When I first planned a trip to the Caribbean with my family, I was incredibly overwhelmed with this responsibility because I didn’t even know what was involved in planning a trip.

But I’ve had the luxury of traveling to over 30 countries now, and through my travels, I’ve completely mastered how to plan the perfect trip ANYWHERE!

From planning so many vacations, I’ve learned how to save the most money while doing the maximum amount of fun things with my precious travel time, and make the entire travel experience as smooth as possible.

No matter where you are planning to travel to, this guide will make vacation trip planning a piece of cake.

The quality of your travel is largely depended on how well you plan it (believe me, I know!) So I’ve created this incredibly comprehensive step-by-step trip planning checklist to walk you through exactly what you need to do to plan a trip (anywhere).

What’s in this trip planning guide?

I’v broken down all the major travel plan items you need to think about and research before you travel. I’ve included a lot of best tips and practices I’ve learned in each step, along with additional resources to get more information and dive deeper into each specific topic.

The major travel planning steps are:

  1. Researching your destination
  2. Plan your travel logistics (flights, accommodations, transportation)
  3. Planing your travel itinerary
  4. Managing your travel finances
  5. Obtaining your travel documents
  6. Organizing your travel technology

I’m so excited for you! Let’s do this!

Step 1: Research your travel destination(s)

The first thing you need to figure out is where you want to go. If you already know your destination, skip to the next section (finding things to do and see)

If you are looking for ideas of possible destinations to travel to, I recommend the following websites to get ideas from:

  • Pinterest | Type in something like “best places to travel solo” or “where to travel to in April”) You’ll get plenty of potential ideas here
  • Google | My favourite place to research places to visit. I like to use general search queries like “best countries to visit on a budget” to get ideas

Pinterest is great because you can save the pins you like very easily and come back to them later to reference. Pinterest and Google is all you’ll need for this step.

How to find fun things to do and see in each city

Probably the most exciting part of travel planning is looking at all the potential things you can do!

For this part, and the rest of your planning, I recommend using an app on your phone to write notes down. A popular app you can use is called Evernote. It syncs with all your devices as well (so if you write notes on your computer, the information will transfer to your phone).

Where to get ideas on what to do

What’s fun to do and fun to see is 100% depended on your taste, right!

So what I want to share with you is WHERE you can go to get tons and tons and tons of ideas. (remember to write anything cool down in a notes app!)

Pinterest is a place where travel bloggers share their travel blog posts.

Specifically, travel bloggers pin posts like:

So what you want to do is type in a search term like “things to do in Paris France”. You’ll get hundreds of pins that will send you to blog posts for endless ideas.

Remember, these are actual travellers, travel influencers, and travel bloggers sharing their personal experiences with you. They will share what they liked, if this attraction was worth the money, and more. I’ve always found these insights crucial to figuring out what’s worth my time or not.

What if you’re only looking for what’s popular in a destination?

To find out what the most popular things to do in a city/destination are, you’ll want to visit a major excursion booking website.

These websites sell paid excursions offered by locals in a city/destination. In other words, the excursion/attraction listed will be among the most popular things to do.

My favourite website to research the top things to do in a destination is Viator.com.

I use Viator to get ideas of what I should be doing in a new place. If you see a tour/excursion you really like, you could also book it through them instead of planning an itinerary for it yourself. But the main idea of using Viator is to find what’s popular to do in a city.

How to find the best places to eat

In my opinion, the best way to find the best places to eat is to ask locals what they recommend. This is what I do most of the time. I HIGHLY recommend you go this route too.

For example, in Florence, I asked a random local on the street for a good place to have lunch. He recommended Florentine beef steak at a nearby restaurant. We went there, and I had the best T-bone steak I’ve ever had, and the seafood spaghetti was also one of the tastiest Italian dishes I’ve ever had.

A lot of amazing local restaurants are NOT very visible on apps or the internet. They tend to be smaller places that don’t advertise much or cater to a big tourist crowd, but you better believe locals know about them and how good they are!

Other ways to find good eats in any country

You may not want to be completely adventurous with your eatery choices and prefer to research a little before departing or even while abroad.

Totally understandable. Here’s how I would approach that.

