THE ULTIMATE TRAVEL PLANNING GUIDE

Disclaimer: This page may contain affiliate links. Please see my disclaimer policy here.

How to plan your next trip from A to Z, including travel resources, practical tips, and tricks for a seamless vacation or journey. 

Travel planning can be a daunting task, especially with the amount of information that we have at such easy reach, it’s so easy to get overwhelmed and frustrated.

During my 1 year trip which became an endless journey as I eventually embraced the digital nomad lifestyle, I did some planning but I also did lots of detours, because that’s when the magic happens and that’s how I love to travel.

However, there are a few important details that couldn’t be left in the hands of chance.

I am quite messy and clumsy, I lose stuff and I have a short memory.

So keeping things in order, taking notes, and having a checklist to tick off every time I moved to a different place, saved me from a miserable story to tell.

And it gave me that peace of mind that allowed me to enjoy my freedom.

It may seem like a paradox, but it’s not, and you will find out why later in this post. I have also improved my planning skills over the years, and in this travel planning guide, I want to share my travel planning process with you with the hope of making your planning easier and more fun.

Whether you are going to become a digital nomad life or you just want to organize a trip, this post will help you do that.

Calculate your budget 

When I set off for my South America journey (or what it was supposed to be), I had left a decently paid job and a solid income.

In that situation, I knew that I wouldn’t be able to have one for many months, nor I wanted to.

Therefore I had to plan very well I had to know how much I would need every month, what kind of expenses I would have to face in the long run including unexpected situations, and for how long I could go on.

I did a very rough estimate and it couldn’t have been otherwise, at least for me.

It was too long a journey and I couldn’t really decide or plan in detail for so many days but it turned out  I made quite a good guess.

I started to save from when I had the first thought about this journey even though I changed my mind so many times but meanwhile I was saving and planning and dreaming, just in case.

Read: Saving money while traveling in Mexico for one year

However, if you are not going to ditch your job and plan a simple vacation, it will be much easier, but you will still need to decide how much you are ready to spend. That will help you also to decide where to go and for how long.

Decide how much you are willing to spend on your trip but at the same time leave some margin in case of any emergency.

Prepare for the worse, and expect the best. That’s my motto. So you need to be prepared in case you have any emergency expenses that you have to face.

That’s why I would not suggest using all your savings for your trip.

Decide where you want to travel 

Now that you know how much you can and want to spend it’s time to decide the destination.

I am sure you have a few already in mind so here is the process I would follow to narrow down your shortlist to the one winning destination.

Phase one: write a list of the destinations you are keen on traveling to

In writing the list keep in mind also how long is your trip going to be and if it’s good enough to make the most of the same destination.

Some of the questions you want to ask yourself are:

  1. Will I manage to see everything I want to see?
  2. Isn’t it too far away for the number of days I have?
  3. Do I want to do one country or more in this trip?
  4. Do I want to take my time and enjoy the places I go sucking it all in or do I want to do a “grab and go” kind of journey, just to check places out of my list? Not my way of traveling, to be honest, but most people do that. So you need to decide what kind of journey you wish to have in order to pick the right place.

Phase two: Check out prices

Now it’s time to do a quick search to have an idea of the possible destination you can enjoy with that budget.

I find all of my flights on Skyscanner, Expedia, Scott’s Cheap Flights, and always remember to compare.

Book hotels with Booking.com or Hotels.com, Expedia.Expedia is also great for packages as well.

In this phase, you don’t have to waste much time with thorough research. You just need to have a quick look at the basic costs of the destinations you wish to travel to and then choose accordingly.

Phase three: decide what kind of journey you want

Now it’s the time you ask yourself some questions to determine the kind of trip you wish to have

  1. Do I have an active vacation with outdoor activities or a relaxing one on the beach?
  2. City and cultural venues or countryside?
  3. What’s the best place for the season?

Phase four: do some research

Now that you know what kind of vacation you want, you will need to match it with the destination. This is when some search comes in handy.

Checking on things to do at a specific time of the year in a specific destination will help you connect the dots.

Phase five: Look up what documentation you will need

Some countries have Vaccine and Visa requirements. Visalist.io  has got you covered. Just insert your passport country and click on search.

It will give you information on the visa requirement of each country. Some countries require a visa application submitted months earlier. Be smart about it.

Phase six: connecting the dots

Now you have plenty of information to help you narrow down your shortlist and decide your travel destination.

I suggest you write down everything you find out in a spreadsheet so that you will have the information laid out right before you.

Research flights

With Airlines you never know… Sure is they constantly change rates, based on many different factors, time of the year, booking window, destination airport taxes, and competition, just to name a few.

