I’m Over 50 and Want to Travel Alone. Where Do I Start?

There comes a point when waiting for someone else to travel with you can start to feel like waiting for your life to begin. Maybe you've spent years assuming you would eventually take that trip with a spouse, partner, friend, sister, or group of girlfriends. But people have jobs, families, health concerns, financial limitations, and their own ideas about where they want to go. Sometimes the person you thought you'd travel with simply isn't interested. And suddenly you find yourself over 50, still wanting to see places you've dreamed about, but wondering whether traveling alone is something you could actually do.

If you've never traveled alone before, the idea can be both exciting and intimidating. It's one thing to imagine yourself strolling through a beautiful town, sitting beside the ocean, visiting a museum, or waking up in a hotel room with an entire day ahead of you. It's another thing to imagine getting yourself through the airport, checking into the hotel alone, figuring out transportation, eating dinner by yourself, dealing with a problem without someone beside you, and making every decision on your own.

Those concerns don't mean you're not cut out for solo travel. They mean you're thinking seriously about doing something you've never done before.

And here's the good news: you don't have to start with the trip of a lifetime. You just have to start.

First, Forget the Idea That You Should Have Done This Years Ago

It's easy to look at other solo travelers and think you're late. Social media doesn't necessarily help. We see women backpacking through Europe, celebrating birthdays in Paris, cruising by themselves, hiking mountains, or posting photographs from some gorgeous beach, and it can look as though everyone else figured this out years ago.

But there are countless reasons someone may not begin traveling alone until later in life. You may have spent decades raising children, building a career, caring for parents, supporting a spouse, paying bills, dealing with health problems, or simply putting other responsibilities ahead of yourself. Maybe you always had someone to travel with before and never needed to consider traveling alone. Perhaps life changed unexpectedly and the person you thought would be beside you isn't there anymore.

Whatever brought you here, you haven't missed your opportunity. There isn't an expiration date on becoming a solo traveler. Starting at 52, 58, 64, or 72 doesn't make the experience less meaningful. In some ways, getting older can actually make solo travel easier because you probably know yourself much better than you did at 25. You know what you like, what you don't like, what you're willing to tolerate, what makes you uncomfortable, and what you need in order to enjoy yourself.

That knowledge is valuable when you're planning a trip around you.

You Don't Need to Be Fearless Before You Book a Trip

One of the biggest mistakes we make when thinking about something new is believing confidence is supposed to come first. We tell ourselves that once we feel confident enough, we'll book the hotel, buy the ticket, or take the trip. But confidence usually doesn't work that way. It often develops because you've done something that once made you nervous and discovered that you were capable of handling it.

Think about other things you've learned during your life. There were probably jobs you didn't feel completely prepared for on the first day, difficult conversations you didn't know how you were going to get through, responsibilities you had to figure out as you went, and problems you handled because there wasn't anybody else available to handle them for you. Travel isn't entirely different. You prepare as well as you can, take the next step, and learn from the experience.

The goal isn't to eliminate every nervous feeling before leaving home. The goal is to make your first trip manageable enough that your nervousness doesn't control the experience. You can be cautious and still travel. You can double-check your reservation three times and still travel. You can call home every evening and still travel. Being nervous doesn't disqualify you from becoming a solo traveler.

Start Small—Much Smaller Than You Think

Your first solo trip doesn't need to involve a passport, an eight-hour flight, or two weeks in another country. In fact, if you've never traveled alone, I wouldn't recommend starting that way unless you're already extremely comfortable navigating unfamiliar situations independently.

Start by practicing solo travel close to home. Choose a place an hour or two away that you've wanted to visit and spend the day there by yourself. Visit a museum, walk through an interesting neighborhood, browse shops, have lunch, sit beside the water, take photographs, or find one attraction you've always wanted to see. The destination itself isn't particularly important. What matters is that you're practicing the mechanics of being somewhere unfamiliar without relying on another person.

During that little trip, pay attention to yourself. Did you enjoy having control over your schedule? Did eating alone bother you? Were you comfortable navigating? Did you wish you had planned more beforehand? Did you become tired sooner than expected? Did you feel lonely—or did you unexpectedly enjoy the quiet?

Those observations will teach you more about your personal travel style than a hundred generic solo-travel articles.

When a day trip starts to feel comfortable, consider staying somewhere for one night. Book a hotel within reasonable driving distance, check yourself in, have dinner, spend the night, enjoy breakfast the following morning, and come home. That counts as solo travel. You don't have to cross an ocean for the experience to be legitimate.

