How to Plan a Trip You’ll Remember Forever

A step by step guide on how to plan a trip that you'll be talking about for the rest of your life. Everything you need to know to plan the perfect vacation.

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So you want to learn how to plan a trip of a lifetime.  Perhaps you’ve gotten started and are feeling in over your head.  Maybe you’re not even sure you can do this.  To that, I say, pshhh.  Yes you can, and it’s easier than you think.

I am going to guide you, step by step, through the entire process.  I personally take an odd pleasure in planning and budgeting out an entire trip.  Sometimes I enjoy the planning process so much, I forget I actually get to go on the trip!  So believe me when I say, you are in good hands.  That being said, you may want to grab a cup of coffee and a notepad, because I’m about to drop some knowledge…


How to Plan a Trip Part 1: Decide where to go

The first thing you need when learning how to plan a trip is an awesome destination.  Are you still flip-flopping between a couple different places?  No problemo, but I am going to have to force you to pick one.  Otherwise, we’ll be here all day, and we got things to do!  Let’s say you want to go to the beach.  You cannot decide between the Caribbean or Hawaii.  Here are some ways you can narrow down this choice:

Proximity to where you live

It’s always best to minimize travel time.  Let’s say you live on the east coast of the United States.  The Caribbean will be much more accessible to you.  Hawaii will take you at least a full day of travel, and you’ll be jet-lagged.

Price

If you live on the east coast of the United States, Hawaii will be a pricier flight since it’s much further away.  However, some of the islands, such as Maui and Oahu, are quite developed and have inexpensive condo rentals.  On less developed Caribbean islands, you may feel more comfortable at a resort, but will pay resort prices.  Peak season (December through April for both), also tends to bring higher prices.

Activities

Pick the place that has activities you are most excited about.  For example, you are almost set on picking the Caribbean in May for shorter travel days and less crowds.  That is, until you find out Maui has whale watching tours in the winter.  You are psyched because whales are your spirit animal!  Decision made.

Atlas and travel books - how to plan a trip

How to Plan a Trip Part 2: Determine Timing

Time of year

Now you need to decide when to go to Hawaii.  It must work with your schedule, but also be when you can do the activities you are most interested in.  Since you are going to be whale-watching, you need to go when the whales are in Maui for the winter.  That means that January through March is your ideal window.  Unfortunately, that’s Maui’s busiest season, but you are willing to tough it out for the whales.  You decide you will travel in January before work gets busy in February and March (I just made you a tax accountant – you’re welcome).

Length of trip

Keeping Hawaii as the example, a large amount of money will be spent on flights and it’s going to be a long trip.  You’ll want to make the most of your investment.  Plus, more time spent at a beach can only be a good thing!  I would do at least a full seven days for this sort of trip.

Be crafty with your vacation days by choosing the earliest flight possible for far destinations, even travelling overnight if it’s an option.  Try to avoid long layovers, especially if they cause the total travel time to be more than a day.  This allows you to have more time at your destination with your precious PTO days.

Kaanapali beach - how to plan a trip

How to Plan a Trip Part 3: Getting there

Flights

I always book my flight before my lodging.  I think of it this way: there’s no point in booking a place to stay if I can’t even get there in the first place.  The only exception to this is if you are dead set on a particular hotel or rental, and it books up quickly.  As mentioned above, I usually look for flights that get me to my destination within one day, and preferably early in the day.

I always use Expedia to book my flights, as I have gotten very good deals with them.  This has especially been true when booking flights and hotels together, as I’ve always coincidentally (or not?) gotten a free upgrade on our hotel room!  You may want to check out my tips on how to find the cheapest flight prices possible.

Transportation

If you are going to a city where you can walk everywhere, you’ll spend little on transportation.  Just be sure you are prepared for any potential taxis from the airport, Ubers, etc..  For a road trip, try to get an idea of how much gas the drive will require.

When flying somewhere that is not easily walkable – basically anywhere other than a large city – you’ll have to rent a car or figure out public transportation.  In Europe, many times there are trains that can connect you between cities.  Be sure to explore your options to get the most convenient yet cost effective choice for your destination.

View of St. John from air - how to plan a trip

How to Plan a Trip Part 4: Choose a place to stay

Lodging

Now it’s time to choose where you’ll be staying during your trip.  TripAdvisor, Airbnb and VRBO are all great resources for finding hotels or vacation rentals.  I personally have been using Airbnb more frequently than ever lately.  It can be so much more cost effective and I like staying in an actual home with a kitchen.  Plus, I can pretend I am a local for a few days!  One tip I have is to read both recent reviews, as well as some from the time of year that you will actually be traveling.  Individual experiences can be pretty different based on when they visited.

