Over 50? How to Plan a Solo Trip in 11 Easy Steps

If you’re a seasoned solo traveler, you may just pack your bag and go. But for many women, especially if it’s your first solo trip, wandering out into the unknown requires “just a little” more prep. An itinerary. A bit of pre-thinking.

I’ve been traveling solo for 55 years, so I’ve got planning down to an art – and I’ve laid it all out for you below.

If you’re reading this, it’s probably because you want some travel planning advice.

You may be someone who needs a detailed itinerary, a ducks-in-a-row kind of woman. Or you may be the kind of traveler who generally goes with the flow, but wants to feel just a tiny bit organized. 

In fact, travel websites everywhere – including this one – will tell you some planning is better than no planning at all, and even a little pre-thinking can make your trip far more enjoyable. This applies to all solo travelers, novice or seasoned!

Maps are an integral part of planning a travel itinerary – can’t live without them ©️WOTR

On a trip to Serbia a few years ago, I decided to go with the flow and hop on the train without travel plans. I ended up backtracking, taking a train to the same destination twice, and wasting an entire travel day.

Not dramatic, but a bit of forethought would have meant spending that day in a lovely city, rather than settling for a quick lunch. Lesson learned.

How to plan a solo trip successfully

When I decided to travel to Central Asia for a month on my own, I decided to plan properly and document the process so I could share it with you.

Following a step-by-step guide is a great way to make sure you don’t forget anything major, while covering most of the minors as well.

So how to plan a trip to Europe? Central Asia? Anywhere? Planning a trip abroad, no matter where, requires a methodical process that doesn’t change much from place to place.

And it’s not even complicated: 11 sweet little steps.

Rome Colosseum at night: when you plan a solo trip, you'll want to choose your "must-sees" first
A good plan means being able to see all the sights – like the Colosseum at night (photo Annabel Haslop)

1. Gearing up for solo travel (it’s a mindset thing)

Never traveled solo? Then please, keep reading… because you may be in need of some mental preparation. (If you’re a little more experienced, then scroll down to #2.)

I took my first trip alone when I was 15, and I’ve so far visited 99 countries on my own. Solo travel has become a part of me.

I’m going to assume you’re already decided to travel solo, and just need a road map to get things organized. If, on the other hand, you’re a little anxious about solo travel, consider WHY a solo trip can be so beneficial for you.

  • You get to see what you want to see. Rather than bending to someone else’s tastes, you’ll do what you want, no questions asked, no compromises to make.
  • You’re forced out of your comfort zone. Sometimes it’s good to stretch ourselves and learn a bit more about who we are.
  • You meet new people more easily. When there’s no one to chat with at lunch, you’re more likely to make friends with strangers. 
  • You can be extra flexible. With no one else to consider, you can change everything at a moment’s notice and take advantage of unplanned opportunities (I ended up in a Bali motorcade with a government minister this way!)
  • Your self-confidence skyrockets. Just one trip where you do everything all by yourself will do wonders for your self-image. There’s nothing quite like knowing you’re capable of a lot more than you thought.

Solo travel changes you in many other incredible ways: here are 16 ways you’ll never be the same

Still hesitating?

Safety issues are often at the top of our list, and that’s a good thing.

I’ve written extensively about travel safety for solo women, and while we should be well aware of potential dangers, we shouldn’t obsess about them.

You can never eliminate all risk, and being abroad is no more dangerous than being at home.

What if you have a disability? I interviewed Carrie Harrington, author of “Barrier Free Travel: A Nuts and Bolts Guide for Wheelers and Slow Walkers”, and she offers great accessible travel tips. Another great travel website for people with disabilities is Curb Free With Cory Lee.

Even if you’re no longer a spring chicken (I’m 70), there’s no reason you can’t enjoy seeing the world on your own should you wish to, as I eventually did in Kyrgyzstan and Uzbekistan on that Central Asian trip.

And in case you think I’m crazy for traveling solo “at my age”, here’s a little compilation of stories from fellow mature women who have conquered solo travel and loved it. 

Onward!

2. Around the world travel: start by choosing a destination

You want to go everywhere, right?

I hate to be the bearer of bad news, but you have to choose. One place or several, but you still have to make a decision.

If you already have a bucket list or a raging desire to see a certain place, perfect. No need to read this section, just move straight to point #3 below.

Are you on the fence about where to go? Do you want the artistic beauty of Florence, or the bustle of Hanoi, or the spicy energy of Morocco?

