What’s the first thing that comes to mind when you hear the word “travel planning”? If it’s beautifully organized spreadsheets, then we’re kindred spirits. Let’s grab a glass of wine and talk about our favorite Excel functions.
If not, you’re in the majority. Travel planning is something non-spreadsheet nerds are happy to delegate. It can be stressful, draining, and ain’t nobody got time for that.
But, my overly-organized self has a theory. People hate travel planning because they don’t know where to start. They feel overwhelmed and like they need a vacation from planning their vacation.
The key to easy travel planning is a game plan.
I don’t think travel planning needs to be overwhelming. There can be so many little pieces that need to come together, like reserving a spot at a coveted campground or securing the right permits. But it’s all about having a game plan. The tiny tasks become much more manageable when you have all your deadlines laid out in front of you and you can check them off a list one by one.
After years of travel planning, I’ve gotten the process down to a science. For me, it’s exciting and inspiring and that’s how it should be for you too.
Every trip I plan uses this process, whether it’s a national park trip filled with day hikes or a road trip down the California coast. While I focus on outdoor travel, these tips will help you plan any kind of trip – even a weekend getaway in New York City!
What tools do you need to travel plan?
I use Google Sheets. It’s free, autosaves your progress, and is accessible on any device (you’ll thank me later when all your details are accessible on your phone!).
For those of you that are anti-spreadsheet, you can use any writing tool. All you need is somewhere to write down all your thoughts and get started travel planning.
So without further ado, sit back, relax, and spend the next 20 minutes learning to simplify the way you plan trips.
The benefits of travel planning
Unless you’re a full-time traveler with an unlimited budget, travel planning can benefit you. Most of us, particularly those in the U.S., only have a limited number of days to travel per year. That’s why I spend so much time researching destinations upfront. I want to spend my time soaking in everything I can instead of frantically planning my itinerary day-of.
Following a comprehensive, upfront travel planning process makes trips a lot smoother and:
- Reduces the amount of time I spent going down Pinterest rabbit holes
- Provides backup plans for rainy days, road closures, and post 12-hour hikes where I’m too exhausted to move
- Allows for unique experiences I’d have otherwise missed, like standing atop the Continental Divide.
Step 1: Determine your destination
If you’re anything like me, you have an ever-growing travel bucket list. So how do you pick from an endless list of inspiration?
Start by asking yourself a few questions:
- Who are you traveling with? A romantic camping getaway looks a lot different than a family vacation with 3 kids. If you’re planning a hike-filled trip, you’ll need to consider the ability level and conditioning of your group. Some campgrounds or backcountry trails have constraints on group size. Figure out who you’ll be traveling with and use that to narrow down potential destinations.
- How long are you planning to travel? The time you can spend away from home depends on your job, family, and responsibilities. For me, the length of my trip involves calculating my remaining PTO after traveling for multiple weddings a year (is my “woman in her mid-twenties” showing?). Figure out what you have to work with and go from there. If you have less than a week to travel, I recommend a destination within a short flight radius. I’m a big fan of using long-weekend trips to explore driving distance destinations in my home state of California.
- When are you planning to travel? The time of year will have a large impact on your destination, particularly for trips where you’ll be spending most of your time outdoors. If you’re limited on when you can travel, ensure this is a good time to visit the destination you have in mind. If you’re able to be flexible, choose to travel at the start or end of the on-peak season for your destination. Straddling the busy season avoids crowds while still traveling during ideal weather conditions.
Make a ballpark budget
Knowing how much you’re able to spend on travel is crucial to planning a trip. Your budget will affect every part of your trip: activities, dining, accommodation, transportation. A ballpark budget allows you to pick a destination that’s affordable for you. A huge perk of nature-centric trips is that they tend to be more budget-friendly than other types of travel.
Once you know with whom, when, and how much you’re spending on travel, you’re ready to pick your destination! Remember that ever-growing bucket list? Take a look at it. Pick a destination that excites you but is reasonable based on the questions you answered.
What if you don’t know where to start when it comes to picking a destination?
No worries! Some of my favorite travel planning inspiration tools are free and easy to use. In fact, most people use them already!
