How to Start Traveling Solo & How It Can Change Your Life

Are you tired of waiting for friends to sync their vacation calendars or fed up with compromising on travel destinations? Well, grab your passport and pack your sense of adventure, because it's time to fly solo! Traveling alone might sound daunting, but it's also exhilarating, liberating, and downright fun. Here's a guide to kickstart your solo travel journey.

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Flying Solo: How to Embark on Your First Solo Travel Adventure

1. Embrace the Awkwardness (It's Part of the Charm)

Let's face it: eating alone at a restaurant can feel like you're wearing a neon sign that says "Table for one, please!" But guess what? No one cares. In fact, dining solo is a rite of passage. Bring a book, practice your people-watching skills, or strike up a conversation with the waiter. Remember, confidence is the best accessory you can wear—besides, you can order dessert without sharing.

When I first started traveling solo I was so nervous about eating alone that for dinner I would order take out and eat in my hotel room. Breakfast was easier for some reason - this can be a great place to start! Eventually I started enjoying getting dressed up and splurging on a fancy dinner for one. I always bring my ipad mini to have entertainment; either a book, movie or social media, depending on my mood. If you decide to go the movie route, just remember to bring your earbuds/headphones so your movie doesn't disturb other diners.

Eating alone at a restaurant can occassionally lead to meeting fun new people - always a perk! Lunch is my go-to meal for meeting new people. I've had the most luck when eating at the bar of a cute café or sitting at a small sidewalk bistro table at a busy trending lunch spot. Just a little food for thought ;)

2. Start Small: Test the Waters

If the idea of jetting off to a foreign country alone makes your palms sweat, start with a weekend getaway nearby. Visit a neighboring city or a quaint town you've always wanted to explore. This "solo travel lite" approach eases you into the experience without the added stress of language barriers or culture shock.

If even a weekend getaway in a neighboring city feels like too much, you can always try a "stay-cation" in your home town. Personally, I LOVE a stay-cation. It can be super fun to be a tourist in your home town - rent a swanky hotel room, go to the spa, do a little shopping (or a lot, it's all good!)... even sign up for Viator or Get Your Guide activities. Why not, right!? You are on vacation afterall, enjoy it with activities that you might consider in another town, city or country.

3. Plan... But Not Too Much

Research your destination, book accommodations, and have a general idea of what you'd like to see. But leave room for spontaneity. Some of the best travel stories begin with, "I didn't plan to, but I ended up..." Overplanning can turn your adventure into a rigid itinerary. Remember, you're the boss of your schedule now—relish that freedom!

Personally I am not a planner and prefer to fly by the proverbial seat of my pants. Earlier this year I had made a plan to meet a friend in Bali for an Erykah Badu concert, which would have been amazing, but less than a week before the concert I discovered a conference in Spain that I really wanted to attend and it was on the same dates as the concert. Luckily my friend was cool with my blowing off the Badu concert at the last minute so I could attend the conference in Spain. Not only did I learn a lot at the conference, but I also made new friends that resulted in my moving to Barcelona - a complete 180 life change for me all because of a spontaneous decision. 

4. Safety First (Not to Sound Like Your Mother, But...)

While spontaneity is encouraged, safety is paramount. Share your itinerary with someone you trust. Keep copies of important documents, stay aware of your surroundings, and trust your gut. And maybe, just maybe, avoid that dimly lit alley that even Google Maps seems hesitant about.

The top two questions I get from people asking about my travels are: 1. what is your favorite destination, and 2. do you feel safe traveling solo (insert here the sometimes said aloud, and always implied "as a woman" - maddening to me!). While safety is definitely important, it is personally not a factor I allow to hamper my travel adventures. I know that I make good decisions (like not ever going down dark alleys), I'm not a big party go-er, so having too much to drink or having my drink spiked is unlikely, and I take reasonable precautions like not carrying large amounts of cash and not being overly flashy with clothes and jewelry. One trick I started doing while traveling in South America is to transfer only a small amount of money into my checking account every morning so if my debit card is lost/stolen it won't break the bank and hinder my enjoyment. For those who prefer to travel with a credit card, this isn't such a big deal.

5. Make Friends with the Locals

One of the perks of solo travel is that you're more approachable. Smile, say hello, and don't be afraid to ask for recommendations. Locals can point you toward hidden gems that aren't in any guidebook. Plus, you might make a new friend—or at least find the best coffee in town.