This list will help you decide.

PRO TIP: Don’t try to see it all. Your travel experience will be that much richer if you try to get to know a place before you move on to the next one.

Start by making a list. You’ll add some places and delete others, but you have to start somewhere.

Is budget a factor? Here are some of the world’s least expensive countries to travel.

Perhaps you’re concerned with safety? Here are some of the safer destinations for solo women.

Do you have special interests? About genealogy or environment or literature or spirituality? There are many destinations to cater to these interests.

3. Know before you go – it’s about the research

This is often a neglected part of planning. Read a few guidebooks, check the cheapest tickets, buy and go.

No no no. What if the cheapest country with the prettiest guidebook is a place with food you absolutely cannot eat or a culture that makes solo women feel uncomfortable?

Yes, of course, read some guidebooks, but go beyond. Here are a few things you can do to acclimate to your destination before you get there:

  • Read books by authors who know the destination intimately.
  • Learn a few words of the local language.
  • Talk to friends who have visited your destination.
  • Join Facebook groups or check out travel forums discussing your destination.
  • Google your destination and click on News.
  • Check out its Wikipedia and Encyclopedia Britannica pages.
  • View some YouTube videos.
  • Read government travel advisories. They’re overly cautious, but at least you’ll be informed.
  • Go to a restaurant near you that serves food from your destination – let’s call that a bit of prep.

In other words, find out as much as you can about your destination before you go. Armed with this knowledge, you’ll make better use of your time, avoid the activities that are tourist traps or not worth your money, and see the country with greater understanding.

This knowledge will also make you feel more confident, which is a valuable trait in a solo traveler.

4. You can’t plan a solo trip without a budget

Generally speaking, the larger your budget, the longer you can travel. But if you’re facing a financial squeeze, you’ll want to find ways to travel on the cheap.

This is why it’s so important to plan: travel invites the unexpected, and those hiccups often burn holes in your wallet. Having a plan of some kind can help reduce the number of “oops…” expenditures.

But how much to estimate? This guide might be helpful. It includes links to all kinds of trackers, estimators and articles which can give you an idea of just how much your trip will cost, all before you leave.

Remember, you’re looking at your airfare, travel and medical insurance, any visa fees, accommodation, food and drink, sightseeing entry fees and local transportation. These are the costs you really can’t get away from. And of course, there will be unplanned extras… I usually budget 10-15% of my trip’s total cost for these “unexpected” expenses.

5. Journey planning and travel practicalities

This involves a lot of odds and ends.

How long should I travel for?

If I encouraged you to create a budget first, it’s because longer trips are generally more expensive. That said, they are also the best way to truly immerse yourself in a culture.

Many first-time solo travelers (any travelers, in fact) want to “fit it all in”. How could you visit Rome and not see every broken marble statue and ancient stone? I understand that, but there are definite advantages to slow travel, at your own pace and on your own terms.

I’ve certainly taken whirlwind trips, but some of my favorite are those where I truly took time to relax and soak it all in, and not rushing from monument to museum at record speed.

Daily life in Cuba, painter
Taking time to observe daily life in Cuba rather than rushing (photo Annabel Haslop)

I was able to meet locals and make friends. I got to glimpse everyday life, with the time to really think and appreciate what I was experiencing.

When to travel

Deciding how long to travel for goes hand-in-hand with when to go: when is the perfect time for your trip?

A good time to travel is during the shoulder or low season; this can cut your expenses by half! You’ll also battle fewer crowds, but there’s a downside too – it’s the low season for a reason, usually the weather.

Also, you might want to time your trip to coincide with a special event, a friend’s wedding, an art festival or concert…

The right gear for your travels

Obviously this depends on where you’re going, but for most trips you’ll need certain staples, for example:

Travel Backpack

If most of your clothes are made for everyday life, you might want to upgrade to some fast-drying travel apparel, including:

For safety, especially in my hotel room, I like to pack a lock, and if I’m headed off the beaten path, which I do relatively often, I’ll want a quality mosquito net and a first aid kit. Another good thing to have along is a flashlight.

I’ve also put together some packing lists which might be helpful and which you’ll find in the top menu bar under Travel Planning > Packing Lists.

PRO TIP: Don’t take more than you need. Whatever you think now, you’ll use far less than you think.

The right paperwork for your destination

Depending on where you go, you may need a visa in addition to your passport. Make sure you order this well in advance from either the country’s consulate or from a specialized visa site.

