How to Plan a Trip: Tips from a Chronic Travel Planner

Are you ready to travel but don’t know how to plan your trip?

I’m a Type-A planner and frequent traveler who does tons of research about travel, and I want to share my favorite tools and resources with you.

You don’t have to be as Type A as I am — even the most spontaneous people can get something out of this!

The goal is to not cramp your style but to help make your life easier with a little planning.

Tip 1: Let the universe choose your destination

Not to sound all mystical, but if you are a budget-first traveler, let the whims of airline pricing guide you in where you choose to go.

How to find the best flight deals from your home airport:

• Head to the explore page on either Kayak.com or Google Flights.
• Set your home airport.
• Look for the cheapest flights for specific dates or for anytime within the next six months.

Have you signed up for email alerts yet on Going, Thrifty Traveler, or Jack’s Flight Club? I’m subscribed to all three (the free versions), and they’ve helped me book very cheap flights without having to do any research beforehand.

Be sure to consider the season and weather of your destination before you book your ticket. There may be a reason those flights to the Maldives are so cheap (it’s during rainy season).

Tip 2: Plan your trip backwards (set dates last)

The traditional way of planning a trip is to set your dates and then think about what to do during that time.

But what if, after you look at all the attractions in the area, you realize that you allotted too many days or too few days?

Instead, figure out how long to stay somewhere by listing out everything you want to do and then roughly calculating how much of that you can do each day.

To make your list of activities, here’s what to do:

• Google “Things to do in [city]”. (I love using Google as a starting point for discovering the most popular attractions in a city.)
• Jot down a few that interest you.
• Search itinerary ideas on travel blogs (like mine!).
• Do you already have in mind a few things you have to see and do? Write those down!
• Are you traveling with other people? Be sure to get their input as well.

Even if something is the most popular thing to do in a city, if it doesn’t interest you, then don’t go.

I’m not at all regretful for missing TeamLab Planets in Tokyo because I really wasn’t that interested.

It’s your time and your vacation, so do what suits you.

Tip 3: Visualize your itinerary on a map

Before searching for hotels or booking any travel, you should map out everything on your activity list.

Why? When you see how close (or far away) your activities are, it can help you figure out how much is feasible each day as well as the most strategic neighborhood to stay in.

Here’s how to create the most effective map for your trip:

• Go to My Maps on Google and create a new map.
• Create a new pin for every activity on your list.
• Once you’ve finished, take a look at where most of your pins are.
• You can even map out how long it will take to reach each place.
• Be sure to also mark any airports, train stations, or car rental places that you think you will be using.
• If you’re planning a long trip with multiple stops, look for the most strategic cities to stay in for day trips.

Having a visual of all these pins can help you group activities into different days — and figure out the amount of days you’ll need to make the most of everything you want to do.

I try to stay at least three days in any one city to cut down on travel days (doesn’t it take up a lot time checking in and checking out, lugging the suitcases everywhere? just me?).

Use Wanderlog for the chaotic trips

If you have a chaotically messy itinerary, I would suggest also mapping it on the Wanderlog app.

I used Wanderlog to organize my intense, 2-week trip to Japan, where I had dozens of activities and restaurants pinned each day.

I don’t think every trip needs Wanderlog. Most of the time I’m fine to write down a quick list of things to do in my phone’s Notes app. But some destinations have so much going on that it’s helpful to have extra organization.

Wanderlog kept me SO organized in Japan, and I definitely plan to use it again on another long trip.

(By the way, this is not sponsored, I just love their app.)

Tip 4: Being detail-oriented will reduce chances of disappointment

Lots of spontaneous people boast about the awesome time they had while following their heart or a stray cat down an alley in a new city.

Well, that’s cool and all, but something us extreme planners can boast about is never having to be turned away from an attraction because it was closed or sold out.

Why? Because we did the research beforehand to know about its hours (it’s closed on Sundays and Mondays and only open until 4 p.m.), and we know to get reservations (a booked time slot is required, and tickets may sell out early).

To avoid disappointment, always find out the costs, hours, and reservation information of every activity on your list.

Yes, it’s tiresome, but it will improve the likeliness of getting to do everything you want to do.

Tip 5: Daydream about your future trip until the plans make sense

After you’ve gathered all your ideas, how do you put it all together?

What if you make one of these classic mistakes?

• Choosing to do too much of one type of thing (like seeing a dozen castles on your trip to Europe and not realizing it until the castle fatigue sets in)
• Choosing to do things in one day that are too far apart (you can see the Grand Canyon and Las Vegas in one day, right?)
• Not allotting time for breaks and meals (or mishaps)

To avoid these types of mistakes, here’s the trick:

Visualize yourself moving through the days you’ve planned. Does it feel doable, enjoyable, fun?

Consider the type of traveler you are: What pace do you want to see and do things?

Are you looking for fast-paced days where you’re doing four or more activities? Or slower-paced days where you may only have one or two activities? It’s up to you, and it may totally depend on the destination.

I’m more of a slow-paced traveler. I like to try for one or two activities a day, ideally one in the morning and one in the afternoon, so that if there are any travel mishaps (missed bus, wrong turns), the whole day won’t be ruined.

