Trip Planning
Planning,  Tips, Tricks, and Hacks

How to Plan A Trip: 8 Easy Steps To Becoming A World Traveller!

So you made some New Year’s resolutions to travel more this year.  But where to start?   If this is your first time heading out on the road, how to plan a trip can seem overwhelming.  There are so many questions:  Where to go? Who to travel with?  How much will traveling cost?  What will I do when I get wherever I am going? 

There is so much information available out there—social media, guidebooks, and Pinterest throw information at you faster than you can absorb it.  Take a deep breath.  My husband and I have been traveling for over 20 years together. We’ve learned a few things that make planning easier and even fun.  This post will walk you through the steps we use when we plan a trip.    

How To Plan A Trip

These are not hard and fast rules, just solid suggestions that will make your planning easier and travels more fun.  Once you master how to plan a trip, you will be ready to travel to any destination with ease and excitement.

For many people planning a trip seems like a lot of work.  We find that planning our travels fills us with anticipation and excitement and is nearly as much fun as the actual journey. 

But, if you find the planning part, grueling fear not.  Many agencies will do this part for you.  You tell them where you want to go and they prepare all the plans, perhaps with some input from you and a small fee, of course.  All you have to do is show up.

This post may contain affiliate links. That means that if you click and buy, I may receive a small commission (at zero cost to you). Please see my full disclosure policy.

#1 – Travel Style:  Everyone Has One, What’s Yours?       

How to plan a trip starts with figuring out your travel style. 

Is it your plan to travel solo or with a partner?  Are you independent in your travels, or do you like to be in a group?  Do you want to be spontaneous? 

Many travelers are adventure junkies and love to hike or bike, or kayak anywhere they can.  Other travelers follow the cultural path and dream of seeing the Louvre, the Rijksmuseum, or the Hermitage.  

The answer to these questions will help you plan your best trip. 

Romantic Cabanas in the Maldives

Suppose you are looking for a romantic week with your significant other. In that case, the Maldives with a quiet hut over the water is a great choice. Still, as a solo traveler, you may not want to be hanging around a place swarming with couples on romantic getaways.

The Greek Islands offer a lot of old-world culture.  However,  Ios (one Greek island) mostly offers young people drinking; this might not be the place you bring your family.

Whatever your style, even if you think you want to be totally spontaneous, you probably need at least an outline to follow.   At a minimum:  Where are you going? How will you get there, and how long will you stay?

#2 – How Long Do You Have to Travel?

This is an essential step for planning a trip.  If you have a limited amount of time, you will want to focus your travel.  Minimizing the travel time from your house to your vacation will give you the most time to enjoy your getaway.

How to Plan A Trip - Vacation Calendar

As your time to travel lengthens, you have a lot more options.  Still, you will want to keep a few guidelines in mind.

If this is your first trip to Europe or Asia, don’t try to fit in a whole continent in two weeks.  You are excited.  There is so much to see, and you want to see it all.  But you just can’t do that in two weeks. 

You will find traveling more fun and relaxing if you set your sights on staying in one location for at least 3 days and 2 nights, longer if you can bear it.  It takes an enormous amount of time and energy to pack up and travel from city to city. 

Try to find an anchor location for your hotel stays in a city that is a “transit hub” to other areas.  For example, London is a great city on its own.  But from London, you can make easy day trips to many more legendary sites.

  • Oxford (think Harry Potter)
  • Portsmouth (the Mary Rose and the HMS Victory)
  • Stratford-upon-Avon (Shakespeare)
  • Avebury or Salisbury (to see henges, like Stonehenge)

The list literally goes on and on and on…

#3 – Decide Where & When To Go

Daydreaming - How to Plan A Trip

If you google how to choose a travel destination, the first page of Google will be filled with “Travel Quizzes.” These quizzes aim to tell you where you should travel based on your answers to 8 – 10 multiple-choice questions.  But deciding where to travel based on an internet quiz is really leaving your fate up to chance.  And we all know how to game the quizzes.

Instead, brainstorm for an hour or so, daydreaming about what your perfect vacation travels look like. 

Mapping Your Trip Ideas

Then pull out a map (it’s good to have a paper one for this unless you are pretty good at annotating Google Maps) and circling the countries and cities that match up with your daydreams. 

Next, read up on the areas you’ve circled.  Check out travel guides from the library, look at travel blogs, scroll through Pinterest.  See what others are saying about the places you want to go.

This may lead to planning more than one trip. That’s a good thing as you’ll be a few steps ahead for your next vacation!

You’ve nailed down where to go. Now when is the best time to travel there?

