How to Plan a Trip to Anywhere on Earth

“How to Plan a Trip” will walk you step-by-step though the most efficient way to plan a memorable trip.  It covers destination decisions,  budgeting, timing, visas, itineraries, flights, lodging, transport, mobile phone access, money, and safety.  It will get you to where you want to be!

I love traveling, and I LOVE planning trips too! 

In the planning phase, the options are unlimited, and I find that an intoxicating feeling.  I can go anywhere!  I can do anything!  What shall I do?  After years of roaming worldwide, I know just where to find the information I need to make decisions.  Here are the steps I follow, and the sites I use, to know how to plan a trip successfully.

How to Plan a Trip:

How to Plan a Trip – Step 1: Decide where you want to go:

Maybe you have a dream destination in mind?  Maybe you don’t know where you want to go, you just know it involves jungles, temples, and beaches.  Or perhaps you prefer ancient castles, cobblestone paths and good beer.  Peruse my destination guides.

How to Plan a Trip – Step 2: Research costs and plan the length of your trip.

The best one-stop-shop for comparing costs in different destinations is the outstanding website: Price Of Travel.  This site lists actual costs based on concrete price data for the cost of backpacking in different destinations.  It tallies the daily cost of: a hostel bed, three cheap meals where locals would eat, one public transport ride, three beers, and entry to one tourist site.

Here you will find that 10 days spent backpacking at hostels in Zurich, Switzerland will set you back about $1,184.  For that same price, you could spend 17 days in nearby, and equally lovely, Salzburg, Austria.  Or you could spend an ENTIRE MONTH just a few miles up the road in gorgeous Cesky Krumlov, Czech Republic.  Or for something completely different, for that same $1,184, you could afford to live in hostels for 65 DAYS in historic Hanoi, Vietnam.

Keep in mind we are comparing apples to apples here; in all of the above cases, you are sleeping in a dorm bed, eating cheap street or market food, having 3 beers for your nightlife, and seeing one touristy museum or castle or whatever each day.  Your standard of living is the SAME in each example, but the cost of living is very, very different in each location.  Even if you don’t want to stay in a hostel, or only eat local street food and markets, this site gives you a sense of the massive difference in cost of living between different places in this world.

How to Plan a Trip – Step 3: When is the best time to go?

This is a really important consideration.  One that I have forgotten to my detriment a couple of times.  I planned a Mediterranean trip in February thinking that even in winter it would be kinda warm there.  Wrong!  Your first stop in making this decision should be WeatherSpark.com.  This site gives extremely detailed weather statistics for everywhere on Earth.  You’ll find out important things like that in August it rains all day, every day in Douala, Cameroon.  Or that in July, it gets below freezing each day in Queenstown, New Zealand.    You should also look up when are the festivals in the place you are going.  For example, traveling in the Middle East during Ramadan is not so great.  People are fasting, and not much is going on in the daytime.   Imagine if you booked a trip to Munich in mid-October, not realizing Oktoberfest is actually the last week of September.

How to Plan a Trip – Step 4: Start saving money, get a travel rewards credit card.

Now that you know how much your trip will cost (not including airfare), you can plan how you will save for that goal amount.  As for airfare, you can start checking Momondo.com looking for the cheapest fares.  You should also try working towards getting there for free, via frequent flyer miles.  I’ve traveled to over 100 countries, nearly always flying for free.  Read my post How to Fly for Free to see how I do it.  (Hint: many, many travel rewards credit cards)

How to Plan a Trip – Step 5: Do you need a visa? 

You can look up visa information on dozens of websites, and for some countries (especially African countries) you’ll find conflicting information.  Even on the country’s OWN OFFICIAL WEBSITE you might find conflicting information.  But, there is “One Site To Rule Them All.”  Timatic is the site that EVERY AIRLINE ON EARTH uses to decide if you can get on the plane.  When you check in for an international flight, the lady at the check in counter is plugging your home country and destination country into Timatic to see what documents you need to get into that country.  Whatever Timatic tells her, is what you are going to have to have, or you will be turned away from the flight.  It won’t do you any good to plead; “But the Burkina Faso website says I CAN get a visa on arrival!”  If Timatic says you can’t, that’s that.  The airline doesn’t want you taking up a seat on their return flight just because you got denied entry. You would normally have to pay for a Timatic subscription, but you can check it for free on the United Airlines website and Star Alliance website.

