the world and it just hit me!

Dee from Well Worn Heels enjoying the autumn colors in Nikko, Japan in 2025.

Presence isn’t always loud, sometimes it’s just noticing the moment you’re in and realizing you don’t want to be anywhere else.

On Heartbreak & Healing 

My newsletter family saw me write out loud that I hoped for a baecation in 2025. Not only did that not happen, but it was on my 3-day weekend trip to Taiwan in February that I had a moment of realization that the relationship I was in would not work out. I felt my heart break in Taiwan and it was also quite rainy most of the weekend. At least when you cry in the rain, people think it’s just the weather and you can cry in peace. The weather was bleh, the food was great, and I had a really lovely guide. But, Taiwan will always be bittersweet for me. Back then, healing felt too far-fetched. Thanks to time, therapy, and reflection, I’m in a much better place, and honestly surprised at how much can change in a year.

On Turning 40 

Turning 40 taught me that celebration isn’t selfish, it’s sacred. As someone who has very often shied away from the spotlight, I made a conscious choice this year: to set aside time, money, energy, and attention. To celebrate myself, and make room for others to celebrate me.

Dee, a global career woman reflets on spending her 40th birthday in 2025 in Morocco with friends.

In August, I had an intimate birthday dinner in the USA. In September, a new friend in Tokyo threw me a lovely dinner and night out, and I celebrated in Morocco with 9 of my girlfriends. Then I celebrated myself with 2 nights in Paris on my return from Morocco. I shared how much each of these celebrations meant to me here. 

Dee reflects on her two day birthday celebration in Paris for her 40th birthday.

Quality time is my love language, and boy did I receive it. My people gave me my flowers, and poured into me with their words, presence, and time. What a blessing it is to be seen, held, and loved by people you choose, and that choose you in return. 

On The Journey

Australia is country #70 for me, particularly on a Nigerian passport and I canโ€™t help but reflect on my year, but also on my journey. Travel teaches me so much about life in a way that really resonates with my spirit. It teaches me about myself, about my relationships, and about the world. Between heartbreak and healing, work trips and celebrations, flexibility and presence, I traveled to 2 new countries this year, bringing my total to 70. This year, I also brought this blog back after a 4-year hiatusโ€”50,000+ words across 21 articles, proof that the journey is worth documenting.

I don’t have a target number of countries for my lifetime, but it would be fun if my country count always stayed ahead of my age: a personal race I’m winning for now.

I made it to my 20th country in 2016 and by 2018, Kenya was country #50. Seven years later, I made it to #70. A lesson in pace, that life happens in seasons, and a reminder to trust that I am where I need to be.

When I told my Japanese teacher I was going to Sydney, she repeated ‘you are so lucky’ over and over. To say Iโ€™m lucky is to put it mildly. I am incredibly blessed to come from where Iโ€™m from, to carry the passport I carry, and to have stepped foot in the places Iโ€™ve been. 

So when I stare up in wonder at Sydneyโ€™s legendary fireworks as the clock strikes midnight, I fully expect to get emotional and for little Dee who dreamed of being in this exact moment won’t quite believe it’s real.

Here’s to all the journeys and lessons of 2025, and to the wonder that awaits us in 2026.

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4 Comments

  1. This post touched my heart. I enjoyed reading all the reflections from the past year. Travel had deeper meaning for you and it is so wholesome to see. I’m glad I made the 2025 visitors to Tokyo batch! Haha. We all had a lovely dinner with you ๐Ÿ™‚ And oh so happy to read that you have loved living in Japan.

    On country #70 – on a Nigerian passport and on turning 40, Congratulations! The pace, the intention, going back to places with fresh enthusiasm, all the memories, heartbreaks and all – what a beautiful life! Here’s wishing you a richer, fuller, joyful 2026!

    1. Thanks for inspiring me to recap my year in themes and go beyond the chronological way I’ve done so in the past hehe! Writing it touched my soul, I think I ever cried (wow, such a G ๐Ÿ™‚ )but i’m glad it touched you as well. Hehehe yes o our Japan queen you did! I loveee my Japan life though it will soon end. Sigh! Thank you thank you for the congrats and for GETTING it! Amen amen and I wish you the same, and thanks for answering all my many blogging questions.

    1. Thank you for reading, I truly enjoyed looking back on the year and seeing the themes and lessons! Happy New Year and AMEN!!!