To search for my flights I have these simple rules:

  • Rule number one is: always search from an incognito window.
  • Use aggregators, which means sites that compare rates from different airlines, which is great for you to see all prices on one page.
  • Compare prices among the aggregators but also on the airline website as well, at different times of the day or night, so you will make sure you are really getting the best possible fare.

If you see a rate that is reasonable to you book it without hesitation because you never know when the offers end.

Once the seats are filled the fares automatically raise.

Once I lost an amazing rate because I wanted to wait…

However be aware that the airline sites use cookies, not the ones that we all eat and love, the ones that track your information.

So the next time you log in from the same computer they know that you have been searching for that destination and the price automatically raise!

Yes, it’s that bad! we live in a dirty world!

But now that you know, what you have to do is either clear your browser history or open an incognito window and search from there.

With aggregators such as Skyscanner you can also set up an alert for your search result, this way you will receive an email every time the rate fluctuates.

Let me know should you need any assistance with this…

Decide and plan what to do

Now, I am sure at this point you know approximately what to do as I guess the reason why you would choose a destination is pretty much related to the things you can do and the places to see there.

However, now it’s time to do thorough research and make a plan, especially if you are going to have an itinerary trip you will need to decide how many days you are going to stay at each destination.

I normally use the following tools to search for a destination:

  • Google “things to do in” or unique things to do in, and tend to check out blogger sites, sometimes I have a pick on page 2 or 3 on Google to find more sources
  • Pinterest
  • TripAdvisor for restaurants and tours
  • Instagram

Since this is not something that I would do once and for all, but I will use some free time here and there I would make notes either on the block note of your phone or google doc and throw everything I find no matter in which order.

Never believe you can possibly remember it.

Always write it down, so that when you have more time you can organize all the information on a spreadsheet to be used when needed.

I confess I also love to take write notes the old way and I would write everything down by pen.

It just feels so much more real.

Book day trips

Although I totally prefer to rent a car and explore on my own, there are some situations in which it’s much more interesting or easier to book a tour.

You would need to research what is most convenient of course but that’s what we bloggers are here for! right? 

If you decide to book an organized tour, the best thing to do is to book in advance in order to save your space and most of all to organize your schedule for the remaining days, especially if you don’t have much time.

There are in fact many tours that combine different destinations, for half days one full day.

They almost always come with a guide which I find useful when you are visiting a historic place and in general to know about the local culture and society.

Viator is one amazing platform that I partner with, that have thousands of different tours available.

Organized Guided Itineraries

There are many reasons why you might prefer to join an organized multiday tour

  • If traveling alone is not your gem
  • if you just want to join a group of like-minded people to travel with for some time
  • or if you just don’t want to be bothered or don’t have time to plan

I totally get you.

Where to stay

Once you have established the itinerary, you have to decide where to stay. Here are my favorite booking platforms for hotels.

VRBO and PLUM GUIDE

In my case, I have been booking the majority of my stays in apartments rather than hotels when I was doing long stays and working while traveling.

That’s just because being on the road for such a long time, I love to cook my own meals and have a cozy spacious place.

Also, you can find great discounts for 7 days and 1-month stays.

Booking.com

However, I love nice and cozy boutique hotels and when I don’t have to work and I am just traveling for leisure, I love to check out in a nice artsy hotel and that’s when Booking.com comes in.

The platform is super user-friendly and straightforward, it offers reviews from previous clients and has a thorough description of the properties, not to mention the great deals that you always get.

Hotels.com

Hotels.com is another great platform, part of the Expedia group, and reliable.

It’s definitely worth checking and comparing prices.

Expedia.com

I find Expedia very useful when you want to purchase hotels+flights packages. That’s because hotels offer great deals if they come in a bundle with flights.

Also, keep in mind that when you book a flight on Expedia you have 24 hrs to cancel it without any cancellation policy.

I will receive a full refund, which is very convenient.

TripAdvisor

I normally use TripAdvisor to check reviews of places and tours, however, it has also become a booking platform for the past few years. It’s actually an aggregator which feeds from other traditional platforms and compares prices. So it’s definitely a great resource to rely on.

Hotel reservation guidelines: how to make a hotel reservation in a smart way.

  • Enter the correct number of people in your party, because room type and rates would vary accordingly.
  • Make sure you read what are all the services included in your rates so that you won’t have false expectations.
  • Remember the taxes are almost never included, so make sure you check all the smallest notes. Normally the taxes are mentioned right before checkout.
  • With Booking.com you can pay directly upon arrival while with Expedia you are asked to choose your preferred method of payment. It’s up to you.
  • Check the cancellation policy, always! Just to make sure up to which date you can have a refund in case you need to cancel?
  • If you are sure you won’t cancel or you have good insurance, you should look for NON-REFUNDABLE deals, where normally the hotel set the price very low but it is subject to cancellation penalties in case you cancel, from the very moment you confirm the booking even if it is a year before your stay. That’s also one of the reasons why purchasing travel insurance is a smart move. But I will talk about in the next chapter.