You may also need certain meds, like malaria pills for example, and a bit of local currency if you can get your hands on it. Make a copy of your important documents, just in case, and check the cost of using your credit cards in a foreign country.

If you’ve done everything this far, you’ve broken the back of your planning process. The rest is important, but it’s more a question of filling in the blanks.

6. Choose your flights or train tickets

Shop for airlines because you’ll find huge differences in prices ©️WOTR

There are some things you have to deal with well ahead of time, especially transportation. There’s no point in planning an itinerary or booking a hotel if you haven’t secured your transport yet!

Flights

If you haven’t made your flight reservations yet, you’d better.

The main reason to plan your trip ahead of time is cost. With the rise of budget airlines, you can find ultra-cheap tickets if you book well in advance, especially by using comparative search engines that include low-cost airlines.

Here are some ways of keeping flight costs down. And if you’re planning a very long trip, start investigating round the world tickets.

If you’re flying long distances originating in the United States, you should give Going a try – they specialize in “error fares” (fares mistakenly published by airlines) and save half the airfare or more.

PRO TIP: Whether you’re flying, taking a train or a bus, be aware of your arrival time. As a solo female traveler, try to arrive in daytime.

Rail travel

If you’re planning on travel by train, you may have to book these now too, especially if you’re traveling in high season on a crowded route. If you’re headed for Europe and plan plenty of train travel, consider getting a railpass.

Other types of transport

Other inexpensive transportation options include traveling by bus or even rental car (great if you’re a road trip planner). Be sure to exhaust all your options if saving money is a priority.

7. How to plan your trip itinerary

While you don’t have to plan out every minute of your solo adventure, a general itinerary is a good idea. You don’t want to waste time or money, and you don’t want to miss out on something because you didn’t do a little research ahead of time.

PRO TIP: Once you have a basic itinerary, leave a copy with a friend or relative back home. Just in case.


Journey planning doesn’t have to be difficult, but you need to start somewhere

If you’ve done the research I mentioned above, the rest is easy.

You should have a starting point and an end point. You should have a number of days. And that’s the skeleton of your itinerary.

That’s me, looking way too cheerful as I’m about to head for Colombia’s interior ©️WOTR

If you’d like some itinerary inspiration or guides to different destinations, these can get you started.

And of course, go to Google. 

Type in “What to do/see in ____” and you’ll find plenty. Then create a list of everything you’d love to see if you could, and reorder the list by priorities. Include all your must-sees, the non-negotiables.

A good way to find the main attractions is to check out what other visitors pay to see: companies like Get Your Guide or Viator organize local tours to major attractions in many countries. Check them out to see which group tour is the most popular.

Once you have a list of your most popular attractions, cost them out. Perhaps you can manage one or two a day, perhaps more.

Use a map (physical or electronic) to mark out what you want to see, and then group the attractions that are close together. Make sure you check to see what’s open, when.

Check The Fork or similar food apps to find nearby restaurants and cafés you might want to try out (rather than head across town and waste precious time).

Add everything to your map, or add it to a spreadsheet. And that’s your basic itinerary. Just keep everything in a single place.

8. Choose your accommodation

On my trip to Central Asia, I reserved a few hotels and homestays ahead of time but dealt with the rest once I arrived. I realize this isn’t comfortable for everyone so if you want to reserve ahead, by all means do so.

There are pros and cons.

On the positive side, if you’re on a budget, booking ahead will usually save you money and let you take advantage of special deals. If you wait for the last minute, hotels fill up and there’s every chance you may have to pay a premium.

One the not so positive side, booking everything ahead locks you in and reduces your flexibility. If an opportunity arises to visit someplace you hadn’t planned, you won’t be able to take advantage of it. This is one of the reasons I use booking.com for my hotel bookings – many listings have a guaranteed no-fee cancellation, so I can change my mind.

PRO TIP: You don’t have to book a place to stay before you arrive, although I always book the first night, especially if I don’t land during the daytime.

Accommodations come in many sizes and shapes and your choice will be dictated by a number of factors, such as whether you want a private room, of if you want to be near the train station, or your travel budget….

Here are guides that might help you decide on the best type of accommodation for you:

  • Airbnb – and what to watch out for
  • Hotels – how to choose the best one
  • Hostels – navigating them even if it’s your first time
  • Monasteries – for some peace and quiet
  • Housesitting – luxury for nearly free
  • Homestays – to get to know people and different places in depth

So now you have a destination, a budget, an itinerary, transportation and accommodation.

