10 Questions to Ask Yourself Before Booking Your Next Solo Adventure

“Are you really going by yourself?” My colleague’s tone hovered somewhere between disbelief, concern, and admiration.

“Yes. Why not?” I replied with a grin. “That’s the beauty of it — I’ve organised everything, and I get to do what I want, when I want. “

This conversation took place many years ago, but it highlights the fact that people can have vastly different approaches to travel. While my colleague valued the predictability and (perceived greater) safety of group tours and family beach holidays, I thrive on the freedom and thrill of solo adventures. Both approaches are equally valid — there’s no one-size-fits-all approach to exploring the world.

For many, solo travel feels like an intimidating leap into the unknown — and in some ways, it is. But that’s also where the magic lies. With the right preparation and mindset, travelling solo can become one of the most liberating and rewarding experiences of your life. It’s a chance to step outside your comfort zone, find your unique rhythm, and explore the world entirely on your terms.

Of course, solo travel doesn’t come without its challenges. On my solo trips, moments of self-doubt and loneliness have crept into the day from time to time. And there are times when you need to figure things out on your own. Yet, these very challenges often turn into the stories you cherish most — reminders of your resilience and adaptability, as well as experiences that you’ll eventually learn to laugh about, even if it doesn’t seem amusing at the time. (You will!)

Whether you’re contemplating your first solo trip or dusting off the passport for another adventure, thoughtful planning and a little self-reflection will be your best allies in crafting a meaningful experience.

I’ve prepared these ten questions based on my experience — use them to help you align your journey to your personal preferences and needs, ensuring your next solo adventure is not only memorable but also perfectly tailored to you.

10 Questions to Ask Yourself Before Booking Your Next Solo Adventure

Q. 1 — Why do I want to travel solo?

Before diving into the logistics of your journey, ask yourself: “Why do I want to travel solo?” Your motivations, both practical and personal, will shape not only where you go, but also how you experience your trip.

Solo travel doesn’t mean you have to be alone all the time. For example, you can combine travel styles within one trip — take a few short day tours, embark on a 2-day ferry crossing, explore cities on foot, all while still travelling independently. Later, we’ll explore different solo travel styles to find what suits you best.

Over the years, I’ve travelled solo, with friends, and in groups. Here’s what I’ve learned about the pros and cons of solo travel:

Pros of Solo Travel

• Freedom: Solo travel offers the ultimate luxury: time for yourself. Whether exploring a city on foot, joining a group tour, or relaxing in a café with a book, you can plan your days exactly as you like.
• Flexibility: Changing plans on a whim is easy when you’re travelling alone. For example, you can switch activities if the weather changes without needing to consult others.
• No guilt: You can do precisely what you want, at your own pace, without worrying about pleasing anyone else.
• Convenience: Solo travel lets you schedule trips at your convenience, without waiting for others to coordinate their availability or budgets.
• No expectations: Visiting places where you don’t know anyone can be liberating. You can wander, engage in activities, eat when, where, and what you please, and even take an afternoon nap — all on your terms.

Cons of Solo Travel

• Accommodation costs: Solo travellers usually bear the full cost of accommodation, often including the dreaded ‘single supplement’. Thankfully, many places are beginning to offer budget-friendly options for solo travellers, so shop around. Finally, singles are beginning to be valued.
• Limited conversation: Sometimes, you miss having someone familiar to talk to. While meeting strangers can lead to fascinating conversations, calling home is a great way to stay connected.
• Loneliness: Feeling lonely from time to time is natural, but there are effective strategies to overcome it. For example, you can read a book or watch a movie (remember to download movies to your tablet or computer before leaving home). You could also visit a café or bar and strike up conversations with people there, book a walking tour or a small-group day tour, or engage in sports or exercise — I love swimming, in particular, and it’s great for boosting my mood. Additionally, calling home for a chat can provide comfort. Another idea is to buy postcards, write something witty on them, and send them to your friends. Fundamentally, I found that doing something will get me out of a funk most times.

There’s a unique empowerment in navigating the world on your own. Solo travel, whether it’s your first time or your hundredth, builds confidence and proves your ability to adapt and thrive independently.

Ultimately, there’s no right or wrong reason to travel solo. Whether driven by adventure, necessity, or self-discovery, solo travel is a deeply personal experience — and the first step is embracing your reasons for taking the leap.

