How to Mentally Prepare for a Long Solo Trip in Retirement
Travelling solo for six weeks or more sounds incredible — but it can also feel overwhelming. From homesickness to navigating family reactions, the mental side of long travel often matters more than what you pack.
I’ve built a set of rituals and systems that keep me steady on the road. Here’s how I prepare my mindset before a big journey, with real stories from my own travels.
Picture Life, Not Just Travel
When preparing for a long trip, don’t just imagine the sights you’ll tick off — picture your daily life.
Morning coffee in a café.
Wandering through a local market.
Evenings by the river.
This shift makes travel feel less abstract and more like life abroad.
Assumptions Behind the Budgets
First Days Matter
The first few days can feel tricky without a plan. I keep it simple.
I’m a self-confessed coffee princess, so I always pin a café on Google Maps before I arrive. On my first morning, I head straight there. It gives me a destination, confidence, and a sense that I’m already making the most of the day.
Not a coffee person? Choose a juice bar, yoga studio, morning market, or riverside walk. One small, walkable anchor is enough to make you feel grounded.
Anchor Expectations
A long trip isn’t about doing everything. I give myself permission to choose anchor locations — staying at least a week in each place.
That way, I can:
Find favourite spots.
Relax into the rhythm.
Let go of the pressure to “see it all.”
First-Morning Courage
In the Philippines, I once stayed at a hotel that recommended a surf coach. It was nerve-wracking — disappearing into the wilderness on the back of his motorbike — but that introduction turned into a trusted connection I’ve kept for years.
For women travelling solo, I’d say this is non-negotiable: start with strong local recommendations. It turns nerves into confidence.
Little Systems That Keep Me Grounded
Pick somewhere walkable each day to give yourself direction.
Book only your first two nights of accommodation to stay flexible.
Keep fewer, deeper calls with loved ones to avoid constant longing.
Lock in hobby highlights (e.g., improv in Chiang Mai on Tuesdays), then let the rest flow.
Research once you’ve arrived — often from a café — instead of constantly planning ahead.
These little systems help you stay present and safe.
Navigating Relationships & Reactions
Not everyone will understand. My dad once asked: “Are you really going for that long?”
The truth is, yes — eight weeks was the minimum that makes sense for me. Courage in conviction is what steadies me. It’s not their story, it’s mine.
When Homesickness Hits
In Nicaragua, I stayed in a homestay that felt unsafe. I locked my door, took a sleeping tablet, and just got through the night. The next day, another surfer joined us, and the energy shifted completely.
Sometimes, you just have to get through the day. For me, tools that help include:
A good book.
A calming playlist.
Booking a structured activity to reset my mood.
Finding Connection
If I feel lonely, I book a walking tour or a food tour. They sound touristy, but they’re the best way to:
Meet locals and hear their stories.
Get recommendations you’ll use again.
Chat with other travellers.
Closing Reflection
Preparing mentally for a long solo trip isn’t about controlling every detail. It’s about clarity:
Picture life, not just travel.
Start small with rituals.
Build little systems that steady you.
Expect both connection and wobbles.
Some people back home may not understand. And that’s okay. Because solo travel at this stage of life isn’t a breakdown — it’s a breakthrough.
Final Thoughts
If you’re planning a long trip in retirement, start with your mindset. The logistics will follow.
What’s your first-day ritual when you arrive somewhere new? Share it in the comments — your idea might be exactly what helps someone else feel at home abroad.