- Pinterest is a visual search engine filled with destination guides and itineraries. Make a dream board of destinations – a visual bucket list. Do you have a lot of pins for a certain destination? It might be your subconscious speaking…
- Travel Blogs are great resources for inspiration and planning. Blogs can provide relatable insight from first-hand experience, unlike some major publications. Plus, bloggers want to help you (me included!). Our passion is to share experiences in the hopes that we inspire you and make your life a little bit easier. I guarantee you that there’s someone out there posting about your dream trip (Hey, it might be me! See if I’ve written about your destination). Find that blog. Subscribe. Search. Consume. Even message for some advice – bloggers will be happy to help.
Step 2: Research things to do
This advice may go against popular opinion, but don’t book your flights and accommodations immediately after deciding on a destination.
Here’s why. The highlights of your trip are the things you’ll see and do. Plan your trip around activities and places. After you’ve figured that out, then book your flights and accommodations.
So how exactly do you figure out what to see and do? Let’s dive into the details.
Attention to all you Type A, spreadsheet nerds: time to get out your spreadsheet and get to work.
Build an activity to-do list
This is my absolute favorite part of planning a trip. It’s what gets me the most excited for the journey ahead.
Generally, the idea here is to start big and narrow down your list later. As you research, write down every activity, hike, landmark, etc. that interests you. I also list out the general location and how many times I read about it throughout my research. Generally, the place everyone says is a must-see is, in fact, a must-see.
Sticking to a few travel planning resources can help you stay on track
- Travel blogs you subscribe to should be your go-to resource. If you already subscribe, you’d most likely enjoy their recommendations for your trip. Check out their site for guides on your destination. While you’re here, check out Well Planned Journey’s posts.
- Pinterest is a great tool for this step. Search for pins related to your destination. Save your favorite pins to a dedicated board to come back to later.
- Google is another great resource. While it may be tempting to open 30+ tabs of search results, stick to the first page or so of Google results. Most often, the first page of results is enough to get a grasp on the top things to see and do in your destination. Searches like these will give you the best results:
- Best things to do in…
- Must-see places in…
- Must-do activities in…
- Itinerary for X days in…
- Lonely Planet publishes great destination guides. Navigate to your destination for top to-dos and tips. You can also buy their comprehensive destination guides to take with you on your trip.
- The Outbound Collective is a site focused exclusively on outdoor adventures. Their content is community-sourced, meaning individuals from all over the world contribute to their site. The Outbound Collective is the perfect site for researching national park trips and other outdoor destinations.
Once you’ve exhausted these resources, stop researching. Don’t beat a dead horse. If you have more than 50 items for a week-long trip, you’ve overdone it.
Pick out your Must-See items
Take a look back over your comprehensive list. What items interest you the most? What items did you read the most about? Narrow down your list to 5-10 “Must-See” items. Pick the things you’d feel guilty about missing. Pick the things that make you most excited.
For those items on your Must-See list, do more research. Do you need a reservation, advanced booking, or a permit? Are there “hacks”, such as going first thing in the morning or paying in cash only?
The things on this list should be your top priority and what you plan your trip around. Make sure you take all steps to ensure you’re able to do/see them.
Sort the remaining items into Interested or Backup
Sort the remaining items into “Interested” or “Backup”. Something you’d like to do but isn’t your ultimate priority? Label that as Interested. Something you don’t want to get rid of but wouldn’t cry about if you missed? Label that as a Backup.
Last, eliminate things that aren’t up your alley – and don’t feel guilty about it! Stay true to your interests.
Step 3: Create a custom Google map
Now that you know what you want to do, it’s time to figure out where you want to stay. Plotting and visualizing your activities can be eye-opening, particularly for road trips. If everything you want to do is in one area, stay in that area. It doesn’t make sense to find accommodation an hour away from where you’ll be spending most of your time.
How to build your map
I like to use Google’s My Maps tool to create a custom map of my activity list. It’s easy to set up and navigate for those who have ever used Google Maps.
- Go to your Google Drive. If you don’t have a Google account, it’s time to join 2020 and make one.
- Create a map by clicking New in the upper left corner, then more > Google My Maps.
- Name your map something that identifiable, like “Destination – Month Year”.
