Originally published December 13, 2025. Updated September 2026 to reflect my developing retirement funding plan and the practical steps I am taking to test this lifestyle.
Why Solo Travel Belongs in My Retirement Plan
When I first published this article in December 2025, I was 62 and had spent 25 years in higher education administration. I enjoyed my career, but I was also beginning to ask what I wanted my days to look like when work no longer determined where I needed to be. There were places I wanted to see, interests I wanted more time to follow, and parts of my life that had usually fitted around the work calendar.
Longer trips had already given me something to think about. In recent years, I had used extended holiday breaks to spend more time away, and during the pandemic I was able to spend a month in Florida. Those experiences gave me opportunities to stay beyond the first few days of exploring a place. I found that I liked having time to settle in, look around more slowly and sometimes simply be there.
My circumstances also shape the possibilities. I do not have children or a partner, and my trusted companion is my dog, Bobo. That gives me considerable freedom to decide where I go and how long I stay, while also making his comfort and care part of every decision. The retirement I am designing needs to work for the life I actually have.
Solo travel is already familiar to me through both work and personal trips. I enjoy making my own choices, meeting people along the way and moving at a pace that suits me. Building more travel into retirement feels like a continuation of those interests. I want to give myself enough time to explore them more fully, with longer stays around the United States and selected cruises woven into the plan.
Staying Longer in One Place With Bobo
My plan is to stay in one place for at least a month, and sometimes longer. That would give me time to get to know an area without trying to fit every interesting place into a few vacation days. I could visit a museum one day, spend another close to the rental and return to somewhere I enjoyed. That is the appeal of thinking about how slow travel works as everyday life: the place needs to support the whole stay, including the ordinary days between outings.
Bobo gives that ordinary life a useful shape. He needs walks, familiar routines and a comfortable place to settle, and I enjoy sharing those parts of the day with him. Watching him discover a new scent and follow it through the woods or down the street is one of the pleasures of being out together. We can both explore a new neighborhood, although his research will be much closer to the ground than mine.
Traveling this way also changes what I look for in accommodation. I want a place where we can live comfortably for several weeks, prepare meals and get outside without making every walk a major undertaking. A location might look appealing in photographs and still be inconvenient for the way we would spend our days. Giving those practical details attention is part of making a longer stay enjoyable for both of us.
Land travel with Bobo will be the core of this plan. Cruises will have their own place, with his care arranged while I am away. I enjoy cruising, but the time apart and the boarding costs belong in that decision. Much of the retirement life I am looking forward to involves the two of us moving slowly from one place to another and finding a routine wherever we stay.
What My Earlier Moves Taught Me About Home
I have owned a home for most of my adult life. My first was a little bungalow that suited me as a single person. When I moved to another state, I chose a larger house that still fitted the way I lived. Now I am in a townhouse that works for the life I organize around my career, although it can feel confining at times. As I prepare for retirement, I am reconsidering what I want a home to provide and how much of my life I want tied to one property.
Moving is also part of my history. My family moved around until I was in middle school, and as an adult I have lived in three states and two countries. Most of those adult moves were connected to work opportunities. I have had to decide what to take, learn unfamiliar surroundings and establish new routines before. Those experiences are part of why creating another temporary home feels possible to me.
My time in Belize belongs in that story too. When I returned to the United States and began life in New Jersey, Bobo and I spent a couple of months in an extended-stay hotel. That was a practical transition between homes, and it gives me another experience to draw on when I think about living somewhere temporarily. I have already had reasons to consider what I need around me, what I can manage without and how a new space fits daily life.
For retirement, I want more flexibility in how I put those pieces together. A furnished apartment or house could become home for a while, with enough space for Bobo, somewhere comfortable to sit and the basics that make a day run smoothly. I am still working through the decisions involved in leaving an owned home. What is becoming clearer is that I want the place I live to support the life I am choosing, including the possibility of moving on when a stay has run its course.
The Places I Want to See on My Own Terms
One of the pleasures of planning my own itinerary is being able to build it around interests that have been with me for years. I grew up watching the NFL, Major League Baseball, and college football and basketball. I want to visit the Pro Football Hall of Fame and Cooperstown, and I would love to attend some March Madness games. With more time available, I could consider how those experiences fit into a longer stay in the surrounding area.
There are also state and national parks, museums, small towns and large cities around the United States that I have never explored. I want time to research what interests me and follow something beyond its most obvious attraction. A museum might lead me to another place nearby, or a town might turn out to be somewhere I want to spend more time. I like the possibility of leaving enough room in the itinerary for that to happen.
Traveling solo gives me considerable freedom over those choices. I can spend longer in a place that holds my attention, change the pace or decide that I have done enough for the day. I still need to prepare, learn about the area and make sensible arrangements for myself and Bobo. That preparation is part of what gives me confidence to enjoy the independence.
