Ultimate Guide to Easy Trip Planning

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There really are two types of travelers…the kind that plan everything down to the T and those that just go with the flow. Look no hard feelings towards those easy-going travelers, but that’s not me (and if you’re reading this, that’s likely not you either).

I like knowing all the details ahead of time. Sure, I think there’s value in spontaneity, but I refuse to travel across the world only to miss out on an activity because tickets sold out a month in advance. If that sounds like you too, then this easy trip planning guide is for you.

I’m going to cover the ins and the outs and trust me when I say, the hyper-planner in me will cover everything you need to know about planning an awesome trip. And beware I said easy, not short. There are a lot of steps and lots of factors to consider, so strap in.

Once you have these basics down, it becomes easy to be able to plan a trip for multiple people, groups, families, and even with colleagues.

So whether you’re new to travel planning, inexperienced, or just haven’t had the time, let’s dive in! (and hit play on the spotify button above to get an epic theme song going)

Why plan your trips?

Organizing the many aspects of a trip is no small feat, so why invest your time, energy, and focus?

Having a plan will make your travels more:

1. Reliable
2. Calm
3. Safe
4. Successful
5. Budget-friendly

Let’s break each of these down.

Reliability

Locking in tickets, reservations, and bookings ahead of time secures your spot. No wondering if there will be room or if you can rearrange your plans to fit something in. With a mapped out trip, you know what you’re getting and there’s no question about it once you’re there.

Calm

Especially if you’re a new traveler, having a sense of calm is huge! If you already have a game plan, you don’t need to worry about the basics. You can focus on all the other stuff that comes up as you travel that you can’t plan for like figuring out new transportation systems and conquering language barriers.

Safe

The more research you can do ahead of time, especially when it comes to lodging, the safer you will be. It’s a luxury to be able to read hotel reviews that discuss a location, security, and amenities. But it becomes really tricky to do that on the fly. So, don’t!

Successful

Not every trip is going to be 100% successful (read my road trip from Hell). This is a fact – one that you’ll become more comfortable with as you travel more. But, having a plan including ticket reservations, background knowledge of the public transportation system, and more will ensure that less things go wrong.

Budget-friendly

Last minute bookings are often more expensive, whether that’s a flight, hotel, or activity. Some things have an ideal booking window meaning X months out (like Disney Reservations), but generally speaking earlier is better. Planning a trip will be more budget-friendly in the long run and even more so if you implement these tips for traveling cheap.

The only downsides are that you might become everyone you know’s trip planner…it’s a blessing and a curse…and it is possible to over-plan.

There is a balance between planning just enough and overplanning so that you end up too busy or don’t allow yourself the flexibility to discover new things or follow local’s recommendations, which is so valuable when traveling (like these Dublin restaurants recommended by locals).

That said, you will make mistakes and you will learn what your travel preferences are, so take deep breaths and don’t be too hard on yourself.

As you read through this guide, grab something to take notes with, something to sip on, and remember that this is a lot of information. You don’t need to remember everything. You certainly will learn along the way and learn by doing. Let’s go!

How to decide on trip duration?

The main factor that usually limits you here is how long you can get away from work or school. If you’re limited to a few days of paid-time-off (PTO) or a week long spring break, thems the breaks.

Another thing to consider here is your budget. The longer you travel, the more it costs. Just keep that in mind.

Generally, the more flexible you can be with the “when” of travel, the more you can maximize your budget.

When should you travel?

When and where to travel really go hand in hand. If you’re a student, the when is more defined as you only have certain breaks (summer, winter, and spring). Those are your chances. But, don’t forget about weekend getaways if you can get away with them (pun absolutely intended).

If you aren’t limited by a schedule in the same way as students, I suggest picking a destination first then you can research the place. Find the off-season and plan to visit then to get the most out of your budget.

*Buzz word: Off-season is the cheapest time to travel, but varies based on location.

*Related word: Shoulder season is the time between peak and off seasons, so if peak season is Winter and off season is Summer, then shoulder seasons are spring and fall.

Where should you travel?

How in the world do you choose where to go? Especially when your list is so long you can’t even see the end. Here are some guiding factors.

Alternating styles

My family traveled a lot when I was growing up and we typically took turns between an adventure trip and a relaxing one. So for example, a trip to Europe for sightseeing one year then next year a trip to Bora Bora to relax at the beach and sightsee if desired.