- Customize your base layer by clicking on the “Base Layer” section on the left-hand side. I like to use a more neutral base map, like Simple Atlas or Whitewater. The icons stand out more against a muted backdrop.
- Add layers to your map to distinguish between types of activities on your list. I like to group into 3 categories: Must-See, Activities, and Food & Dining.
- Add everything from your list by typing each item into the map’s search bar. Click on the icon that pops up on your map and click “Add to Map”. You can drag and drop the item between different layers on your map.
- Format your map to make it easy to read. To do this, click “Individual Style” listed underneath your layer name. I like to use the uniform style and display the name of the item, but the formatting world is your oyster.
Check out Google’s full tutorial on how to use Google My Maps.
Analyze your map
Study your map. I’d be willing to bet that the map you develop has natural clusters of activities. These clusters will dictate where you stay and for how long.
Your map will also show you isolated activities. Unless the isolated activity is a Must-See, I’d recommend skipping it. The time you’d spend in transportation to that activity is not worth it.
Step 4: Book your flights
Most likely, getting to and from your destination will be the most expensive part of your trip. If you’re traveling further than a 5-hour drive from your home or internationally, look at flights. Flexibility is the key to finding flight deals.
- Flying is usually cheapest on weekdays. Check prices for different departure/return days.
- One airport may be cheaper to fly into than another. Check prices for nearby airports.
- Different trip lengths can mean different flight prices. Check out flight prices for varying trip lengths by adding/subtracting a day or two to your trip.
The best resource for researching flights
Skyscanner is my favorite tool for researching flights. They show you flight itineraries for all major airlines. You can search for flights at nearby airports for various date ranges. Use the price calendar feature to find the cheapest flights in your travel period. Click the small print “Show whole month” option under the search to access it.
Write down all flight options, including varying travel dates and airports. Pick the one that best suits your budget and schedule.
It’s cheapest to book domestic flights roughly 7-12 weeks ahead of your departure date. For international flights, you should book roughly 3-6 months out. I’ve read plenty of times that Tuesdays are the cheapest days to book flights, but that’s a myth. You may save a few bucks, but it’s not worth waiting around for $10 off a $500 flight.
Frequent flyer programs
Another travel tip? Always enter your frequent flyer number. You can gain or use miles with international partners of domestic airlines. If you aren’t a member of the airline’s frequent flyer program, sign up. Below are the codeshare partners for major US airlines:
- American Airlines: Air Tahiti Nui, Alaska Airlines, British Airways, Cape Air, Cathay Pacific, Etihad Airways, Fiji Airways, Finnair, Hawaiian Airlines, Iberia, Japan Airlines, LATAM Airlines, Malaysia Airlines, Qantas, Qatar Airways, Royal Jordanian Airlines, S7 Airlines, Seaborne Virgin Islands, SriLankan Airlines
- Delta Airlines: Aeroflot, Aerolineas Argentinas, Aeromexico, Air Europa, Air France, Alitalia, China Airlines, China Eastern, China Southern, Czech Airlines, GOL Airlines, Hawaiian Airlines, KLM Royal Dutch Airlines, Korean Air, Seaborne Airlines, Transavia, Virgin Atlantic, Virgin Australia, WestJet
- United Airlines: Aegean, Aer Lingus, Aeromar, Air Canada, Air China, Air Dolomiti, Air India, Air New Zealand, ANA, Asiana Airlines, Austrian, Avianca, Azul, Boutique Air, Brussels Airlines, Cape Air, Copa Airlines, Croatia Airlines, Edelweiss, Egypt Air, Ethiopian, Eurowings, Eva Air, Hawaiian Airlines, LOT Polish Airlines, Lufthansa, Olympic Air, SAS, Shenzhen Airlines, Silver Airways, Singapore Airlines, South African Airways, Swiss, Air Portugal, Thai, Turkish Airlines
Step 5: Book your accomodation
So let’s recap: so far you’ve figured out your destination, what you want to do there, and booked your flights. Now it’s time to figure out where you want to stay.
Figure out where you want to stay
Use the map you created in Step 3 to figure out where to stay and for how long. I like to spend a minimal amount of time commuting. I’d rather stay in a few different areas than spend hours a day getting to and from activities.
