I’m 62, I Travel Solo, and AI Has Changed How I Explore the World

By Jennifer Pietrzak-Wahl

At 62, I’m retired, living in Costa Rica, and planning more international adventures than I ever did when I was working full-time. I travel solo, make my own decisions, and have discovered an unexpected travel companion: artificial intelligence.

I’m not talking about asking ChatGPT to generate a generic vacation itinerary and blindly following its recommendations. I use it to research destinations, discover unusual experiences, coordinate transportation, communicate with local providers, and solve the logistical puzzles that come with independent international travel.

After spending much of my professional life working in technology, I’m comfortable experimenting with new tools. But what fascinates me about AI isn’t the technology itself. It’s what the technology makes possible.

I can plan a complicated international trip from my home in Costa Rica, communicate with providers halfway around the world, and make informed decisions without handing control of my vacation to someone else.

Most importantly, I can create trips that reflect what I actually enjoy doing.

Scotland: When AI Became My Travel Logistics Assistant

In September 2026, I traveled solo through Scotland on a trip organized by a professional travel company.

The company arranged my hotels, transportation passes, and excursions, but I discovered that having reservations wasn’t quite the same as having a practical, day-by-day travel plan.

Which train should I catch? How far would I need to walk? Would public transportation be practical, or should I take a taxi? Could I realistically fit everything into the allotted time?

I uploaded my travel documents and confirmations to ChatGPT and asked it to develop a detailed itinerary.

For my journey from Edinburgh to Stirling, ChatGPT recommended a train departure window, considered restrictions on my rail pass, and suggested how to reach my hotel with luggage. It also developed a self-guided walking route through Stirling’s historic Old Town, including estimated distances and time allowances.

But the most valuable assistance came when ChatGPT identified problems in the original arrangements.

Catching a Scheduling Conflict Before Departure

While reviewing excursion confirmations, it flagged a scheduling discrepancy involving two activities that appeared to be booked for the same day: a Jacobite Steam Train excursion and a tour of Glen Affric, Culloden, and Clava Cairns.

I raised the discrepancy with the travel company, which subsequently issued a corrected voucher confirming the Glen Affric excursion for a different day.

A problem that could have become a major inconvenience was resolved before departure.

ChatGPT also noticed that my visits to Stirling Castle and the National Wallace Monument were scheduled unusually close together.

Rather than simply highlighting the tight connection, it recommended leaving the castle earlier, arranging a local taxi, and using the shuttle to reach the monument. It even helped identify a taxi company and a suitable pickup location.

These were specific planning problems with practical solutions.

The experience demonstrated that even when someone else organizes a trip, AI can help turn a collection of reservations into a workable itinerary and identify potential problems before they become problems on the road.

Chile: Designing an Adventure Around My Interests

My next major adventure takes me to Chile in March 2027.

I’ll spend ten days traveling from Santiago into the Colchagua Valley before finishing along the Pacific coast near Viña del Mar and Valparaíso.

Unlike Scotland, this trip is entirely my own creation, with ChatGPT assisting throughout the planning process.

I began by describing what I wanted: horseback riding, spectacular scenery, interesting local experiences, comfortable accommodations, and the freedom to explore independently.

I wasn’t interested in a conventional itinerary filled with museums and obligatory tourist stops. I wanted to ride horses in the Andes, experience Santiago from above using its funicular and cable cars, explore the countryside, and spend time along the coast.

ChatGPT helped research possibilities, compare experiences, and gradually shape an itinerary around those interests.

The process was conversational. I rejected suggestions that didn’t appeal to me, explored alternatives, and refined the schedule as new opportunities emerged.

Discovering Something Unexpected

One of the most interesting additions to my Chile itinerary came from a suggestion I hadn’t anticipated.

While researching activities in the Colchagua Valley, ChatGPT introduced me to Viña Santa Cruz’s Sunset Eno-Astronómico experience.

The excursion combines a cable-car ride into the hills, sunset views, and a visit to an astronomical observatory for guided stargazing.

Astronomy wasn’t on my original list, nor was it something I would necessarily have thought to search for. But once I learned about the experience, I loved the idea. I researched the details, contacted the provider, and made a reservation.

This is one of AI-assisted travel planning’s greatest advantages. Instead of limiting my research to activities I already know exist, I can describe my interests and discover possibilities I might never have considered.

Sometimes the most memorable part of a trip begins with something you didn’t know you wanted to do.

Finding Private Drivers

Chile also presented a transportation challenge.

My itinerary crosses multiple regions, with activities spread across locations that aren’t always convenient to reach by public transportation.

I didn’t want to rent a car, but hiring one private chauffeur for the entire journey seemed unnecessarily expensive.

ChatGPT researched transportation options, identified private drivers serving the areas I planned to visit, and provided contact information so I could reach them directly.

I contacted the drivers, explained my plans, compared proposals, and arranged transportation appropriate to different stages of the trip.

ChatGPT also helped coordinate the logistics, including grouping activities geographically and avoiding unnecessary backtracking.

The result is a transportation plan built around my itinerary rather than an itinerary dictated by transportation limitations.

For me, that’s a significant advantage. I can spend more on the experiences that matter most while making practical decisions about getting from place to place.

Bordeaux: Finding Experiences Beyond the Obvious

In May 2027, I’m heading to France, beginning in Saint-Émilion, continuing through the Médoc countryside, and finishing in Bordeaux.

