How to Plan Traveling

I sometimes forget that not everyone likes to plan a trip. For me, it’s one of the biggest joys of the process of travel - getting into the nitty gritty, researching the hotels and things to do around a city. All of that lights me up, but as I’ve heard from many people, it’s definitely not everyone’s cup of tea. It can feel overwhelming to figure out flights, which hotels to stay in, sticking to a budget, and activities. There are a lot of decisions to make when traveling.

Travel planning becomes a lot easier when you break down the steps and do things one at a time. There’s no need to put together your entire trip all at once, but making one important decision and then another will lead you to a whole vacation. First decide the destination, then the days you want to travel, flights, hotels, and so on. This can be a marathon and not a sprint.

One thing I’ve learned in my many years of travel and planning is that you don’t have to (and I would not recommend) schedule every day with things to do. Most trips I go on have plenty of “free time” and room for surprise and whimsy, as I like to call it. Leave time to wander around, get a little lost, change your mind, and eat somewhere you didn’t have a reservation nor planned.

I’m going to share with you my general guide to planning a trip, from choosing where you want to go to booking your flights and creating an itinerary. Whether it’s a weekend trip or a bucket list destination, these steps will help make the whole journey feel easier and more enjoyable. Enjoying the process is part of a good trip, and knowing how to plan traveling is included in the journey.

A Day I Left Totally Up to Whimsy

When you’re thoughtful about travel planning, it makes a huge difference in how the entire trip turns out. I’m not recommending making a detailed spreadsheet (unless that’s your jam) with every meal, activity, and moment you’re there. What I would do is focus on making decisions that will be the highest impact on your trip ahead of time. These considerations include where you’re going, how much you want to spend, where to stay, how you’ll get around, and what are your non-negotiable activities or must-sees. After you’ve sussed that part out, you can decide how much more and if you want to plan for the rest of the trip.

My trips come with a loose list of things I want to do, and my absolute favorite thing to do is to leave time for unexpected things to happen. Truthfully, it’s in those times that I have the most enjoyment and fun, and that goes for most of my trips. Of course I book a few things that are important to me, but having some surprises along the way only enhances a trip. I want to be able to stay extra time somewhere, eat at a restaurant a local recommends, or walk a neighborhood I had no idea about before I arrived. Your perfect vacation may look totally different. I’m sharing my own methods to my madness, and you should absolutely create your own.

There have been trips I’ve planned months in advance and trips I’ve planned rather last-minute. Both are acceptable, depending on your circumstances, but planning in advance definitely has its advantages. A spontaneous weekend trip nearby is a fun idea. Planning a European Christmas market trip at the last second is somewhat of a nightmare. There are some very practical reasons to consider when planning a trip.

You Have More Choices

On one of my Christmas market trips, I waited too long to book a hotel in Salzburg, a popular destination for the markets, and was left with very expensive options or crummy hotels. I ended up ditching the city in the itinerary because it made no sense. This is a good example of why planning early makes a lot of sense. Outside of hotels being booked up, flights can increase in price, and activities fill up. If you want good choices, plan as early as possible.

You Can Create a Realistic Budget

When you have nothing in the works, it’s almost impossible to make a budget worth anything because you don’t actually know what things cost. Looking at theoretical airfare, accommodations, transportation, food, travel insurance, activities, and incidentals will help you narrow down a proper budget. Sometimes things surprise you in a good way. Maybe that dream destination is well within your price range, or when you book flights they are actually less expensive than you originally thought. Doing some research and planning ahead of time will give you the answers to the questions you’re looking for in creating a budget.

You Can Spread Out the Cost

If you’re like me and like to earn points on your credit cards, planning ahead and booking things in steps prevents you from having everything hit the card at once. One month you can pay for the vacation rentals, and the next you can book the tours or your rental car. By the time you get to your trip, it’s almost completely paid for, making it “free!” That’s the girl math coming out in me.

