How to Plan Your Own Trip

Have you always wanted to travel independently without taking a group tour or using a travel agent? While there is nothing wrong with those things and they can be fantastic given the right circumstance, there’s a great deal of satisfaction inherent in planning your own trip. I realize that this can be a daunting task but after many decades of travel and mostly planning my own trips, I am going to share what I hope are helpful tips and my process for how to plan your own trip.

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Where to Start When Planning Your Own Trip?

Ok, so you’re going to plan your own trip. Congratulations. This doesn’t have to be awful and scary but I will admit, it’s going to take some time and effort on your part but it will be worth it. I would choose your location wisely if this is your first time planning on your own. For example, start with somewhere in western Europe or even within your own country but maybe not Mongolia or Zambia. Let’s not go crazy. There will be plenty of time for crazy in the future.

I think there are two kinds of travel planners. The ones who have some vacation time in a certain month and need to decide where to go OR the ones who definitely have a destination in mind, but then need to figure out when to go. I’ll talk about both.

Choosing Your Destination

Perhaps you already know you’ve always wanted to go to the Greek Islands or hike in Patagonia. Great, you can skip this step (but you do need to pay attention to the time of year). Let’s say you have a week of vacation time in mid-October and you don’t know where to go. You live on the East Coast of the United States. I realize a week isn’t that long for an international trip but for most Americans, this is the reality of our vacation time situation.

In one week you can do a trip basically anywhere in the United States and mid-October is a great time of year in most places. You can also go to Canada, Mexico, or the Caribbean but you would have to check hurricane trends for that time of year. You could also go to Europe but with one week you would have to be strategic. I gave you this random example to show how your time frame, time of year, and place of origin will all factor into your choice of destination. Some destinations are good in any season. You just have to find them.

Choosing the Time Frame for Your Trip

Perhaps you already know where you want to go. You are most definitely going to the Greek Islands next year. Great. So will you go in May or August? Will you spend a few days or 2 weeks? Which islands will you go to? This is when a Google search is your best friend. You can very easily google things like “best time of year to go to X” or “how much time do I need in X”. I will talk more about resources later in this post for how to obtain this type of information but obviously, you can’t just go anywhere any time of the year. Some places are literally shut down in the winter or maybe August is just completely overrun with tourists and you’d rather avoid that drama.

So essentially the first step with travel planning is research!

Make Your Itinerary

What places will you fly in and out of?

Ok, so you have the destination and dates! Some people may just book flights at this point and that could be the next step before the Itinerary IF your trip is more simple such as going to a resort in the Caribbean for a few days or visiting London and surrounding areas. This type of trip requires one round trip flight to one city, so easy peasy. Some trips may require you to fly into one place and out of another. This is called a multi-city option on most flight planning tools. This is why if you are doing a longer multi-country trip or even one country that is very big, you can look into flying into one city and out of another. It’s just one of many considerations.

Making your itinerary also sort of helps you decide how much time you need. You may have thought you only needed 5 days at a certain place but maybe your research tells you to squeeze in another couple of days. If your flight is not yet booked, you will have more flexibility with this matter.

How to Make This Itinerary?

This may be the most challenging part of the process but once done, other things fall into place. My favorite resources is talking to other people who have been there. I also check google for reputable blogs but another avenue I find helpful is looking at tours! Look up a well-known tour company and peruse their itinerary. This can be a good place to start. I find it useful to see where the most popular places are in a certain country and also it lets you know what is possible in a given time frame. You can Google “Two Week Tour to Thailand” or “10 days in Italy” and see what comes up. Then you can customize this for your own preferences. Maybe you prefer a slower pace or maybe you want to jam-pack as much as possible.

Base yourself in One City and Do Day Trips

This is a fantastic option if you want to keep things simple. You will only need one hotel and won’t have to constantly check in and check out. You can wait and plan day trips when you get there if you want. This is an option I choose when I’m tired and don’t feel like running around. And it doesn’t have to be just one city. This will depend on the length of the trip. If you only have 5 days in Paris, you can stay there and do a day trip to the Champagne region, a day trip to Versailles, etc. Another example, I’m going to Puglia, Italy later this year and over a 2-week period will stay in 4 different places, doing day trips from various “bases”. I do not feel the need to “stay” in every city on the itinerary. I chose a few places to base myself in to make it easier to just take a day tour or hop on the train and visit another city. Many tours and itineraries have you doing 1 night here, 2 nights here. This is fine for some people but it involves tons of running around, tons of unpacking, repacking, checking in, checking out, etc. That is time-consuming. Also when planning, it means more hotels you have to research and book.

Just Wing It

Planning your own trip can involve…not planning! Maybe just book the flights and then decide when you get there. Many people do this, especially backpackers who have more time and stay in hostels or are not super picky about lodging. This is not MY preference but it can be done. You don’t need a strict itinerary.

How Will You Get Around?