If you do need a visa BEFORE you arrive in the country, get going on that right away.  It shouldn’t be a problem with most countries, but there are a handful that are slow in responding, and even a few that might just say no!  Saudi Arabia, Angola, and Eritrea come to mind.

How to Plan a Trip – Step 6: Plan a rough itinerary for your trip.

So let’s say you’ve decided you want to travel to Berlin, through the Czech Republic, Hungary and Austria.  Does it matter to you where your trip starts and finishes?  Would you be just as happy to start in Berlin and end in Vienna, or vice-versa?  If you are trying to book with frequent flyer miles, seats can be hard to find.  You should plug-in every destination city that reasonably fits into your planned itinerary.  Maybe you can get a seat into Berlin, but not one out.  Ok, that’s fine, now try to get one out of Budapest.  Or Vienna.  Or Prague.  Just keep trying every possible combination of cities until you get flights that you are happy with.  It helps if you have miles accumulated on multiple carriers.  Maybe Delta has lots of flights into Berlin, but only United has flights out of Budapest.  The more variables you have to work with, the higher your chances of success.  Don’t be the guy who just plugs in a search for a roundtrip ticket to one city on one airline, on one particular set of dates, finds no seats, and thinks “Oh, frequent flyer tickets are impossible to book.  Forget it.  I’ll just pay for a ticket”.  Using miles takes some research, some flexibility, and some determination.

How to Plan a Trip – Step 7: Book your flight.

Ideally you want to book your flight for free using the frequent flyer miles you accumulated in Step 3.  If that’s not possible, you want to go to Momondo.com to get the best fares to anywhere in the world.  It is the best flight search website, as it searches all the fare aggregators as well as airlines. The best time to book your flight has scientifically been proven to be about 70 days out, on any day of the week, at 5am.  Seriously!

How to Plan a Trip – Step 8: Book your accommodations.

If you have a short trip, and you know exactly where you are going each day, go ahead and book all your accommodations now.  Waiting will just allow your first choice spots to get sold-out.  If you have a trip longer than three weeks; you should allow yourself some flexibility.  You don’t know which stop you’ll love so much you can’t leave.  In this case, just book the first few days.

• If you have really maximized the travel rewards credit card game, you might have many free nights saved up with Hilton, Marriott, and IHG properties.  If so, you should find out which of those chains have properties in the places you are going, and take advantage of the free nights.  When I backpacked across Africa, I stayed in ramshackle $12 guest houses all through Madagascar (which has NO international chain hotels), but then at $100 a night Holiday Inns in Zimbabwae, just because it was free with points.
• If you can’t swing rooms for free, You want to be looking for hostels and hotels on Booking.com.  Booking.com is the best overall platform for finding budget hotels and guesthouses. They have the biggest inventory and best deals.

  

• Before you book, you should also see what is available on AirBnB.  I always check it out, and find it especially useful when staying in very expensive locations.  The local people are often struggling with the cost of living in those cities as well, and renting a room or apartment from a local helps everyone.

If you’ve never used it, sign up for Airbnb HERE and get $40 off your first $75+ Airbnb stay!

How to Plan a Trip – Step 9: Plan how you are going to get around.

There are many options to get around this big world:

• Flying is the fastest and easiest.  But you don’t see anything that way.  Airports are all the same.  Nevertheless, if you must fly, make it happen on Momondo.com
• Train travel is my favorite.  Big windows to look out of.  No bumps or potholes.  No drunk drivers.  You can get up and walk around.  Night trains have comfy fold out beds, and save you paying for a hotel night.  You wake up in a new place, feeling refreshed.  I’ll choose a train every time.  The ultimate authority on any train journey, anywhere; is The Man In Seat 61.  You won’t need any other website than his, trust me.
• Cars are fun sometimes.  You can fit four people in most of ’em, so if there is four of you, it might be the way to go.  Rentalcars.com is the undisputed heavyweight champ of finding the best car rental deals.  Another site worth checking out is Turo.com.  Turo is “The AirBnB of Car Rental”.  You can rent someone’s personal car from them, usually for much cheaper than a commercial car rental agency.  Some Turo hosts can throw in free or cheap extras like tents, sleeping bags, beach gear, etc.

