Trip planning can be overwhelming, right?

It takes countless of hours to plan a trip, and even after spending all that time, you are still uncertain if you have covered all your bases.

When I first planned a trip over two decades ago, I had no clue what I was doing.

I dove into the deep end head-first and hoped to pop out alive.

At least that is what it felt like.


My trip did go well, but in hindsight it could have been better.

Much better.

These days, you would think that it would be easy to plan a trip with all the information that we have access to.

But it’s simply not the case.

Trip planning is like any other skill.

You need to perfect it.

Years after planning that very first trip, I have now fine-tuned a system that allows me to plan my trips efficiently.

Trust me, you can do it too, and I’ll show you exactly how.

Let’s get to it.


STEP #1 - Budget

Set your maximum budget.

How much can you afford to spend on your trip?

This is very important.

Of course we would all love to have bottomless bank accounts, but this is not most people’s reality.

In fact, according to Forbes, most Americans are taking vacations they cannot afford.


I truly believe that it is necessary to create a vacation budget.

So think about what your finances look like and set a maximum budget that you are comfortable with.


STEP #2 - Length of Your Trip

How long do you want to go away for?

Or perhaps more importantly, how many vacation days can you take?

Unfortunately, a GlassDoor survey found that Americans don’t use half of their earned paid time off.

Do not let this be you.

You have earned your vacation days, so use them.

It is crucial to your mental health to take that much needed break away from the pressures of work and to de-stress.

Your mind and body will thank you.

So, go for it.

Set the length of your trip.


STEP #3 - Decide Where to Go

London? Phuket? Bora Bora?

The choices are endless.

If you don’t already have a destination in mind, now is the time to brainstorm.

What type of vacation are you looking for?

Beach? City? Cultural? Food centric?

Once you have decided on the type of vacation you want, next write down all the destinations that you would like to visit.

For destination ideas, talk to friends and family who travel to get their recommendations, read articles that highlight travel destinations or look through social media to find ideas.

Then narrow down your list further to your top two destinations.

Budget tends to be the main factor that will impact the destination you pick.

So you will need to do some preliminary research in order to determine the approximate costs for flights, accommodations, activities and food in your top two destinations.

For example, I’m thinking of going on a beach vacation in February.

My top 2 beach destinations are Maldives or island hopping in Thailand.

My budget is $2000 USD for 10 days.


Based on my preliminary research, my budget is just too low for Maldives BUT Thailand can be done.

So Thailand it is!

If your top two destinations are above your maximum budget, then move on to the next two destinations on your list and conduct your preliminary research on approximate costs.

Continue this process until you have picked a destination that you are excited about!

Always pick a destination that you simply cannot wait to visit.

Our time off can be so limited, so you want to make the most of it.


STEP #4 - Pick a Time to Travel

Unless your vacation dates are already set, I would recommend being flexible with your dates while you research the best time to travel to your destination.

You will want to consider these three things:

  • Peak Season: This is the time of year when most tourists will visit a location. This is often due to good weather and holidays surrounding it (e.g. Europe during the school holidays in July or August). Flights and accommodations tend to be the most expensive during this time. 
  • Off-Peak Season: This is when the majority of tourists aren’t visiting a destination, typically due to weather (e.g. Hurricane season in the Caribbean). You will normally find very affordable flights and accommodations during this time, but on the flip side, there’s usually a reason for it being “off-peak.” In some countries, off-peak can mean that a torrential downpour happens nearly every day, all day long. 
  • Shoulder Season: This is the time between peak and off-peak. This time is usually a good time to take advantage of the benefits from both seasons.

Start searching for flight prices.

I recommend using Google Flights and Skyscanner.

Depending on the destination, flights and hotels are going to be more expensive if your travel dates land on a major holiday.

For example, expect to pay premium prices if you are planning to visit New York City on New Year’s Eve.

Play around with your dates until you find a flight price that you are comfortable with, during the travel season that you would like to visit the destination.

Now this part may take some time, but it will be worth it!

This is all a part of the trip planning process, and it will ensure that you are able to make the best decision possible with all the information you have on hand.

Once you have picked a time to travel, write down your travel statement.

My statement is:

I am going island hopping in Thailand for 10 days during the second half of April with a maximum budget of $2000 USD.

Keep this statement handy and continuously refer to it during your trip planning process, in order to keep you in check.

Because let’s be honest, it is very easy to get ‘carried away’ when trip planning.

You see one cool activity after another and you just want to do it all!

But, unless you win the lotto during your trip planning process, sticking to your maximum budget is KEY.


Source Lonely Planet

STEP #5 - Create a Rough Itinerary

Now it’s time to decide which cities/towns you are going to visit.

Are you going to stay in one city/town your entire trip or will you move around?

If you plan to move around, just remember to be realistic.

Yes, we would all love to see every single spot in each country we visit, but this is just not always reasonable.