This is an important consideration when planning your own trip and may play into your itinerary because you can do different things if you have a car. If you are absolutely uncomfortable driving in a certain country, then a certain type of itinerary is already off the table. Not a problem, you just have to adjust your plans. If you are going somewhere that doesn’t have great public transportation, you will likely need your own car or hire a driver. These are sometimes the situations in which I may look into a tour if I REALLY can’t figure out a good way to get around. For example, I wasn’t sure how I’d get from Uzbekistan to Tajikistan to Turkmenistan on my own so I just found a tour. But I have NEVER done a tour anywhere in Europe because getting around on my own is so easy. Jordan is a place where I didn’t want to at first, but I found that renting my own car was the only way to go and it was a fantastic trip!

Flying Between Cities vs Public Transport or Rental Car

Perhaps you are only going to a few big cities in Europe or Southeast Asia. In this case, the train or bus trips between may be too long and you will have to fly. (Side note: I met many young backpackers in southeast Asia that took buses EVERYWHERE even if the trip was 2 days long so…there’s that option). However, many of us don’t have the luxury of time and 2 days on a bus is nota viable option. If this is you, I suggest you take a look into various flight routes between the places you want to go.

You may find that there is no direct flight from say Hanoi, Vietnam to Jakarta, Indonesia but there IS direct a flight from Singapore. This type of information is invaluable for planning your itinerary. For example, I spent a few weeks in the middle east and there were no direct flights from Oman to Jordan but pretty much anywhere in the larger region is accessible via Dubai, so I sort of used that as a hub and spent a night there in between the other places. Finding these “hub” cities in different parts of the world is a great strategy. Within Europe places like London, Paris, Munich or Vienna can act as such hubs. Dubai or Doha, even Abu Dhabi can work for central or South Asia and even Africa. For Southeast Asia, Singapore or Hong Kong are good hubs.

Back to the rental car question. You may want to visit some obscure castles in Germany or different wine chateaus in France or hike in the mountains of Italy. This may be difficult with public transportation and these are the kinds of trips that may require a rental car. (not so subtle segue)

Tips for Renting Car and Driving Abroad

Nervous about renting a car and driving abroad? It’s understandable but don’t let nerves get the best of you. I got you covered with another recent post with tips for international car rentals

Pitfalls of Travel Planning

What you don’t want to do is get married to a strict itinerary, book nonrefundable hotels and then find out that getting from one place to another is virtually impossible or is going to take a ridiculous amount of time and money. You may find that certain flight routes only operate twice a week or every other day. I have found this for Greek Islands, smaller airlines in Asia, or even some European routes, especially since the Pandemic when many airlines decreased the number of flights. I had to change my entire Africa itinerary because of flight routes that weren’t as simple as I had envisioned (ask me to tell you about this..it’s a hilarious and cringeworthy story).

TLDR: It’s definitely worth checking into whether or not a flight from point A to point B even exists at all and especially on the day you intend to travel.

Booking Lodging

This is one of the last steps UNLESS the whole reason I went somewhere was for a certain special resort or spa or something like this. I have been known to change my itinerary because the hotel I want wasn’t available on certain dates. But that’s just me. Booking lodging can be easy if you’re not super picky or can take DAYS of painstaking research.

I am more of a hotel girl. Airbnb has abysmal customer service so I’ve used them less and less, but I do enjoy staying in apartments, especially for longer stays. You can find many apartments on Booking.com…the same ones that advertise on Airbnb. Just so you know. Regardless of what type of lodging I choose, I always research the neighborhood. I will pay more for convenience (and safety) much of the time, especially if I don’t have a car. I like to walk everywhere, easily find meals, a pharmacy, etc.

Again, google is your friend here as well as travel forums (I summarize these resources below). Google “where is the best neighborhood to stay in Mexico City or Buenos Aires”. For bigger cities, this is more important than for smaller ones. Many of the hotel search engines allow you to put in filters such as price and neighborhood as well as others such as parking.

To Summarize: How to Plan Your Own Trip

• 1. Choose Destination
• 2. Choose Time of Year
• 3. Choose Length of Time
• 4. Make an Itinerary
• 5. Figure Out How You Will Get Around
• 6. Book International Flights To and From Your Destination
• 7 Book domestic flights, obtain a train pass, look at bus schedules or rent a car
• 8 Book hotels at each place you are staying overnight
• 9 Decide what daily activities you’ll do in each place. Make your tour reservations or restaurant reservations.
• 10 Figure out what you need to bring.

Other Considerations For Planning Your Own Trip

What Will You Do Each Day?

Once you have an itinerary, hotels, flights, and other transportation sorted, now comes the FUN part. What will you actually DO at these places? This is the part where I wing it a bit, depending on the location. Sometimes I don’t want too many plans. I just want to walk around and see where the wind takes me. Other times I KNOW that I must visit XYZ historical ruins or scuba dive one day or whatever, so I book a tour. I recently visited the Champagne region of France and I knew that I had to reserve cave tours and tastings ahead of time. Some locations are better for winging it than others. And if you don’t know…just ask google.

Do You Need A Visa?

Americans can travel visa-free to Europe within the 26 Schengen countries for 90 days. You can get all the information about visa-free European travel for Americans here. We are definitely privileged when it comes to visas because many other people don’t have it this easy. Most countries in the world are actually Visa-free for Americans.

