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Real talk – trip planning can make you feel overwhelmed as hell.
From researching the cheapest ways to get from point A to B to scouring the web for the best places to visit, it’s easy (and totally normal) to feel anxious.
But planning your next adventure should be as stress-free as the trip itself.
Over the years of planning my own international, backpacking and road trips, I’ve made plenty of mistakes. I've learned from these experiences to fine-tune and simplify the planning process. I want to share this easy and robust way to plan your next adventure that so that it fits your budget and travel style….without any of the stress.
In this in-depth guide, I’m going to show you step-by-step how to plan any kind of trip. Using a trip I planned to Hawaii in 2017 as an example, I’ll show you exactly what you need to do to get the most value out of your time and money, while minimizing any potential risks as you prepare for your trip. You’ll learn how to do the following in a simplified and affordable way:
So let’s start planning your adventure.
If you want to follow along using my trip planning template, you can download it here.
“What am I supposed to plan?”
“How much am I supposed to plan?”
These are common questions I hear all the time. But the answer to both really depend on what you want out of your trip.
Do you prefer to travel with a structured day-to-day itinerary or a more “let’s go with the flow” kind of style? A day-to-day itinerary will be more detailed and require additional research than one that’s more spontaneous.
Are you looking to catch up on some rest and relaxation or trying to see as many cities as you can? Your pace will guide you as you start planning the activities you want to do on your trip.
A trip with your family can be quite different than one with your significant other. If you decide to travel with your family, you may want to shy away from traveling to popular honeymoon or party destinations.
Who you will be traveling with will influence decisions around where to go and what activities to do.
Although Hawaii is a top destination for family vacations, it’s also a hot spot for honeymooners. As my family and I traveled through Maui, The Big Island, and Oahu, there were several times when people made comments about my brother and I being a couple. Yeah…it’s as awkward as you think!
In Maui, I asked a couple of honeymooners to take our photo in front of a stunning sunset. Everything was cool and all, until they just had to say “What a beautiful couple… kiss each other!” Hence, why our body language is so awkward in this picture.
“I’m too poor to travel”
“I don’t have enough time to go anywhere”
These thoughts are enough to stop a lot of people from adventuring. But remember – YOU are in control of how much it costs to travel.
In order to figure out how much you can spend on your trip, take a look at:
Your budget will provide direction and focus as you start planning. Deciding on what you can and can’t do on your trip is much easier when you have your budget telling you what’s feasible.
Working a full-time job, I have a limited number of personal days off. I decided in December 2017 to budget the majority of my vacation time (10 days) to spend with my family in Hawaii 2018.
I also a personal goal to spend less than $1,500 on the trip. As I worked hard to save, I planned around this budget. I found it easier to figure out what accommodations I could afford and what types of activities fit my budget. More on that later.
Most of the time, we already have our destination picked out – whether it’s a place off our bucket list or from a scene in a Netflix documentary we just watched.
But no sweat if you don’t have one picked out…this is the exciting part! There are so many places to get inspiration from to help you decide where you want to go.
Hawaii had been at the top of my parents’ bucket list since they got married in 1989. They finally decided to turn the idea of Hawaii into a reality 28 years later and wanted me to plan the trip. During my googling fury, I found that reading through other travelers' recommendations to be incredibly insightful for determining which islands to visit within my time frame. As suggested, we set our sights on Maui, The Big Island, and Oahu.
Pinterest and Instagram are overflowing with stunning pictures. If you find some places that tickle your fancy, google them and learn more.
Oddly enough, the first road trip I ever planned was actually inspired by a picture an ex posted of Zion National Park on social media (yes – I was stalking, don’t pretend you don’t…). The breathtaking view of the canyons against the sunset was enough motivation for me to get off my ass and travel out there to see it myself.
What’s a better way to know where to go than from suggestions by other travelers? Research travel blogs and reddit (subreddit r/travel) and start building your bucket list.
You can find yourself in some incredible places (for cheap!) if you book a flash deal for a flight you like. Tons of flight search engines will send you alerts on flash deals if you subscribe.
I’ve been subscribed to The Flight Deal and Fare Deal Alert since 2012 and have been receiving daily notifications of flights that cost $0.06/mile or less. I scored a $75 round-trip flight from Houston to Boston for a weekend getaway.
