The most common question I get when I tell someone where I will be going on an upcoming trip is, “Are you going with a group?” My answer is, “No, I’m going by myself.” Occasionally I go with a friend, but usually by myself. I know many people are scared to go off on their own, not knowing anyone or sometimes even the language. But another thing that draws many people to organized trips is that someone else does all the planning.


I find the planning process to be almost as enjoyable as the trip itself. Yes, it can feel overwhelming at times, especially for my longer trips. But looking online, seeing all the possibilities of the places I can go and the things I can do is exciting. I learn a lot about where I am going, even from reading about the places I don’t end up going. If someone else were to do all the planning, I would not be anywhere near as familiar with the places I travel.


How to Choose a Place

Usually from looking at pictures online and talking with people, a place peaks my interest and I eventually settle on where I will travel on any given trip. Sometimes the destination is chosen  only a month or two before I leave, while other times it is close to a year in advance.


Planning the Trip

One of the first things I think about and look into is passport and visa requirements. Beware that it is usually a good idea to have a passport that is good at least six months from your return date. You won’t be allowed into a lot of countries without this.

Before going on a trip, I read a lot about where I can go and what I can do. Through this process, I learn a lot about where I am going, and come up with a large list of things I would like to do. I figure out which things I definitely want to do and which ones I would enjoy but would still be happy if I didn’t do them. I do not like to plan every minute of a trip ahead of time as it limits my flexibility to do other things I learn about when I get there. It is important to look into the things you definitely want to do when you arrive as some experiences require booking ahead of time, sometimes well in advance. I don’t typically do a lot of this, but I have missed doing some things from not doing it.


While planning a trip where I will be staying in hostels or hotels, I typically book in advance. Not necessarily when I am staying at cheap hotels on a road trip in the US, but otherwise I do. Hostels in many places book well in advance, especially at peak times, which is when I have time to travel. This is the most stressful part for me because it involves a lot of planning how long I want to be in each place, then reading reviews of each hostel. I don’t like having such a firm plan because sometimes I want to stay longer, and sometimes I book too much time. But when going to places such as Europe, I would likely end up in an expensive hotel if I didn’t book ahead. Also, while traveling abroad, I don’t use the data on my phone, making it difficult to find a place last minute when only using wifi. So, it is actually less stressful to plan that part ahead of time, knowing I have a place to sleep each night.

A hostel in Hawaii

It is also important to look at transportation options. If you’re renting a car, make sure there are rental companies where you will be. This is often quite easy, especially if you are picking one up from the airport. When using public transportation, you must ensure there is good transport where you want to use it. For regular routes that have service hourly or better, you can usually book the ticket at the train or bus station. For other, less frequent routes, it might be a good idea to book in advance. It all depends on where you are going. For example, this is true in Europe, but in lesser traveled places like, say, Morocco in the off season, it is unnecessary. Sometimes a quick flight is cheaper and/or saves you a day or more, depending on how far you want to go.

What it can really look like in popular tourist destinations.

Important Step

When traveling alone, I always find a friend to share my travel plans with and communicate with daily. I provide this friend with a digital calendar with all the places I made bookings with listed, color coded by what it is (lodging, transportation, etc.). While traveling, I message this person daily, letting her know I got to where I was going, advising of any changes to my plan, an update on what I plan to do each day that I didn’t already have something booked, and a confirmation that I made it to my hostel again at night. That way, if anything were to happen to me, someone knows where I was last and what I planned to do. It is important to let this person know when I expect to have difficulty finding wifi so they don’t worry or alert the authorities too soon.


What do you do when planning a trip? Share in the comments below.

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Planning a Trip
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2 thoughts on “Planning a Trip

  • September 15, 2017 at 10:28 AM

    Love your post and can resonate with it since I also travel mostly alone.
    Like you I pick the ideas from pictures on instagram, other blogs and so on. I check distances on map since I usually get a car, and then try to plan my days in high level.
    In case it’s a long trip, more than 3 weeks (didn’t have one of those in many years) I won’t reserve accommodation in advance but otherwise I will…

    • September 15, 2017 at 6:31 PM

      That’s great! I’m happy to hear the connection. Yes, if I reserve my lodging ahead of time depends on where I am going. Busy places tend to book early (like Europe), especially hostels, so I will book those. But places that are more off the beaten track, or if I am staying in motels off the highway, I won’t bother. I like the freedom it gives me not to book in advance!


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