Don’t forget the puppies (or kitties)!

Make sure your fur baby will be taken care of while your gone.  Websites like BringFido.com can help you find pet-friendly places to stay.  Sometimes there is a fee, but it’s worth it to have your little fuzzball with you during your trip.  If you are unable to bring them, you just have to find someone to watch them while you’re away.  Our little puppy stays at a place with his own room and outdoor space.  There’s even a camera that lets my husband and I watch him while we’re away!  Yes, we are a little obsessed with our dog and spoil him to no end…

Kaanapali beach - how to plan a trip

How to Plan a Trip Part 5: Dining and Entertainment

Food

The next step in learning how to plan a trip is to research all the delicious food options in your destination.  Some popular places may require reservations, so it’s good to plan ahead.  When doing research, vary your sources, as taste in food can be highly subjective.  There are so many paid recommendations out there, and sometimes a place can just be completely overrated.

Here is what I usually do.  First off, when researching, my rule of thumb is if I see a restaurant recommended in at least three different sources, it’s probably good.  Second of all, I avoid anything that remotely looks like a chain restaurant.  I try to pick out at least one casual option that offers something unique that I wouldn’t normally find at home.  Then I pick out one nicer place for my husband and I to eat at for more of a date night.  Thirdly, I give the menus a once-over to make sure the food actually looks good.  Some places serve some icky stuff, like sheep’s head in Iceland.   Whatever you do, don’t google those pictures…

Activities

Finding awesome experiences is the most important part of knowing how to plan a trip.  These experiences are the reason why we travel.  For our Hawaii example, this would be making sure you book that whale watching tour.  Since you are going for a whole week, you still have six other days to plan amazing things to do in paradise!  You should look up what other unique adventures your destination has to offer.  In Maui, this would include beaches, hiking, and the Road to Hana.  Just be sure to also give yourself a little downtime during your trip as well.

kaanapali beach - how to plan a trip

How to Plan a Trip Part 6: Pack The Essentials

Passport

If you are leaving the country, make sure you bring your passport!  Make this one of the first items you pack.  It’s also wise to make a photocopy of your passport to have on hand in case the original one gets lost or stolen.

Converters for small appliances

Different countries use different voltages for their appliances.  Bring a converter or your hairdryer will catch fire.  Kidding!  I don’t even understand electricity stuff, so don’t listen to me!  All I know is that you will need a converter for any small appliances you bring.  They may not catch fire, but they could fry and never work again.  An adaptor could be needed as well, as the plug shapes can vary across counties.

Appropriate clothing

Check the weather before you go so you know whether you need shorts, jackets, umbrellas etc.  Also, keep your planned activities in mind, as things like hiking boots or bug spray could be necessary.  Comfortable shoes are always a good idea if you’ll be walking a lot.

outfits laid out on floor - how to plan a trip

How to Plan a Trip Part 7: Finishing Touches

Money

If you are leaving the country, check to see what currency your destination uses.  It’s just good to be aware of the difference in exchange rate and where you can easily get cash upon arrival.  It seems in most cases you can just use an ATM at the airport, but it’s always good to be sure.

Look up the sunset/sunrise schedule

I always go to timeanddate.com before all of my trips and take note of the sunset and sunrise times.  This is so I can plan, for example, to eat at a waterfront restaurant while the sun is setting.  Also, I can make sure I wake up early enough to watch the sunrise at least once.

Secure your house

You don’t want people to catch on that you’re out of town.  Things like mail piling in your mailbox and a dark quiet house may signal an opportunity to those thieving youths in your neighborhood.  To be safe, see if someone you trust can get your mail and keep an eye on your house while you’re gone.

Prepare for your travel day

Pick your plane seat at least a month in advance of your flight.  Remember to check into your flight the day before your trip and print your boarding passes.  You will need this and your passport with you when you get to the airport.

Stack of travel books - how to plan a trip

• • •

If you made it to the bottom of this page, you are ready now grasshopper.   You now know how to plan a trip, and I must set you free to go plan your travels on your own.  Go on, and get started already!

Are you planning a trip soon?  Share where you are heading below!

A step by step guide on how to plan a trip that you'll be talking about for the rest of your life. Everything you need to know to plan the perfect vacation.
A step by step guide on how to plan a trip that you'll be talking about for the rest of your life. Everything you need to know to plan the perfect vacation.
A step by step guide on how to plan a trip that you'll be talking about for the rest of your life. Everything you need to know to plan the perfect vacation.

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