Once again, I’m using ChatGPT to design an itinerary around my interests rather than someone else’s list of must-see attractions.

I enjoy horseback riding, exploring historic villages, finding distinctive accommodations, and experiencing a destination from different perspectives.

One discovery was Château L’Eperon, where I’ve arranged a horseback riding experience at the estate. ChatGPT helped identify the opportunity, research the experience, and prepare questions for the provider.

Another possibility was a hot-air balloon flight over the countryside near Saint-Émilion.

ChatGPT helped me identify operators, determine where flights were offered, and find contact information.

I recently contacted an operator in French to inquire about a sunrise flight during my stay. The reservation isn’t confirmed yet, but the process illustrates how I use AI to turn an interesting idea into a practical possibility.

I don’t need to know which companies operate balloons in southwestern France before beginning my research. I can describe what I’d like to experience, investigate the possibilities, and decide which ones are worth pursuing.

Knowing When to Book

Another benefit I hadn’t anticipated was using AI to develop a booking strategy.

Some experiences have limited availability and should be reserved months in advance, while others can wait until closer to departure.

For Chile and France, ChatGPT has helped me research booking windows, prioritize difficult-to-replace activities, and organize outstanding reservations.

The balloon flight is a good example.

Because flights depend on suitable weather, we considered not just which day I preferred but which date would leave opportunities to reschedule.

I chose to inquire about a flight early in my Saint-Émilion stay, allowing additional days as alternatives.

I also asked about weather-related refunds before committing. As someone visiting the region for only a few days, an open-ended voucher wouldn’t be particularly useful if the flight couldn’t take place.

AI helps me consider these questions before making commitments rather than discovering complications afterward.

Communicating Across Languages

Living in Costa Rica has given me a new appreciation for the importance of communication when navigating another country.

My Spanish is improving, but I’m far from fluent. In France, I’ll face another language entirely.

ChatGPT helps me prepare messages to hotels, transportation providers, and activity operators. I can explain what I want to communicate in English and request a natural translation appropriate to the country and situation.

Before sending my balloon-flight inquiry, I reviewed an English translation to ensure the French version accurately reflected my questions about availability, pricing, solo participation, and cancellation policies.

This allows me to communicate directly with local businesses without depending entirely on intermediaries.

It doesn’t eliminate language barriers, but it makes them considerably less intimidating.

What I’ve Learned About AI’s Limitations

Of course, ChatGPT isn’t infallible.

It can provide outdated information, misunderstand transportation arrangements, or confidently recommend an activity unavailable on the dates you need.

I’ve encountered suggestions that required correction and arrangements that needed further clarification.

That’s why I treat AI as a research and planning assistant, not the final authority.

For important reservations, pricing, schedules, and cancellation policies, I verify details with the providers. I retain written confirmations and distinguish between activities I’m researching, arrangements I’ve requested, and reservations that are confirmed.

The responsibility for making good decisions still belongs to me.

Seven Ways to Use AI for Your Own Travel Planning

You don’t need a technology background to benefit from AI. The best approach is to treat it like a conversation with a research assistant.

Here are seven practical ways to get started.

1. Describe the trip you actually want. Instead of requesting a generic itinerary, explain your interests, preferences, budget, and what you’d rather avoid. The more specific you are, the more useful the recommendations become.

2. Ask AI to discover unusual experiences. Describe your interests and ask what distinctive activities are available near your destination. Don’t limit yourself to attractions you already know about.

3. Research local transportation providers. Ask AI to identify private drivers, transportation companies, and contact information. Compare arrangements directly with providers.

4. Review your existing reservations. Upload your itinerary and confirmations, then ask AI to identify scheduling conflicts, unrealistic connections, missing information, and possible solutions.

5. Research booking windows. Ask which activities should be reserved early, which can wait, and how cancellation or weather policies might affect your schedule.

6. Communicate with local providers. Use AI to draft inquiries, translate correspondence, and review replies in your own language before making commitments.

7. Maintain a master itinerary. Keep confirmed reservations, transportation plans, payment deadlines, and outstanding questions organized. Periodically review the information for accuracy and retain original confirmations separately.

One additional suggestion: Don’t hesitate to challenge AI’s recommendations.

I’ve found that some of the most useful conversations begin when I respond, “That’s not really what I had in mind. What else have you got?”

A Different Kind of Independence

Retirement has given me the time to explore the world at my own pace. Technology has made that freedom easier to exercise.

At 62, I’m not particularly interested in following someone else’s idea of the perfect vacation. I know what I enjoy, and I’m willing to put in the effort to make those experiences happen.

I want adventures that challenge me a little, introduce me to interesting places and people, and leave room for unexpected discoveries.

AI hasn’t changed my desire to travel. It has changed how confidently I can organize the experiences I want.

It helps me manage complicated details without giving up the independence that makes solo travel so rewarding.

And when I arrive in Chile next March or France next May, I’ll be following an itinerary I’ve created for myself.

That’s the kind of freedom I imagined retirement would bring.

And I’m just getting started.

About the Author

Jennifer Pietrzak-Wahl is a retired technology professional now based in Costa Rica. She writes about independent travel, practical planning, and exploring the world on her own terms. Read more at Jennifer’s blog.