You may have figured out that I love to travel—not just vacation, but extended stays in one place for a month or longer. My current career lets me get away for a few weeks each year, but not in those longer, slower chunks that really feel like living. And when I do retire, most of my time won’t be spent hopping from place to place overseas—it’ll be slow travel around the USA, with three or four cruises sprinkled in each year.

As I’ve gotten older, it’s occurred to me that I can reinvent myself (again) and design a semi-retirement that supports what I love—without sacrificing a quality of life that makes travel sustainable. So as I move toward that day, I’m building this retirement on purpose. No chaos. No “we’ll figure it out later.”

I genuinely enjoy trip planning—making lists, mapping out the best way to get there, choosing where to stay, and yes, deciding what I want to eat. But with slow travel, the planning can’t stop at the fun parts. You have to account for the boring stuff too: the bills that keep running, the logistics that don’t disappear, and the real costs that show up around the edges. And then there’s Bobo—my not-so-little reality check—because his care has to be part of the plan, not an afterthought.

I’ve learned a lot over the past few years about my travel patterns and what I actually need to feel comfortable traveling solo. In this post, I’m sharing my top five rules—simple, repeatable, and built for real-life solo travel planning.

Rule 1: Baseline First. Always.

This is the rule that keeps everything else from turning into wishful thinking.

Before I price a cruise, before I browse Airbnbs, before I even start a packing list, I make sure I know what my life costs me in a normal month. Not my “ideal” month. My real month. It is important to remind myself that bills don’t stop just because I’m not in my own kitchen.

For me, baseline includes the things that keep humming in the background whether I’m home, on the road, or at sea: insurance, phone, subscriptions, pet expenses, and all the little life-admin costs that are easy to forget until they show up on a statement.

Here’s why this rule matters so much: if baseline isn’t covered, travel becomes stress. Even a “great deal” stops feeling great when you’re trying to make the rest of life work around it.

I’ve learned I don’t need a perfect budget. I need one clean separation:

• what life costs me anyway, and
• what travel adds on top.

That one shift takes the emotion out of the decision.

---

Rule 2: I Budget the Entire Month, Not Just the Trip.

A trip price is not a month cost. And that difference is where a lot of people get blindsided.

It’s easy to look at a cruise fare and think, Oh, that’s doable. But a cruise month isn’t just the cruise fare. It’s everything that wraps around it—the stuff that doesn’t make the brochure.

For cruise months, the “extra” costs that matter most are often the predictable ones:

• gratuities / tips – most cruise lines put that on top of the fare
• flights or repositioning travel to the port
• one night pre- or post-cruise – arriving the day before eases stress and allows for calm boarding
• transportation: home → airport → hotel → port
• and yes, dog boarding (which is real money, not “misc.”)

For slow travel months (which will be most of my retirement rhythm around the U.S.), the monthly cost looks different, but the principle is the same. The rental is only part of the story.

You also have:

• pet fees (and sometimes deposits)
• parking and laundry – though I generally opt for all inclusives
• groceries and supplies (which don’t magically disappear)
• local transportation
• and the occasional “transition month” where moving between places adds a few expensive days

This is why I like rules. Rules keep me from talking myself into things that only work on paper if I ignore the fine print.

If you’re planning extended travel, here’s the practical takeaway: pick one month—just one—and calculate what it costs when you include the whole month, not just the fun part. That single exercise will likely surprise you and tell you more than a hundred inspirational Pinterest quotes ever will.

A quick cruise-month reality check (5 minutes)

Here’s the way I keep myself honest when I’m pricing a cruise. I total my baseline first—mortgage, car, utilities, cell phone/internet, HOA, gym, insurance averaged monthly, travel insurance, credit cards/loans, and Bobo. Then I add the cruise layer: fare + gratuities, transportation to the port, one hotel night before/after if I want calm boarding, transfers, and dog boarding.
Once you see your true month cost on paper, the decision gets calmer. You’re not guessing—you’re choosing.

The 10-minute exercise

• Write down your baseline categories.
• Estimate your baseline total for one month (best honest estimate).
• Pick a month type: cruise month or monthly rental month.
• Estimate the travel layer (for cruises: gratuities, transportation, hotel night, transfers, boarding).
• Add baseline + travel layer.

---

Rule 3: I Build in a Buffer (Because Life Happens)

I’m a planner, and I still get surprised. So, I’ve stopped acting like I can predict every cost perfectly. My goals are to stay within a range and that range includes a buffer. This isn’t pessimistic, it is protection if you are planning a retirement without the $1M safety net.

When I’m planning a month of slow travel or a cruise month, I add a cushion—because there’s always something that changes:

• a price change
• a last-minute Uber
• a pet fee I didn’t expect
• an extra hotel night before or after a cruise because a flight time makes no sense
• a “small” expense that becomes five small expenses

My simple rule:

• If I’m feeling confident about my estimates, I add 10% to my travel layer.
• If I’m feeling even slightly optimistic, I add 15%.

The buffer is what keeps me from resenting the trip later. It’s the difference between “I can handle this” and “Why did I do this to myself?”

---

Rule 4: I Keep the Plan Simple Enough to Use

I love details. I love spreadsheets. I love a good list. But I’ve also learned that if a plan is too complicated, I won’t use it consistently—and inconsistent planning is where things start slipping.

So I aim for simple enough to repeat.

That means:

• a baseline with clear categories (not 47 micro-categories)
• a travel layer that captures the big costs and the usual suspects
• a total that tells me the truth without requiring a finance degree

I’m not trying to build a perfect budget. I’m trying to build a sustainable lifestyle.

If you’ve ever created a beautiful plan… and then quietly stopped updating it because it was too much, you already understand what I mean.

I’ve learned I’m more consistent when the system is easy to repeat—so I keep my categories simple and my process the same each time. Not because budgeting is exciting—but because making it easy to repeat is what makes it work.

---

Rule 5: I Run Small Tests Before I Go “All In”

This is where the “retirement isn’t a leap — it’s a series of tests” mindset shows up in real life. Instead of planning the whole future at once, I run small, practical tests that teach me what I actually need.

Examples of tests that matter:

• Calculate one “true month cost” (baseline + travel layer) and see how it feels.
• Do a one-month stay somewhere within driving distance and learn what you underestimate.
• Plan a cruise month and include all the real costs around it—flights, boarding, tips, transfers.
• Track one month of actual spending and compare it to what you thought you spent.

Even if I can’t be away for a full month, a two or three week stay away from my home base will provide valuable information. Every test gives you data. And data gives you confidence.

I don’t need certainty about every year of retirement right now. I need a system that helps me make good decisions and adjust as I go.

That’s how you build a plan that lasts.

---

If you’re designing a retirement that includes extended travel—especially solo travel—the planning has to hold up in real life. Not just in a dreamy version of life where bills pause and logistics magically handle themselves.

These five rules are how I keep the dream realistic and the planning calm. They help me choose trips I can enjoy without stress, and they keep me focused on the kind of retirement I actually want: slow travel around the U.S. most of the time, with a few cruises each year sprinkled in—planned on purpose.

And this is the line I come back to when I’m tempted to ignore the boring parts:

If I can’t afford my life and my travel on paper, I don’t get to call it a plan.

I have a free Baseline Budget Template (starter version) if you want a simple way to get your baseline number clear. And if you’re comfortable sharing, I’d love to know:

What’s the one “boring” cost you refuse to ignore when you travel?

---

Want the spreadsheet I use? Get the Two-Layer Budget Template here.