When I'm traveling I'm walking around town, or riding a scooter, with the biggest smile on my face because I'm always so excited to be exploring someplace new. I no doubt look like the village idiot with the big ass grin, smiling and waving at pretty much everyone I see - it works for me because it's my personality, I think it also makes me very approachable, and I almost always make new friends in every country I visit, so something is working. Next time you're walking down the street just start smiling and you'll be amazed at how receptive and welcoming people are with you.

6. Join Group Activities

Just because you're traveling solo doesn't mean you have to be alone all the time. Join a walking tour, take a cooking class, or participate in a local workshop. It's a fantastic way to meet fellow travelers and maybe pick up a new skill (salsa dancing, anyone?).

I absolutely LOVE taking classes and joining group activities - it's SO much fun and a wonderful opportunity to meet people from around the world. In Rio I signed up for a tour with Viator and spent the afternoon seeing sites and making new friends. In Buenos Aires I went to a Get Your Guide cooking class that led to an asado. (Asado is a traditional Argentinian social event that involves cooking meat over a fire pit and is considered a core part of Argentinian national identity.) These are just two examples of the many, many group activities and classes I have attended around the world.

7. Pack Light (Do You Really Need Those Five Pairs of Shoes?)

Channel your inner minimalist. Lugging around heavy suitcases can dampen your adventurous spirit—not to mention your arms. Stick to the essentials; your back will thank you, and you'll have room for souvenirs. Plus, navigating public transport is infinitely easier when you're not burdened like a pack mule.

As much as possible I try to travel with only a carry-on suitcase. This year I traveled for 6 months in South America, Asia and Europe with only one carry-on suitcase and a personal bag. The clothing options are more limited, but it makes getting around much, much easier than lugging a huge suitcase.

8. Document Your Journey

Keep a journal, start a blog, or make vlogs about your experiences. Not only will this help you process your adventures, but it's also a great way to make your friends back home just a tad jealous. Years from now, you'll appreciate having a record of your courage and the memories you made.

It feels awkward at first to take photos and videos of yourself, trust me, I've been there! However, every time I feel too embarrassed to take photos and videos of myself I regret it later. So do like Nike and just do it, it gets easier and you'll thank yourself later.

9. Get Comfortable with Being Uncomfortable

Traveling solo pushes you out of your comfort zone—and that's precisely where the magic happens. When you venture into the world on your own, you're not just exploring new places; you're exploring new facets of yourself. Every step you take without a familiar companion by your side is a step toward self-discovery and personal growth.

Embrace the unexpected and view challenges as integral parts of the adventure. Perhaps you missed the last bus back to your hostel. Instead of seeing it as a setback, consider it an invitation to experience something new. Maybe it's a sign to explore that lively street market you passed by earlier—the one buzzing with colorful stalls, tantalizing aromas, and the hum of local chatter. You might stumble upon a hidden gem of a café, meet fellow travelers with fascinating stories, or witness a street performance that becomes the highlight of your trip.

These unplanned moments often become the most cherished memories. They teach you resilience, spontaneity, and the art of going with the flow. Navigating through the unexpected not only boosts your confidence but also makes for great stories to tell when you return home. You'll find that some of the best experiences happen when you deviate from the itinerary and let curiosity lead the way.

Stepping outside your comfort zone might feel intimidating at first, but it's in these moments of uncertainty that you truly come alive. You learn to trust your instincts, adapt to new situations, and appreciate the beauty of serendipity. So, the next time a curveball comes your way while traveling solo, smile and say "Yes" to the adventure it presents. After all, the journey is not just about the destination but the exciting twists and turns along the way.

10. Celebrate Your Independence

At the end of the day, solo travel is all about you—it's your journey, your decisions, and your chance to truly prioritize yourself. It's an opportunity to be delightfully selfish in the best possible way, focusing on your own desires and interests without having to accommodate anyone else's schedule or preferences. Want to spend an entire afternoon wandering through a museum that fascinates you? Go for it. Feel like changing your plans on a whim and heading to a different city that caught your eye? The choice is entirely yours. This freedom allows you to go where you want, do what you like, and fully immerse yourself in experiences that resonate with you personally. There's an unparalleled joy in reveling in this autonomy, embracing the spontaneity and self-discovery that come with charting your own course. You've taken the leap into the unknown, stepping out of your comfort zone to explore the world on your own terms, and that's an achievement worth celebrating. Not everyone has the courage to embark on such an adventure, so take pride in your boldness and let it fuel your journey ahead. This is your time to shine, to explore, and to connect with the world—and yourself—in a profoundly meaningful way.

