Although I’m not a Digital Nomad and do jiggle my many trips and travels around a day job, I did my share of travel planning and organizing. I definitely know how to plan a trip from scratch, believe me.
After countless trips – long and short – I was really surprised when I read the other day a lady asking on Social Media for help where to begin planning her trip.
But come to think of it, helping others planning their trips has been one of the main reasons I started to write a blog, after all.
So I was analyzing and structuring what I’ve been doing without much overthinking for years now and I put it in words and in chronological chapters so that everyone who is a newbie to travel planning can design the trip of their lifetime without the help of any of these big, costly companies.
And once you’ve done it for one destination, it will be a piece of cake doing it for the next one – and all the coming ones. Because, actually, life is long enough for more than just the one trip of a lifetime.
The concept and structure can be adapted to a shorter trip or even just a weekend.
If you are travelling for more than a month, you might not need to get that organized beforehand since getting stuck in a place or ‘losing’ a couple of days won’t affect you so much.
If you have only a quite limited amount of time and you want to see as much as you can without racing mindlessly, the following approach will certainly help you make the best of it.
I’ve sketched in the following four steps how I do it and how it works best for me.
I leave it to you to copy my strategy step by step or just get some inspiration or new ideas. Anyway, there is an extra-chapter at the end supplying you with a safety-net – just in case….
All I want is to encourage you by this thorough planning to try travelling by yourself – if I can do it, there’s no reason you can’t – and I’m glad to assist!
Choosing a Destination
I guess that everybody has a bucket list of places to be visited before…kicking the bucket. If you will be travelling by yourself – and possibly for the first time, there are places more recommendable than others.
I guess Europe should be easy everywhere, no matter which means of transportation you choose: there is an extensive system of public transportation basically everywhere, and of course, you always have the option to rent a car.
In the US you’re fine as long as you’re driving, which might make you not only a single traveller, but a lonely one, too. Since I’m not driving, I did everything by public transport which can be a bit complicated and tricky. So since travelling the US by yourself, you’re most likely to really stay entirely by yourself, I would first recommend another region where you’re chances of meeting other travellers are bigger.
Japan is a very safe place – but you’ll probably be quite isolated and prone to get lonely. Although Japanese are very polite and friendly, they are not as open, and also the traveller community is not as developed as in other South East Asian countries such as Thailand or Viet Nam.
Actually, in Asia, I’d recommend Thailand to you newbies, since there are many single travellers – men and women alike, you’ll find a decent system of public transport and you have the option to join organized trips to remote points of interest, which allows you to get in touch with other individual travellers, if you like.
For the same reasons, in South America, I’d go for Peru. Here you can buy a bus ticket that brings you from Lima all the way down to Lake Titicaca along the so-called “Ruta del Gringo”, i. e. passing all the destinations of interest where you can individually stay as long as you wish before taking the bus to the next stop.
Composing an Itinerary
A assume that you don’t want to spend your entire vacation at a beachfront hotel. To do this, the only advice you need from me is to stock up on sunscreen.
If you want to see as much as comfortably possible over a limited amount of time, I suggest you get a good guide book and consult the internet. Since I’m living in Germany, I cannot recommend guide books in your language, in German I like Dumont a lot, but they are quite conservative. A good guide book will already trace a certain route, so that will give you a first direction how to travel.
According to your interest, you can skip or add stops or travel the suggested route in the opposite direction. But a book will be only the basis of your planning, you should cross check and double check your itinerary and the stops on the internet. Here you can also inquire how long it takes to go from one place to the another.
Don’t even think about calculating your travels based on distances in miles resp. kilometers: going from Hamburg to Berlin takes 90 minutes by a rapid train. The same distance by bus in a Latin American country will take like 6 hours. So the best way is to look for the bus and train schedules online and verify how long it actually takes to go from A to B.
I’d recommend foreseeing at least two nights for a city, if it’s a good gateway for day trips, add one more night for each trip.
Unless it’s a big city with a large number of points of interest, I plan to arrive in the (early) evening so I can go for a short walk and grab a bite. Then I spend an entire day and leave at noon or in the early afternoon of the third day – to arrive at my next destination again in the evening.
At beach destinations, I add about two nights to relax. In addition, this gives me the opportunity to run some errands like for instance doing laundry. Although most laundrettes will have your laundry ready within 24 hours, it’s always safer to slate for an extra day.
Talking ’bout clothes: Like I wrote before, I’m not doing backpacks, especially when I’m meandering a country and don’t stay long in one place. My experience is that after a while you either a) carry a big load of mixed mess around because all your stuff cluttered, or b) you are repacking your junk at every destination anew, or c) you end up wearing the same clothes day by day to avoid a) and b). I’m using a large travel bag with wheels.
Note: Starting your planning, keep the time difference in mind, especially when travelling East; you will lose a couple of hours. It happened to me on my first trips to Asia: I didn’t consider that I’d arrive only in the evening, in addition, tired from the long flight, so I just crashed. This way, having booked two nights, I had only one day for a big city.
Actually, a little visualization helps, so maybe you want to download one of these free calendar templates
A great tool to compose an individual trip is Tripwolf. You can pick a country, a region, or a city and you’ll get many useful information and ideas on what to visit. It’s not as complete as a guide book, but it’s a good supplement to your other sources. You can use it on your computer or download the app that is working also offline.
Good for you: If you happen to go to one of the countries I’ve travelled – you’ll find them all categorized on the homepage – there is an itinerary. It’s embedded in a dynamic map which gives you a good overview and allows you to follow it as it is – or easily alternate it to your needs.