What’s left?

9. Buy travel insurance

I mentioned this earlier but this is one of those major items many travelers are tempted to forgo – I can never talk about it enough.

The “it’ll never happen to me” mindset can be costly. If I’d had that mindset, I’d be $25,000 poorer right now because it DID happen to me.

You’ll probably never have to use your insurance but – IF YOU DO – you’ll be ever so grateful you have it, if you lose your bags, your hotel room is burgled or if you break a leg. I’m now testing out a variety of age-friendly insurance companies.

Most travel insurances have a 24/7 toll-free number which you can call from anywhere. They’ll usually find someone who speaks the local language to communicate, so if you end up in a foreign hospital, language won’t be a barrier. As a solo traveler, it’s important to have someone you can reach out to if you’re ill.

10. Pack your bags

I always travel carry-on, period. Either with wheels, or with a backpack. I simply don’t put anything into the belly of the beast, ever. My bags have gone astray too often.

So first, what are you using to pack? If you can’t decide, I’ve got some buying guides for carry-ons and for anti-theft backpacks which you might find useful.

But my ONE secret (and you’ll nod your head in agreement if you have these!) are –packing cubes! I have no idea how I traveled before I discovered these but they allow me to pack light and more, and stay better organized when I travel.

My suitcase, “neatly” packed thanks to my packing cubes! ©️WOTR

Regardless of when you start packing, you shouldn’t have to start over from scratch each time you travel. So yes, a list.

Print out one of my packing lists (click Travel Planning > Packing Lists in the menu at the top of the page) and check off each item as you put it aside.

11. Enjoy the ride (and the unexpected)

There is one more element to getting ready for your trip: travel-proofing your attitude.

Because, as you probably know, travel rarely goes according to plan.

If you tend to get upset when plans change, take a moment before you head off to the airport to breathe deeply and remind yourself why you are traveling. Getting out of your comfort zone and experiencing new things are two wonderful benefits of travel, and having your bus break down is part (albeit not the nicest part) of the process – inconveniences, yes, but disasters? No.

Part of travel’s joy is being able to accommodate the unexpected. There’s a bit of fear that grips some of us before we go so we may tend to plan every single detail. Try not to! There’s nothing wrong with a bit of planning, but don’t let your schedule take over your journey.

Take it as it comes and remember, if all were to go according to plan, the stories you tell after your trip wouldn’t be half as interesting!

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Essential tips for the international traveler

Once you’ve planned your trip and taken care of the basics, this is when to remember those last few tips that will make your journey easier, more fun, more rewarding.

Learn a bit of the language

Whether you’re exploring new places for a week or a year, try to learn a few words of the language. No need to go overboard. Even ‘please’ or ‘thank you’ will send a signal that you care and that you respect your host country. 

Notice how society functions around you

Things like clothes and manners can take on a much larger meaning overseas. Halter tops and shorts may be commonplace at home but in some countries they may attract a lot of unwanted attention. When in doubt, look around you and do as local women do. Learn to cope with culture shock. Find out about basic cultural etiquette. Notice the cultural differences around you.

Be open

Things will be different from home, so be prepared. Some things will be better, some will be worse. The food may be unfamiliar, and you may be almost invisible as a woman in some societies. Take it in stride. If what you want is a carbon copy of what you left behind, then back home is where you’ll find it, not on your travels.

Change your sense of time

Western societies place a great premium on time and punctuality. Many societies do not. If you can’t adapt, your frustration level may rise. ‘In a moment’ may mean tomorrow, and tomorrow could mean next week. In Madrid, my mother once invited friends for dinner. By 11pm we finally went to bed. They appeared well after midnight, chipper and hungry! 

Tread your politics lightly

Political discussions can turn into minefields. Just be prepared for it and remember, there’s always more than one way to see things. In some countries, discussions can rapidly spin out of control – and can also get local people into trouble. Speak your mind respectfully but be aware of the realities of where you are.

Remember how little you know

Those of us who come from economically well-off countries may have a tendency to think we know what’s best for the rest of the world. Travel light. Leave that piece of baggage at home.

A few final words…

I love solo traveling but I understand that even if you’re tempted, you might not feel 100% ready yet. Head over to this article if you think finding a travel companion would be better for you… until you’re ready to go it alone. 

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