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Solo Journey: Your 11-Step Guide to Perfect Travel Planning

Women on the Road
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World travel... some people are spontaneous and others love to make lists (me), the more color-coded the better.

If you’re reading this, you may be among those who need a detailed itinerary, the ducks-in-a-row kind of woman. But you may also the kind of traveler who generally goes with the flow but just wants a tiny bit of organization for your trip. 

In fact, travel websites everywhere – including this one – will tell you some plan is better than no plan at all and even a little bit of pre-thinking can make your trip far more enjoyable.

detailed map to create travel itineraryMaps are an integral part of planning a travel itinerary - can't live without them! Photo Lucian Milasan

Recently I visited the Balkans and in while travelling Serbia, I decided to go with the flow and hop on the train without checking ahead. Which is why 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 allowed me to spend that day in a lovely city, as opposed to settling for a quick lunch.

How to plan the perfect trip successfully

You can organize your trip any way you want. But following a step-by-step guide like this one will at least make sure you don’t forget anything major, while covering most of the minors as well.

So how to plan a trip to Europe? 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.

how to plan an overseas trip - Rome Colosseum at nightA good plan means being able to see all the sights - like the Colosseum at night (photo Annabel Haslop)

1. Gearing up for solo travel (even if it’s your first time)

If you’re a seasoned solo traveler, you probably don’t need to read this section so just head directly to choosing a destination.

Never traveled solo? Then please, read on...

I took my first solo journey when I was 15, and to date have visited 93 countries. So 50 years of solo travel later, it’s become a part of me.

If you’re trying to wrap your head around solo travel - if you’re anxious or a first-timer or simply suspicious about traveling on your own, consider this:

Solo travel means...

  • You get to see what you want to see. If you’ve ever taken a family trip or traveled with friends, there might have been a “travel guide” figure in your group. The one who felt duty-bound to direct your every move. Or you just couldn’t turn into those interesting little corners because they’re not interested.
  • You’re forced out of your comfort zone. Sometimes it’s good to stretch ourselves and learn a bit more about who we are. In fact, it can be great.
  • 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. 
  • 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.
  • You become 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!).

And that's just a taster, because solo travel changes you in 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, but being abroad will be 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 67), there’s no reason you can’t enjoy solo travel and have a tremendous time, as I did for a month across four Eastern European countries recently, or last yea around Kenya and Colombia

And in case you’re curious about how other women travel as they move forward in life, here’s a little compilation of stories from fellow mature women who have conquered solo travel and loved it. 

Solo travel it is. Onward!

Age introduces new challenges - like travel insurance. Although World Nomads will cover you until 66 (70 in some countries), here are several companies that will watch over you at any age.

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

You want to go everywhere, right?

If you already know your destination, perfect. No need to read this section.

But if you’re less than certain about where you’re going (and just want to GO SOMEWHERE DIFFERENT), start by making a list (this is possibly my favorite sentence in the universe, other than “Here’s your invitation to a three-star Michelin restaurant”). Write it all down. It helps.

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

Do you have special interests? About genealogy or environment or literature or spirituality?

Here are some fabulous travel ideas that will help you decide where you want to go, however undecided you might be.

Once you’ve decided where to go...

3. Determine your 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.

You can download this handy budget planner to write down your estimated costs for everything from flights to accommodation to food. Once it’s down on paper, it’ll start looking less daunting and you can begin playing around with the numbers.

But how do you know 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.

A few tips for budget travel

While I recommend you start with a figure from the beginning, what if you’ve looked at even the cheapest destinations and realized you just don’t have the money you need?

There are other ways to stretch your funds if they don’t cover your travel budget.

One way is by living more cheaply, if that’s at all possible. I’m always amazed at the amount of money I waste on things that I don’t need… these are no-brainers and we should all be able to find something we're willing to go without in exchange for travel.

  • Spend a lot of money eating out? Try searching Pinterest for some seriously delicious recipes and turn your evening into a single-contestant master chef (and invite your friends, of course!)
  • Stop the Nespresso capsules or the Starbucks habit and substitute some freshly-ground Colombian coffee instead.
  • If there’s any way you can manage this, try to trade in your car for public transportation (although depending on where you live, this might not be possible).
  • If you’re really serious, cancel your Netflix (noooo!) or Hulu subscriptions and join the library instead. I substituted books for my late evening film and had a great time reconnecting with books!

If all the saving in the world is still not enough and you plan to travel for a length of time, you might consider working abroad. Consider teaching English overseas, or finding online jobs you can do remotely.

No? Here’s a list of other jobs you can do while you travel.

4. Journey planning: decide how long you’re going 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 travelers want to “fit it all in”. How could you visit Rome and not see every broken marble statue and ancient rock? I understand that, but there are definite advantages to slow travel.

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, those where I wasn’t rushing from monument to museum to attraction at record speed.

Cuban painter in HavanaTaking 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.

And then there’s the opposite end of the spectrum - how about a round-the-world adventure? If you need to know how to plan a trip around the world (much different than taking a two-week jaunt across Europe), this guide will unpack it for you.