We’ve all heard of peak season, i.e., DisneyWorld during spring break is very crowded.  Avoid this if possible. 

June, July, and August are some of the busiest travel months anywhere.  This means lots of people, and at least in the northern hemisphere, it will be hot.  Prices for airfare, accommodation, etc., will also be at their highest during this time.  When you are thinking of how to plan a trip, these are things you might want to avoid.

“Traveling on the shoulder” the months just before or after summer is a good alternative.  These times of year offer fewer crowds and somewhat lower costs.  But this easy travel hack is now well used by almost everyone, and some of the perks are gone.

#4 – The Hardest Part of How to Plan A Trip – Research Costs Set and A Budget

Time to Budget

Knowing what things cost and how much you have to spend is essential to help you determine how to plan a trip.  These factors will have an impact on where you go and how long you can stay.  When learning how to plan a trip, researching the cost and setting a budget are challenging.

There are so many resources out there today to find travel costs.  You have Google, TripAdvisor, travel blogs (like this one), Pinterest, Instagram, and Facebook. If you go old school, there are real travel guide books by Lonely Planet,  Rick Steves, DK Eyewitness Travel, etc., for nearly every location on earth. 

Only You Know How Much Money You Want To Budget

In our household, travel is an on-going expense.  To ensure we always have funds, we set up a separate savings account and deposit a set sum into that account each month.  How much we deposit changes from time to time based on our future travel plans, but we are always setting aside money.

Travel Savings

You know your finances, now you have to set a budget.  Travel is wonderful for so many reasons, but please don’t go into debt for a trip.  Once you know the average costs, you can set a budget for the trip and start saving.

Let’s say you are planning a two week trip to England and Scotland.  Your costs include airfare (economy seat @ $750 round trip), $200/day for accommodations, food, and adventures, and a  Eurail Pass for $275 to get around the UK.  Your total trip will cost about $3,825 per person.  You leave in 12 months.  You will need to put away roughly $320.00 per month to cover your costs.

Chances are you already have some funds earmarked for travel, or you wouldn’t be planning a trip.  But it’s never too late to start saving for future travel

There Are Ways To Help Afford Travel

Get a Travels Rewards Credit Card with no Foreign Transaction Fees.  Many credit cards give you points for purchases that you can redeem for airline travel, hotel accommodations, and other travel expenses. Examples of these cards are Chase Sapphire, Costco Anywhere Visa by Citibank, and the Capital One Venture One

Credit Cards

These cards often come with high annual fees – ranging from $95 to $550.   But you get part or most of that back in perks like instant reimbursement for travel expenses, credit for your TSA precheck or Global Entry fees, and No Foreign Transaction Fee.

This last one foreign transaction fees can be significant if you do a lot of overseas traveling.  This is a fee that the credit card companies charge you for the convenience of not having to convert your money.  According to CreditKarma, the average credit card foreign transaction fee is 3%.  If you are using your credit card nearly exclusively when you travel, that is an extra $30 for each $1,000 you spend.

Airlines and hotel chains offer “branded” credit cards that give you miles or points that you can redeem for flights on their Airline or accommodations at their hotels. If you choose to go in this direction for your credit card, pay close attention to the major airlines that fly from your home airport.  Chances are this is the Airline you will be using most. 

Switch to No-Fee ATM Cards.  Several Banks have checking accounts that offer no fees on international ATM Withdrawals.  These banks are often the same as those that offer no foreign transaction fees on credit cards:  Chase, Capital One, Citibank, etc.

#4 – It’s Time to Book Your Trip! 

Yay! You’ve made it this far and are almost ready to book your trip.  But first, if you are traveling outside of your home country, internationally that is, there are a few more questions

Passports, Visas and Shots – Oh My!

International Driving Permit & Other Travel Documents

Do you have a passport?  Is a visa required for your destination?  Are you traveling to an “exotic” location, and do they recommend or require “shots?”

Check your home country’s websites for answers to these and many more travel questions.  In the US, the State Department offers up information on Passports, visas, and more travel resources.  The following are links for our friends in the UK, Canada, and Australia.

It typically takes four to six weeks to get your first passport.  Renewals take a little less time.  But if your passport will be expiring within 6 months of your travel, you should renew it before you leave. 

To determine if you need a visa to travel to a particular country, I usually head over to my favorite resource for everything site, Wikipedia.  If you find you need a visa, you will need to contact that country’s Embassy and start your application.   It can take several weeks to get visas, so plan accordingly. 

Note:  There are some countries like Jordan, Egypt, Paraguay, and Laos that allow you to get your visa on arrival or have an eVisa application process.  When you check with the Embassy, they will provide you with this information. 