I recommend two ways to research good eats:

1. Food app | Search the app store on your phone and download a few food apps. They are wildly popular and will give you tons of recommendations on where to eat depended on what type of food your craving, budget, and typically rate eateries/restaurants by a star rating system, and they typically have user reviews of the restaurant too.

2. Google maps | Google maps is also a very easy way to find food near you quickly. All you’ll need to do is type in “Sushi restaurants” (or whatever you’re looking to eat). Google maps will show many sushi restaurants near you. In Tokyo, we wanted conveyer belt sushi and my friend found one near us in the Shibuya district using this exact method. It was the BEST Japanese food I’ve ever had (for an incredible budget price too). Google will also show you user reviews and a star rating too.

One last tip

Many restaurants (especially in touristy places) have a green Trip Advisor sticker on their door/window. I’ve found they’re usually good bets. Use your phone and quickly look up their reviews. If it’s 4 stars or better you’re usually in good hands.

Step 2: Planning Vacation Logistics (flights, accommodations, transportation)

Now it’s time to work out your logistics. I personally like to have as many things booked and reserved beforehand as possible.

This guarantees I have a bed to stay in and a way to get around – which can become difficult to secure if you leave it last minute, especially during busy season.

Here I’ll go through how to approach securing flights, hotels, and figuring out transportation (at the most cost effective way possible).

Booking your flight (and finding cheap flight deals)

I’ve found the two best ways to get the cheapest price on flights is to book well in advance or wait for a special seat sale.

Booking in advance | If you are planning your travels ahead of time, now is the time to look for flights. Flights are almost always cheaper when you book earlier (start looking as early as 6 months is reasonable).

Here’s an easy way to get the cheapest flight price:

1. Check flight booking websites like Expedia.com once a week or so to monitor flight prices to your destination. Flight prices will fluctuate depended on how many seats are sold (among other things) and new flights can be added too. Manually checking a few booking sites per week (or even every few days) is what I recommend (make sure to do this at least a few months in advance).

2. Use a flight monitoring system like airfarewatchdog.com where you enter the flight(s) you are interested in, and they will alert you if the prices of the flight drop (through email).

I’ve found flight prices generally go up the closer it gets to your departure date. It is very difficult to determine if flight prices will increase/decrease. What I recommend is if you see a price you’re happy with, consider booking it now.

Waiting for last minute deals | Last minute deals, whether we’re talking flights, vacation packages, or hotel rooms, will save you a ton of money.

The problem is that “last minute offers” are unsold inventory that are reduced in price to fill them up quickly. It’s next to impossible to plan a trip based on last minute pricing because you can’t predict it.

If you can pack your bags any time and are open to going to all sorts of places, you are the perfect candidate for last minute travel – and all the huge travel savings that come with it too!

How to find the best accommodation for your budget

Where you stay during your vacation is absolutely critical. It can make or break your trip.

Here are three very important accommodation points I wan to make:

  • Pick a very central location in a city (or central to many places you’ll be exploring)
  • Pick an accommodation close to transportation
  • It’s not just hotels anymore (apartments and rental homes are great value too)

The two most important points here is to find a place to stay that is close to the things you will be doing or has nice things in walking distance nearby, and also has quick access to a major point of transportation.

Booking a central location | The most important factor I look for when booking a place to stay is how central the place.

For example, in Barcelona, I rented an apartment just off Barcelona’s most famous street Las Rambla. The street itself is filled with touristy things to do, a nearby large shopping mall, the beach, La Boqueria food market (bought food to cook in our apartment from here) and a nearby underground train! It was the perfect location. We could walk out the apartment anytime for a stroll, food, entertainment, etc.

I absolutely feel it’s worth spending a little more money to stay in a better location. Your quality of travel will drastically improve.

Booking a location close to transportation | If your destination requires you to take trains, busses, and any other public transportation, you want to make sure you are as close as possible to them.

This is important because time is everything and you want to limit transit time. Plus, you’re probably going to be super tired from all the walking you’ll be doing, the last thing you want is to walk another 20 minutes to your room after you get off a train.

For example, in Tokyo, the main train line JR Yamanote (runs most often and circles the main points in Tokyo) is the line I knew I needed to be closest to (I was going to be taking the train everywhere daily). So I specifically searched for a hotel within walking distance to one of their stops. I found a hotel 8 minutes walking distance at a price I could afford, which a good rating, and that’s the one I booked!

how to find accommodations close to transportation?