I would recommend sticking to 2-3 destinations in a 10 day trip.

You want to be able to get a good flavor for the country, without feeling like you are constantly just traveling from place to place.

After all, you should come back from your vacation feeling rejuvenated, not exhausted and needing a vacation from your vacation.

Look up the major international airports in your destination and from there determine if you will be flying in and out of the same airport, or if you will fly in to one airport and out of another.

Typically, it is cheaper to buy a round trip ticket versus 2 one-way tickets.

However, if flying in and out of different airports allows you to save time or possibly see an extra town, then the additional cost may be worthwhile.

Next, pick out the top cities/towns that you must see on your trip and determine how many days you will stay in each spot.

Figure out the travel logistics between each city/town.

Will you take a domestic flight? Is it better to rent a car and drive yourself? Can you take the train?

The transportation that you pick between each city/town will most likely boil down to your budget.

For example, I can take a 55 min domestic flight from Phuket to Koh Samui for $100 USD or I can take a 6.5 hrs bus and ferry ride with a combined ticket cost of $14 USD.

You want to look at all your transportation options and then pick the one that suits you best based on your budget, time constraints and safety.


STEP #6 - Book Your Flight

Do you have a travel rewards credit card?

If not, consider signing up for one. 

You can earn sign-up bonuses to redeem miles and points for free flights and hotel stays.

Most cards even have bonuses of up to 50,000 points when you meet their minimum spending requirement (often $1,000 within a three-month period).

That’s enough miles for a free flight almost anywhere in the world!

Collecting points and miles (“travel hacking”) is something you can do to cut your costs.

If you have a travel credit card, consider using your miles to book your flight.

Keep in mind that it is harder to use miles these days due to less availability, so make sure to book early to ensure you get your desired flight.

If you don’t have a travel credit card, search for cheap airfare on the following sites:

  • Momondo – A great platform for finding really cheap flights.
  • Skyscanner – One of the best websites for searching multiple destinations at the same time.
  • Google Flights – Quick and easy way to search for a flight. After you enter your departure and arrival airports, the calendar pre-populates with prices so that you can target dates with lower fares.

Be mindful of what’s included in the cost of airfare.

Sometimes what appears to be a good flight price ends up costing you a lot more, if you have to pay extra for baggage, meals, etc.

Typically, airfare and accommodations have more availability and are less expensive the earlier you book.

Depending on your destination, I usually find that the best time to book a trip is about 3 – 6 months prior to your travel dates.

However, if you will be traveling during a destination’s peak season, it’s best to book even further in advance to avoid hotels, transportation or activities selling out.

And make sure to read our tips for a long flight as well.

Enjoy your vacation even in-flight!


STEP #7 - Book Your Accommodation

Once you know the dates you will be in your destination, there is no real reason not to book your accommodation.

I find that waiting will simply just lead to you losing your top picks.

If you have a travel credit card, you can determine if you can use your points to book hotels.

If you do not have a travel credit card, the following booking sites offer the best rates for accommodation:

  • Hostelworld – Has the largest selection of affordable hostels online.
  • Agoda – Has the best results if you are heading to Asia and has the widest selection of properties in the region.
  • – The best overall platform for finding budget hotels and guesthouses. They have the biggest inventory and best deals.
  • – They have accommodations ranging from uber-luxury hotels to small mom-and-pop bed and breakfasts. Also, frequent users can earn a free night in a hotel.
  • Airbnb – An online marketplace that connects people who want to rent out their homes with people who are looking for accommodations in that locale. You can find many different kinds of properties, such as single rooms, apartments, houseboats, entire houses or even a castle.

STEP #8 - Book Your Local Transportation

If you are going to multiple spots on your trip, book your transportation between each spot.

Make sure you know how long it will take you to get from place to place, so that you can plan accordingly.

Google Maps is typically a good resource to calculate travel times between spots, as is Rome2rio

Don’t book a flight for 7 am, if it will take you 6 hours to drive from your accommodation to the airport.

It happens.

Unfortunately, I know from first-hand experience.

You live and you learn, right? 🙂


STEP #9 - Plan Your Activities

It’s always nice to be able to fly by the seat of your pants, however there are times when this does not always work to your advantage.

For this reason, I recommend deciding what are the must do activities on your list and determining if you need to book anything ahead of time.

Popular attractions like Alcatraz in San Francisco or the Sydney Harbour Bridge Climb are typically fully booked well in advance, so you can’t show up the day of and expect to get in.

For ideas on things to do in your destination, check out the following resources:

  • Ask family & friends who have been there
  • Facebook (put out an update asking for tips)
  • Twitter & Instagram (hashtags)

STEP #10 - Get Your Documents in Order

If you don’t have a passport or if your passport is expired, begin the process to obtain one NOW.

Without this very important document, international travel is out of the question for you.