Groupon features flash deals for travel experiences and hotels all around the world. My friends I snagged a 5-day trip to Iceland in 2015 for our group of four for $5,000! The trip included flights, accommodation, transportation and a few different regional tours.
When you travel will make a difference on the kind of experience you have. Do some research on your destination and weigh out the pros and cons to help you decide when you want to visit.
Traveling during high tourist season means you'll enjoy the best weather your destination offers. But this also brings more crowds and higher prices. In contrast, low season is when the least amount of tourist activities take place, usually due to weather conditions. However, you’ll enjoy a much quieter experience at a lower cost.
For a nice balance between the two, consider traveling during shoulder season. This is the time period between high and low season, where you can still enjoy mild weather without overpaying.
For instance, visiting Hawaii during high season means paying for accommodations at prices that are as much as 67% more than prices during low season. And depending on which island you visit, crowd levels can be 25% to 50% higher than low season.
Since travel seasons vary by region, research your destination ahead of time to figure out when it’s best for you to visit to get the experience you want.
Cultural events, like Washington DC’s Cherry Blossom Festival or Brazil’s Carnival, attract people from all over the world. Yup - more crowds, more expensive. Check the Travel Event Calendar for your destination to plan appropriately.
Ya’ll don’t want to end up like my parents when they accidentally crashed Queen Elizabeth II’s Diamond Jubilee (60th anniversary celebration) in 2012. Because London wasn’t originally on their itinerary, they had no idea this event was going on until they showed up and couldn’t book a single hotel or hostel!
Time to make your trip officially official…let’s book that flight! As someone with a low-key fear of commitment, this is one to be excited about. Especially when you get a good deal!
Since 2015, CheapAir.com has published annual airfare studies to provide insight on the best times to buy an airline ticket. The 2019 Annual Airfare Study analyzed 917 million airfares in over 8,000 markets. Here’s what they found:
Find a cheaper flight with a long layover? If it's in a city you find intriguing, take advantage of that time and explore.
Because flight fares change constantly throughout the day, knowing the perfect time to buy can be tough. Price alerts are a simple way for you to get notified when prices change for your desired flight.
Subscribe to your favorite flight search engine and receive alerts to better your chances at booking your flight at the right time.
Because I check my phone notifications more frequently than email, I prefer alerts from Hopper. It’s a free mobile app that’s easy to use without annoying ads and alerts are sent directly to your phone. The best part? Each alert provides a recommendation on whether to book the flight now or wait. As a person that struggles with on-the-spot decision-making, this features makes it easier for me to pull the trigger. Hopper claims to have a 95% accuracy on flight price predictions up to 1 year in advance.
Many credit cards offer several ways to earn points from every day spending, which can be redeemed for travel.
Credit card sign-up bonuses are a way quick way to earn as many as 60,000 points, which is enough for a free round-trip flight anywhere in the world! So why not earn points from your regular spending and start traveling for free.
It was total Amateur Hour the first time my mom’s friend told me how she traveled to Thailand on pennies. Fresh out of college with my first credit card on hand, the concept of points and miles was so foreign to me.
But I started studying the strategies on Million Mile Secrets, which broke down the art of earning points without overspending. I also learned how to get the most value from points for travel so I could make them last longer. I found their in-depth "Beginner’s guide to credit cards, miles and points" the perfect place to start learning and earning.
Thanks to Million Mile Secrets, I was on my way from Houston to Hawaii (and back) for 74,000 points and no cash out of my pocket. Can I get a “hell yah”?!
You know how people say time is precious? Well, it’s even more so when you’re traveling.
Don’t waste time in your hotel each day Googling what you should spend the day doing. Instead, prepare an activities list to bring with you.
Your activities list will serve as a quick reference guide of your top activities you want to do on your trip. Doing the research before you go will allow you to spend more time actually enjoying these activities in your destination.
A few good things to research are:
At first, your list will be a hot mess – cluttered with details for every single thing you want to see and do. But focus on the pace and budget you set when you started planning. This will help filter out and prioritize your top activities.
Here is the list of activities I prepared before heading to Hawaii. It’s short, sweet, and informative enough for me to make quick decisions on where to spend my time for each island.