If you decide to stay in more than one area, figure out how long you want to spend in each area based on your to-do list. Make sure you stay there long enough to check off all your Must-Sees.
Another factor to consider is the type of accommodations you enjoy. Some people (*cough* my parents *cough*) are hotel loyalists – Airbnb is too hit or miss for them. If this is you, there are endless options to search and quote hotels.
Resources for booking accommodations
Hotels.com is my favorite site for booking hotels and motels. They give you access to “secret” prices. The best perk? You accumulate rewards as you book with them. After 10 stays in a single year, you get a free night for the average value of your 10 stays.
I generally opt for an Airbnb or VRBO. They are great for families or groups. I’ve also found they are better options for more remote destinations. If you’re looking to save money, getting a place with a kitchen can be a great way to limit eating out. Use the search by map feature on Airbnb or VRBO to find places in your areas of interest.
If you’ll be camping or backpacking during your trip, I recommend doing lots of research through the parks system for your destination (i.e., National Park Service, California State Parks, Bureau of Land Management, etc.).
Reservation capabilities and platforms can vary tremendously based on region and park system, so make sure you know what to expect for your destination. If you’re particularly risk-averse, I recommend finding a campground that allows advance reservation instead of first-come, first-serve.
Keep track of your research
As you research accommodations, write down your favorites. Also keep track of price, pros/cons, and general amenities.
Regardless of your accommodation type, pick a place that fits within your budget and your needs. I don’t recommend splurging on accommodations.
Step 6: Determine how you’ll get around
Understanding how to get around once you arrive at your destination is crucial. If you don’t plan, you could end up spending way more than you intended on rental cars or taxis.
If you’re traveling to a city:
Make a plan to get from the airport to your accommodation
Research the cost of a ride from the airport to your accommodation ahead of time. The last thing you want is to start your trip by getting ripped off on a taxi ride. Google search the average cost from the airport to the neighborhood you’ll be staying in. TripAdvisor can also be a great resource for these types of questions.
Check the price of parking at your accommodation
If you’re renting a car and staying within a city, ensure that your accommodation offers parking. This may come at a hefty premium. If you only need a rental car for a day trip outside of the city, don’t rent for your entire trip. Consider a day rental or use services like Zipcar or Getaround.
Determine the best way to get around your destination
Public transportation is a viable option for getting around most major cities. Cross-reference the google map you made in Step 3 with public transportation maps. Find stops that are convenient for your accommodation and points of interest.
Walking is also a great way to explore your destination for short to mid-range distances. A word of caution: be smart, do your research, don’t walk through an area you shouldn’t.
For domestic travel, I recommend Uber or Lyft for trips that aren’t walkable or off a public transit line. Shorter trips can be affordable, particularly if you use the pooled ride feature. Using Uber and Lyft internationally is more difficult if you don’t have an international data plan. In most European cities, taxis are a simpler way to get around.
You don’t have to map out the exact way to get to and from every place you plan on visiting. Have a plan to get from the airport to your accommodation and a general idea of how you’ll get around while you’re there.
If you’re traveling to a national park, going on a road trip, or traveling to a more remote area:
You’ll be renting a car or driving your own. I’d recommend booking a car around the same time that you book your flights and accommodations. You might find better deals at non-airport car rental locations. It’s worth checking out both airport and non-airport rental options to find the best rate, but I typically opt for the airport location out of convenience.
The best resource for booking rental cars
Hotwire.com is my favorite resource for booking rental cars. They offer “Hot Rate” deals where you book a car at a lower price without knowing the exact brand. Hotwire also lets you cross-reference other search sites like Expedia and Kayak. You can also use Hotwire to research rates and book directly through the renter’s site.
Book a rental car that meets the needs of your trip. For any trip where non-paved roads are even a remote possibility, book an SUV with 4WD.
Regardless of your accommodation type, pick a place that fits within your budget and your needs. I don’t recommend splurging on accommodations.
Step 7: Build an itinerary
Now it’s time to put it all together. Those who prefer more spontaneous travel might be inclined to skip this step, but they shouldn’t.
Building an itinerary is a key piece of travel planning, but probably not in the way you think.