If you’ve never used Turo, sign up HERE and get $25 off your first Turo rental!

• Taxis are the most common way for travelers to get around worldwide.  Uber has disrupted the taxi market in many cities and is growing every year.  I LOVE using Uber in foreign countries.  This past year I used it all over Kenya, South Africa, Belarus, and Ukraine.  In all of these places I would surely have paid much more for each ride going by taxi and getting screwed with the “tourist price”.  With Uber, I don’t have to haggle, and I don’t have to explain where I need to go to someone who might not speak English.

If you have never used Uber, sign up HERE to get $5 off your first ride.

• Walking is going to be a major part of your transportation.  Make sure you have the right backpack and shoes.  Read my Worldwide Travel Packing List for tips.

How to Plan a Trip – Step 10: Solidify itinerary – plan activities for each day.

Now is a good time to buy a Travel Guide, so you can start deciding where exactly you want to go, and what you want to see and do.  I tend to just buy whichever guide is most highly rated on Amazon for my destination.  I prefer paper guides to Kindle, but I’m trying to change that…  My two most purchased are Lonely Planet and Rough Guides.  Rick Steves guides are always the best for budget travel.  Bradt Guides are great for off-the-beaten-track places, especially in Africa.  You can also check out my Destination Guides.

How to Plan a Trip – Step 11:  Pack your bag.  Do you have all the gear you need?

The weather of your destination will decide what you need to pack, but above all, aim to PACK LIGHT!  I travel with a 45 liter backpack, and a 17 liter daypack, and that is plenty for any trip outside of Antarctica.   Don’t buy the largest backpack in the store and fill it to the brim!  It will make you tired and sad.  Read my Worldwide Travel Packing List for a comprehensive list of everything you need to pack, and what you DON’T need to pack.

How to Plan a Trip – Step 12: Plan How to Stay Connected: 

When I land in a new country, I want to get mobile data access immediately.  One way I achieve this is by using Google Fi as my telecom provider.

I highly recommend that anyone planning to do a large amount of international travelling switch their service provider to Google Fi. Google Fi allows you to use your same data plan, at the same domestic usage price ($10 per 1GB, with data free after 6GB) in 164 countries!  With Google Fi, you don’t have to sign up for a pricey “International Plan”. And you don’t get worthless 2G data speeds internationally like T-Mobile’s “One”, you get data at whatever the top speed the local cell towers can offer, which is always at least 3G, and usually 4G.

I just switched to Fi, and it has made traveling sooo much easier.  In developed countries like Western Europe, Japan, and Korea the cost of Google Fi is about the same as getting a local SIM card, so I can skip that whole hassle and just use my phone like I would at home.  In developing countries where data is super cheap, I’ll still get a local SIM to save some money and have a local number.

At home in the U.S., Google Fi uses the cell towers of both T-Mobile and Sprint, switching between whichever has the best signal, so you have more cell coverage than just about anyone else.  I have a Pixel 3XL, which is built specifically to use Fi, but most Android phones and iPhones also work with Google Fi. If you sign up through my referral HERE, you’ll get $20 off your first bill, and I’ll get $20 off my next bill. Everybody wins!

In places where Google Fi doesn’t offer coverage, that usually means buying a local SIM card as soon as possible, preferably in the airport arrivals area.  Before I take off, I always check out this amazing website – Prepaid Data SIM Card Wiki.  It lists all the telecom providers in every country on Earth.  It tells you who has the best coverage, and which is cheapest.  For more info, check out my guide on how to Get Cheap Mobile Phone Service Worldwide.