Q. 2 — What is my primary goal for this trip?

Every journey has a purpose, and understanding what you want from your trip can make it truly memorable and meaningful. For years, I dreamed of visiting Finland to explore my family heritage, and Iceland because it’s, well…cool! I just wanted to go there.

When planning, I considered where and why I wanted to go, desired activities, and the time needed for each.

Whether you’re seeking relaxation, adventure, self-discovery, or connection, clarifying your main goal provides focus and shapes your experience.

Clarifying your intentions

Identifying your primary objective ensures your trip gives you the experience you want:

• Adventure: You might want to do active things like hiking the Scottish Highlands, exploring Japan’s vibrant cities on public transport, or embarking on a train journey through South America.
• Relaxation: Perhaps you feel drawn to tranquil destinations such as spa towns, seaside retreats, or countryside getaways. A week in Provence or a secluded retreat in Bali might be perfect.
• Self-discovery: Choose places that interest you, like historic sites, pilgrimage routes, or meditative landscapes. A solo walk along Spain’s Camino de Santiago or a retreat in New Zealand’s fjordlands might be just the ticket.

Balancing multiple goals

Solo trips can combine various objectives, such as adventure, relaxation, cultural immersion, and personal growth. Mornings might be spent hiking or exploring, afternoons engaging with locals through group tours or classes, and evenings unwinding with a good book.

Honouring the purpose of your journey

Travel is about more than ticking destinations off your bucket list. It’s a chance to honour what matters most in your life right now. By defining your trip’s purpose, you transform it into a meaningful adventure.

Ask yourself: “What do I truly hope to gain from this journey?” Let the answer guide you toward experiences that will ensure your trip is both enjoyable and rewarding.

Q. 3 — Am I too old to travel?

I’ve seen comments from people in their 20s and 30s asking “Am I too old?” [really??]. I’m seventy, and don’t consider myself ‘old’. My body might be past its prime, but (fortunately), I’m still healthy and fit enough to do most things. Sure, I might need to pace myself a bit more than in the past, I get the odd niggle in my joints, and travel insurance is more pricey, but never would I consider myself too old to travel.

The notion of being ‘too old to travel’ often stems from societal expectations or personal doubts — but these can be challenged and overcome, even if you live with a disability — there are travel options for you, too.

Redefining travel at any age

• The freedom of later-life travel: With age often comes greater freedom — fewer work commitments, grown children, and for some, the ability, financially, to prioritise personal passions. This is the perfect time to embark on the adventures you’ve always dreamed of.
• A different pace, not a lesser experience: Travel doesn’t have to mean climbing Mount Kilimanjaro or backpacking through Southeast Asia (though it could if that’s your dream!). It’s about finding the style of travel that suits your energy and interests.
• Physical fitness and health concerns: One of the biggest worries about travelling as we age is physical capability. But today’s travel industry offers a wealth of options to accommodate all levels of fitness and (dis)ability. There’s something for everyone, and even some ‘adventure’ trips need not preclude you from taking part. I remember when I was in my late forties, I went on a backpacking tour around Bali. On this tour, there was a 74-year-old gentleman who used a walking stick. He understood that he couldn’t handle the mountain biking portions of the trip, so he chose to ride in the minivan when needed. Nevertheless, he fully engaged in all other aspects of the journey. His participation was truly inspiring, and the younger members of the group looked up to and respected him.
• Feeling self-conscious: Some older travellers worry about standing out, especially when travelling solo. However, the reality is that people often admire those who pursue their passions, regardless of age. Rather than trying to dress or act like someone in their twenties, which can make you stand out more, embrace your own style and confidence. Remember, confidence grows with experience, and as you continue to travel, you’ll become more comfortable in your own skin.
• Navigating technology: Technology can feel daunting, but it’s an incredible tool for modern travellers. Apps for navigation, translation, and trip planning make travel easier and safer than ever. If you’re not confident, take time to learn — ask a tech-savvy friend to help, or many libraries and community centres offer tutorials on using smartphones and travel apps.

Travelling solo doesn’t mean you’re alone; it means you’re brave enough to explore on your own terms.