How NOT to build an itinerary
A quick origin story: If you haven’t already figured it out, I’m an ultra-organized planner. My apartment may be a mess, but my spreadsheets are color-coded and labeled to perfection. A few years ago I was planning a trip to visit all 5 Utah national parks in one week. I was so excited for this trip and had done so much research that I put together the most intense itinerary. Everything in my itinerary was scheduled down to 15-minute increments. I felt so accomplished until I showed it to my boyfriend. His only reaction was “When am I supposed to go to the bathroom?”.
The moral of the story is this: don’t build an itinerary to schedule every second of your trip. That leaves no room for error or delays or bathroom breaks. That only ends in unnecessary stress. I now use itineraries as a way to identify where I’ve overcommitted myself and then narrow my priorities.
How to build your itinerary
Estimate the time needed for activities and transportation
Group your activities by location. Then estimate the amount of time each activity will take by doing a Google search of “How long should I spend at X?”
For hiking trips, use All Trails to estimate how long a hike will take you to complete. All Trails allows hikers to record elevation profiles and times for their hikes. Looking at actual hiker’s recordings gives you a realistic idea of how long it will take you to finish.
Use Google Maps to figure out the best way to get from point A to point B and roughly how long it will take you.
Overestimate how long it will take you to do anything. My rule of thumb is to multiply the time it will take me to do something by 1.5. Worst case scenario you have some extra time on your hands to explore a nearby vantage point or eat a trailside PB&J. Some days you will be grateful for a few extra minutes to grab a snack or rest on a bench.
Put it all on a schedule
Put activities on a daily schedule and block out transportation time as necessary. When I build an itinerary, I group things by location first. Then I fill in any activities that have any scheduling constraints. This is anything from scheduling a breakfast spot in the morning to arriving at a trailhead by sun up. Fill in the rest of the day with other activities in the area. Make sure to build all your Must-See items into your itinerary.
Make sure your itinerary is realistic
After you’ve put it all into an itinerary format, check to see if it’s realistic. Here are some indicators that you may be over-committing yourself:
- You’ve scheduled more than 12 hours per day.
- You’re walking more than 10 miles on consecutive days (or less depending on your fitness level!).
- There’s no time to relax. Even for a restroom break or a cup of coffee.
- Seeing it all written out makes you feel stressed.
If your itinerary is too busy, go back through and take out things that aren’t an absolute priority. Don’t forget about them though! Change those activities to Backup status in your planning document. Save them for days with inclement weather or more free time.
Step 8: Figure out the details
The final, and most important, part of your planning process is figuring out insurance, visas, and vaccinations. Without a doubt, this is the least fun part of planning your trip. But it’s essential to ensure your trip is as safe and stress-free as possible.
So you may be thinking, I already have health and car insurance, what else could I need? Travel insurance.
Travel insurance covers everything from medical emergencies to trip cancellation to stolen property.
Your health insurance may cover you for domestic travel, but you’ll have limited coverage if you’re traveling abroad. Travel insurance will cover medical expenses if you’re injured on an international trip.
Travel insurance policies also cover flight delays, flight cancellations, and delayed baggage. Most policies also cover trip cancellation for unforeseen circumstances.
Are you taking expensive gear with you on your trip? You should cover anything from a cell phone to photography gear with travel insurance.
Travel insurance costs vary by destination, country of origin, and age. It’s best to get an online quote to understand the cost of coverage for your trip.
The best travel insurance
I recommend World Nomads. It’s recommended by top travel sites, like Lonely Planet, Nomadic Matt, and The Blonde Abroad. World Nomads gives you many coverage options and makes it easy to get an online quote.
Never skimp on travel insurance. You never know what could happen on your trip and it’s worth the peace of mind.
Will you be renting a car on your trip? If so, you might need extra car insurance. Here are some general guidelines:
- If you have a domestic car insurance policy and are renting domestically, your current policy may cover you. Check with your current car insurance provider.
- If you have a domestic car insurance policy and are renting internationally, most likely you aren’t covered and will need to purchase additional insurance.
- If you do not currently own a vehicle and don’t have a domestic car insurance policy, you’ll need additional coverage for both domestic and international rentals.