Use Google maps. All you need to do is type in the name of your accommodation and look on the map for transit services/busses/trams, etc (Google maps is great for this). You can map out walking distances through Google maps too.

You have more accommodation choices than hotels | Hotels used to dominate the booking scene, but that’s so far from the case today. A lot of people are choosing different accommodations specific for their needs.

Here are popular booking ideas other than hotels:

  • Airbnb – One of the best places to rent someones home, however you can book all types of accommodations here
  • Renting apartments – A great idea if you have a group or a family
  • Hostels – Excellent choice for budget travellers, solo travellers, and if you’re looking to meet others

Finding cheap accommodations

Just like with flights, searching for accommodations ahead of time is the safest way to find the best place for the best price.

With accommodations, you have way more options than flights, so it’s not necessary to book anything immediately unless you see a fantastic deal.

I personally like to check a few hotel websites every few days to compare prices and to see if anything new pops up. If you are close to departure time, I recommend booking sooner rather than later, because places fill up and prices (overall) tend to rise when less inventory is available.

Figuring out how to get around countrywide

Whether you’re visiting several countries clustered together or visiting many cities within a single country, you’ll want to transport yourself around as cheaply and conveniently as possible.

The best way to travel around will be entire dependent on what modes of transportation is available and what Country/Continent you are visiting.

Planning transportation when you’re traveling to several countries

Flying | If you’re exploring several countries, you’re likely going to want to fly. Check with budget airlines who often can get you between countries for less than $100 (especially in places like Europe). I flew from Budapest to Athens on Air Serbia for about $60 in a few hours, whereas taking a train was just as expensive and would take 12 hours or so.

Train | The train is also a fantastic way to cover a lot of ground and to avoid the hassle of airports. Trains generally take longer than flying (when going across to another country) but may be more convenient.

Planning transportation when traveling to several destinations in a single country

Flying and train travel can both make sense. Typically, you’ll want to fly if the distances travelled is far (for example, you’ll want to fly if you’re traveling across the massive country of Canada).

Train travel makes sense when you need to travel shorter distances and/or there is reliable high speed trains available. For example, in Tokyo, I took the train everywhere, including the bullet train (high speed fast train) between Tokyo and Osaka. Even though it was more expensive than flying, it was more convenient to get me between cities.

Trains or flights – what makes the most sense? It will come down to convenience and money. I prefer to pay more money to get from point A to point B faster and more conveniently (as long as the other option isn’t dramatically cheaper).

There are also other options like ferries and water taxis depending on where you will be visiting.

How to rent a car

Renting a car makes the most sense when you explore places that don’t have public transportation or you want to explore places at your own pace and generally wander all around.

You can rent a car online before you arrive at your destination, or rent a vehicle when you arrive.

Typically, you’ll get cheaper car rental rates when you rent online before your trip begins (lots of deals to be found online). You’ll also avoid the hassle of no available vehicles (or out of stock of the type of vehicle you want) though I’ve found this to be rare.

Step 3: Planning a trip itinerary

You’ve figured out what cities/countries you want to visit and have researched all the things you want to do in each place. You have a good idea of where you want to base your travels out of and how you’ll get around.

Now it’s time to plan a travel itinerary!

How I like to plan an itinerary (and what I recommend for you as well) is to break what I want to do by each day.

For example, my travel itinerary for Berlin looked like:

Day 1

  • Arrive noon, taxi (should cost $20) to hotel
  • Check in to hotel 2pm
  • Check out nearby restaurant area and eat 5pm
  • Walk the local area check out the street art, maybe go out if not tired (will be a Friday)

Day 2

  • Grab food. Lots of local places in area
  • Rent a bike at Mike’s rentals. Ride to Alexanderplatz (should take 25 mins)
  • Explore Alexanderplatz, grab lunch
  • Ride west to Alexanderplatz, then Potsdamer Platz, and then back to bike shop
  • Grab food again, check out nearby Gorlitzer Park
  • Head out to possible night clubs Traffic or Berghain maybe

Day 3, 4, 5, 6, etc will contain bullet points just like above so I can easily follow my schedule.

