5 Questions You Must Ask Before Traveling Solo (Especially as a Woman)

Have you ever dreamed of taking a trip just for you—no compromises, no negotiating with anyone else’s schedule, and no waiting for the “right” time or travel partner? If you’ve felt that tug to explore on your own terms, you’re not alone. More and more women—whether single, married, divorced, or widowed—are realizing the freedom, clarity, and happiness that comes from solo travel.

But let’s be honest: it’s not near as simple as throwing clothes in a bag and heading out the door. To feel safe, confident, and prepared, there are important questions you must ask yourself before you take that first (or even next) solo trip in today’s world. As a solo traveler for over two decades and your guide to joyful solo travel (Hi, I’m Joy) at TravelWithJoyTV.com, I’m here to help you think through those essential details before you go it alone.

Here are five questions every woman must ask herself before traveling solo—and how the answers will shape a safe and successful journey.

1. How Will You Get To Your Destination?

Whether you're hopping on a plane or hitting the road, your mode of travel matters more than you might think. If you're flying, consider not only ticket prices but also checked bag fees and the costs to park at the airport while you’re gone.  You also want to consider whether your flight times allow for arrivals (& departures) in daylight hours. If you’re driving, is your vehicle in good shape for a long-distance trip? Do you feel comfortable navigating unfamiliar roads solo following directions from your maps app?  What is your plan if an indicator light like check engine came on in your vehicle?  

No matter how you travel there's trade-offs—and part of traveling solo smartly is preparing for those "what ifs." As a travel coach, I help women think through all the different scenarios you could encounter.  If you have little to no solo travel experience, you won’t have thought of everything.  But I have.  

2. How Will You Get Around At Your Destination?

Once you arrive, how will you get around? Will you use your own car (which you’re familiar with) if you've driven there, rent a vehicle, rely on rideshare apps like Uber or Lyft, or other transportation?

This is a huge part of travel safety that’s often overlooked. For example, are you confident using public transportation in a new city? Have you researched parking options, so you don’t go over your budget right away with expensive valet parking at your hotel? What about a backup plan if you lose your purse with your Driver’s License, credit cards, and health insurance card?

These questions aren’t meant to overwhelm—they empower you. Because when you’ve thought through the “how,” you walk through your trip with far more ease and peace of mind.

3. How Long Will You Be Gone?

This question isn’t just about taking the time off from work or arranging childcare—it’s also about timing. The length and timing of your trip affects your budget, energy, and even the crowd sizes you’ll encounter. Want to enjoy a quiet spa weekend or tour wineries without the chaos of weekend traffic? Consider a midweek trip instead of weekend.  For tight budgets, you can do an overnight or a couple nights away vs. a week or longer.  

Short getaways can be just as refreshing as longer escapes, especially if you’re new to solo travel. As your travel coach, I can help you map out a trip that aligns with your comfort level, time availability, and financial goals—all while avoiding overwhelm, fear, and panic.

4. How Will You Decide What to Do on Your Trip?

One of the best parts of solo travel? You get to explore your interests, on your schedule. But a successful trip isn’t totally unplanned—it’s thoughtfully designed.

I always recommend requesting a free Visitor’s Guide for your destination. These guides often include insider tips, events calendars, money-saving coupons, and maps that are pure gold for trip planning. Whether you want to visit local breweries, enjoy shopping, tour historic sites to learn about the area you’re visiting, or simply relax, having a clear plan helps maximize your time and enjoyment.

As your travel guide, I will help you narrow down the best options based on your goals—whether that’s rest, adventure, or a mix of both.

5. How Will You Pay for Your Travels?

With no one to split costs with, it’s essential to plan your finances wisely. Will you charge expenses and pay them off later? Use savings? Take advantage of prepayment discounts?

Solo travelers need to be especially mindful of cancellation policies and hidden fees that can add up fast. You’ll also want to track your spending, plan for meals, and possibly budget for some "splurge" experiences (because you totally deserve it!).

I provide a travel budget tools and real-world advice in my private coaching sessions so you can travel smarter, not just cheaper.

Ready to Go From Fine to Phenomenal?

Traveling solo is one of the most empowering things you’ll ever do—but it doesn’t mean doing it all alone.

That’s where I come in. I don't want your trip to be "just fine."  I want it to be phenomenal!

I have over 20 years of very successful solo travel experience.  My trips are the envy of family and friends who ask how they can solo travel confidently too once they see my pictures and videos and hear about my unique experiences.  I help women just like you navigate all the details, boosting your confidence and planning getaways that fit your lifestyle, budget, and dreams.

Whether it’s your first trip or your fifteenth, I’m here to help you make it safe, stress-free,and absolutely unforgettable.

🎒 Book your private coaching session today here …because you’re not just planning a trip—you’re reclaiming your time, your joy, and your freedom.

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