HOW TO PLAN A TRIP FROM SCRATCH

Although I’m not a true digital nomad and juggle my many trips with a day job, I’ve done my part in planning and organizing trips. Having organized probably a hundred trips—from weekend getaways to week-long road trips—I’d argue that few people know better than me how to plan a trip from scratch. Planning from step one has become second nature to me.

And in fact, helping others plan their trips was one of the main reasons I started writing a travel blog—always true to the motto If I can, you can do it, too.

Nevertheless, I carefully analyzed and then structured what I’ve been doing automatically and without much thought for years to make my travels smooth and fun from day one.

I’ve put the structure into words and divided it into chronological chapters. This way, even those who are completely new to travel planning can plan the trip of a lifetime. Of course, without the help of large, expensive companies. But I’m sure that even experienced globetrotters will find a tip or two in this post on how to organize even more perfectly.

Once you’ve mastered it for your first destination, the next one will be a breeze. And all the trips to come, too. Because organizing a life long enough for more than just the one trip of a lifetime is important.

If I Can, You Can Do It, Too

The strategy outlined is based on a roughly two-week trip. It can be applied to solo travelers, couples, families, or groups. The concept and structure, however, can be applied to short trips like a weekend getaway, as well as to month-long trips across continents.

If you’re traveling for a longer period, you may not need to plan quite as rigorously in advance. Getting stuck somewhere or losing a few days obviously doesn’t matter as much on a long trip as it does on a multi-day excursion.

If you have limited time and want to see as much as possible without mindlessly rushing, the following approach will certainly help you make the most of it.

In the following four steps, I’ve outlined how I do it and how it’s worked for me for years.
I’ll leave it up to you to follow my strategy step by step or simply get some inspiration and new ideas. There’s an additional chapter at the end that offers you a safety net—just in case. If you’re still a bit unsure, my encouraging strategies in the post “How to Surpass Pre-Travel Anxiety” will certainly help.

With this thorough planning, I only want to inspire and encourage you to try solo travel. If I can do it, there should be no reason why you can’t, too – and I’m here to help!

Choosing a Destination

 I’m presuming everyone has a specific dream destination, or perhaps even a whole list of places they absolutely want to visit. I certainly don’t need to give you any ideas. However, for your first self-planned trips, some places are more recommended than others. This is especially important to consider if you’re traveling alone.

Traveling through Europe should be very easy and convenient everywhere, regardless of your choice of mode of transport. There’s a well-developed public transportation network practically everywhere. And finally, you can, of course, rent a car.

In the US, everything is fine as long as you’re traveling by car. However, solo travelers should keep in mind that traveling by car is inevitably lonely. Trains, long-distance buses, and ferries are good places to meet fellow travelers.

I don’t drive, hence, I always use public transportation. So far, that’s been possible practically everywhere, even where even locals claimed it wasn’t possible. Admittedly, it can be a bit complicated and tricky in places. However, I have had decades of experience that with a little research, good preparation, and a bit of flexibility, it is possible to travel by public transport almost anywhere.

Solo Travel Across the Continents

Traveling solo in Asia is generally a very good idea. However, not all Asia is the same. There’s a huge difference whether you’re traveling solo through Japan and South Korea or exploring Thailand and Vietnam.

I would only recommend the first two countries mentioned if you’re really comfortable being alone for extended periods of time without significant human interaction. While solo travel doesn’t necessarily mean being alone, in Japan and South Korea it certainly does. It’s generally more difficult to connect with locals in Asia. But in Japan and Korea, interaction between fellow travellers is also minimal. This is different in other Asian countries due to the distinctive travel cultures. You’ll meet backpackers in simpler guesthouses, there are bars frequented by travellers, and everything is much more open and communicative.

However, I need to highlight that Japan and South Korea are the best places in the world if you’re concerned about safety. Everything is super-organized, there’s no vandalism, you won’t be accosted. You certainly won’t become a victim of petty crime, even if you’re not constantly watching your belongings like a hawk. As a long-time solo traveler, I’ve found this to be an incredible relief and a great luxury!

Travelling in Gaggles

Nevertheless, since the traveller community is far more developed in Southeast Asian countries such as Thailand, Viet Nam or even Malaysia, I highly recommend those for your first self-organized trip. Even as a solo traveller, you’ll meet many fellow travellers – individuals, couples, and groups, both, men and women. At the same time, there is a decent system of long-distance buses shuttling travellers comfortably between the most popular destinations. In Malaysia and Thailand, you can even travel by train.