Budget first

If you absolutely need to prioritize your budget, one technique is to let that guide you. Look for cheap flights and pick the cheapest! Full time travelers often do this to maximize their budget so they can travel longer or do more activities. Sometimes any destination will do!

Schedule restricted

If you are limited by your schedule like an academic year, then you’ll obviously need to keep that in mind. For cheaper trips, look for destinations that have their off and shoulder seasons during your breaks. For example, summer break in the USA actually falls during winter in New Zealand, which is their off season.

Trip duration

Similar to the above, you want to make sure that you’re picking a destination that you can experience for whatever trip duration you landed on in the previous section.

For example, you can easily do Las Vegas in a weekend, but you really need at least a week for New Zealand’s North Island. You obviously don’t want to spend the first and last days of your trip flying all day if you only have 3 days.

You can go back and forth, however. So if you really want to visit a place that requires 2 weeks, you can always wait until you have that time frame to work with in your schedule…if possible.

If you aren’t sure how long is recommended to visit a place, you can search in Google “destination + your desired trip duration + blog” and see what comes up. If you don’t see itineraries or only a couple, that might not be the best combo.

You can also try to Google “recommended amount of time to visit X” but make sure the source is using an itinerary you are interested in. Obviously a backpacking trip around Europe is going to take weeks but if you only want to hit the highlights, the backpacking itinerary and trip duration wouldn’t fit your needs.

A final tip is to plan it yourself, hypothetically. Not everything you plan needs to be set in stone right now. Test it out.

If you think you can do Thailand in one week, try to make a sample itinerary and see if it seems doable. I’ll cover how to do all that in later sections so keep reading.

Can’t decide?

If you have no limitations and no mental (or physical) bucket list to check off, how do you pick a destination?

There are plenty of places to get some inspiration!

1. Entertainment – Let TV and movies be your guide. Even if the sets may be fake, it could stir up a new obsession for a destination. For example, after watching Lost, I really wanted to visit Hawaii! Here are my favorite TV shows for travel inspo. I even went on a full Harry Potter themed road trip in the UK and it was magical!

2. Photography – I actually have a post with dedicated photos meant to inspire your travels! Check it out here.
3. Social Media – Of course, there’s no shortage of inspirational travel photos and ideas on the socials. I personally like Instagram for this purpose because you can search by hashtag or location. You can literally type “travelideas” then select the Tags menu header and a bunch of spots will pop up! Planning a trip on Pinterest is another way to get inspiration and travel ideas.
4. Books – Don’t forget about books to inspire you! My favorite that sparked my wanderlust for the South of Spain and North Africa was The Alchemist, which is my pick for as one of the best books about Spain. I highly recommend. You can also swing by a library or book store to peruse their travel section.
5. Listicles – A final tip is to Google search “top places to visit during X month/season” and see what comes up. You can also add “in the US” or any country, continent, or region you’re interested in.

Flights

Once you have a destination and a time frame, you get to dive into one of the most important parts: flights!

If you’re taking a road trip, carry on…this section isn’t for you.

But if you need to fly to your destination, here’s how I like to plan flights.

Flight Search Engines

I have two favorite search engines for flights.

I like Skyscanner to get a general look at things. It compares LOTS of different websites and has this awesome feature where you can set your destination to “anywhere” so it will just show you the cheapest places to fly to.

You can also search by “cheapest month”! This really frees up the searching parameters.

All you need is your home airport and it will tell you where you could go and when and how much it costs.

It’s a great starting point!

However, I wouldn’t limit your search there. Sometimes, the results would have you book through shady websites that have poor reviews for customer service.

I have booked through some weird places via Skyscanner and although I’ve never had a hiccup, there are more reliable ways.

My other go-to is Google Flights.

If you click on the map, you can set your home airport and it will leave the “Where to?” field blank.

Next, set the calendar for a time frame by selecting your desired month or “All” if you want to search any month and duration such as weekend, 1 week, or 2 weeks.

Then you can zoom in and out of the map to browse flights and destinations.

How to choose a flight?

