The Complete 10-Step Trip Planning Guide

The Complete 10-Step Trip Planning Guide

Confused on how to plan a big trip? Flights, hotels, transportation, excursions, oh my!

Let’s be honest, there is a lot to think about and that’s where I come in!

Disclaimer: This post contains affiliate links. If you book or buy something through these links, I earn a small commission (at no extra cost to you).

Statistically speaking, we are leaving a lot on the table every year in regards to a life/work balance. But Nick, isn’t it called a work/life balance? Not in my book! In other words, we are not traveling enough in America and PTO goes unused or unpaid and – it’s heartbreaking!

I believe that one of the many reasons why we don’t travel is because, planning is hard. But, planning is NOT hard, it just takes some effort and time. This step-by-step guide makes the process easy so you can plan your dream getaway. For the best (and most affordable) results, get started as soon as you can.

1. Choose your destination

Start with your dream list of locations. Go old school, write them down or better yet- get a dry erase board. First things first, decide on the time of year that you would like to travel because weather is always a factor. It could even influence your plans. Another thing to consider is the cost of your destination.

Now, going anywhere around Christmas or USA’s spring break is going to be very expensive. And, the amount of time that you have off, will factor into how much time you have to travel. For example, unless you live close to Indonesia, you wouldn’t want to travel to Bali for only a week. That’s because you would spend so much time getting there, you wouldn’t have enough time to enjoy it before you had to head back home.

To recap, time of year, weather patterns and cost are the most important factors here. Hawaii is an amazing value in April and September. Why? April and September are shoulder seasons for Hawaii. Actually, a lot of places are of great value during these months.

Traveler Tip: The shoulder season is a great way to save money!

Note, some destinations require you to bounce around, like Thailand. Other places, like Maui, have everything there is to do on one island. Keep this in the back of your mind during planning.

Taking road trips and multi-destination getaways into account, be sure to allow enough time at each place. Plan on two full days at any major city hubs. You don’t want to overfill your schedule like I did. Read my story at the link below.

Related: The Longest Road Trip of My Life 

Having trouble narrowing things down? Here are some questions to ask yourself.

  • What time of year or month do I want to travel?
  • How much time off do I have?
  • Do I want to check out a new place or return somewhere I know and love?
  • Do I have enough time and budget for international travel, including long flights and jet-lag recovery, or is a short road trip from home a better choice?
  • Am I looking for beaches, hiking, biking, relaxation or adventure?
  • What is my goal of the trip? Do I have a goal or do I want to just relax?
  • Would I prefer to be surrounded by nature, spending time at the beach or immersed in urban culture?
2. Estimate a budget to value travel

Personally, I dont set a hard budget. I love traveling so much that I make it a priority in my life. With this in mind, I’m always setting aside money so that when I plan my trip, I’m not flustered and worried about the budget. However, I am financially responsible and I do keep notes on my estimated costs while planning. Some destinations, you just can’t get away with doing on a budget or it will devalue your experience.

I like to meet somewhere in the middle, between budget and luxury travel, I call this “Value Traveling”. Value traveling is what I preach on all of my social media outlets, blog posts and when I talk to others about traveling.

For example, when I’m looking at booking accommodations, I will search high and low for my favorite places. If I really love a boutique hotel or a Yurt on the side of a mountain, I’m going to stay there! It may cost me more, but I’m paying for the experience. I will counter this with booking a cheaper and more budget friendly place for the next few nights. I won’t sacrifice on clean sheets and comforts, but I will sacrifice on amenities and location, to a certain degree. In the end, you will notice that you will get more value for your money by splitting your time between accommodations – luxury and budget.

If you’re not familiar with my travels, it’s very rare that I stay in the same location for more than two nights. In doing so, I get to experience a lot more of my destination and those luxury stays don’t add up as quickly on my budget.

To get an idea of how much your trip will cost, research prices for airfare, hotels, and activities before you make any nonrefundable purchases or reservations. Here are some tips for finding the lowest prices:

  • Consider using a travel credit card to earn points for your future trips. The Capital One Venture card is a fantastic travel rewards crdeit card to start of with. If you’re a pro, use the Chase Sapphire Preferred card.
  • Try multiple dates. Flights are often cheaper in the shoulder- or off-season. Check prices for different dates within your travel window. A sale on airfare may help you afford a destination that’s otherwise out of your reach.
  • Avoid holidays, festivals, and other large events. Crowds can inflate hotel rates, overwhelm popular sights, and make it difficult—and costly—to get around.
  • Compare midweek to weekend prices. Hotels in big cities tend to be more affordable on the weekends when the business travelers have gone home, while resorts in vacation destinations may be less expensive midweek.