I am also interested in how I describe myself when work takes up less of the conversation. As I have extended some of my trips, I have noticed that I can think of myself as a traveler and explorer as well as an administrator. That feels significant after so many years in a career that has shaped my schedule and identity. Retirement would give those other interests more time and a larger place in my everyday life.
Making Room for Movement, Curiosity and Community
One thing I have noticed during my travels is that arriving somewhere without knowing anyone can draw me into the place. I pay attention, ask questions and look for ways to participate. When I return to familiar places or people, it is easy to fall into familiar patterns. Both experiences have value, but I am looking forward to the different possibilities that come with spending time in a new community.
A longer stay could give those connections time to develop. I would like opportunities to recognize people, return to places I enjoy and perhaps take part in a local activity or a small volunteer commitment. I do not expect every stay to produce lasting friendships. I do want enough time to discover whether there are people and activities I would enjoy seeing again, with room for company as well as time on my own.
The physical setting matters too. Having lived in Central America and the northeastern United States, I have experienced both intense heat and cold winters. For retirement travel, I want to pay closer attention to the seasons and choose places where being outside is comfortable for Bobo and me. Access to walking routes, nature and everyday errands is part of that choice. My aim is to build more movement and curiosity into the day in ways I will actually enjoy and continue.
How I’m Planning to Pay for Retirement and Travel
When I first wrote this article in December 2025, I imagined using remote work, income from the blog and YouTube, and my retirement savings to support the transition while delaying Social Security. My thinking has developed since then. As of September 2026, Social Security is part of my retirement planning, and I am separating the resources I already have from income I am still working to establish.
While I am employed, my salary supports my current life and preparation. My retirement savings are assets I already have, but I still need a plan for how to use them over time. Social Security belongs in the projections as an estimated future benefit, with its timing considered alongside the retirement date. Any contribution from selling my home will depend on the proceeds remaining after the closing expenses and debt are paid. These are different sources of funding, and they need to be accounted for separately.
Part-time work and business income are intended to make a meaningful contribution to the retirement I want. That includes the work I am developing through Solo Travel by Design and YouTube, along with other suitable paid work. Those plans require a different kind of evidence. I need actual work commitments or a record of earnings before treating a projected amount as dependable monthly income. I also need to understand what remains after the expenses of doing the work and taxes.
That gives me practical questions to answer before leaving full-time employment. How much income can I establish? How much time will earning it require? Can I maintain that work while traveling at the pace I want? I need to see what the budget looks like when those earnings are lower than hoped or take longer to develop. Building the income is part of preparing for retirement, alongside deciding where I would like to go.
The cost of slow travel needs the same attention. A furnished monthly rental may cost less per night than a series of hotel stays, but I need to compare actual accommodation for the dates and locations I am considering. Cleaning charges, pet fees and other costs can change the total. Utilities and Wi-Fi may be included, charged separately or subject to limits, so I would confirm those terms for each property.
The rental is only one part of the calculation. I will still need to pay for food, transportation, insurance, healthcare, Bobo’s care and the costs of moving between locations. Any expenses that continue at home also belong in the budget while they remain my responsibility. I have written more about the expenses a slow-travel budget needs to include, because those details will help determine which version of this lifestyle I can sustain. I want the plan to rest on costs and income I can explain and test
Keeping Purpose and Useful Work in Retirement
I expect useful work to remain part of my life after I leave full-time employment. Higher education has given me years of opportunities to contribute, solve problems and help move ideas into practice. I would like to carry some of that experience into work that fits a different schedule, while making more room for travel and interests that have usually occupied the edges of the calendar.
Writing, making videos and developing practical resources give me ways to share what I am learning. I want that work to be useful to someone weighing a travel decision or trying to understand how retirement might fit their own circumstances. I also want it to earn income. Both purposes matter, and the amount of time the work requires will be part of deciding how it fits into the life I am designing.
There may also be room for volunteering, sharing professional experience or taking on a limited project while staying in one place. I do not need to know the exact combination yet, but I want to leave space for those possibilities. People have different reasons for continuing to work or choosing to retire. My task is to understand my own circumstances well enough to make that decision, then build a life with enough purpose, income and flexibility to support it.
Testing the Retirement Life I Want
The next stage is to test-drive a retirement lifestyle while I still have time to adjust the plan. I can use longer trips to learn how I respond to a different pace, and I can test parts of the routine at home. What I spend, how I use my time, how work fits into the day and what keeps Bobo comfortable will all help shape the decisions that follow.
A useful test can start with one part of the proposed life. I might try a planned spending level for a month or give a day the shape I imagine it having after retirement. The point is to pay attention to what happens: what feels comfortable, what costs more than expected and what I would want to change. That gives me something concrete to work with before making a larger commitment.
If you are beginning to shape your own retirement, choose one part of the lifestyle you would like to try. My free checklist helps you identify possible tests involving routines, spending, housing, travel pace and support. You can request it by email through the resources page: Retirement Test-Drive Checklist.
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