Aside from budget, here are some things to consider:

1. Airline – If you’re going somewhere domestic, it might be worth it to just suck it up for a budget airline, like Frontier or Spirit. Just watch those extra fees for bags, seat selections, and food. However for longer flights, read airline reviews. If you have a loyalty account with an airline, don’t forget about it. If you don’t have one, start one! They’re free! You can rack up miles and exchange them for free flights.
2. Baggage fees – Ugh. I hate that airlines charge for baggage, but it’s standard so don’t forget about those extra fees. Most airlines allow up to one 50 lb. bag for $30 but double check before you book. Sometimes you can also save money by buying your bags ahead of time.
3. Amenities – Not all flights are created equal. Make sure that if you’re on a long haul flight that you’ll get meals included. Does the airplane have outlets to charge your devices? Can you choose your seat ahead of time? Lots to think about.
4. Layovers – Love ‘em or hate ‘em, layovers are important considerations when choosing a flight. If your flights including the connecting ones are domestic, be sure to give yourself enough time to deplane and go to your next gate. I shoot for at least 45 minutes. If it’s an international flight, you definitely want longer, because you often have to go through customs before catching your next flight. I’d aim for at least an hour and a half.

I’m ready to book! Now what?

Yay! Before you hit book here are some things to remember:

• Double check your dates, to/from destinations, and flight times
• See if adding your luggage now saves money
• Check the cancellation policy (we’ll chat about traveler’s insurance in a bit)
• Choose a highly-rated booking site just in case

Accommodation

The next big ticket item is your accommodation. Whether you opt for something basic to act as a base camp or a more unique stay like these movie-themed ones, there are lots of options here: hostels, Airbnb or Vrbo, hotels, and even bed and breakfasts!

I personally open a tab in my broswer for each type of stay. Hostelworld is the best site for hostels. Obviously Airbnb itself, although you can also check Vrbo. There are some differences between the two…for example, Airbnb has more listings than Vrbo. And lastly for hotels, I go with Booking.com or Hotels.com.

I punch in the general location and my dates to get a feel for all my options. I don’t really have a preference most of the time so I like to browse by budget.

Here are some things to consider when choosing your lodging:

1. Location – If you know where you’d like to be, that’s a good place to start. I typically try to stay central to many things so I can access them easily via public transportation, a ride share, or via walking. I also will pay attention to how close my stay is to downtown or the beach, for example. Be sure you can get to your hotel from the airport as well, via public transportation or otherwise.
2. Amenities – Obviously this is a big one. You want to make sure your accommodation has everything you need. Do you need beach gear? WiFi? a mini fridge and microwave? free breakfast to save for other meals?
3. Hidden Fees – Don’t get swindled by hidden taxes & fees. For hotels this is often a daily charge that you pay when you arrive. For Airbnbs this can be the cleaning fee and service fee.
4. Safety – If you aren’t familiar with your destination’s neighborhoods, it can be helpful to search “safest neighborhoods in X” or conversely “most unsafe neighborhoods in X”. Just a baseline to get an idea. You can also read reviews and “walk around the area” via Google maps by placing the little yellow dude on the map!
5. Cancellation policy – You definitely want to make sure that wherever you stay has a flexible cancellation policy if you need it. Better safe than sorry, I think. Plus, most of the time even if one place doesn’t have it, there will be another that is just as awesome and does have flexible cancellation.

Transportation

We’re almost past the big stuff, so stick with me! For transportation once you’re in your destination, there’s a few options to think about.

Rental Cars

First, do you need a rental car? If you’re visiting a city and there’s great public transportation and ride sharing, you’re probably fine without one. However, if you’re road tripping around a country, obviously you’ll need a car.

Where to book rental cars online?

I usually stick to RentalCars.com because it’s straight forward and they check with multiple top rental car companies to compare prices and options.

Another choice is Kayak.com if you wanted to look further.

There’s not a lot of bells and whistles that goes into choosing a car. Obviously make sure it’s the right size, is automatic not manual if needed, can fit your luggage, and has unlimited mileage.

You also want to make sure that there are free shuttles to take you between the rental car company and the airport. Most have it, but it’s still good to check.

Important rental car information

Here are some things to note.

First, you do need to be 25 years old in the US to rent a car. However, if you are younger you can often still rent one, but for an additional daily fee. It can get pricey so consider only renting when you actually need the car. For example, you can save tons during a trip to LA by only renting a car when you visit the farther beach cities like Malibu.

The legal rental car age varies by country so be sure to specify when booking.

Second, in terms of legality, you do need a valid license to rent a car. Depending on your destination and country of origin, you may need an international driver’s license. Check with your rental car company in their FAQ’s (or call) to be sure as it varies.

Third, it’s important to understand your rental car coverage and whether or not you need to buy additional insurance. Many people already pay for coverage under their personal car insurance, so it’s worth a call to ask. You want to see if your liability coverage (another person’s medical bills or property caused by an accident) extends to your rental car and any other coverages you may have opted in for, such as comprehensive (for damage via theft or natural disaster) or collision.