Ultimately, solo travel isn’t bound by age; it’s about mindset, preparation, and confidence. Travelling solo in midlife and beyond often comes with unique advantages, such as life experience, a clearer sense of priorities, and often, more flexibility in how you spend your time.

Q. 4 — How do I feel about being ‘out of my comfort zone’?

Solo travel often means stepping into the unknown and embracing new experiences. Assessing your comfort level with unfamiliar foods, languages, public transport, and environments is key to shaping your travel experience.

Assessing your adventure threshold

Ask yourself: Do you thrive on spontaneity, or do you prefer a structured itinerary? A mix of structure and free time is an ideal compromise for many of us. These days, my ‘adventures’ are more modest than in the past, but it doesn’t make them any less adventurous. It’s simply that I prefer a little comfort when I travel these days!

Understanding your limits helps you plan an adventurous trip without it being overwhelming.

A personal story: Tokyo Metro Triumph!

I’ll never forget navigating the Tokyo Metro for the first time. The map looked like an intricate web of coloured spaghetti, and the myriad array of ticket types was confusing. But I’m someone who likes to thoroughly research before leaving home — forewarned is forearmed — so the experience was less overwhelming than it might have been. Even so, trying to figure out which ticket to buy and which line to take took a while.

But by asking for help when necessary (Google Translate to the rescue!), referring to the magic that is Google Maps, exercising patience, and taking it one step at a time, I made it to my destination without mishap. The next day, it was easier. By the end of my stay, I was navigating the Metro (almost) like a pro. The initial challenge and subsequent triumph become one of the most rewarding aspects of my trip to Japan!

Striking a balance

If you’re unsure about embracing uncertainty, ease into it with these steps:

• Research, plan, or organise one activity in advance for your first day in a new place so you hit the ground running.
• Join a small group tour, such as a city walk or a day excursion.
• Start with short, direct trips on public transport to build confidence.
• Don’t hesitate to ask for help. Most locals are happy to assist, and Google Translate can bridge language gaps.

Potential rewards of embracing the unknown

Stepping out of your comfort zone can create unforgettable memories and a sense of accomplishment. Even small wins boost your confidence for future adventures. It’s not about avoiding challenges but finding a balance that lets you enjoy the journey while feeling prepared and capable.

Q. 5 — What is my budget? And how flexible can it be?

Start with the essentials

Knowing your budget is vital. Begin by researching destination costs and balancing them with what you’re willing and able to spend. Having a realistic idea of expenses helps avoid nasty surprises.

When I planned my trip to Iceland, I quickly realised how expensive it (and most Nordic countries) was. Accommodation, meals, transport, and activities added up, so I carefully planned my stay around what I wanted to do and what I could realistically afford. In contrast, Japan proved more budget-friendly, with lower costs (at the time) and a favourable exchange rate stretching my money further.

Flexibility is key

After estimating your budget, consider areas where you can trim costs, like dining at local markets. I would rather skip the pricey restaurant in favour of a thrilling excursion. It’s a reality that the cost of flights and accommodation, ground transport, activities and day trips, food, phone and internet, and travel insurance add up quickly.

Adaptability, and spending a few hours researching your destination and the available activities and accommodation costs ensures your stay will be everything you want. Remember, the most valuable moments often don’t come with a hefty price tag.

Q. 6 — Finding your ideal travel style: What suits you best?

Solo travel offers the freedom to set your own pace and choose your travel style, whether you prefer excitement, relaxation, or a mix of both.

Group and guided tours

If you enjoy activity and want the security of structured plans, guided tours — whether in a group or customisable solo format — are a great option. You can choose between coach tours with frequent travel or self-drive tours that allow for more flexibility.

Resorts and cruises

If you need time to unwind and recharge, resorts and cruises provide a leisurely pace with everything arranged for you. Spend your days lounging by the pool, taking part in spa activities, or enjoy the onboard entertainment. However, cruises can involve additional expenses that might catch you by surprise (e.g. shore excursions, tips, single supplements, onboard currency, etc.), so consider your budget before setting sail.

True solo travel for independent explorers

True solo travel offers the ultimate freedom, with no fixed itinerary to follow, other than the one you decide! This is the choice for the independent wanderer who enjoys choosing where to go, what to see and do, and how long to stay. It’s perfect if you want flexibility and freedom to explore at your own pace.