I find scheduling activities for specific days of the trip makes me feel too constrained. For instance, if I chilled at the beach longer than anticipated or ended up getting stuck in traffic while riding the public bus, it’s easy to fall behind schedule. And when this happens, I start to feel anxious (I know, it’s a personal problem).
Instead, I prefer take this list with me and decide day of (or the night before) what I feel like doing. This gives the flexibility I need to adjust to things out of my control like weather, travel delays and my energy level.
This was a lesson I learned the hard way. Making my way to Nepal, my first of two flights was cancelled due to heavy fog in India. Because my itinerary was jam packed and didn’t leave enough flexibility, I experienced a domino effect of missed flights, rescheduled accommodations and a cancelled trek reservation. It was stressful trying to figure out new plans on the spot.
Avoid the stress and leave room for flexibility in your itinerary!
Figuring out your travel situation before hand will not only save you time and money, but also minimize your risk of being a victim of scam!
Now that you have an idea of the things you want to see and do, research transportation options for getting around.
“Is public transportation available?”
“Should I get a rental car?”
My family decided early on to rent a car in Maui and The Big Island. Not only were our top activities spread across the islands, but we also wanted to personally drive the Road to Hana in Maui. The famous twists and turns of this drive were ones we wanted to experience at our own pace.
However, as I researched transportation options in Oahu, I found that public transportation was readily available in central Waikiki, where most of our top activities were located. So we skipped on the rental car in Oahu to save money.
Some cities offer daily, and even weekly, passes to purchase at a set price for unlimited rides. If you plan to use public transportation often, this can help you save major cash.
Although a convenient option, the total cost of renting a car can sneak up on you quickly when you take into account parking fees, tolls and gas.
Keep in mind that convenience always comes at a price. Cheaper transportation options typically take longer to get to your destination while faster, more direct options are often more expensive. So which do you choose? Reflect on how much your time is worth while keeping your budget mind.
Don’t take time away from exploring to wait in long bus lines or stuck in traffic.
Depending on your style and travel group, you may choose to book accommodations ahead of time or none at all. If you make reservations, make sure you print out (or screenshot) your booking confirmation and contact information in case any issues arise.
I prefer to make accommodation arrangements ahead of time to avoid running the risk of everything being booked once I get there. To make sure I get a comfortable and enjoyable experience within my budget, I dig pretty deep through customer reviews and price comparisons.
I tend to wait for last-minute hotel deals to book day of.
I’ve had positive experiences booking last-minute deals from Priceline’s Hotel Express Deals. If you don’t mind not knowing which hotel you’re booking until you make the reservation, you can save up to 60% (honestly, the element of surprise adds to the excitement!).
The great thing about camping is that you can find a campground for any budget. Private campgrounds are typically more expensive, while publicly owned campgrounds (federally and state-run) are more on the cheaper side. If you want to camp for free, consider dispersed camping. This is where you camp anywhere outside of a developed campground. There are now services, like trash or restrooms...but hey, it's free!
Another benefit to camping is that there are many that operate on a first-come, first-serve basis. So if you decided to visit a National Park at the last minute and all of the reservable campgrounds are unavailable, look for a first-come, first-serve campgrounds to stay at.
I prefer to camp at public campgrounds. Recreation.gov is my go-to when searching for campsites and lodging across the United States.
Arriving in a new, unfamiliar location can be confusing and overwhelming, especially if you don’t speak the language. Having a plan of where you want to go and how you’ll get there will make your first experience in your destination seamless, positive, and scam-free.
If you’re using public transportation, figure out which bus or train lines you’ll need and the hours of operation. I also recommend to have the address of where you want to go handy, in case you need to ask for directions.
If you plan to take a taxi, it’s a good idea to get an estimate of how much it will cost to get to your destination so you don’t get ripped off in the haggling process.
If you’ve got some time until you can check-in to your accommodations and want to explore the city, find services that will safely store your luggage.
Picking up the rental car in Maui and The Big Island gave us the freedom to go anywhere once we arrived. However, our arrival in Oahu required more preparation since we were relying on public transportation to get to our AirBnB for check-in. I compared prices for airport shuttles, buses and Ubers, but ultimately decided to take the #19 bus towards Waikiki.
Nobody plans on getting sick, injured, missing a flight or having valuables stolen on a trip. But it can happen to anyone, anywhere. Preparing for the unexpected can help protect you from health, safety and financial risks.