For other countries, it is recommended that you have certain vaccinations.  Here in the US, the CDC (Centers for Disease Control and Prevention is an excellent resource to find out if you need to Get Vaccinated Before You Travel.

On the CDC’s site, you can see what vaccinations are required and recommended for nearly all countries and why.  The site also provides a wealth of information on what you should and shouldn’t do in each country to stay healthy.  This is a great resource.

Book Your Flights First

Flights are probably the single most expensive and least changeable part of your vacation.  Your tickets may come with some pretty heavy restrictions (read fees) for changes or cancellation if you want the best airfare.  Once you have your flights booked, you can move on to booking accommodations and any sort of ground transportation.

There are a lot of recommendations and myths about the best time to book a flight.  There are some general guidelines to follow domestic flights, international flights, and if you are trying to find an “award seat.”

A general rule of thumb for Domestic Flights is to book no more than 90 days but no less than 21 days (three weeks) in advance of when you want to fly.

However, if you are traveling over a hectic holiday such as Thanksgiving or Christmas, booking sooner rather than later gives you a better chance of getting a seat.  For these heavily trafficked periods, you may need to book up to 6 months in advance and not worry about the price as much as availability.

How to Plan a Trip - Flight Board

For International Flights, you should start doing your research as much as a year in advance, especially if you are looking to be in a premium cabin.  Pay attention to the trends watching the ups and downs.  Around the 6th month mark, you should have a clear picture of the pricing over time and be ready to make the buying decision.

Note for both Domestic and International flights:  Airlines are aware of when Business flyers are traveling.  Fares will typically be better if you leave mid-week and stay over a Saturday night.  Business travelers usually want to be home for the weekend. 

Lastly, Award Travel – Can I Ever Use My Points?

Those little points that airlines and credit card companies issue for our loyalty.  Can you ever really use these points?  Well, it’s not easy, but here is what you should know.  Airlines usually release their “Award Seats” between 362 and 330 days out ( that means before the flight).  You will need to check with your particular Airline to see their timing. 

If the release date is 330 days before your flight, you better be on the Airline’s website at 12:01 am.  These seats go super fast, and generally, there are no more.  Airlines are in the business of selling seats, after all.  However, if you need to fly from San Francisco to London next week, it doesn’t hurt to check.  If a flight has many unsold seats close to takeoff, an Airline will often release a few more awards to fill up the plane.

Here are Some Other Tips for Getting Good Prices on Flights

  • When you are thinking of how to plan a trip – Play around with breaking up the flight.  If you are flying from San Francisco to Rome,  instead of searching for a direct flight, think about a layover.  Try San Francisco to New York, spend a few days living it up on Broadway, and then head on to Rome.  You have a fun layover, less jet-lag, and the flights can be cheaper.
  • When searching for flights, use a site like Skyscanner initially.  This will allow you to search across different airlines to find the best flight for your needs. These sites offer price alerts that will email you when the fare goes down so that you can jump on it! 
  • However, once you’ve found a fair price,  you might want to move over to the Airline site and directly book your flights.   Booking directly with the Airline will give you a better understanding of their policies for changes and cancellations. 
  • Understand why a flight is cheap.  You may arrive at your final destination at 2 am.  There is nothing open at 2 am, sometimes not even the shops at the airport.  If you don’t have a friend picking you up, you’ll have to wait for hours even to catch a train. 
  • If the Airline you end up flying on is not your usual Airline, sign up for their frequent flyer program.  Many airlines are part of a network like StarAlliance Oneworld or SkyTeam, and the miles are often transferable.

#5 – Now’s The Time to Book Your Accommodations, Or Not!

Where To Stay: Hotel, Hostel, AirBnB?

There are as many options for lodging as there are ways to plan a trip.  We find Booking is a useful resource for all types of lodging: hotels, apartments, vacation homes, and resorts.

More Traditional Accommodations

Hotel Resort in a Tropical Location

Hotels and resorts are the higher-priced forms of accommodation. These properties offer the most amenities but the least personal of stays. 

Unless you are a high-value loyalty member of a hotel, you won’t get a lot of staff attention.  If you value your privacy above all else, hotel lodging is the style for you.

Apartments and vacation homes offer the feel of actually living in the city you are visiting.  You also get a kitchen, a bonus if you like to cook that can save you some money, since you don’t have to eat out for every meal.  Also, these types of accommodations are usually for more extended stays.

Less Traditional Accommodations

Airbnb - A Great Way to Book a Stay

Airbnb has become a popular option for vacation stays over the past decade.  What started out as the online search for “couch-surfing” has become a mainstream provider of privately held vacation rentals.  While some of the rentals are still in personal homes, many are now private apartments or houses being rented out by the owner.  