You Have Time to Research the Destination

Not doing enough research on a particular destination has both worked in my favor and worked against me. I’ve arrived at a place, wishing I had gone sooner. I’ve also arrived wishing I would’ve done more due diligence and realized that city was not the right choice for me. My advice? Do some prior planning so you know where you’ve chosen is the right fit for you and your desired outcome for your trip. Look beyond the social media Instagrammers and TikTokers of the world and figure out if YOU like what you are seeing/reading about a place. Don’t take someone else’s word for it. Unless it’s mine.

You Can Reduce Stress During the Trip

I remember the first time I went to Europe at age twenty. My friend and I went with the book called “Let’s Go,” with not much of a plan and places booked. Because we are the generation of very little parent involvement, we were basically on our own with this trip. Our first few days of our month-long backpacking adventure were spent planning our entire trip. Instead of doing it on the front end, we scrambled to find places to stay, things to do, and every other thing you can think of. I look back and laugh now, but I’ll be damned if I ever do that again. I still have a little of that 20-year-old left in me, but overall I’m reducing my stress by planning as early as I can.

Christmas Market Planning

I’ve found that a lot of people have their own methods for planning a trip, if they are seasoned trip planners. If this is your first or near-first rodeo, I’ll give you some basic steps you can follow for planning a successful trip, and then I’d encourage you to customize as you see fit. There’s no right or wrong approach, or one way to do it.

1. Decide Where You Want to Go

Making the decision of where you want to go could be easy or could take some deliberation. There have been times I knew exactly where I wanted to go, no question, and then other times where I knew I wanted to travel, but where? Sometimes starting with what you don’t want to do or like is a good place. For example, I’d rather not travel if it means camping. Not really even glamping. But I sure do like Italian wine, cheese, and looking at water. How much time you have will also play into where you might choose, and certainly how much it will cost.

2. Determine Your Budget

When you have a destination in mind, it’s time to figure out if you can or want to afford it. A few things to consider regarding budget are:

• Flights or other transportation
• Hotels or vacation rentals
• Food and drinks
• Local transportation
• A rental car, if needed
• Tours and attractions
• Travel insurance
• Shopping (I always go a bit overboard with this one)
• Tips
• Pet care or airport parking
• Incidental cash

A general budget will usually do, so you don’t have to get down to the penny for every category. Having an idea is going to help your perfect vacation stay perfect.

3. Choose Your Travel Dates

I’m lucky because I usually have pretty flexible travel dates. Not everyone does, as sometimes you have to schedule with work, around school, or something else. The more flexible you can be, the more options you will likely have and may find great deals. Flights and hotels can be considerably less or more expensive depending on the day of the week or time of year. A cheap hotel might be a nightmare if it’s 30 minutes outside of everything you want to do in a place. Give yourself some options with when you can travel, if you can.

4. Check Entry Requirements

One of my more famous snafus was showing up to the airport to go to Brazil without a valid visa. Talk about a mess. When you’re traveling to any destination, my best advice is to check the requirements of entry so you aren’t left hysterically crying as the Delta desk agent kindly consoles you and helps you get a refund you might not have deserved. Different requirements will depend on destination and nationality, so be sure to do your research before booking everything else.

5. Book Flights

Booking the flights is such a good feeling. You’ve settled your dates, where you’re going, and you’re ready to hit “purchase” on the airline ticket. Through my years of learning how to travel solo, I’ve realized that I like to get to a destination midday if possible so I don’t have to putz around a city, gross and dirty from a long flight. Whenever that is available at a reasonable price, I take it. You might not mind and want to get there as early as possible. Whatever your preference, you have that luxury of choice. And if you haven’t flown much before, here are my tips for first time flyers that can help you understand what to expect before you get to the airport.

6. Decide Where to Stay

Where to stay is very important to some, and not as important to others. For me, it’s very important because I like to be relatively central, and I like to be comfortable. You will not hear me say “you only sleep there” ever in my life of booking a hotel or other accommodation. Check on Google Maps to see where the things that you want to see are, and make some decisions from there. You might be into luxury, you might be fine with a roach motel. This is a purely subjective topic that I’ll leave up to you.

7. Figure Out How You’ll Get Around

Depending on the type of place you are going, you’ll want to know how you’re getting around. If you’re going to sit on a beach and veg out all week, no car might be okay. Coming to Paris, you’ll want to know all the options of how to get around Paris (because there are many). Not everywhere is the same, and knowing what you’re dealing with is a very good idea so you’re not scrambling at the last minute or paying taxis or ride shares a fortune because of poor planning.