My schedule is a general guideline of what I can do each day so I don’t waste time figuring out what to do while abroad, and so I don’t forget/miss things I wanted to do.

I can omit items, add items, and change days I do things depending on how I feel, what I learn there, and unavoidable situational circumstances (like a museum closure).

How to plan a travel itinerary

Remember I told you to note down all the things you want to see and do? Now it’s time to figure out WHERE all those things are.

Google maps (again!) is your friend. Type each item down into the map and figure out where it is located. Find out the best time to visit the place, if you need tickets, hours of operation, etc. by visiting the destinations website or reading reviews (on a site like TripAdvisor or Viator).

Google will also show you a location by neighbourhood. I recommend visiting places by neighbourhoods rather than zig zagging all over the city each day.

For example, in a massive city like Tokyo or Osaka, I trained to the center of a neighborhood, and explored all the places I wanted to visit by foot. Sometimes I’d cover two/three neighbourhoods and they were generally neighbouring ones.

tip: a great way to find out what to do in a specific neighbourhood is to type in to Google “thing to do in Kreuzberg Berlin”. You’ll get a ton of ideas specific to that hood.

If there are museums and attractions you want to visit, find out if there is a cost and if it’s cheaper to buy tickets online or to buy a package deal that gets you into many attractions and a bundle. Find where they are on a map and logically plan which days you’ll be seeing which attraction.

Planning a trip itinerary each day is as simple as making bullet points of what to see and do each day (like in my above example). Or you can use one of these travel itinerary templates as well. Whatever keeps you on track the best.

Step 4: Preparing & Managing Your Travel Finances

The three main money things you need to get handled before your trip is:

  1. travel budget
  2. travel insurance
  3. how you’ll use your money abroad

How to figure out your travel budget (your cost of travel)

A travel budget is important because it helps you figure out how much money you’ll need for your entire travel. It will also help prevent you from overspending (which will likely happen anyway but hopefully not by any disastrous amount!)

If you’re really into traveling and want ways to make money traveling, read this post about getting paid to travel.

I like to break down the cost of travel by calculating my “average daily cost” which averages every cost of my travel (including flight, hotel, unexpected costs, etc).

Here’s a rough idea of what my budget to Japan looked like:

  • $200 flight (because I used credit card reward points!)
  • $1500 capsule hotels
  • $700 train rides
  • $1000 food
  • $300 excursions, entry fees, etc.
  • $300 miscellaneous costs

That totals $4000 for 1 month of travel in Japan. Divide that by the 30 days I spent there, my daily average cost comes to $135 per day (I went over budget on food but that’s a story for another day :P)

You should calculate your costs the same way. Write down all your:

  • hard costs (hotels, flights, city transportation, etc)
  • soft costs (items like food, shopping, tourist attractions, etc)

Estimate unknown costs as best you can. Add it all up, divide by the number of days you’ll be traveling, and that’s your estimated daily cost.

You now know how much money you need for travel. If you don’t have enough saved, now is the time to start saving!

Travel insurance

Travel insurance is protection from unexpected travel costs like if you get sick and need medical help or if your flight gets delayed and you have to stay at a hotel overnight until the next flight in the morning. Both of these things happened to me.

Here are two examples of how travel insurance helped me:

  • I got sick in Greece and needed stayed in a private hospital for a day, which costed $1000. That’s actually cheap because it’s Greece. Imagine if it was a country like the US
  • My connecting flight to Cancun was late and I was forced to stay a night in Atlanta because the next available flight was the next morning

I had travel insurance so I didn’t have to pay for the costs above.

So the question you’re probably asking yourself is, do you really need travel insurance?

In all likelihood, something is probably NOT going to happen. But when it does, you’ll wish you had travel insurance. Especially if you get sick and need medical care (this can be incredibly expensive depending on which country you are in).

I do recommend travel insurance for everyone (I always buy it).

How to get travel insurance

First, check your credit card perks. If you have a premium credit card (usually has an annual fee), you likely have some sort of travel insurance. I’ve found many credit cards cover you for the first 14 days abroad or so. This may be all you need.

Otherwise, buy travel insurance for the duration of your trip.

How to use money abroad

You’ll want to know how to pay for things in the country you’re visiting and how much money to bring.