Another way you may have coverage already is via a travel credit card. Again you’ll want to call and ask, but typically for this to work, you’ll need to book the rental car with this specific travel credit card.

All this to say, don’t fall for their up-sells without doing your own research first.

Public transportation

Ahhhh, a traveler’s best friend and worst enemy rolled into one. I’d be lying if I said I loved public transportation but I do love the price tag and that’s often hard to beat (read how we saved $$$ in South Beach Miami with public transportation).

Before you travel somewhere, do a little research before your trip to see what options there are. Does the city have subways? busses? free bikes? trolleys? trains?

I recommend downloading any public transportation apps specific to your destination as well as a Google Map offline so you can access it whenever. And see if you can get a multi-day pass for cheaper.

Your boots were made for walkin’

I cannot stress this enough: you can walk. Yep, you heard me. I know it might seem like a long ways and everyone has their walking limits, but I bet you’ll find something cool along the way!

Activities

Yay! Onto the fun stuff…not that all that wasn’t fun, but planning your vacation activities is the best part of travel planning in my option. It’s also the part where you can go overboard and book too much for yourself in one day.

How do you find the best activities?

Google

I always start with Google’s Travel portal. In the “Things to Do” tab, you can enter any destination and it will pull up a bunch of activities. I like to look through them at the pictures and reviews.

Really try to keep an open mind when browsing activities. It will help you find hidden gems and activities you might not have chosen for yourself otherwise.

Travel Blogs

Call me biased but I like to hear it from travelers. I like to search “destination + things to do + travel blog”.

I think travel bloggers find some awesome things to do and often have high quality photos to go along with their suggestions…which, no offense, beats some guy who happened to visit and snapped a photo on his flip phone. They also usually have lots of tips and insights on logistics!

Tourism Websites

Who knows a place better than locals of the place itself? Look to tourism websites for their recommendations.

I’ve personally found great beaches and museums that way, like Piha Beach in New Zealand via NewZealand.com.

Where do you book said activities?

Of course the most direct way is via the actual activity itself. For example, you can book tickets ahead of time for the Guinness Storehouse in Dublin on their website for cheaper than in person the day of.

Booking directly through an activity’s website is my preferred method.

Another popular website for booking activities is Get Your Guide. They have awesome tours, activity tickets, and combination tickets. Plus they also have reviews so you can see what other people experienced.

Don’t forget about Airbnb, who has an Experiences section, which has neat local-guided options.

If you have it, I also like to book through TicketsatWork.com, which pairs with many companies to provide their employees discounted attraction tickets and other travel benefits.

Lastly, you can book multiple activities at once if you get a CityPass. However, make sure you really want to do the activities included in the CityPass, because the price tag is only worth it if you use it to its fullest potential.

How do you know how much to squeeze in a day?

This is a tricky question because aside from the obvious time constraint, a lot of it boils down to personal preference.

I recommend choosing one morning activity and one afternoon activity for a local sightseeing day. Of course you can do more!

You want to give yourself lots of time between activities for meals and the time it takes to get from point A to B.

If you’re planning an excursion, I’d stick to one a day.

For example, when we were based out of Dublin, we took a one day trip to the Cliffs of Moher. Although we had time in the evening to tour around the Temple Bar District in Dublin, we were tired and wouldn’t have wanted any extra pressure to make it on time to another timed activity.

With this part, it’s really your personal preference and you’ll learn how much you can comfortably squeeze in a day.

Just to give you an idea…as I’ve traveled on my own, I’ve learned that an hour and a half is plenty of time for me to experience most art and history museums, but I need more time in science museums like observatories, aquariums, and botanical gardens.

If you’re ever in doubt though, go to the place’s website, browse through the details. Get an idea how much there is to see because it can vary a lot. For example, the Biltmore Estate in Asheville is a whole day thing. You tour the house, gardens, shops, farm, winery, and grounds! But, the Atlanta History Center, which has a couple historic homes can be seen in 2-3 hours even with the home tours.

Food

The last big thing we have to discuss is food! This might just be me (although, I doubt it), but I love to know where I’m eating and what I’m getting before I even get to a place. I’m that person that shows up to a restaurant and doesn’t need the menu because I know what I want already.

Well it’s no surprise that with travel, I’m the same. I like planning my travels around food. Before I arrive at a destination, I like researching the best restaurants.

