How to Choose the Perfect Time for Your First Solo Trip as a Woman

When Do You Want to Solo Travel?

Have you ever sat down and asked yourself: "When do I want to vacation on my own?"
If you’re a woman who’s dreaming of solo travel — not someday, but now — then this question is your first gateway to freedom, fulfillment, and fun. But there are important things you need to consider when choosing the ideal timing of your trip. Read on to learn more!

You Don’t Need to Wait for Others

One of the most freeing aspects of traveling solo is: you don’t have to coordinate your schedule around anyone else. No one else’s calendar dictates your adventure. When you travel with friends or family, there’s always the juggling of everyone’s commitments, moods, budgets, and desires. Solo means you schedule based on you.

So ask:

• When in the year will you best be able to step away from work or volunteering?
• When are your personal commitments lighter?
• What time of year in your home region AND destination will serve you best? For example, I don't love to travel in the winter living in the Midwest. I don't want to ice-skate potentially to the airport in freezing rain or snow. Also I want to minimize the chance that my first departing flight will be delayed or cancelled with wintry weather. So I tend to hibernate somewhat in Winter. I daydream about where I want to go. I order my visitor's guides to evaluate the different options, and plan with my hot chocolate by the fire. I'm also working and saving a bit from paychecks to fund the fun so I don't come home to a huge credit card bill!

Consider Work, Weather & Your Energy

If you’re working full time, chances are there are busier‑and‑slower seasons. Maybe you know which weeks are quieter. Maybe the end or first of the month is hard to get away? Carving out the right time for your solo trip means choosing when stepping away won’t create unnecessary stress.

Then there’s the weather part:

• If you live in a region with heavy winters or unpredictable travel disruptions (icy roads, flight delays, convoluted airport logistics), might a different season serve you better? If you're trying to fly out of the snowy tundra to somewhere tropical, be prepared for disappointment if your flight is cancelled and you can't get to your location. Also driving in bad weather just tends to add stress, and that's not the solo trip experience you want!
• At your destination — are you choosing peak season (beautiful, popular, and so maybe super expensive and crowded) or just after peak (almost the same vibe, fewer crowds, better prices)?

For instance: I once travelled to Wisconsin Dells arriving on the Monday of Labor Day — cruising the Dells, relaxing at Sundara, exploring the downtown shops — when many families were checking out to travel home for the start of the school year. Same climate, fewer crowds, and lower cost. That’s really smart solo travel.

Align with Your Personal Significance

Here’s where the deeper “why” comes in as to why you're traveling when you choose: when you travel solo, you have the space for reflection, significance, and personal rewards. I speak from extensive experience. After facing a stage 4 cancer diagnosis in my 30s and the years of hard-hitting chemotherapy that followed, I realized I did not want regrets. I realized that I would travel sooner rather than putting it off — and not wait until “someday.”
So I picked dates that mattered to me — times that others might overlook — to mark, honor, and celebrate how far I’d come. Solo travel became my tribute to myself. I try to travel on the date I was diagnosed with cancer (It's helped turn around the worst day of my entire life.), for National Cancer Survivors Day (Yes, that's a thing! It's in early June.), and around the date I found out my cancer was in remission.

You can do the same. Choose travel dates that matter to you— and then build a solo plan that honors your journey: your resilience, your purpose, your dreams.

The Step‑by‑Step: How to Make Solo Travel Happen

1. Pick your timeframe.
   Look at your calendar. What days can you realistically step away from work, family, and commitments? Do you have a “shoulder week” (just before or after a popular trip time)? Block it out.
2. Choose a destination that feels familiar — but solo.
   For your first solo trip, I highly recommend picking somewhere you’ve at least visited before with friends or family. The familiarity gives you comfort; the solo     element gives you freedom. You know the main routes, and you know how to navigate the area. But this time it’s all about you.
3. Consider your mode of travel.
   Flying can be rather stressful: checked bags (fees, weight limits), airport hassles (flight delays and cancellations), rental cars in the dark (How do I work the rear windshield wipers??), and unfamiliar roads. Instead, if you’re within driving distance of a desired destination, drive yourself. You know your vehicle, you control the schedule, you set the pace. This can reduce anxiety greatly, boost confidence, and make the journey itself part of the fun as you set the radio to what you want to listen to (singing along loudly is encouraged).
4. Look at weather & crowd patterns.
   Avoid the stress of extreme weather or being flooded by crowds. Consider going just after peak season, when prices drop and you still get a great experience (Make sure attractions haven't closed yet for "the season."). Less waiting, fewer people, more you‑time.
5. Make the date meaningful.
   Tie the trip to something personal — your birthday, a milestone, a symbolic date that holds meaning for you. You’re not just checking off a trip, you’re celebrating you. If you weren't recognized on Mother's Day, maybe you do an overnight or weekend away this next year and disappear. Absence could make the hearts that take your constant presence for granted grow fonder?  
6. Plan solo‑friendly fun.
   You want freedom. So tailor the itinerary your way. Want sunrises alone with a steaming hot beverage of your choice, late check‑out, afternoon naps, multiple course dinners for one (Yes, I will get dessert finally before the others eat it all up!), and random spontaneous stops pulling over to explore what looks intriguing to you? Do it. Your schedule is yours. No compromises. And no one is complaining about not wanting to do it!  
7. Build confidence around solo safety & budgeting.
   Yes, you’re solo. But you’re not helpless. Research safe neighborhoods, book accommodations with good peer reviews, know your route ahead, and think through some "What ifs?" so you can plan for them just in case. And remember: traveling solo doesn’t have to break your budget. Think about what's important to you and spend on that. If you're not a foodie, maybe you won't spend as much on your meals. You can put more towards your experiences or shopping.

Why This Matters — For You

You deserve more than “just getting by.” You deserve your own adventures. Now is the time when you take your own seat at the table of life. Solo travel becomes a statement: I value myself. I invest in myself. I choose fun, freedom, and fulfillment for me.

If you’ve been watching others’ social media travel posts wondering, “Why not me?”, then this is your cue. You can turn that “why not” into “why yes.”

Ready to Take the Next Step?

If the thought of solo travel excites you but you have additional questions, I’d love to help.
📍Book a private coaching session with me and we’ll talk through your dreams, your fears, your calendar, and build a step‑by‑step plan that’s customized for you to make the most of your limited vacation days and budget.
🎤And if you attend a women’s conference, church group, workplace retreat, or visit a spa or resort — suggest me to speak at these events sharing solo travel tips and building your confidence to help create the life you can't stop dreaming about.

You don’t have to wait for someone else to say yes to traveling at that time you want to vacation. You can say yes to yourself today.

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