Plan travel logistics

Now it’s time to get into further details of your trip, those details that would make you waste so much time during your holiday instead of enjoying it if you didn’t prepare for them. Here is a list.

Find out the following information.

Local Currency

Can you exchange money in your bank or do you need to do it there? Where you can do so? Normally it’s advisable not to exchange money at the airport and get to the banks or Money exchange bureau in the city, but you might be in a place where you don’t have a choice. You need to find it out before flying.

Local transportation

How do you get to your hotel once you arrive? Is Uber an option there? or is it better to pre-book a transfer?

In this case, the Viator platform is also a useful place where to book transportation.

Organize your reservations confirmations

You won’t know if you get WIFI in the airport, even if you research before, you cannot be 100% sure that’s working or you can accidentally end up without a battery on your phone. Whatever.

I always love to make sure I have all the information handy when I get there.

So, here’s what I do.

Take a screenshot of your reservations and save it in all your electronic devices.

I am not fond of printing out and wasting paper, so don’t do it if you are sure that one of your device batteries will make it to your arrival, otherwise print just the necessary sheet of paper with the information needed.

Inform your family and friends of your itinerary

You never know what can happen when you are away from home. It’s very important, besides purchasing travel insurance, to inform your close friends and parents about your itinerary and where they can reach you, besides your phone number. Also, inform them if you will be staying with no phone reception for some time so they won’t worry.

Stay informed

Stay up to date on the news and be aware of there are any political tensions or unsafe situations. There is so much to see in this world. There is no point in putting yourself in danger. It’s also an ethical practice not to support governments with little or no respect of human rights

Pack an adaptor

I will go through a complete checklist later on in this post.

However, here it’s important to remind you to make sure you search which kind of adaptor is used and remember to pack it.

You don’t want to spend the first day of your trip playing treasure hunt in the city (if you are even in a city) to find where to find one, to be able to recharge your phone and other devices, do you?

How to move around

I find google maps the best way to find your way around.  It’s always with me but you need to make sure you have data on your phone or do your itinerary search when you have WIFI.

In Europe, I also use it to find out the best transportation combination to reach one place as public busses are connected to the app. However in Latin America, it’s not working, yet,  not sure in Asia.

Sometimes you can find applications for the local transportation bus that can be efficient as well.

Maps.me is also an app that can be used online but you need to download the region that you are interested in, when you have WIFI.

To move from one city to another some travelers suggest Rome2rio. To be honest I have never used it personally but I have tried a few routes just for a test and I didn’t find it very accurate. You can still use it though, but take it with a grain of salt and do cross-checks with other sites.

Do you need a car rental?

I always prefer to get a car and drive around, everywhere I go, from Jamaica to Mexico, anywhere I feel safe I do it.

I just find it simply the best way to find remote places and secret corners where public transportation can’t reach for many reasons.

Of course, it’s not always the case and that’s why planning ahead is always advisable, hence this post.

If you chose to rent a car here are the sites I recommend.

Discover Car Rentals

MY PICK
Best Car Rental Deals w/ Free Cancellation, Compare & Save! | Discover Cars

Find the best car rental deals and explore around freely, at your own pace. My favorite way to enjoy a destination!

Best Car Rental Deals w/ Free Cancellation, Compare & Save! | Discover Cars
VIEW DEALS

Local car rental companies (depending on where you go)

I would suggest you check them all out, try to make a quotation, and see what is most convenient for you.

They might have a special deal in the country where you want to rent.

I have used Discover Car Rentals for my trip around Baja California and I really felt great about it.

The thing that I love the most is that each site compares rates among different car rental companies.

Beware though, that you need to check out the insurance too if you need it.

Bear in mind that those sites are only aggregators and they are not responsible for each company policy.

First, check how much it is and then what it includes. When you ask for full insurance (which I recommend), always ask what they mean for FULL, because most of the time the windows or tires are out and sometimes you have a deductible, in which case it doesn’t make it a FULL insurance.

Therefore more than the initial price which is normally very low, you will need to dig a little deeper and ask what is included in that price. Also, the DROP OFF tax is important. If you pick the car up in one place and drop it off in another city, for the majority of the time your bill will inflate significantly.

Read: The honest truth about renting a car in Mexico 

Make sure you are safe

Before starting to explore and get lost in the city, make sure you do some search and compare reviews and comments about the safety of the place you are in. Don’t let bad episodes scare you but also be mindful and cautious.

Common sense is never out-of-date.

And here comes the next chapter.

Keep reading…

Consider unexpected mishaps (how to minimize the risk)

Buying a travel insurance is a gamble. You don’t want that anything happens to you on your trip but at the same time, you know there are things that are out of your control, like a missing bag a canceled flight, an accident, and many other mishaps. We want to make sure that if anything happens we are covered. But at the same time if nothing happens, we think, we have wasted money in travel insurance that we didn’t even use.