Build Your Confidence Instead of Testing It

I like to think of first-time solo travel as a confidence ladder. You don't have to jump from the bottom rung to the top. You can move up one level at a time until you discover where you're comfortable.

Maybe your first step is simply having lunch alone in your own town. The next might be driving somewhere unfamiliar for the afternoon. Then you could take a day trip, followed by one night at a hotel. After that, perhaps you try a two- or three-night road trip. Eventually you might take a short direct flight to a destination where transportation is easy. International travel can come later if that's something you want.

The important part is that you decide how quickly you climb. You don't need to prove anything by forcing yourself into a trip that scares you so much you can't enjoy it. A successful first solo trip should leave you thinking, I could do that again. Then you can make the next trip a little bigger.

You might also discover that you don't want to climb all the way up the ladder. Maybe you love three-day solo road trips but have no desire to fly internationally alone. That's perfectly fine. Solo travel isn't a competition, and there isn't a prize for going the farthest.

Pick an Easy Destination for Your First Real Solo Trip

Your first destination can make an enormous difference in your confidence. This isn't necessarily the time to choose somewhere that requires multiple flights, several hotel changes, complicated transportation, or constant problem-solving. Save the challenging destinations for later, when you've already developed some travel experience.

For your first trip, look for a destination that makes things easy. Consider somewhere with hotels close to restaurants and attractions, reliable transportation, plenty of things you're genuinely interested in doing, and an environment where you feel comfortable. A destination you've visited before can actually be an excellent first solo trip because some of the uncertainty has already been removed. You may know the airport, understand the neighborhood, or recognize the general layout of the city.

And don't choose a destination simply because everyone says it's a great place for solo travelers. Choose somewhere you want to go. If you love museums, choose a museum city. If you want quiet mornings by the water, choose that. If you hate crowds, don't book a destination famous for crowds just because it's popular on social media.

Your first solo trip isn't supposed to impress anybody. It's supposed to work for you.

Plan the Parts That Make You Nervous

Some people are natural planners, while others prefer to arrive somewhere and figure things out. For your first solo trip, I'd suggest planning the things that would cause you the most stress if you had to solve them on the spot.

For example, don't wait until you land at an unfamiliar airport at 9 p.m. to figure out how you're getting to your hotel. Research that beforehand. Know whether you're taking a hotel shuttle, taxi, rideshare, rental car, train, or bus. Have the hotel address saved in your phone and written somewhere else in case your phone isn't available.

Know roughly what you want to do each day, but don't turn your vacation into a military operation. Give yourself breathing room. If you're planning three days away, perhaps choose one main activity for each day and keep the rest flexible. That gives you direction without creating pressure to race from attraction to attraction.

The more stressful something feels to you, the more useful it is to prepare for it beforehand. Planning isn't a sign that you're afraid to travel. Good planning can be exactly what gives you enough security to relax once you're there.

Learn to Enjoy Making the Decisions Yourself

One of the strangest parts of first-time solo travel can also become one of the best: nobody else gets a vote.

When you travel with another person, even someone you love, almost everything involves some degree of compromise. What time should we get up? Where should we eat? How much should we spend? Should we go to the museum or the beach? Do we stay another hour or leave now? Is everyone tired? Is someone hungry?

When you're traveling alone, those negotiations disappear.

If you wake up and don't want breakfast until 11, that's fine. If you love a museum and want to stay for four hours, nobody is standing beside you looking bored. If you decide at 2 p.m. that you've had enough sightseeing and want to go back to the hotel, you can. If you want dessert for lunch, I certainly won't tell anybody.

At first, having complete control can feel surprisingly unfamiliar. But learning to listen to yourself—to ask, What do I actually want to do today?—can become one of the most rewarding parts of traveling alone.

Get the gumption and solo travel is an article that will give you more confidence to vacation on your own.

Practice Eating Alone Before You Leave

Eating alone is one of the most common concerns I hear about solo travel, and it's worth practicing before your trip. If sitting alone at a restaurant feels uncomfortable, start with breakfast or lunch at home, when restaurants tend to feel more casual. Take yourself somewhere you like, ask for a table, order what you want, and simply observe how you feel.

You may be convinced that everyone is noticing you're alone. They're probably not. The couple at the next table is thinking about their own conversation. The family across the room is trying to get their children to eat. The server is doing their job. The person looking at their phone isn't analyzing your relationship status. Most people are far too busy with their own lives to wonder why you're eating by yourself.