Once you’ve estimated your trip’s flight and accommodation cost, start considering the cost of transportation. Public transportation or renting a car could eat into your overall budget. Make sure you have an efficient and reliable way to get around. If you’re considering hoping from town to town, it’s best to rent a car in most cases. For centrally located cities and small towns, plan to walk or use public transportation.

Related: The Best Spain Road Trip Ever

Next, get an idea of your food budget. Everyone has to eat and stay hydrated. I’m a foodie lover, so more likely than not, I’m finding new, fun, and interesting places to check out. Some people opt to save on their food budget and hit the local market or neighborhood store. This can also be a really cool experience in itself.

Pro Tip: You may even find a really cheap and authentic souvenir at one of these local markets.

Pizza at La Gallina Bianca in Seville, Spain.
La Gallina Bianca – Seville, Spain

Half the fun of being in a new place is being able to experience new things. Don’t skimp on your tours and excursion expenses, plan on doing them. You will regret not taking that authentic tapas tour in Spain or sailing on a ship in the Mediterranean or horse back riding through the Costa Rican jungle or zip lining through the Caribbean… I could go on and on!

It’s a good idea to break up your excursions and line them up for at least every other day. This saves your budget and allows downtime throughout your stay. If your itinerary is jam-packed, that’s not fun either. You need downtime around the campfire or relaxing on the beach, by the pool. etc.

Check out my absolutely favorite excursions that I love below!

3. Research & book flight(s)

It’s important to check flight prices as soon as you have a few destinations in mind. It’s super easy to get started with SkyScanner. The best part is, you can track prices as they fluctuate to learn patterns and price drops. Track multiple flight options with just a click of a few buttons.

SkyScanner Flight Tracking Website
SkyScanner Flight Tracking Website

A question I get often is, “when should I book?”. There’s not a science to booking the right flight, at the right time. However, there are patterns to be aware of. For example, flights in June-August will always be high. USA Holidays will always be high. Shoulder season is the best time to book (April & September). Flights within your country are best booked around 30-45 days out. Flights booked for International travel should be booked around 80 days out.

Furthermore, all of this information above is hearsay if market trends are out of whack or you’re currently living in a pandemic (see Covid-19 pandemic). Plan accordingly.

Pool at the Tifakara Boutique Resort, La Fortuna, Costa Rica
Tifakara Boutique Resort, La Fortuna, Costa Rica
4. Plan your hotel, yurt, glamping tent, boutique, or cruise

Once your flight is booked, it’s best to start locking in accommodations.

Browse Hotels.com, AirBnb, HomeStay and other hotel, loding, camping and resort locations. Favorite, star, heart, or write down your favorite accommodations before making a final decision. Base your decision on location, price, style, features and amenities.

If you’re booking a cruise, ask all the right questions before booking with your travel agent, travel portal or company website. Heck, you can ask me, I’ve been on 5 cruises!

  • How big is the cruise ship?
  • What does the cruise cost?
  • How many passengers can it hold?
  • Is the cruise line reputable?
  • Does this specific cruise have good reviews?

Before making any kind of payment, make sure you know the cancelation policy. And if you think you need it, purchase trip cancellation insurance. Most major travel credit cards include trip protection, such as the Capital One Venture card or the Chase Sapphire Preferred card.

Another reason to book using your Capital One or Chase card is collecting miles and points for future traveling. That’s right, more benefits for you! Every time I travel, I’m already checking my new mileage chart for my next destination.

So, use those travel reward credit cards to get a jump start on your future travels. You may even get a round trip to Hawaii (or similiar) for free by just using your sign-up bonus miles. I did!

The wildly gorgeous hotels, amazing infinity-pool-view villas, yurts on a seashore cliffside, glamping tents -will all book up far in advance. Generally, their prices don’t swing and there will be no deals to be had. Expect to pay for what you get at these luxury and off the beaten path stays.