Checking Schedules and Determine Length of Stops
Putting together your itinerary doesn’t mean only checking domestic flights, trains, and busses. You should also check Public Holidays in the region you’re travelling to avoid getting stuck or pay too much (e. g. Semana Santa, the “Holy Week” before Easter, it’s the peak holiday season in Latin America. Don’t even think about not booking beforehand or you won’t get tickets and end up at the most expensive accommodations).
You should find the answer to all your questions regarding your trip such as visa regulations, vaccination requirements, flights, and accommodations, voltage – or public holidays – in the links I put together in my World’s Most Complete Traveller Information.
You should also check visit info of attractions you want to see like for instance museums or even national parks. In the US, at many museums, there’s a – sponsored – day where the entrance is free or on a ‘pay what you wish’ basis so you might want to take advantage of that. In Europe, most museums are closed on Mondays – and some originally enough on Tuesdays, so you better check their website thoroughly beforehand.
You should also pay the official online tourist info a visit to check if there’s something special on like a theater play, an exhibition, or a sporting event you’d like to see.
So after checking all this, you’ll be able to determine how long you’ll stay in each place – and possibly adapt your itinerary accordingly.
The same way I determine the route crossing a country I sketch strolls through cities and neighborhoods, i. e. I check where the points of interest are, what’s a good time being there (it doesn’t make sense to plan to go to a museum that opens only at 11 a. m. at the beginning of your day)
My early booking – and early packing for that matter – are legendary. All my friends make me look like a fool laughing at me booking flights and accommodations and sometimes bus and train tickets months ahead. And in the end, they are all jealous when I get the best seats for the best prices.
Same goes for accommodations whereby I actually do prefer those where I can cancel the booking free of charge up to let’s say a week before arrival. Although I seldom change the route and dates, it does happen that I still stumble over an even better deal after I booked so it’s good to be able to alter or cancel. If the deal is too good and cannot be changed – I still go for it.
An often heard argument against my way of booking so much ahead is that it makes me all inflexible. Yes, that’s true, but think about it: if I have three weeks, i. e. 21 days, and want to see let’s say six to eight places – how flexible can I be? I will have only two to four days for each destination, and checking beforehand usually gives me a pretty good idea, where I can happily leave after 36 hours and where I should stay for a couple of days. A limited amount of time for a road trip doesn’t leave too many options to be ‘flexible’, anyway, so why not booking ahead an saving time and money?!
I probably don’t need to list all the websites like Skyscanner and kayak and expedia where you can find flights at reasonable to cheap prices.
Unfortunately, there is no such thing like the best site, and blogs that claim their recommendation to have the best deals might be right: the best deals for them for advertising. So if you want the best deal, there is no way around checking all the different sites plus the airline’s pages.
The same goes for accommodations. I already wrote in an earlier post that there is definitely no website comparing all the other pages plus all the hotels’ sites an showing you the best price. This can be an orientation, but you might always find a better deal on another site. Another thing that I already wrote in that post is, that booking in advance might be worse in certain areas like some Asian countries, Peru, Mexico – places where you can easily negotiate a good bargain on the spot. So here you have to do a little research, too.
Although Airbnb has conquered the lodging market almost ten years ago, I’ve never ever stayed with them. Simply because I enjoy having someone cooking me breakfast and making my room while I’m gone – I love hotels. But if you are travelling by yourself and do want company from time to time, why not give it a try?! But quite honestly – I’ve never heard from any of my friends that stayed somewhere through Airbnb that they made Pizza with their host or all the great stuff the company promises in their commercials. My friends often found the key behind an old flower pot or had to pick it up at the dry cleaner’s next door and don’t even have a clue what their host looks like; there was no Pizza involved.
Another thing you should consider when booking accommodation is a convenient location (or you will end up in one of the places I described earlier). This is another thing I check beforehand on google maps and print it out.
If you intend to use public transport, just search the city and key in ‘public transport’ and you’ll be surprised. This way I’ve even found online bus schedules for posh beach destination Naples in Florida where yet local people were convinced they had no public buses – here’s the proof.
I love the Internet and every wonder that comes with it – I’m writing a Blog, after all!
Still, there are things I want on paper: I’m hauling big books around the world, and I like my plans and information and confirmations and tickets in paper. So I’m printing everything out (like for instance maps like those map excerpts I posted above). It came handy more than once being able to show the cab driver quickly a piece of paper with the hotel address (and sometimes even a small photograph) on it instead of desperately waiting for an internet connection while smiling at him apologetically.
Plus I like how from stop to stop the folder holding all the printed info gets lighter and lighter.
Solo Travel with a Safety Net
Maybe it’s your first trip by yourself and you feel a teeny bit insecure. Or you want to make sure to get in touch with other travellers. Or you are simply a bit lazy and want to leave the planning to others. Well, you still don’t need to go on an All Inclusive hotel vacation. There are agencies organizing either the entire route or a part of it for you. It works like the Hop On Hop Off system you know from cities: You buy a pass and you can join the tour on certain days at certain stops. Sometimes there are even some day trips and tours included.
The biggest one covering every continent is www.bambaexperience.com. In Asia, you have www.straytravel.asia, and www.greentoadbus.com drives you through South America. You can travel in Europe by www.busabout.com, Australia by www.greyhound.com.au, and in the United States, www.amtrak.com offers travel passes.
Although it’s convenient and fun, you should compare the prices to individual booking and reconsider: Especially the tours in Asia and South America are really pricey compared to what you would pay if you organize your trip by yourself.
But it is definitely an option.
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