If you already have your passport, keep an eye on your passport’s expiration date. 

Most countries require that your passport is valid for at least six months after your ticketed date of return.

This means that even if your passport doesn’t expire for a few months, you may still be denied entry in to a country.

You may also need to ensure that you have enough empty pages for stamps/visas.

Always be sure to understand your destination country’s entry requirements.

I do visa research on Google and double check the information against the destination’s embassy website and/or my own country’s embassy website.

I encourage you to do the same for your destination.

I also recommend that you make copies of important documents (passports, visas, driver’s license, credit cards, birth certificates, marriage certificates, etc.) and keep them in a secure but easily accessible spot.

In case a document of yours is accidentally lost, it typically speeds up the process if you have copies of your documents.

Or in case you need to apply for a visa while abroad, you will not need to worry about not having all the appropriate documentation (if copies of the document is accepted, of course).

I personally suggest scanning your documents and keeping them in an online location like Dropbox, Google Drive or some other secure, high-tech cloud service. 

Hard copies of certain documents are important as well, as you won’t always have access to the internet to search through your email.


STEP 11 – Get Your Immunizations

Depending on where you are traveling to, it’s important to get the right advice for any necessary vaccinations before you travel.

Your safety and health are essential, and in some instances, you can’t travel unless you have proof of being vaccinated.

Talk to your health care professional about travel vaccines.

Visit them at least two months before your departure, as some vaccinations need to be started six to eight weeks before departure and require more than one shot spread out over time.

Make sure to carry your vaccination records when you travel, as certain countries require proof of vaccination in order to be able to enter the country.

Zimbabwe, Zambia, Botswana … I’m looking at you!


STEP #12 - Buy Travel Insurance

According to a lot of experts, travel insurance is a must.

Nobody expects something negative to happen when we travel.

But, we don’t live in a perfect world, so anything is possible.

It’s always best to be prepared for the worst case scenario.

This is why I strongly urge you to at least consider purchasing travel insurance.

Many credit cards will include some level of travel insurance.

However, coverage is often limited and might only apply to trips or items purchased with the card.

I suggest that you first check with your credit card company to determine if you have any travel insurance coverage.

If you do not or you want to supplement your travel insurance, check out the following tried and tested travel insurance companies:

Keep in mind that some countries do require you to show evidence of a medical insurance policy, with a minimum amount of coverage valid for the period of your stay as a part of the entry requirements. 


STEP #13 - Money

International transaction fees can be high when using the wrong credit and debit cards.

That’s why I suggest switching to a no-fee ATM card.

Charles Schwab is a popular card for Americans, but there are lots of other banks (don’t forget to check your local banks) that don’t charge ATM fees too.

Do your research and pick a card that best suits you.

These days, you will typically need a credit card when traveling in order to book flights, rent cars, book accommodations, etc.

I suggest looking for a credit card that has:

  • No international ATM withdrawal fees
  • No currency conversion fees
  • No fees on cash advances
  • No annual fees
  • Reward points for airlines and hotels

Is your destination still a cash-based society? Or can you use your credit card for most purchases?

Make sure you know this information before your trip, so that you can be prepared.

I recommend that you always have a combination of debit cards, credit cards and cash on hand.


STEP #14 – Phone & Internet Access

These days everyone seems to travel with at least one smartphone, in addition to other gadgets that require an internet connection.

If you have an unlocked phone, you can consider purchasing a local SIM card.

Simply research the data plans and how to get a SIM card for your destination.

Or, you can do what I do, and simply use your phone only when you have access to free WiFi.

If you need to use your laptop, I recommend using the free WiFi in your room or at a café.


STEP #15: Learn Some Basic Phrases in Your Destination's Language

It is always a good idea to at least learn a few phrases before you travel to a country that does not speak your mother tongue.

Trust me when I say that the locals really appreciate the effort, and they may be more inclined to help you if they see that you are at least trying.

You can purchase a phrase book such as Lonely Planet’s Phrasebook & Dictionary.

Or you can use an app like Google Translate, which can translate more than 100 languages and several dozen languages offline. Just remember to download the language(s) you need before you leave for your trip, so you can use the app even without a data/WiFi connection


STEP #16: Think About Your Electronics

Make sure you have the right equipment needed to use any electrical gadgets you will bring on your trip.

If you are traveling overseas, you need to know what type of voltage is used in the country you’re traveling to and what type of adapter or plug is needed to plug your appliances into the outlet.

Otherwise, you may end up with an overheated straightening iron or a fried camera charger.

Most American-made electrical appliances work at 110 volts.

While Japan, most of North America and parts of South America and the Caribbean use voltage between 100 – 125, the vast majority of the world uses 220 – 240 volts.

For a complete list of voltage requirements by country, visit Power-Plugs-Sockets.