It’s worth a search. You can do a similar search for food as you did with activities by searching “destination + best places to eat + travel blog” or just search “restaurants in destination”.

Of course, Yelp and TripAdvisor are other good spots to check.

Regardless of how you find spots, read those reviews, look at photos and start salvating write it down!

Other travel planning tidbits

Do you need travel insurance?

Look, lots of travelers may say it’s a waste most of the time, but those one-offs where it comes in handy…it really comes in handy.

Especially as an inexperienced traveler, I say travel insurance always. I use Safety Wing every time. They’re easy to use, cover travel and medical needs, and even include some more extreme sports, which are usually excluded from standard insurance plans.

Once you get more comfortable, you can opt for travel insurance on international trips only at your own risk of course.

I personally seek outside travel insurance for international trips. World Nomads is my favorite. Although I haven’t (thankfully) had to use it, I’ve heard lots of good things from those that have had to. They also include health insurance so you don’t need to add your own travel plan to your personal health insurance.

For domestic trips, I tend to opt for insurance just for my flight.

Similar to rental car insurance, you likely have some covered travel insurance via your travel credit cards, so again, call and ask.

TL;DR: As a beginner, yes. Once you’re more comfortable, no for domestic trips and still yes for international trips.

…basically there are no magic wands to fix everything on a trip, but Traveler’s Insurance is as close as it comes.

Are city passes worth it?

They absolutely can be! Some big cities offer city passes that bundle admissions into one ticket to save money and sometimes they even have a private bus fare included.

My top tip is to go to their website and look what admissions are covered. If they sound like things you were going to do anyway, then it’s likely worth the price!

Personally, I’ve never used them only because I don’t love to just do the touristy things and overall it hasn’t been worth it for my trips.

How do you stay organized once the bookings start accumulating?

I use Excel to track my overall budget and take notes along the way, including links when appropriate. I have a whole guide on how to use Excel for trip planning. Plus click here for my free spreadsheet to get started.

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Aside from Excel, I recommend creating a separate email or folder within your email. Once you have that, immediately move everything there. That includes bookings, restaurant reservations, tickets, insurance confirmation and terms, and EVERYTHING else!

My favorite travel app is Trip It where you can connect to your travel booking related email. They’ll recognize all your bookings and compile them all into the app for a step-by-step itinerary of your bookings in timeline order. It’s a life saver!

@periodicadventures

This travel app is a game changer especially for my planners out there. Its called Trip It and will make your travel planning process so much easier! Not an ad, just genuinely love it! #tripit #tripitapp #travelplanner #travelplans #travelplanning #travelapps #travelapp #travelplan #travelplannerlife #travelplanningtips #travelplanningmadeeasy #planyourholiday #planyourtrip #howtotravel #organizationapps #organizationapp #traveltips

♬ Don’t Let Me Down – The Chainsmokers

Don’t forget:

1. Transportation to/from your home airport
2. Parking at your home airport. I like to check Way.com for hotels that accept parking on site for a fee, just make sure there’s a shuttle to the airport when booking.
3. Do these things before your international trip.
4. Make sure you pack the essentials for your flight.
5. Breathe! You’ll get the hang of it as you plan more trips!

My final tip is to not be afraid to start small. It’s okay to plan a day trip, weekend getaway, or short road trip nearby to see how you do. It’ll get easier!

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My Travel Essentials

• Travel Insurance – Going on an international trip? Don’t forget travel and medical insurance with SafetyWing.
• Travel Card – If you’re new to travel hacking, fear not! My favorite card for beginners gives you $750 in rewards when you spend $4,000 in the first 3 months, plus lounge access, 10x points on hotel bookings, and free TSA pre-check!
• Get Your Guide – Check out Get Your Guide for a one-stop-shop for booking travel activities.
• Booking.com – This is my favorite hotel search aggregator, specifically for reading reviews. On Booking.com, the reviews can be searched for keywords like WiFi, breakfast, pool, amenities, etc.! So helpful!
• Anti-pickpocket bag – Worried about having your valuables swiped? PacSafe makes the best travel bags with zippers and straps that lock and with mesh steel enforced fabric.
• Give the Gift of Travel – This is the perfect gift for travelers in your life! Tinggly allows you to gift experiences around the world, perfect for birthdays, weddings, or anniversaries.
• Staycation Idea – Check out Resort Pass, which gives you day passes to resorts so you can use their pool, spa, and fitness center, a great staycation idea!

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