There are Airbnb locations in 191 countries.  If you like the idea of spending your dollars giving directly to the providers and not a big chain or corporation.  Airbnb is the way to go.

Hostels - How to Plan a Trip

If you are younger and planning to backpack your way through a country, a Hostel may be a good choice. But don’t rule hostels out because you think only young people hang out there.  Today, while there are still the dormitory setups with bunks, hostels will often have a private room or two with private baths.  So you can have some privacy save a bit of money, and still enjoy the camaraderie of the other travelers that is a natural benefit of hostel stays. 

Don’t know where to find a hostel?  Look into HostelWorld, with over 36,000 properties in 178 countries, you will find a good location for your stay.

Be Spontaneous!

Last but not least, permit yourself not to book accommodations.  If you are traveling off-peak and to less popular locations, you can live on the edge and just show up and ask for a room!

Travel By Train – Not By Car

When you start learning how to plan a trip, your thoughts immediately go to renting a car to get around.  Driving is always an option, but there are many good reasons not to.

You don’t know the driving laws and often can’t read the street signs.  And in the US, we drive on the right. In the UK and Japan (and other locations), they drive on the left. Gasoline in other countries is outrageously expensive. For example, in France, the average price is around $5.54 per gallon according to CNN/Money. Of course, you will need to do the math to know this because gas is sold by the liter and Euros in France. Lastly, renting a car in foreign countries is very expensive. 

Suppose you decide to rent a car after considering all this. In that case, you definitely want to get your International Driving Permit.

If you are traveling in Europe or Asia the best way to get around the countries is by train. We’ve used trains throughout Europe, China, and Japan.  The rail systems are easy to use, very punctual, and very clean.

Train Pulling into Oslo Station

In Europe, get a Eurail Pass.  You buy the pass based on your need for “x” number of days of travel in a month-long period.  The pass can be used in 33 participating countries.  Note: Even when using the Eurail Pass, you may need seat reservations.  There is often an additional charge for this.

Japan Rail Pass

In Japan, you can buy a Japan Rail Pass.  This pass covers all Japan Rail Trains, the Tokyo Monorail to/from Haneda airport, and the JR Ferry to Miyajima.  The pass also allows you to make seat reservations for free and so much more. By the way, you really need to go to Miyajima; it is mystical!

You generally need to buy these passes before you travel as they are not available in-country.

Travel by Air To Save Some Time

Once you are in Europe or Asia, you will find many inexpensive Airlines that can transport you from city to city.  These no-frills Airlines like easyJet and Ryanair in Europe and AirAsia in Asia offer relatively cheap flights. London to Rome might only cost you around $100. 

But it would be best if you were prepared to carry on your luggage (and the bag should be small) and take your chances on where you will sit on the plane.  If you want to check your bags or choose your seat, it will probably cost you.   

These flights can be a real time-saver if you want to visit two destinations that are not close, like London and Rome. 

#6 – Plan Your Activities

How to Plan your Trip Arrival

As minimal as this sounds, a good plan for arrival at your destination sets the tone for your whole vacation.  Remember above when I talked about one of the reasons for a cheap flight was its arrival time?  That matters! 

We try to book flights that arrive mid-morning whenever possible.  First, If you are on a “long-haul” flight, you’ve probably been able to get at least a few hours of sleep. Mid-day is still early enough to collect your baggage,  make your way to ground transportation, and get to your lodging, with several hours of daylight left.

How to plan a trip and avoid Jet Lag

Why is this an essential step in how to plan a trip?  Jet Lag! Jet Lag is a killer for first-time travelers (and the rest of us too!)  You learn how to plan a trip to avoid Jet Lag as much as possible. One of the best ways to get your body adjusted to the current time zone is to walk in the sunshine. 

So drop your bags at your hotel, clean up a bit, and get outside! Walk around this new city, orient yourself to the local transit.  If you are at a tropical resort, put on your swimsuit, go for a swim, and enjoy the sunshine. 

Once you’ve had a bit of exercise and dinner, head back to your hotel. Hopefully, you will fall asleep until the next morning when your adventures begin.

Planning What to Do & Where to Go

Chances are you have chosen your destination because there are several activities in the area that call to you.  Often you can wing it and see where things take you. But if there are must-do items on your list, you will want to book these in advance.

Suppose you are in St. Petersburg and must see the Russian Ballet, book in advance. You’ve always wanted to see a Shakespeare play performed at the Globe Theater in London, make sure you book in advance. 