I find it to be a tricky one.

Somebody asked if it’s possible to get a refund from the insurance at the end of the trip if you didn’t use it. I had a good laugh. And if you are wondering too, the answer is NO. This is how insurance companies make money.

They are gambling too.

They bet on your health and your lucky star.

And you will need to decide what is more important. Insurance would cost an average of 35 to 50 USD per month. I would pay this price for some peace of mind, to know that if anything happens I will be taken care of, and I wouldn’t have to face extra costs.

Of course there are many factors that you need to look into when you choose and travel insurance and I will get to it on another post.

Now I am just suggesting a couple of travel insurance companies that I trust.

Safetywing

Another company that I just happen to find and will try myself is Safetywing. It’s been used by many other travelers and digital nomads especially because it’s made by nomads so they know our needs. The comments that I am seeing are nothing like praise. So I will let you know about my experience when I will use it. But I can just tell you I love their website, it’s cute and super user-friendly.

GET A QUOTE WITH SAFETYWING

Generally speaking though, before signing up, make sure you read through what’s included and not included and if in doubt reach out to the company and ask questions.

Pack wisely

When it comes to packing my favorite phrase is ” Just in case” and my bagpack or suitcase is never going to be light. I gave up trying.

However, ironically enough, I do know how to pack light. I just don’t follow my own advice. You can do it or not.

Here some guidelines:

Clothing

Pack wisely When it comes to packing my favorite phrase is ”Just in case” and my backpack or suitcase is never going to be light. I gave up trying. However, ironically enough, I do know how to pack light.

I just don’t follow my own advice. You can do it or not. Here some guidelines: Clothing Deciding what to wear is always related to what kind of vacation are you having and the ability to find  a balance between my “just in case” and “just a carry on”.

So supposing that we are going on an itinerary trip which includes beach, hiking, elegant hotel, and outdoor activities. Overwhelming, right? Not so much.

Now that you have decided what activities you will do, it should be easy to decide what to wear. Think about how much hiking will you do versus beach time, and therefore decide how much spare clothes to change would you need.

What the weather is supposed to be like.

But also what items can be combined in multiple ways so that you can feel like you keep changing your look with a few items.

Also think about layers, t-shirts, jumpers, a scarf, or one neckless that might be nice to wear on a night out.

I am all for keeping it simple and essential but as a woman, I also love to look nice every now and then.

Decorative elements don’t hurt. they are small and light.

Grab your travel essential packing list here

Also remember:

  • that you will find laundry places anywhere you go
  • use packing cubes to optimize space

Toiletries

I am not a maniac of face creams and other super complicated toiletries so I would go with the essential. Toothbrush, toothpaste, facial soap, and moisturizers. Hair comb, shampoo, and conditioning. Deodorant. I don’t use makeup so I cannot really say anything about that but if you do I don’t think it will add lots of space.

Always bring a towel with you, you never know.

Electronics

Depending on how techy you are, and how much you love photography, or if you really need to bring your laptop with you. I really can’t tell, you only know.  I cannot travel without my camera, and lenses, no matter how bulky they are. And my laptop. Just make sure you keep it safe and protected.Read: How to find the best camera bags

Travel Essentials

There are a few items that will make your life easier if you travel with them and that I would always pack:

  • first aid kit, if small, such as bandaid, disinfectant, and paracetamol, besides my homeopathic essential remedies.
  • a wrap, which can be multifunctional, if you get cold on the plane, or on a chilly night or if you need to enter in a sacred place and need to cover up, for instance.
  • a microfiber towel, of those that are very thin and super absorbent. You might need it if you go on a couple of days trek or on the beach.
  • money belt, it’s always good to have cash with you for any emergency. However, you will need to have the minimum needed handy while hiding beneath your clothes the rest of it. This belt is just perfect, slim, and with RFID Blocking Sleeves Set to keep your passport and credit cards safe as well.
  • lightweight packable backpack for daily trips or beach.

Check out the destination packing lists I have created.

Travel resources full list

I have been mentioning sites and apps  all over the place – In this section I am just giving you a full list of my travel resources for your convenience.

Booking flights

Find accommodation

Things to do

Travel Reviews and info

Moving Around

Travel Insurance

Budgeting

Travelspend App

Travel Shopping

Travel Packing Lists

About the Author

Hello there! This is Isabella, the author of this blog, and a cat lover. I am an Italian expatriate with a Mexican permanent Residence. After 7 years of living in Cancun, I have decided to leave my job and explore my beloved Mexico and the rest of this beautiful world, starting from South America, while sharing my travel stories and offering useful travel tips about traveling as a solo female traveler and digital nomad.