8. Research What You Want to Do

Some of you are going to have a detailed list of all the things you want to experience, as well as times and days you’re going to do them. Others are going to go with zero research. I’m going to say meet in the middle and make the effort on the front end to see if there is anything you might like to do while visiting a place. There’s nothing worse than leaving a place, wishing you had done this or that. For example, saving the Louvre for my last day the first time I came to Europe turned out to be a big mistake, as it was the one day it was closed for the week. Oops.

9. Book Anything That Requires Advance Reservations

Once you’ve got your priorities down, it’s time to decide what to book ahead of time. This is an unsolicited piece of advice, but I almost never book more than one thing in a day, no matter how much I think I want to do. Inevitably you end up exhausted, unable to enjoy the activities remaining, and grouchy. Book what matters most to you and leave the rest of the day to just be wherever you are.

10. Create a Loose Itinerary

Creating an itinerary (loose one, mind you) is where the fun really starts to begin. The trip is becoming more tangible, and you can start to see your days unfold. Pinning all my desired places to go in Google Maps has greatly helped me move around my destination geographically, and reduced wasted time running around cities or countries without much of a plan. Once you save all your spots, you can see where you’re going in any city or destination you choose.

11. Think About Safety

Males and females alike, safety should be part of your planning process, especially if you’re traveling alone. It’s good to know common scams, transportation options, areas to stay away from for tourists, and where your accommodation is and how to get back to it at night. If you are taking a solo trip, my guide on how to travel solo will come in handy, and you can also read solo travel safety tips as well.

12. Consider Travel Insurance

I’ve written an entire guide on how to decide if you need travel insurance, and I would read it before deciding you do or do not need it. Not every trip requires it, but if you’re going on an expensive, non-refundable one, you might want to consider it. Also check with your credit cards and the benefits they provide for your travels, if any. There are several ways to skin this cat (what a gross saying).

13. Organize Your Travel Information

Along the way, so you don’t lose anything, creating a folder (physical or electronic) is a good idea. I always like to have all my confirmations in one spot, and I can tell you now it makes life a lot easier when you do this.

Some items you might add to the folder:

• Flight confirmations
• Hotel or vacation rental details
• Travel insurance information
• Tour confirmations
• Restaurant reservations
• Train tickets
• Rental car information
• Passport or visa information
• Emergency contact numbers

14. Make a Packing List

Friend, do not wait until the 11th hour to pack your bags for your trip. Start checking the weather about a week or so out, and at the very least mentally decide what you want to take with you. I’m excessive. I’ll try on outfit after outfit, take a picture, and then put it aside until it’s time to pack the packing cubes. If you need to buy comfortable walking shoes, travel toiletries, a portable charger, or converters, it’s best to do that ahead of time. Packing isn’t just clothes - it’s the whole shebang of traveling.

15. Leave Some Room for the Unexpected

I’ve said this throughout this guide and I’ll say it again. Make sure you don’t pack your schedule so much that you don’t leave room for the whimsy and surprises that can be the most delightful part of your trip. You never know who you may meet, want to stay and talk to, or decide to scratch a museum you originally planned to go to because you found something more desirable to do. Planning free time might sound counterintuitive, but it’s the best way to not ruin a vacation.

Let's Go!

A perfectly imperfect trip is the kind of trip you will never forget. You’ll expect the unexpected, enjoy the surprises along the way, and roll with the punches that come with travel at times. There are flight delays, rain, fatigue, and other things that happen sometimes. None of these should ruin your beautifully planned trip. That’s part of travel (and life for that matter).

Learning how to plan traveling is not about controlling every part of the experience. It’s about mitigating as many frustrations as possible, and taking care of the big decisions ahead of time so you have the freedom to enjoy your trip. Choose a place that excites and lights you up, set your budget, and reserve the important things. And then give yourself permission to enjoy. That’s the whole goal, right?

If you liked reading this, you might also like reading what to wear to the airport or about my favorite travel bags.

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