Then, you also have the option to join organized trips to popular points of interest. This allows you to get in touch with other individual travellers, if you like. You’ll find a plethora of tours’n’trips for instance on getyourguide*:

Another great region for solo travellers who don’t want to be lonely are Central and South America. This is also a region where backpackers and other open-minded travellers tend to flock in gaggles which grants pleasant encounters.

My Tip

Peru Hop Bus: The Flexible Way to Travel Peru

Peru Hop is a popular hop-on hop-off bus service designed for travelers who want a safe, flexible, and social way to explore Peru. Founded by backpackers, the company offers a unique alternative to public buses or rigid tours, connecting major destinations across the country — from Lima and Paracas to Huacachina, Nazca, Arequipa, Puno, and even into Bolivia.

What makes Peru Hop stand out is its flexibility. Travelers can choose passes that cover different routes and durations, allowing them to “hop off” at any destination, stay as long as they like, and then “hop on” the next bus to continue their journey. This system gives the convenience of an organized route with the freedom of independent travel. All passes include pickup and drop-off from hostels or hotels, making the experience smoother — especially for those new to South America.

Safety and comfort are key priorities. The buses are modern and well-maintained, featuring reclining seats, Wi-Fi (on most routes), air conditioning, and English-speaking guides. This makes Peru Hop a reliable choice for solo travelers, especially women or first-time visitors. The staff on board are known for their friendliness and helpfulness, offering local insights, travel tips, and recommendations for activities and accommodations.

Peru Hop also integrates sightseeing into the journey. Instead of simply transporting passengers from one city to another, the service includes free stops and tours at hidden gems along the route — such as the Paracas National Reserve, the Nazca viewing tower, or the Huacachina desert oasis. These short excursions help travelers experience parts of Peru they might otherwise miss if using standard transport.

Another benefit is community. Since most passengers are fellow travelers, the bus naturally fosters social connections. Many backpackers meet friends and travel companions through the service, which adds to the fun and friendly atmosphere.

While Peru Hop is slightly more expensive than public buses, the added safety, convenience, and experience make it an excellent value for money. It bridges the gap between independent travel and guided tours, appealing to those who want to explore at their own pace without the hassle of logistics.

Overall, Peru Hop is more than just transportation — it’s a flexible travel experience that helps visitors discover Peru’s highlights and hidden treasures with ease, safety, and a sense of adventure.

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”. It is passing all the destinations of interest. At each of those, you can then stay as long as you wish before taking the bus to the next stop.

Composing an Itinerary

After choosing a destination, the first step is planning, followed by preparation.

First, determine the length of your trip. If you only want to spend a short time in the place where you land, be sure to consider the possible time difference: If you fly west, you’ll gain a few hours. For eastbound flights, the time difference can cost you an entire day if you arrive only in the evening. You need to take this into account when making plans for your first destination. I made this mistake on my first couple of 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 actually had only one day for those big mega-cities.

After gathering as much information as possible from the internet—like from my blog, for instance—or a good old travel guide book, decide what you absolutely want to see. It’s handy to make a list of those places. Using a regular paper map or Google Maps, you can sketch a convenient route. Mark all the places you want to travel to and then see how you can visit them in the most time-efficient order possible. If you have a Google account, you can also create a Google My Map. You can then save your itinerary and adjust it anytime you want. I’ll show you in detail how to plan effortlessly with this fantastic tool in my post Travel Planning With Google My Maps.

When sketching out your itinerary, you should build in enough buffer for unforeseen events and also plan stops where you can treat yourself to some rest, for example, at the beach or in a spa. Don’t overpack your trip.

Where to Go?

Consider how many days you have available and then divide them according to the places you want to visit. Of course, this doesn’t have to be evenly distributed: You’ll need to allocate more days for a bustling city than for a traditional village. Perhaps your travel time isn’t enough for all the places you’ve chosen. In that case, you should reluctantly eliminate places instead of putting together an overly tight itinerary. Don’t forget that you’ll still have to travel from one place to another, and public transport might only run once or twice a day. It’s better to leave a little extra time. Trust me, you’ll be able to fill unexpected time slots with ease; you won’t get bored!