Reading reviews online of other travelers experiences should give you a good idea on the experience you can expect. Take them with a grain of salt though, everybody has an opinion. Not everybody likes their tea the same way. Some people don’t even like tea at all!

Last but not least, compare all of your favorites before making a final decision.

rental car booking in Costa Rica
Booking a rental car
5. Book a rental car, hire a driver or map public transportation

I love the freedom of being able to come and go on my own time. The freedom to hit the open road to get away from the big city. The freedom to explore more than one place in a short amount of time. Booking a rental car allows you to have flexibility. It saves you time and it could save you cash.

Waiting around for public transportation is just not my thing. Guided group tours that make you wait for a packed bus full of tourists -nope! I mean, if there are no other options, I guess I have to go with the flow. But otherwise, I’m renting my own car to explore. When estimating your rental car costs, remember to add up tolls, fuel costs, parking fees, and charges for dropping off the vehicle in a different location, if applicable. You don’t want to be stuck at a Costa Rican toll booth without any colones (been there!)

So, when does public transportation make sense? It makes sense when you’re in a major city where parking is scarce. Usually the major cities will have some kind of fastpass card or bus/train pass. You pay for a card and get so many times to ride either the bus or the train for a smaller fee than paying for individual rides.

Steals and Deals

Just like anything else, it’s important to shop around for rental car deals. Some rental cars you can get for free with using points from your Capital One or Chase credit card. It never hurts to sign up for the rental car programs that Enterprise, Hertz or Budget offer. Each company sends an email from time to time about current or upcoming specials. Every penny counts.

When choosing your rental car, make sure it has enough space for all passengers and all of your stuff. Consider price of the vehicle, model, and gas milage your top three priorities. If you know you’re going to be in a muddy situation (literally), like camping or off-roading, make sure to get something with four wheel drive and height clearance.

Note, renting a car is not for the faint of heart in another country. If you’re outside your home country and you don’t know the local laws, plan to study them and feel comfortable or opt for a private driver or public transportation. Most rental vehicles outside the US are only offered in a manual transmission. Automatic transmissions are harder to find and book up much further in advanced, not to mention they are more expensive. Take both of those things intro consideration when planning your trip.

Caminito del Rey Hiking Tour in Spain
Caminito del Rey Hiking Tour, Spain

7. Plan and book your daily adventures

You could say this is the home stretch and the most fun part in the planning process. It’s during this phase that you can begin to paint a picture on what your dream getaway will look like on a day to day basis. And, while there are a hundred ways to bake a cake, this is all up to you.

When I have a destination in mind, it’s usually because I have some must-do adventures that I came across. This is why I chose my destination in the first place. If you’re looking for ideas, Viator.com can help you out. Another idea is to scour Instagram using the destination hahstag to see what other people are doing. Because, if you didn’t photograph it and post it on Instagram, did it really happen?

I like to explore as much as possible when I’m in a new destination so generally my days are full with adventure, with little down time. Since I have a lot of experience planning trips, I even know when to schedule downtime or nothing at all. It’s an art form and balance is key. Leave space for power naps, unexpected discoveries, and spur-of-the-moment detours. 

From the moment I start planning a trip, I jot down all my ideas in Apple Notes, Google Drive, etc. This idea list is also my mobile itinerary. I always refer to it abroad and use it as a guide. I like to go further into detail in my trip notes by making subheadings for things like food, photo spots or a cultural experience. My idea list keeps me organized (even without internet) and helps when I’m in a pinch when trying to find something to do, eat, entertain myself, etc. The internet will not always work, so never rely on it. Don’t expect to always be able to “Google it” on the fly.

Planning Tip: As soon as you settle on a destition, start an Apple Note or Google Drive document to keep track of your ideas and your mobile itinerary.

Another benefit to having an ongoing note is being able to visualize how everything will fit in during your stay. However, more likely than not, you will still not have time for everything. Being a visual learner, seeing it in my notes and on a calendar (if necessary) is extremely helpful.

Passport and documentation for travel

8. Gather your travel documents

At least two months before your departure, make sure your ID and other necessary documents are in order.