The best way to minimize the risk of injury, illness and crime is to know how to protect yourself. Whether you’re traveling abroad or camping in the wilderness, start by asking yourself these questions:
Was I scared sh*tless when I crossed paths with a black bear as I hiked down Half Dome? Yes. But was I relieved to know that I was supposed to make as much noise as possible to scare it away? HELL YES.
I’m definitely guilty of saying “I’m healthy, I won’t get sick” and “I’ve never had an issue with flights before”. If you’re guilty of this too, don’t let these be your famous last words.
Traveler’s insurance financially protects you for a wide range of risks - from trip cancellations to overseas medical expenses to damaged or stolen gear.
The cost of traveler’s insurance depends on a few factors, including length of travel, age of travelers and coverage type, but you can expect to pay 4%-10% of your total trip cost. For instance, if your trip is worth $2,500, you’ll likely pay in the range of $100 - $250 for coverage.
True…this is an added cost. But you can travel stress-free knowing you won’t have to pay tens of thousands of dollars in medical bills if you have an emergency abroad.
Although I haven’t had personal experience with them, World Nomads seems to be highly recommended by fellow travelers due to their wide range of coverage options. You can easily get quote by entering a few pieces of information about your trip.
Nomadic Matt provides a thorough guide for finding the best travel insurance that fits you.
An astounding number of American passports (300,000 to be exact!) are reported lost or stolen each year. Making photocopies of your passport and other ID makes it easier to prove your identity and get a replacement passport abroad.
You’ll also want to make photocopies of any credit cards (front and back) you’ll be bringing in case they are lost or stolen.
Email yourself these documents to have a digital version you can access at any time. Or print them out and carry them with you.
In case of an emergency, it’s important that others know where you plan to be and when. Email your itinerary to a trusted friend or relative.
Planning my trips in Excel makes it easier for me to email a single file with all of my trip details to my family and significant other.
The best kind of decisions you can make when it comes to traveling are informed decisions. STEP is a free service you can enroll in to receive updated information on emergencies, civil unrest and evacuation instructions in your destination.
Enrolling is simple. All you have to do is create a free account and provide your traveler information and emergency contact.
All of the hard work in planning your trip is finally done. Your trip initially started off as just an idea or dream, but you’ve turned it into reality.
But as you wait to depart, there are a few loose ends to tie up to make sure you’re as prepared as possible.
If you’re traveling internationally, make sure you have a valid passport and any required visas and immunizations before you go.
For U.S. travelers, Travel.State.Gov is your one-stop-shop for finding out your destination’s requirements.
Avoid being blocked from accessing your account and stop wasting money on foreign fees while traveling abroad.
Don’t get blocked out of your own account! Let your bank and credit card companies know when and where you will be traveling.
You don’t want to be sh*t out of luck if your primary credit or debit card is lost, stolen or flagged.
Store your backup card away from your primary card to minimize the risk of both being stolen. For example, while you're out exploring, keep your primary card on you and your backup card in your luggage at your hotel.
Fees are charged every time you use a credit card or withdraw from an ATM while abroad. Fortunately, many credit cards offer no foreign transaction fees and many debit cards also offer no foreign ATM fees. Save your dollars from foreign fees and put them towards fun things on your trip!
Using my Chase Sapphire Preferred for credit card purchases abroad, I never pay a cent for any transactions. Another advantage is Chase’s customer service. After I found fraudulent charges on my account after returning from Nepal, I found Chase’s process to dispute these charges quick and easy. The money was even reimbursed that same day.
For instances where I need to withdraw cash while traveling, I’ll use my Ally Bank debit card. Instead of being charged the typical 3% - 5% foreign transaction fee, I am charged a much more reasonable fee of up to 1%. I even save on withdrawal fees for domestic travel - regardless of which ATM I use, I’m charged $0 in ATM fees.
The opportunity to learn new cultures is the beauty of traveling. But it’s important for us to be respectful and open-minded of the cultures welcoming us as guests.
Hand gestures are a common way to communicate, especially if you’re in a country where you don’t speak the same language. But not all hand gestures are universal. Popular gestures in your culture may be extremely offensive in others. Don’t be that person giving the thumbs-up to the taxi driver only to find out you just gave the middle finger!