If you're still uncomfortable on your trip, there are plenty of options. Sit at a café, eat at the bar, choose outdoor seating, have lunch as your main restaurant meal, visit a food hall, or occasionally bring dinner back to your room. Solo travel doesn't require you to sit through an elegant three-course dinner alone every evening to prove you've mastered it.

Over time, however, you may be surprised by how normal eating alone begins to feel.

Safety Should Make You Prepared, Not Terrified

Safety deserves serious attention when you're traveling alone, but fear shouldn't be the entire foundation of your trip. The objective isn't to convince yourself that nothing bad could ever happen. It's to reduce avoidable risks and know what you'll do if you encounter a problem.

Research the neighborhood where you're staying rather than choosing a hotel solely because it's cheap. Think about how you'll get back to your accommodation after dark. Keep someone you trust informed about where you're staying and provide them with your basic itinerary. Save emergency contacts in your phone, but also keep important information somewhere else in case your phone is lost, stolen, or damaged.

Be thoughtful about how much personal information you share with strangers. You don't have to tell someone you just met that you're alone, where you're staying, what room you're in, or what you're doing tomorrow. Be mindful of alcohol, particularly when you have to navigate yourself back to your accommodation afterward.

Most importantly, give yourself permission to leave situations that make you uncomfortable. Women are often taught to worry about appearing rude. Your safety matters more than a stranger's opinion of your manners. If something doesn't feel right, move, leave, ask for help, call transportation, speak to hotel staff, or change your plans.

Being prepared isn't being paranoid. It's part of taking care of yourself.

Check out my article, Solo travel--Safety on the road will get into my experiences as a solo traveler and how I handle safety when I travel.

Have a “What If?” Plan Before You Go

Sometimes the fear of traveling alone isn't really about the trip itself. It's about the question lurking in the back of your mind: What if something goes wrong and I'm by myself?

Instead of trying not to think about it, answer the question.

If your flight is canceled, what would you do? If you lose your wallet, do you have another form of payment stored separately? If your phone dies, do you have a charger or portable battery? If you lose access to your phone entirely, do you have important phone numbers written down? If you become ill, do you know where you could seek medical help? If you take prescription medication, do you have enough for the trip plus a little extra in case you're delayed?

You don't need contingency plans for every bizarre situation imaginable. Concentrate on the problems that would have the biggest impact on you personally. Having a few backup plans changes the question from What if something happens? to If something happens, here's what I'll do.

That's where preparation starts turning into confidence.

If Your Body Has Changed, Change the Trip

Traveling after 50 can look different from traveling at 25, and there's nothing wrong with acknowledging that. Some travelers can still walk ten miles a day without thinking twice. Others have arthritis, chronic pain, mobility limitations, fatigue, medication schedules, dietary requirements, or other considerations that need to be part of the plan. Read, Make the trip work for your body, your budget and your life for info on how your vacation can work for you.

Don't build an itinerary for the body you used to have, the body you wish you had, or the body somebody on YouTube has. Plan for the body you're traveling with.

If you need airport wheelchair assistance, request it. If you need an aisle seat, prioritize it. If staying closer to the attractions means paying a little more for the hotel but saves you hours of walking and transportation, consider whether the extra cost is worthwhile. If you know you'll need an afternoon break, don't schedule activities from 8 a.m. until 10 p.m.

Rest isn't wasted vacation time. Neither is sitting at a café, taking a scenic drive, spending an afternoon beside the pool, or going back to the hotel early.

A vacation isn't successful because you managed to exhaust yourself in a different ZIP code.

Spend Your Money Where It Makes the Trip Easier

If you're watching your budget, it's tempting to choose the cheapest option every time. But the cheapest option isn't always the best value, especially when you're traveling alone for the first time.

A $20 cheaper flight with two connections may not be a bargain compared with a direct flight. A hotel that's $25 cheaper per night but miles away from everything could end up costing more once you add transportation. Arriving at midnight because the airfare was cheaper may create stress you could avoid by paying a little more for an earlier flight.

Decide which things matter most to your comfort and confidence, and spend strategically there. Save money on things you don't care about. Maybe you don't need a fancy hotel room but want a safe, convenient location. Perhaps you'll eat inexpensive breakfasts and lunches so you can afford reliable transportation. Maybe you don't care about shopping but are willing to pay for a guided tour on your first day so you can become familiar with the destination.