Also, don’t even think about calculating your travels based on distances in miles or kilometers. Going from Hamburg to Berlin takes 90 minutes by rapid train. The same distance by bus in an Asian or Latin American country will take up to 6 hours. So the best way is to look for the bus and train schedules online. There, you can verify how long it actually takes to go from A to B.

I’d recommend staying at least two nights in 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. This way, I can still 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. Hence, I 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, 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 in 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 is 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.

Actually, a little visualization helps, so maybe you want to download one of these free calendar templates

Obviously, if you happen to be planning a trip to one of the countries I’ve travelled, I can supply you with a ready-made itinerary that you only need to adapt to your needs’n’wishes. You’ll find all the places I visited over the past years categorized on the homepage.

Checking Schedules and Determining the Length of Stops

Putting together your itinerary doesn’t mean only checking domestic flights, trains, and buses. You should also check Public Holidays in the region you’re travelling to avoid getting stuck or paying 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 assembled 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. You might want to take advantage of that. In Europe, most museums are closed on Mondays. However, others choose 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 like a theater play, an exhibition, or a sporting event taking place that you’d like to see.

So after checking all this, you’ll be able to determine how long you’ll stay in each place. Possibly, you might want to 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, and what’s a good time to be 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)

Booking

My early booking – and early packing for that matter – are legendary. All my friends make me look like a fool laughing at me for 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.

The 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. Therefore, it’s good to be able to alter or cancel. If the deal is too good and cannot be changed, I bite the bullet.

An often-heard argument against my way of booking so much ahead is that it makes me inflexible. Yes, that’s true, but think about it: If I have three weeks, which equals 21 days, obviously, and I want to see let’s say six to eight places – how flexible can I be, anyway?

I will have only two to four days for each destination. Hence, checking beforehand usually gives me a pretty good idea of where I can happily leave after 36 hours. Respectively, 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’. So why not book ahead and save time and money?!

I probably don’t need to list all the portals where you can find flights at reasonable to cheap prices. However, you’ll find some of them in my World’s Most Complete Travel Information.
Unfortunately, there is no such thing as the best site. However, blogs that claim 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 other pages and showing you the best price. This can be an orientation, but you might always find a better deal on another site.

Another thing is that booking in advance might be more costly in certain regions. Some Asian countries, Peru, Mexico – these are places where you can easily negotiate a good bargain on the spot. So here you have to do a little research, too.

Although Airbnb conquered the lodging market about 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?! Nonetheless, quite honestly, I’ve never heard from anyone who stayed at an Airbnb that they made Pizza with their host or all the exciting stuff the company promises in their commercials. Normally, you find the key behind an old flower pot or have to pick it up at the dry cleaners next door. To this date, I don’t even have a clue what some of my hosts looked like. By no means was there ever Pizza involved.

One of the most important things you should consider when booking accommodation is a convenient location. Otherwise, you will end up in one of the places I described in my post xxx. Obviously, I’m speaking as someone who doesn’t drive and relies on public transportation. If you have a car, things are completely different, of course. In that case, you can easily choose accommodation even in the most remote areas.

This being said, you’ll always find accommodation recommendations in all my travel guides, along with a map showing where the accommodations are located and how much they cost. This allows you to easily choose the accommodation that best suits your needs*:

So this is another thing I check beforehand on google maps and print 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 found online bus schedules for the posh beach destination Naples in Florida. Even local people were convinced they had no public buses.

I love the Internet and every wonder that comes with it – I’m writing a Blog, after all! Yet, 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 on paper. So I’m printing everything out – for instance, also those map excerpts I’m showing above. It came in handy more than once, being able to show the cab driver quickly a piece of paper with the hotel address instead of desperately waiting for an internet connection while smiling at him apologetically. Sometimes, it even has a small photograph on it.

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 city tours. 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 the Bamba experience. In Asia, you have Stray Travel, and GreenToadBus 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 bookings 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.

If you need a final little push to step out of your comfort zone and dip your toes into the solo travel pool, I highly recommend reading my post How to Surpass Pre-Travel Anxiety.

There’s More

I’m sure this detailed guide will be a great help to you in your trip planning from scratch. However, I also put together a guide on how I plan a trip with the help of Google MyMaps. Since Google MyMaps is such an amazing App when planning any kind of trip, you should definitely check it out: Travel Planning With Google My Maps.
I’m certain you’ll agree that it’s a great addition to this article.

Pinnable Pictures

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Note: I’m completing, editing, and updating his post regularly – last in December 2025.

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