Refine your manners even more by learning a few common words like “hello” and “thank you”. It's incredible how far this small effort can get you on your travels…it can even earn you respect from the locals.
It’s also recommended to learn (or write down) phrases that will help you communicate any dietary or medical conditions you may have. This will minimize any potential risks to your health and safety.
“I’m allergic to nuts.”
“I have diabetes.”
Offline maps gives you the ability to get directions and know where you are even without mobile data or WiFi available. All you need to do is turn on your phone’s GPS.
Google Map’s “My Maps” is a digital and highly customizable web mapping tool. Create your own map with points of interest, share it with your travel group, and download it offline.
A badass trip is one of those things that’s actually exciting to save money for. With your trip budget established, you have a clear goal of how much you need to save.
However, it’s hard to know where to cut back and save if you no idea where your money is going in the first place.
Understanding your money habits will make it easier for you to take control of your money and have it work towards your goals.
Write down all of your expenses over the last month or so. Soon, you’ll have a clear picture of where your money is going.
When I did this, my mind was blown when I saw the amount of money I’d blow on dining at restaurants, clothes and getting my eyebrows threaded (although I still feel like this is an essential…).
Take control and tell your money exactly where you want it to go by creating a monthly budget. For each dollar of income you plan to receive for that month, allocate it to your different categories, like housing, utilities, food, and transportation. I personally create a category for travel as well.
This exercise challenges you to cut back on unnecessary spending to save more for things that are important to you.
Track each transaction against your budget to make sure your spending aligns with your plans.
Saving money is challenging. So don’t worry if you’re having a hard time at first. After a few months of being disciplined and sticking to your budget, you’ll be saving money in no time! Remember, it takes 21 days to create a habit. So be patient with yourself.
One trick that helped me change my spending habits was to think about my goals every time I wanted to buy a non-essential. I’d ask myself “Would you rather spend your money on this dinner when you have food at home? Or use this money on your trip to Hawaii?” Forcing myself to actively put money into perspective made it easier for me to cut spending.
The two apps that have personally helped me budget and track expenses are Inuit’s Mint and Dave Ramsey’s EveryDollar. Both apps are free, intuitive to use, and have powerful infograms that provide detailed insight on your money habits.
Shit. Is getting. REAL.
It’s almost go-time and the only thing separating you from your adventure is packing.
I used to feel overwhelmed by packing when I first started traveling. I didn’t realize how much “stuff” I needed for my typical, every day routine. And I didn’t know how I was supposed to pack all of it.
It’s easy to over pack, especially with all those “just-in-case” items. But remember, YOU will be accountable for carrying around everything you bring. So the lighter, the better!
The more trips I went on, the more I figured out exactly how much I truly needed. I learned that I can always do laundry or buy items I forgot to bring while traveling.
After a few trips, I evolved from a self-proclaimed over-packer to an efficient traveler.
Regardless of where I’m going or the kind of trip I’m on, here are the essentials I never leave without:
As a “pack less, travel light” kind of girl, my rule of thumb is to bring no more than what can be packed into a carry-on bag, especially for trips that are less than one month.
I’m also going to let you in on my secret sauce for packing efficiently enough to travel with just a backpack. The rolling technique. I roll my shirts, pants and even underwear to save space and keep my clothes wrinkle-free. Finally, those egg roll rolling skills my parents taught me when I was younger finally came in handy.
How and what to pack will be unique to you. I recommend packing a few days in advance to give you enough time to strategically pack what you need without feeling rushed.
To get through the packing process, I always think about what Bubba Sparxxx said in my favorite 8th grade song, Ms. New Booty:
“Get it right, get it tight.”
This part is simple – Embrace the experience. Feed your soul. Do what makes you happy.
You deserve it. You did all of the hard work up-front for a stress-free adventure. Now go out there and LIVE.
When you plan your own trip, you are in control of how much you spend, what you do, and where you want to go. Planning helps you make the most of your time and money while minimizing risks as you travel.
Your first thoughts about planning your next adventure can be overwhelming, but it doesn’t have to be. Taking it step-by-step makes the planning process easier, less stressful and even enjoyable. Planning a trip is simple enough that anybody can do it.
Even if you’re not a travel expert.
Even if you’ve never planned a trip before.
Even if you don’t know where to start.
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