How to pay for things | Most countries accept credit cards (Visa, Mastercard, etc). This will likely be your primary form of payment. I always carry cash with me for emergency purposes and some places (especially not so touristy ones) only accept cash.

I would not use a debit card abroad. You (generally) have zero protection with debt cards when things go wrong.

Keep around $100 in cash with you at all times. You never know when you’ll need it. Also keep a few hundred dollars in cash in a safe place for emergency purposes (hotel safe, suitcase, backpack are all good ideas).

Overall, I recommend using your credit card for as many things as possible. You’ll earn points, have buyer protection, and it’s convenient.

How much money to bring | If using a credit card is your main form of payment, then bringing a few hundred dollars worth of currency should be sufficient in most cases. Make sure it’s in the currency of the country you are visiting and make sure to have this money in your wallet before you depart.

If you are visiting a country where cash is widely used to perform daily transactions (like Japan, Colombia or Indonesia), I would recommend bringing at least half of the cash you need when you depart for your trip. And to take out more money (from an ATM or bank) as you need during your trip.

Step 5: Get Your Travel Documents Sorted

There are a few important travel documents you need to get sorted before you travel. These are extremely important so don’t overlook this step.

Passport | If your passport is expiring soon, get it renewed ASAP. A common rule in many places is to have your passport valid for at least 6 months prior to your travel. I had a family member be denied passage onto a plane because she had 1 month left before her passport expired. She had to stay back to fix this while we boarded for Europe (this included the cost of express shipping of a new passport and booking a new flight. Ouch!)

Visa | A Visa is a piece of paper that will be placed in your passport that gives you permission to enter and stay in a country for a specific period of time. Many countries require Visas to enter. Some countries require you to pay for your Visa upon arrival and some require you to obtain your Visa before entering. Check for Visa requirements before you travel.

Drivers License | If you plan to rent a vehicle abroad, at a minimum you will need a valid drivers license from your home country. Make sure you bring it and that it has not expired. It’s also important to have a second piece of I.D. to take with you abroad.

Make photocopies | I recommend taking photographs of all your important documents (passport, visa, drivers license, etc) to store in your phone, in an email to yourself, and perhaps on an app. Also make physical photo copies of these documents to bring with you abroad. You need to be able to identify yourself in case unfortunate events like getting pick pocketed, lost luggage, or natural disasters abroad.

Step 6: Get Your Travel Technology Sorted

Travel technology is a huge deal. I always make sure I have all the right tools and gadgets for the type of trip I want.

I’ll be covering the main technologies to consider here.

Phone | Your phone will be integral to a success trip, of course. Your daily itinerary will be on there, and it will be your access point to documenting your travel through taking photos and journaling, and it will be your primary way to navigate your way around a city. I think it’s a good time to upgrade your phone to a reliable high quality smart phone before you travel (if your phone is old).

How to use internet on your phone abroad | Many countries will have public wifi widely available. You can find a Starbucks, McDonalds, or any other major chain that offers free wifi. If you’ll be accessing private information frequently I recommend getting a sim card when you land in your new country. Your internet connection will be “private” which will protect your data. Otherwise, simply use your hotel room data to access sensitive information (not fool proof safe, but much safer than public wifi).

Making phone calls abroad | You can make phone calls using internet (wifi) with an app like WhatsApp. This is what I recommend doing for calls. If you need to make phone calls randomly throughout your travels and can’t rely on wifi, then purchasing a minutes plan from your carrier back home before you travel is likely the right move.

Buying a sim card | I only recommend buying a sim card if you need to make phone calls or need data on demand while abroad (or if data is very unavailable). If these things matter, make sure your cell phone is unlocked (so you can use any sim card around the world in it). When you arrive at your new country, you can usually buy a sim card right at the airport, and all around the city like in shopping malls.

Travel camera | Your phone may be the only camera you need. However, if you want to step that up, get a good travel camera to document your travels. Head over to a local camera store to get ideas and help on choosing the right one for you.

And that’s it!

It will take you a little bit of time to do the research and put it together. All your hard work will make your vacation go incredibly smoother!

No matter where you are planning to travel to, this vacation trip planning guide will help you!

If you have any questions, leave me a comment below.