Planning what to do on your vacation is one of the best parts of all the planning.  I love searching Instagram, reading guidebooks, and flipping through Pinterest.  TripAdvisor is the OG now, but still a great place to search for popular activities and attractions. There are so many content providers out there with excellent guides on nearly every location on the planet.

Not sure where to start?  Tours by Locals is a resource we use for local guides and excursions to arrange private tours or join a group adventure. From cooking lessons at a farmhouse in Tuscany to snorkeling at the Great Barrier Reef in Australia, these folks have you covered.

#7 – How To Plan a Trip With  Minimal Risks

Automate Your Bills

You can automate payments for everything in today’s Internet world, from utilities to credit cards.  Take advantage of this luxury.  The last thing you want is to forget to pay your credit card bill and have the card cut off while traveling. 

Tell Your Card Companies You’re Traveling

Let your credit card company and bank know where you are traveling.  This will minimize the chance that foreign transactions will be seen as potential fraud and help keep your card active during your trip. And even save you from a potentially embarrassing situation.

Buy Travel Insurance

When you buy travel insurance, you aren’t just covering yourself for lost expenses, like cancellation fees.  This can be a hard ticket to swallow as you learn how to plan a trip.  But you are buying protection for a myriad of problems that can occur.  Delayed and canceled flights and complete trip cancellation if you can’t travel due to loss of job, injury, or illness.  Most importantly,  medical emergencies while you are abroad.   

Suppose you get injured or develop an illness while traveling. In that case, your regular medical insurance (assuming you have some) isn’t going to cover the costs.  Say you are hiking the Inca Trail to Machu Pichu and fall and break your leg.  You will need to be evacuated to a hospital; the cost could literally be in the 10’s of thousands of dollars.    If you want to get back to your home country, the price keeps going up. 

Many companies offer travel insurance. We’ve used AXA for several of our trips; their pricing is good, and customer service exemplary.  Get travel insurance and peace of mind; you’re worth it!

Register Your Trip With Your Country’s Traveler Program

US Citizens can sign up for the Smart Traveler Enrollment Program (STEP) through the state department.  Once you “enroll a trip,” STEP will send you alerts about conditions that might affect your travels, such as safety conditions,  bad weather, or civil unrest.

Being enrolled in STEP also gives you easy access to your Embassy in the country you’re visiting. Most importantly, if something terrible happens while traveling, it is easier for the Embassy to find you.  And in dire situations, get you in touch with your family, or out of the country if need be. 

Check your country’s travel department for similar programs.

Copy And Scan Your Travel Documents

A lesson hard-learned on how to plan a trip is to have many copies of your travel documents. A few years ago, a friend when to Italy for the first time.  Two days into their vacation, they were pick-pocketed.  The thieves got their passports, credit cards, and other ids.  Without cash, credit, or IDs, they spent several days holed up in their hotel waiting for new credit cards and many hours at the US Embassy to get new passports.

Scan and copy your passport, visa, yellow card (not the one in Soccer, but your vaccination record), and any credit cards you’re bringing on your trip.   We make it a practice to laminate a hard copy of these items and keep them in a secure place online (DropBox, OneDrive, GoogleDocs). 

Also, give a trusted friend or family member access to the online vault.  If you do not have internet, your trusted person can access the vault and get copies of these documents to you. 

Do the same with your travel insurance documents, Airline tickets, and train passes. It’s also a good idea to copy the receipts for all these items along with any significant valuables you’re carrying. If anything happens to these items while you’re traveling, you’ll have an electronic version.

#8 – Packing:  Keep It Simple

In my post on how to pack a suitcase, I go into detail on packing.  Here is the short version.

When traveling with carry-on bags only, make sure your gear is compliant with the Airline’s regulations.  There are different size guidelines for American carriers than for European and Asian carriers.  Even more critical overseas is the weight of your bag.  You will be charged for overweight bags.

Make a list.  You want to ensure you don’t forget anything you won’t be able to buy when you’re abroad.  But don’t overcompensate.   You can buy toothpaste, shampoo, and aspirin everywhere. 

Shoes are bulky and take up a lot of space.  Try to bring no more than three pairs of shoes and one of these should be the pair you are wearing.

An old saying is to set out everything you want to pack and then remove half. It’s true; you won’t need as much as you think.  Work on being able to mix and match your tops and bottoms to create different outfits.  Stay with neutral colors, so everything works together. 

Ready – Set – Go!

You’ve researched, planned, and made your bookings.  It’s time to go!  Yay, enjoy your trip, and may this be the first of many!

How To Plan A Trip

VickieDe has eaten her way through more than 300 cities in over 40 countries. Learning along the way that food and culture go hand in hand. Read More

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