My Life Changing Midlife Solo Travel Journey

... it can work for you too!

In a word, transformative! Before setting out on my midlife adventure in 2023 I was not necessarily miserable, but pretty darn close. Nothing specific was wrong with my life, there was just a general malaise, my once zesty self had become a shell of a person going through the daily motions and counting the hours until I finally got to go to bed for a brief reprieve from the monotonous boredom I was living. Adding insult to injury was the oh-so-joyous perimenopause symptoms (sarcasm!!) that had me sitting in front of the freezer half the day, waking up at night roughly every hour, and moody as fu** most of the time.

One of the best desicions of my life was buying the one way ticket to Bali that started my midlife solo travel adventure. Travel has always been a passion for me, even as a child, so much so I stayed married to a type A, narcissistic and abusive pilot for far too long - hello first class flight benefits any time and anywhere I want, for free! It certainly wasn't for the sex which was horrible at best, and thankfully mostly non-existant, phew.

The first stop of my midlife solo travel adventure was Bali - life for me on this beautiful island was very introverted "doing the work" (apparently that's what healing is called these days). My mornings consisted of drinking coffee while listening to nearby chants and prayers before the sunrise, and making some real estate phone calls (obviously less about "the work" and more about being able to pay for "the work"). After coffee I would walk on the beach for hours, usually listening to books on Audible, like The Surrender Experiment and Build the Life You Want. I also enjoyed frequent road trips on my scooter to Ubud and Uluwatu. Ecstatic dance, cacao ceremonies, fasting, weekly masssage and meditation all became a part of my regular routine.

Read more about Bali here.

I didn't know it at the time, but living in Bali was the start to my personal midlife transformation and new 2nd act as a midlife & travel writer. Since Bali, I have visited around 20 other countries over the course of less than 2 years. You might be asking yourself, "So what? Why do I care about how many countries you have visited and what you have learned?" It matters because you can benefit from the life lessons I have learned throughout my travels. My top 3 lessons from my midlife solo adventures are: 1. love and self acceptance, 2. greater understanding of others, and 3. letting go of attachments. To some extent I should probably also add gratitude, but I am very much still working on this one.

Love and Self Acceptance - Solo travel has a unique way of teaching self-love and self-acceptance. When you’re alone on the road, there’s no one but you to navigate challenges, celebrate wins, and reflect on your own company. You begin to appreciate your strengths as you overcome unexpected obstacles, and you learn to accept your quirks and insecurities without judgment. As you embrace solitude, you become more compassionate with yourself and begin to find joy in simply being who you are. Solo travel becomes a journey to understanding and embracing your own worth.

Greater Understanding of Others - Traveling solo opens the door to seeing the world through a new lens, which naturally fosters greater compassion for others. When you’re out of your comfort zone, navigating foreign cultures, languages, and ways of life, you come face-to-face with the rich diversity of human experience. Witnessing different perspectives firsthand encourages empathy, as you recognize both the beauty and challenges others encounter daily. This journey shifts your worldview, reminding you that everyone has a story, and broadening your ability to connect and appreciate those around you.

Letting Go of Attachments - Solo travel is a powerful way to learn the art of letting go. Away from the comforts and familiar rhythms of home, you discover the value in releasing attachments—whether it's to belongings, routines, or even expectations. With every lost item or unexpected change in plans, you begin to see that these attachments don’t define you or your experience. Instead, the focus shifts to embracing the moment, staying open to what’s unfolding, and allowing the journey itself to be the reward. This newfound freedom teaches resilience, adaptability, and a lightness of being.

In summary, my midlife solo travel journey has been a profound transformation, proving that travel can offer a revitalizing second act to anyone feeling stagnant in midlife. Starting in Bali, I took time to reflect, heal, and grow, discovering new lessons in self-love, compassion, and resilience along the way. Each destination offered unique insights and valuable experiences that reignited my zest for life. My hope is that these lessons inspire others over 40 to take the leap and embrace the life-changing power of solo travel—because this journey can work wonders for you, too!

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xo, ChaCha