But sometimes if you’re in a big city where things are very condensed, it will be easy to knock out several activities in the morning.

Don’t make your itinerary too restricted (or too loose)

Mix it up — schedule some open activities (like a hike that doesn’t require reservations) alongside more restricted ones (theatre tickets, for example).

Tip 6: If all else fails, default to spontaneity

There have been times that I’ve done all the research and been truly stuck as to whether or not to include an activity on my itinerary.

For example, when planning my trip to York, I had no idea if I should make a day trip to Chatsworth House or just spend a second day in York. Would I need two days in York? I had no way to know what my future self would think.

So, I put it off for my future self to decide. When the day came, I eventually decided that yes, I did want to go to Chatsworth House, so I booked the train tickets and admission tickets online the night before.

As a hardcore planner, I don’t often leave it up to spontaneity, but sometimes, it truly is the best option.

Tip 7: Do your homework on your destination

You’ll save a ton of time by researching these four things before your trip:

• Money
• Transportation
• Phone service/data
• Language

Here are my best tips and resources for these four major things when traveling:

Currency:

• Want an easy way to estimate currency exchange rates? For iPhones, calculate exchange rates on your Calculator app (yes, really). Select the “convert” option and then select your two currencies. So simple.
• Get a debit card that refunds any ATM fees. Changing currencies and dealing with money can be simple if you have the Charles Schwab debit card (U.S. based). I’m obsessed with this bank, and I hope they never drop their benefits. Not only do they never charge ATM fees (anywhere in the world) but they REFUND any ATM fees that are charged to you. Also, you get the best currency exchange rates whenever you withdraw cash (in any country). Amazing.
• Get a credit card with no foreign transaction fees. I also recommend getting a credit card with no foreign transaction fees (Capital One’s Venture X card is my ultimate favorite). I’ve had my Capital One Venture X credit card for a few years now, and accessing airport lounges is my absolute favorite perk of the card. Every lounge is different, but most have a buffet available where you can eat and drink to your heart’s content. The annual fee of this card is high, but it evens out with the $300 annual travel credit and 10,000 anniversary miles you get (on top of lounge access and free TSA PreCheck or Global Entry)!

Transportation: Research how the subways/buses work before you go. How will you pay? Will you need an app? Remember that some countries use different apps altogether.

In the UK, we could tap on/off the subways with our contactless credit card. In Japan, we had to use a digital IC card. Every country is different, so don’t assume it’s one way and then get stuck in a station wasting time trying to figure it out.

Phone data: Will your plan cover you abroad? Do you need to buy data? I’m lucky that my current phone plan has global data. But if yours doesn’t, look into digital sim cards. Also be sure to pack a portable charger (this is the one I use).

Language:

• Learn the language, at least some of it. Research a few key phrases to say during your trip, if you’re visiting somewhere where the official language is different from the one you speak. “Please,” “Thank you,” and “Excuse me” will take you far, so those are some good basics.
• Use translation apps. I also recommend using the image tool on the Google Translate app. Google Translate has come a long way, and I found it to be helpful to get a general idea of translations on street signs and posters during my most recent trip to Japan.

Tip 8: Maintain your best attitude no matter the circumstances

Planning a trip properly takes a lot of time and effort, but it will be worth it to have a smoother, less worrisome travel experience, allowing you to see things you could only have seen if you planned.

However, I don’t want to make it seem like planning will solve every eventual problem on your trip and that you won’t ever run into difficulties or disappointment.

The world is an imperfect place, and we don’t travel so that everything will be fine and dandy, we travel to experience new cultures and new places.

These places will have their own problems, such as natural disasters, cockroaches, and delayed flights.

Yes, I have slept in rooms infested with cockroaches (twice in Hawaii), and I have been turned away from restaurants for not having a reservation (I’m not the best about planning meals), and I have had my group trips cancelled and I have even been yelled at by a French bus driver (for reasons I still don’t quite know).

It’s all part of the adventure. Develop skills to help you adapt, pivot, and problem-solve on the go. Maintain your best attitude throughout because, in the end, no matter how much you plan and prepare, there’s nowhere in the world where you can escape all of life’s problems.

The more you travel, the more you will realize this fact and accept it. So whether you are planning your first trip or your fiftieth, plan to have fun, no matter what happens.

What to Pack: Favorite Travel Essentials

• I really recommend these compression packing cubes. They’re very thick and durable and allow you to pack more than you expect.
• I also love this travel backpack that opens like a suitcase, fits almost as much as a carry-on, and has tons of pockets as well as a strap to attach to your luggage handle. It makes traveling so much easier and more organized. It also fits nicely under the airplane seats.
• I bring this AirFly receiver for AirPods with me on long-haul flights, so I can connect to the plane’s video screen with my own AirPods.
• I no longer hop on a flight without wearing my Sockwell compression socks because they really do help relieve/prevent leg cramps from sitting so long in one place. I have the lotus pattern, but there are other patterns to choose from, such as this cat pattern or this flower pattern. See all sock patterns in the Sockwell storefront.