Volunteering and conservation trips

These trips add purpose to your travels, whether by contributing to conservation or teaching abroad, while also connecting you with like-minded people.

Mix and match for your perfect journey

Travel isn’t a one-size-fits-all experience. Take time to reflect on what you need to get the most out of your adventure, and don’t be afraid to mix styles and adjust the pace as you go. Your journey is a reflection of your own unique travel spirit. 

Q. 7 — What type of accommodation do I prefer?

When travelling solo, your accommodation isn’t just a place to sleep — it shapes your comfort, safety, and overall experience. Choosing a stay that aligns with your preferences can make a big difference.

Assessing comfort and safety

Do you prefer the security and convenience of a hotel with 24-hour staff? Or would you prefer the cosy charm of a B&B and a friendly, local host? If independence is key, a vacation rental may be your ideal choice, offering privacy and flexibility.

For some, the idea of staying in a bustling hostel, where you can meet fellow travellers and exchange stories, is an exciting social opportunity. Others might long for complete solitude and a peaceful retreat. The choice is yours. 

Exploring unique accommodation

Imagine staying in a historic monastery, a fairy-tale castle, or glamping under the stars. Or perhaps the idea of sleeping in a yurt, a traditional Mongolian structure, stirs your sense of wanderlust? These unique types of accommodation can immerse you in local culture and create memorable stories.

Matching accommodation to your trip

Your trip type often dictates your accommodation. Backpackers might gravitate toward guesthouses or pilgrim hostels, while city visitors may prefer centrally located hotels or short-term rentals for easy access to attractions. Cruises offer you a ‘home away from home’ where you only have to unpack once at the start of your journey.

Practical considerations

If you’ll be relying on public transport, staying near stations or bus terminals can be a real lifesaver, especially if you’re arriving late or need to catch an early train or flight. Consider how much time you’ll spend in your accommodation: basic options offered by hotels and B&Bs may suffice for active days, while amenities like a kitchen or laundry might enhance longer stays.

Evolving preferences

My preferences have evolved over the years. I’ve stayed in everything from tents under the stars to (moderately) luxurious hotels. These days, I favour mid-range hotels that balance comfort, convenience, and budget. However, I wouldn’t shy away from a pilgrim hostel if I ever walk the Camino de Santiago — it’s all part of the adventure.

The right accommodation can make your solo travel more enjoyable, offering a secure and restful base for each place you visit. Take time to research and choose wisely for a comfortable and memorable trip.

Q. 8 — What activities or experiences am I looking for?

Solo travel lets you indulge your passions without compromise, whether they’re lifelong dreams or newfound curiosities. You’re in control, free to shape a trip that excites and inspires you.

Embrace your interests

What excites you most about your destination? Whether it’s savouring street food at a night market in Taiwan, exploring ancient ruins in Scotland, or attending a live concert in Seoul, the possibilities are endless. Consider a painting workshop in Tuscany, wandering under the cherry blossom in Kyoto, or dog sledding in the Arctic — the possibilities are endless.

When advance bookings are advisable

For high-demand or seasonal activities, planning ahead is often essential. Reserving tickets ensures you won’t miss out on bucket-list experiences like an evening at the Paris Opera House or a hot air balloon ride. I nearly missed visiting Tokyo’s teamLab Planets because I didn’t learn of its existence until arriving in Tokyo. Although advance bookings were a necessity, I was fortunate to secure a ticket for my last afternoon in Tokyo.

Leave room for spontaneity

While planning is helpful, some of the best memories come from unplanned moments: stumbling upon a street festival, joining an impromptu local tour, or relaxing at a hidden café. A balance of planned activities and free time keeps your trip exciting.

Tailoring activities to your needs

Solo travellers often enjoy activities like group tours or workshops, which blend social interaction with independence. If mobility or accessibility is a concern, look for options that accommodate your needs, ensuring every activity feels welcoming and safe.

Create your dream itinerary

Start with a list of “must-dos”, prioritise them, and leave space for exploration and relaxation. Your thoughtfully chosen experiences will make your trip unforgettable.

Q. 9 — How will I stay safe and connected?

When travelling solo, safety and staying connected go hand in hand. A little preparation and awareness can help you feel secure and enjoy your trip to the fullest. Here’s how to travel smartly and confidently.