Even if two countries operate on the same voltage, their outlets might not take the same shape of plug — that’s where an adapter comes in.

An adapter will allow you to plug your gadget into another type of outlet (not change the electrical voltage).

To see what kind of adapter you’ll need for your destination, check out Power-Plugs-Sockets.

Travel stores often sell convenient and inexpensive kits with five different-sized adapters that will work with nearly any outlet in the world. You can also buy all-in-one adapters that include the most common plugs.


STEP #17: Be Mindful of Your Manners

Certain gestures you might use everyday, like a thumbs up or okay sign, are offensive in some cultures.

Avoid awkward situations by researching some basic manners in the country you are visiting. 


Source TripSavvy

STEP #18: Know Common Scams

Be aware of common scams in your destination.

Simply knowing of the popular scams in your destination is often all you need to avoid falling victim to them.

A graphic about taxi scams as an international travel tip

Source Real Simple

STEP #19: Download Useful Apps

The following are apps that I personally find very helpful while traveling:

  • TripIt – TripIt organizes all your travel itineraries and documents so that you have everything in one place before you even get to your destination. Just have your reservations automatically sent to TripIt, which will let you view travel confirmations, flight itineraries, tickets, hotel and Airbnb booking info, etc. in one easy place. The app also makes it simple to share your trip plans with others.
  • XE Currency Converter – The XE Currency app quickly provides live, up-to-the-minute currency rates. Make sure you update the rates before you leave, so you can perform exchange rate calculations on the fly with or without data or a WiFi connection.
  • Google Translate – Google Translate can translate more than 100 languages and several dozen languages offline (make sure to download your desired language while still connected). The instant camera translation allows you to hover your camera over text and it will automatically translate, along with multiple other functions.
  • Google Maps – Google Maps is easily the best mobile navigation app, and one you’ll likely use every day on the road. This app not only makes it easy to discover places near you, but its navigation function is top notch. Google Maps maps out walking, driving and public transportation routes, along with pretty accurate time estimates. Make sure to download maps of your destination in advance, so you can navigate even without a data/WiFi connection. Google Maps is pretty data-heavy otherwise.

STEP #20 - Plan your Arrival

The last thing you want to do after a whole day of travel is to figure out how you are getting from the airport to your accommodation. 

I don’t know about you, but I am usually not in the mood to use my brain after a long journey.

For this reason, I strongly urge you to already know how you are getting from the airport to your accommodation.

It’s also a good idea to have the address of your accommodation written out in your destination’s language, so that it makes it easier for the taxi drivers, bus drivers or locals to know exactly where you need to go.


STEP #21 - Let Your Card Companies Know You Are Traveling

No matter how long you will be gone for, it’s always a good idea to let your credit card companies know you will be traveling internationally.

This way any transactions you make aren’t flagged as fraudulent and your card is less likely to be blocked.

You don’t want to spend your vacation stuck on the phone with your credit card company, possibly spending a lot of time and money in order to rectify the situation.


STEP #22: Pack Your Bags

It’s time to pack for your trip!

The airlines are constantly changing their baggage allowance, so I would start off by confirming the following:

  • How much weight can you travel with?
  • Are there extra baggage fees?
  • What are the maximum dimensions for checked and carry-on baggage?

Once you have that sorted, let the packing begin!

My number one tip when it comes to packing is to avoid over-packing.

Of course what you pack will depend on where you are going, but keep in mind that you really do not need to pack everything you own.

Even if you forget an item, you will survive.

No really, you will.

If you have no idea what to pack, the folks at Smarter Travel have created The Ultimate Packing List


STEP #23: Trip Planning is Now Officially Done. Time to Go!

Always try to check in to your flight online.

Typically you can check in online approximately 24-48 hours before your flight’s departure time.

When it’s time to head to the airport, make sure you give yourself enough time to make it to the airport with plenty of time to spare.

It’s better to be early, than to have the plane doors close just seconds before you arrive at your gate.

For international flights, aim to arrive at the airport about 2-3 hours before your flight’s departure time.

Once you have checked in, dropped off your luggage and made it past security, sit back, relax and let the adventure begin!

You have probably spent countless hours trip planning, so it’s time for all that hard work to pay off.

And it will!

I guarantee that you will have the trip of a lifetime.



After decades of trip planning, I find that the above guideline works for me.

Every. Single. Time.

It ensures that I cover all my bases, and that I’m not left to rely on my memory in order to make sure that I haven’t missed a crucial step in trip planning.

No stone is left unturned.

I assure you that you can use this formula over and over again to plan the most epic trips for yourself.

So why wait?

Start planning your next trip now.

There is no time like the present!

What’s your process for trip planning efficiently? Do you have any tips and tricks that I didn’t mention in this post?

If you are still feeling overwhelmed, or simply do not have the time to plan your next trip, why not let us help you? We will create the perfect bespoke itinerary just for you!


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