Deciding how long to travel for goes hand-in-hand with determining WHEN to go. What time of year is the best time to visit Berlin or New York or Hong Kong?

For some people, travel and weather go hand in hand - avoiding the tropics during hurricane season, or a ski resort when there’s no snow. (Here are my recommendations on the best times to visit various parts of the world.)

For others, it’s about density: the better the weather, the more packed the destination. Want some breathing room? Go during the off season: prices will be lower, and you'll have some places all to yourself.

5. How to prepare for your journey

Before you go on a trip, especially a longer one, there are quite a few things you need to consider on the practical side.

Planning your travels - be practical

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:

If most of your clothing is 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 netfirst aid kit and flashlight at the very least.

The right visa for your destination

Visa rules are different in every country and for residents of every country, but one this is certain: it’s vitally important for you to find out if you need a visa prior to planning a trip to a country. If you need one and arrive without it, you'll be turned back. If you're flying in, you won't even be allowed to board the plane (and the insurance won't cover your missed flight, either).

The easiest way to find out is to check out a specialized visa site that has all the latest information - because yes, thing change.

6. How to plan a trip itinerary

While you don’t have to plan out every minute of your journey, 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 adequate research ahead of time.

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

  • Travel forums often post all kinds of questions from travelers and are a great resource for your research needs. User-generated content sites like Tripadvisor are also worth a look (but with a grain of salt).
  • I know they may seem outdated, what with apps and videos and podcasts, but a travel guidebook is designed to help with exactly this: it’s the original travel planning guide. Buy one (or yes, download one) or find one at your local library and take notes. 
  • If you have a friend or acquaintance who has been to your destination, you can get help planning a trip by picking their brains for recommendations.
  • Next, check out travel blogs! Where are seasoned travelers going and what are they doing once they get there? Here are some of my favorite women's travel blogs.
Happy to travel - much research to do beforehand

If you'd like some itinerary inspiration or destination guides, 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. 

Afterwards, decide what you can afford based on your budget and how long you’ll be traveling.

Use a map to mark out what you want to see, and then group the attractions that are close together (make sure you do your research to find out what’s open and what isn’t).

Be sure to include nearby restaurants and cafés you’ll be stopping at to eat.

Want an easy way to keep track of your itinerary once you sort it all out? Get help from trip planning websites and trip planner apps like TripIt, which let you share your itinerary with anyone  back home.

7. Choose your flights or train tickets

Fly to your destination - plane in the sky

Once you know where you’re going and when you need to be there, you can start making transportation plans. Obviously the more specific your itinerary, the more flights and train rides you can book ahead of time. If you’ve allowed wiggle room for adventure, you may only be able to purchase your round-trip ticket home and will have to buy as you go the rest of the time.

Another good 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. If you're planning a longer trip, start investigating round the world tickets.

If you’re planning a trip to Europe, I’d strongly suggest you consider taking the train rather than flying. You can buy a rail pass before you leave home, or you can buy individual tickets once you get to Europe. Either way, the train is far more convenient: it goes to just about every corner of the continent, and takes you right into town rather than delivering you to a distant airport (not to mention the extra baggage allowance).

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.

8. Choose your accommodation

You don’t have to book a place to stay before you arrive, although I would at least recommend booking your first night, especially if you don’t land during the daytime.

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 feel you need to reserve ahead, by all means do so (I use for my hotel bookings because most listings have a guaranteed no-fee cancellation).

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. (On the other hand, there is a small chance you could get a good deal from a hotel trying to sell out rooms at the last minute.) That said, if you book ahead, you may also run the risk of paying for a room you won’t use if your travel plans change (and they might).

Accommodations come in many sizes and shapes so choosing what's right for you is a challenge - and I’ve written a few guides that might help you decide on the best type of accommodation:

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

What’s left?

Map of Europe - choosing your destination

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.

As I said above, I always bought World Nomads for my travel insurance, but if you’re over the age of 66 (that's me now), check out my reviews of travel insurance agencies for seniors, which are more than happy to insure you later in life (some even if you have preexisting conditions).

10. Pack your bags!

You did it. It’s finally time to fill your new carry-on bag with everything you’ll need for your adventure. What kind of packer are you? Two weeks ahead of time or two hours before your flight?

Regardless of when you start packing, you shouldn't have to start over from scratch each time you travel.

The solution? You guessed it: a list! For long-term trips, I’ve created the ultimate packing list you can use for your journey. Going for a shorter trip? Use the list and cross off items you don't need.

Don’t think you can possibly fit everything you need into a carry on? Here’s the photographic proof of everything I packed for a month in Central Asia.

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 undoubtedly know, travel rarely goes according to plan.

If you tend to get upset when plans change, take a moment before you drive to 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 or your bag end up in another country is part (albeit not the nicest part) of the process – inconveniences, yes, but disasters? No.

All the planning in the world can’t ward off the unexpected, so 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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