Research and prepare

Before you leave, research the safety of your destination. Check government travel advisories, read recent reviews from other solo travellers, and learn about areas to avoid at night or common scams. If you’re unsure, ask at your hotel or accommodation — those people are locals and should be able to advise you.

Make sure you have comprehensive travel insurance that covers medical emergencies, cancellations, and theft. Keep copies of your important documents (passport, travel insurance, flight tickets, etc.) both digitally and in hard copy, and share these with a trusted friend or family member.

Trust your instincts

Listen to your intuition. If something feels off, it probably is. Adjust your plans. On one trip, I felt a distinct chill come over me while walking through an area of New York — there was ‘something’ making me feel unwelcome, like I was being watched. Perhaps it was just my imagination. To this day, I can’t explain it, but I certainly felt very uneasy, so I walked away, retracing my steps until the uneasy feeling passed — a decision I’ve never regretted.

Practical tips:

• Stick to well-lit, populated areas, especially at night.
• Don’t enter an empty train carriage — choose one with lots of other people.
• Walk confidently and avoid looking lost, even if you are.
• If you’re lost, go into a hotel or department store and ask for directions.
• Keep valuables like jewellery or electronics discreetly stored.

Staying connected

Staying connected is vital for safety and convenience. Use an eSIM or local SIM card for affordable data access, ensuring tools like Google Maps work seamlessly. Free WiFi is increasingly available in cities, worldwide, but more remote areas may not offer it, so it’s worth having your own data access.

Bring a portable charger to keep your devices powered throughout the day. If possible, travel with a lightweight laptop or tablet for extended communication, emails and journaling, or entertainment.

Travel insurance: A must-have

Travel insurance is non-negotiable, in my opinion. It offers peace of mind and financial protection in emergencies. Sure, it costs more as we get older, but think of the consequences if something goes wrong. Some years ago, some of my family members managed the consequences of a mugging in Italy with far less stress than they might have had, thanks to their travel insurance. When something like that happens, the emotional drain in enough to deal with, without worrying about money, as well.

Share your itinerary with someone at home and check in regularly. Knowing someone is aware of your plans adds a layer of security.

Quick safety and connectivity checklist

• ✔ Research destination safety tips and customs.
• ✔ Purchase comprehensive travel insurance.
• ✔ Keep digital and hard copies of documents.
• ✔ Use an eSIM or local SIM card.
• ✔ Carry a portable charger.
• ✔ Trust your instincts and adjust plans if needed.
• ✔ Share your itinerary with a trusted contact.
• ✔ Stay alert and secure your belongings.

By taking these steps, you can enjoy your solo adventure with confidence, knowing you’ve prioritised safety and communication. Being prepared isn’t about paranoia — it’s about empowering yourself to explore the world independently and on your own terms.

Q. 10 — What will make this trip meaningful for me?

You don’t have to have it all figured out to take action.

Solo travel is a personal journey, offering the chance to design an experience that reflects your aspirations, values, and desires. Whether you’re seeking adventure, relaxation, personal growth, or the joy of exploring, defining your purpose will create a fulfilling trip.

• Defining your purpose: What’s driving your desire to travel? Your purpose doesn’t have to be profound — even the joy of planning or the thrill of discovering a new place can be reason enough.
• Focus on what matters: A meaningful trip isn’t just about lofty goals or soul-searching. It can be found in simple pleasures — a weekend stay in a nearby country town, for example — spontaneous laughter, or quiet moments of reflection. Take time before you depart to consider what will make your trip ‘perfect’.

Your solo adventure awaits!

Reflecting on these ten questions is about more than trip planning — it’s about ensuring your journey is everything you want it to be. With thoughtful preparation, your trip can bring joy, lasting memories, and a sense of accomplishment.

Whether immersing yourself in a new culture, conquering a challenge, or recharging in solitude, solo travel lets you create a journey that is uniquely yours. Planning is part of the adventure, so trust yourself, embrace independence. Your time is now!

Bonus: Free Printable Worksheet

To make this process easier for you, I’ve created a free printable worksheet featuring these ten essential questions. The worksheet includes space to jot down your answers and notes, and bonus tips to inspire your journey.

Download it today by signing up here. Use it as your guide to crafting the perfect solo adventure.