In the global south, some countries will require a visa. Sometimes this is easy to do online, called an E-visa and you can obtain it just days before you travel. Many countries have a visa on arrival where you just show up at the airport, fill out paperwork and pay a fee. Unfortunately, sometimes it is much more complicated involving a trip to an embassy or consulate or mailing your passport (ugh, and can also get expensive).

You can even pay agencies to do this visa work for you but always be careful with this. Google their reputation first. I got very screwed going to Vietnam because I was only given a single entry visa but needed a multiple entry visa…what an ordeal. This is also part of the reason I took a tour to Central Asia (all the “stan” countries) because they helped with this complex visa process for multiple countries.

One tip for people who travel a ton is to keep a collection of passport-style photos handy because this will save you the time and cost and effort of constantly obtaining these for various visas, international driving permits, etc.

How Will You Access and Spend Money

Oh, I conveniently just wrote a post full of Tips for Using Money Abroad. I think I cover every possible situation here because trust me, I’ve been through most of it.

What Will You Wear?

This is such a loaded topic, one that goes beyond the scope of this blog. My tips are to prioritize comfortable shoes but never bring more than 3 pairs because these are heavy and take up space. Always be comfortable and ready for several weather situations. Bring things that coordinate so that all your clothes sort of work together. Try to respect local customs when it comes to not showing too much of certain body parts. All of this type of information is easily researched on google. I will type “what to wear in Italy in October” or “what is the weather in Mexico City in December”. There are many blogs dedicated to this “what to wear” topic. Some are more “fashion” conscious than others so keep that in mind. My intentions with travel are not to be a fashion model. I prioritize packing light to looking amazing.

Travel Resources for Planning Your Own Trip

Here are the resources I use. I hope this helps.

Flights

Google Flights is my starting point. I find it the most simple and thorough flight search engine. It will alert you if your same route is cheaper on another day that same week. Once you choose a flight you have to choose where to book it. I will always go directly to the airline unless it is a complicated small airline in Indonesia that won’t take American credit cards or something like that. At that point, I will use Expedia. If I’m going to try to use airline points, I now will take several other steps but that is a post for a different time! But now I at least know what flights exist for my destination.

Skyscanner is another great flight research tool. This allows comparing destinations to see which is the cheapest from your starting point. I like the “everywhere” option when I know the date but trying to decide where I should go or what are some good options.

How to Get From Place to Place

www.Rome2Rio.com is fantastic. I don’t know what I’d do without it sometimes. You put your point A and point B and it tells you all the various ways to travel from the flight, to train to bus to the car and even gives price estimates and links for booking.

Traveling around Europe by train? Look into the types of Eurail passes and once you buy one you can link it to the Rail Planner app this makes both planning and obtaining the ticket for each ride so easy.

Hotels

These are really the only 2 sites I use. Sometimes I will find something and then actually go directly to the hotel page and see if rates are comparable. I prefer booking directly than with 3rd parties but I do use 3rd parties for hotels quite a bit because, for every 10 nights, Hotels.com gives you one night free. Make sure you read reviews and change the settings to the most recent otherwise you will only see the good ones! I avoid Airbnb and if I see something there, I will see if the owner has a personal website or I look for it on booking.com. You can get the same things sometimes!

www.booking.com

www.hotels.com

Itineraries and Things to Do in Various Places

Because I’m a blogger and I know many other bloggers, I will turn to certain blogs first for information.

This is not an all-inclusive list by any means but a good start and a good set of references.

France, especially Paris www.solosophie.com

Solo Female Travel, Italy, Mexico www.adventurousKate.com

Greece/Middle East/Solo Female Travel www.highheelsandabackpack

Dubai/Abu Dhabi/Qatar www.expatpanda.com

Sri Lanka/Hong Kong www.yogawinetravel.com

Colorado/Southwest www.organizedadventure.com

Traveling with points and miles/Luxury Family Travel www.worldtraveladventuruers.com

NYC/Netherlands www.wanderlustingk.com

Diving Trips (also tons of Crete and Morocco info) www.midnightblueelephant.com

Backpacking/Partying www.thepartyingtraveler.com

All things Food/Nice Hotels www.theculturetrip.com

Also, look into Lonely Planet forums. You can just ask a question there and other travelers answer. Someone may have already asked your question. It can very helpful for things like “How many days should I spend in this city vs this city” or “What is it like to drive in Sicily?” “Does anyone know a driver for Malawi?”. Another option is Fodor’s. I truly don’t like Trip Advisor but I will use the forums sometimes.

Another source of advice. Facebook communities and groups. I joined a group called “Backpacking Africa” even though I wasn’t backpacking but spent 3 months there and needed tips for how to get around and I actually got great advice and even contact information for drivers. You can search there and find a group for just about anything.

Well, that’s all I got. Ready to plan your own trip now? It will get easier each time, I promise. And it’s ok to ask for help. I still do all the time! Knowing your resources is half the battle.

What questions do you still have? What resources should I add to my list?