  • Driver’s license: Starting in October of 2021, federal agencies, including the U.S. Department of Homeland Security and Transportation Security Administration, will accept only Real ID–compliant driver’s licenses, U.S. passports, or other forms of TSA-approved identification to fly domestically. Before you travel, check with your state’s licensing agency to make sure yours is complaint. If not, you’ll need to get a Real ID, which can take months in some states, or use another form of accepted ID to travel.
  • Passport: Applying for or renewing a passport typically takes six to eight weeks, sometimes longer, according to the U.S. Department of State. However, you can pay an additional $60 expedited service feeOpens in New Window to get it renewed in two to three weeks, if desired. If you plan to travel outside the U.S., you should note that many countries require your passport to be valid for the duration of their traveler’s visa—even if your stay will be shorter. Make sure your passport will not expire for at least six months after your trip is scheduled to end. Some countries also require passports to have one to two blank pages for entry.
  • Visas: If you’re traveling to another country, you may need to apply for a tourist visa. This could require paying a visit, or sending your passport, to a foreign embassy or consulate in the U.S. Schebor recommends researching the entry requirements of your destination and giving yourself enough time to apply. Two months is a good rule of thumb, she says. Application fees typically run from $50 to $200. Visit the U.S. Bureau of Consular Affairs to learn more about passport and visa requirements for Americans worldwide.Visa requirements vary depending on the passport you hold, so if you’re a permanent resident with a passport from somewhere else, your requirements may differ from your travel companion’s.
  • TSA PreCheck and Global Entry: Travel Credit Reward Cards like the Chase Sapphire Preferred or Capital One card, give you up to a $100 credit towards these programs. These programs can help you zip through airport security lines. Before you apply, give yourself a few weeks to fill out the online application and visit an enrollment center for fingerprinting and an ID check. Confused about the two programs? Here’s the difference: TSA Precheck ($85) puts you in a faster security line at U.S. airports. Global Entry ($100) includes TSA Precheck and adds expedited customs screening upon your return from international trips. You must already have a valid U.S. passport to apply for Global Entry, and you must participate in an interview at a designated enrollment center. Once you’re approved, your status lasts five years.

Before you leave, it’s a great idea to photograph or scan your driver’s license, the I.D. page of your passport, medical insurance card(s), and credit cards (including the back, with the phone number to call if your card gets lost or stolen). Store them in a secure folder in Google Docs, Dropbox, or other cloud storage.

Enroll in STEP. The Smart Traveler Enrollment Program (STEP) is a free service to allow U.S. citizens and nationals traveling and living abroad to enroll their trip with the nearest U.S. Embassy or Consulate. If there is ever an issue when traveling internationally, the US Embassy will be aware and can aid you if needed. This is extremely important!

Traveler tip: Before you leave town, check your mobile phone plan to avoid incurring any unforeseen roaming charges. International travelers should also alert their bank(s) and credit card companies to their travel plans to avoid unnecessary hassles, such as blocked charges for unusual activity on an account. 

Overhead view of suitcase being packed for vacation
9. Plan what to pack

Each adventure requires a different packing list. If you pack last minute, you can skip this step.

Traveler Tip: If you’re a film nerd like me, don’t forget your GoPro at home! Follow this link to my Amazon store to grab the latest GoPro Hero 9 Black.

Everybody knows the basics of packing, like, you need underwear! You also need pants, shirts and bathroom essentials. But, if you want to pack like a pro, I highly suggest to start thinking about it an advanced. And this is for a few different reasons. The most important being that you dont want to forget anything, obviously. The second, maybe you need to purchase something for your trip and shipping delays happen often. Am I right, Amazon? Lastly, staying organized will save you time, money and headaches once you reach your destination.

Related: Packing Cubes vs Rolling – Which is Best?

Backpack and book hanging from a tree
Backpack and book hanging from a tree
10. Entertainment

It’s a known fact that while you’re traveling, you will experience some down time. Consider bringing some form of self-entertainment to keep you busy like a book, magazine, iPod or a tablet, or a combination of these things.

Note, not all flights have TV/DVD screens. Be ready to sync your device to the airport or plane Wifi to gain more digital entertainment options.

Questions? Do you have something to add that I missed? Let me know in the comments below!


2 thoughts on “The Complete 10-Step Trip Planning Guide

  1. Great comprehensive guide Nick! This is a great checklist – reminds me that I need to stay in a yurt at some point :D!

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