The easiest route is purchasing insurance through the rental provider. You’ll pay a premium, but have peace of mind that you’re covered under regulations for the country you’re renting in.
Another option is to discuss additional coverage with your current insurance provider. They can help you understand your current coverage and recommend coverage options for your situation.
Your credit card may cover a portion of car insurance
Some credit cards will cover collision insurance for rental cars. This coverage is a common benefit for credit cards targeted at travelers, like the Chase Sapphire Reserve. Check with your credit card company to see if they cover collision insurance for rental cars.
Credit card companies will not cover the liability portion of auto insurance. If you have an existing auto insurance policy, you may be covered. If not, you will have to purchase this separately. I usually do this through the rental car company.
Do your research on vaccinations for international trips. This is so important. I can’t reiterate it enough. Do your research on vaccinations.
This is an easy step to ensure your health and safety while traveling abroad. It’s particularly important when traveling to developing countries.
You should look into vaccinations at least 2-3 months ahead of your trip. Do not wait until the last minute.
The CDC has great information on recommended vaccinations. While some vaccinations aren’t mandatory, most countries have recommended vaccines. You should get every single vaccination recommended by the CDC.
At the risk of sounding like a Big Pharma commercial, talk to your doctor about vaccinations. Your physician can recommend vaccinations or medications specific to your destination.
If this is your first international trip, you’ll need to get a passport. Check with your country’s government for information on getting a passport.
Here’s more information on the process for U.S. citizens. The U.S. Government states that it takes 6-8 weeks after application to receive your passport. Give yourself plenty of cushion to receive your passport before your trip.
Many countries require advance visas. The U.S. Government maintains a list of visa requirements for Americans traveling abroad. This site also gives you information on:
- Travel advisories
- Required vaccinations
- Locations of U.S. Embassies
- Safety and crime
- Health coverage
- Laws and customs
International Data Plan
I don’t recommend an international data plan unless you’re traveling for an extended period. For shorter international or remote trips, set your phone to airplane mode and rely on wi-fi. But… since you’ll have limited data access, make sure you plan.
Before you depart, identify wifi access locations. This could be your hotel or a coffee shop nearby.
Step 9: Download your details offline
Before you depart, be sure to download everything offline. If you’re visiting a remote location, you’ll be without a cell signal for most of your trip. Make sure your itinerary, planning document, reservations, and other confirmation details are available without an internet connection.
It’s also a good idea to scan your passport and credit cards and download these to your device. Google Drive is great for this. You can make documents available offline and accessible from multiple devices.
Download Google Maps offline for your destination. Offline maps allow you to navigate without a data connection. To do this, go to your Google Maps app, select Offline Maps from the menu, and click Custom map. Select the area you’d like to download offline and click Download. I can’t tell you how many times this has saved me on trips when I’m driving through remote areas.
A Quick Travel Planning Recap
Congratulations! You made it through 5,000+ words devoted to planning your next vacation. I hope these steps make your travel planning process less stressful and more exciting.
- Consider when and with whom you’re traveling when picking a destination. Stick to your budget!
- Create a Must-See list before you book flights or accommodations.
- Use Skyscanner to compare flight options, including varying dates, airports, and trip lengths.
- Book your accommodations near the things on your Must-See list. Use sites like Hotels.com, Airbnb, or VRBO to read reviews and book. If you’ll be camping or backpacking, find out details through the respective park service.
- Know how you’ll get from the airport to your accommodation ahead of time. Make sure you know the best way to get around your destination.
- Build an itinerary. If your itinerary has you scheduled for 12+ hour days or gives you anxiety, you’re overbooked.
- Always purchase travel insurance. World Nomads is a great option. Consider additional car insurance if you’ll be renting a car.
- Make sure you’ve gotten all recommended vaccinations and visas ahead of your departure. Check with the CDC and U.S. Government for necessary information.
- Download all your crucial information offline, like itineraries, important documents, and Google Maps.
More Travel Planning Resources
- The Best Road Trip Planning Tools & Apps
- The Complete Road Trip Packing List
- 10 Hiking Essentials: The Ultimate Hiking Gear Guide
- 7 Best Hiking Apps on the Market