Budget travel should help you travel more. It shouldn't make every part of the trip unnecessarily difficult.

Don't Let Someone Else's Fear Decide What You're Capable Of

Once you tell people you're thinking about traveling alone, you may discover that everyone has advice. Some of it will be useful. Some of it will be based entirely on their own fears.

You may hear, “You're going by yourself?” or “I would never do that.” Someone may immediately start telling you about something terrible they saw on the news. Others may genuinely worry because they care about you.

Listen to reasonable safety concerns and do your research. But remember that another person's discomfort with solo travel doesn't determine your ability to do it.

Sometimes people can't imagine doing something themselves, so they have difficulty imagining you doing it successfully.

You don't need everybody's permission.

And Yes, You Might Feel Lonely Sometimes

Solo travel isn't a magical cure for loneliness. You can have an incredible day and still feel a little lonely when you sit down for dinner. You might see friends laughing together or couples walking hand in hand and suddenly wish someone were beside you. You might return to your hotel after a wonderful day and realize the room feels very quiet.

That doesn't mean you shouldn't have gone.

Loneliness is an emotion, not necessarily evidence that you've made the wrong decision. If it happens, have ways to reconnect. Call someone at home. Send photographs to a friend. Join a walking tour or small-group excursion. Sit somewhere lively instead of returning to your hotel immediately. Take a class, visit a local market, or strike up a conversation when it feels natural.

You can also remind yourself that people traveling with companions experience difficult moments too. Couples argue. Families get tired of each other. Friends disagree about money and schedules. No style of travel guarantees happiness every minute.

The goal isn't to have a perfect trip. It's to have your trip.

Your First Solo Trip Is Allowed to Be Imperfect

Maybe you get lost. Maybe you pick a restaurant you hate. Maybe you spend too much money on something. Maybe you book a hotel you wouldn't choose again. Perhaps you plan too much, or not enough. Maybe you have a lonely evening. Maybe you get nervous and wonder why you ever thought this was a good idea.

Then the next morning you wake up, figure it out, and keep going.

Those moments are part of learning how you travel.

Don't judge your entire ability to travel alone by whether every part of your first trip goes perfectly. Instead, when you get home, ask yourself what worked, what didn't, what you'd change, what surprised you, and what you'd like to try next.

That's how you become a more confident traveler—not by avoiding mistakes, but by learning what works for you.

The Most Important Thing You Bring Home May Be Proof

There is something powerful about returning home from your first solo trip.

You unpack your suitcase. You look through your photographs. You think about the restaurant you found, the hotel you checked into, the road you navigated, the airport you figured out, the decision you made when plans changed, and the moments when you were completely responsible for yourself.

And you realize:

I did that.

That feeling is different from somebody telling you that you're capable. You now have evidence.

Maybe your first trip was only 90 minutes from home. Maybe it was two nights instead of two weeks. Maybe you never left your state. None of that diminishes what you accomplished.

You stopped waiting.

And the next time you plan a trip, you aren't starting from zero anymore.

So, Where Do You Start?

Don't begin by asking yourself where you should go for the ultimate solo vacation. That's too much pressure.

Choose one small experience you feel capable of doing now.

Pick a town you've always wanted to explore. Spend an afternoon there. Take yourself to lunch. Visit an attraction. Navigate home. Then consider an overnight trip. When that feels comfortable, make it two nights.

Give yourself time to become the traveler you're trying to become.

You don't have to be fearless. You don't have to be wildly adventurous. You don't have to travel cheaply enough, far enough, long enough, or often enough to qualify as a “real traveler.”

And you certainly don't need to wait until somebody else is ready to go with you.

At this stage of life, maybe the question isn't “Why would I travel alone?”

Maybe it's “How many more places am I willing to miss while I wait for someone else?”

Start small. Prepare well. Listen to yourself. Take the trip that works for your body, your budget, your comfort level, and your life.

Then see where you want to go next.

Ready to Try Your First Solo Trip After 50?

If you're thinking, Okay, but what exactly do I need to do before I go?, I've made it easier.

Download my free “My First Solo Trip After 50” Printable Checklist at the bottom of this article and use it to work through your first trip one step at a time—from choosing an easy destination and planning your transportation to safety, packing, backup plans, and building confidence before you leave.

You don't have to figure everything out today.

Check off the first box. Then the next one. Your first solo adventure can start from there.

The Single, Sick & Broke Traveler
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Travel stories for the brave and budget-conscious.

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