How to Plan a Trip – Helpful Tips

by shortgirlontour
How to plan travel

Where to go? when to go? where to stay? what to do? These are some of the most common questions that need to be answered when planning travel. Being a massive planner and with 29 countries and counting, I’ve had my fair share of planning trips and my fair share of ‘I wish I had known that’. This post covers how to plan a trip and some of my tips and tricks for an smooth and amazing trip.

Where to Go and When to Go?

These are the first two questions you will have to answer. I usually start with my bucket list which I’ve been compiling for a few years now. I go through my list and think about what kind of vacation I am looking (i.e., adventure, culture, R&R). Then I narrow down my list of places.

Next consider the seasons. Summer may not always the best time to visit a place. For example, although July is winter in Peru, it is the best time to take the Inca Trail to Machu Picchu. Even though most tropical countries don’t have seasons, rain and the monsoon period is something to consider before planning a vacation.

How to plan a trip
July, although Winter in Peru is one of the least rainiest months and the best time to visit the Inca Trail

If you are looking for less crowds and cheap rates, travel during off peak for that destination. (“off peak” may mean different things depending on the destination). If you are thinking about Europe, avoid visiting anywhere from mid June to late August. The trick for Europe, is to travel during transition months like May and September. The crowds are less this time and the heat is not unbearable. I make at least 1 trip to Europe each year and visit in May. I’ve found this to be my sweet spot for Europe.

Also, regardless of whether you’re a warm or cold weather fan, the different hemispheres make it possible for you to always travel in your climate of preference.

Book your Accommodation Immediately

Book accommodation the minute you book your flight or if you like to wait for a good fight deal, book accommodation the minute you decide on a destination. You can do this using a flexible booking tool. This way you can make changes if you find a cheaper rate or better option later. is my favorite booking tool for hotels. You can cancel most places up to a few days before arrival. They also have a good loyalty program that offers discounts and other benefits like free breakfast and airport taxis. The cancelable rate is sometimes higher than the non-refundable rate but you can always change this the minute your plans solidify.

Book Accomodation with a 24/7 Reception or Lock Box

This is something I learned the hard way during my trip to Spain last year. Luckily, I was able to alter my course without a disruption to the trip but of course it came at a cost. If you have early morning or late night flights/trains, make sure your accommodation option has a 24/7 reception or lock box. It doesn’t hurt to confirm that they are able to check you in or out at the time you want.

What to See and Do

Here is what I do to when I am planning.

The first question I answer is if I am are going to multiple countries, one country with multiple cities, or just one city.

The second question I answer is if I have a set number of days or if I have the freedom to let the destination dictate how many days I will be in each city/country.

Next, I use several sources to figure out what to see and do starting with a plain and simple Google search. My query starts with a “places to see in x”. X here can be a country or a city depending on step 1. From there I make a list of all the places Google tells me and do in depth research on each place. This research includes the following;

  • How to get there
  • Opening days and hours of attractions
  • Best time of the day to visit
  • Where and when to buy tickets for attractions (online, months prior to my visit or on the day of)
  • How much time to spend at each place/attraction
  • If I need a guided tour or not

Then I map out everything on Google maps sequentially and chronologically in a geographical sense. For example, during my Spain and Portugal trip last year, I flew in to Barcelona and flew out of Lisbon and visited cities like Madrid, Granada and Seville in the middle. This is so that I don’t waste time zig zagging.

Once I have mapped out things to do in a city, I layer in things I learned like opening days and hours to make any tweaks to my sequence of places to visit.

Then, I figure out places I need to omit or add based on the time my research said I need in each place (my research usually involves multiple opinions). I do this keeping in mind the overall time I have for the trip.

After this, I map my accommodation with things I want to do in a city to ensure my accommodation is not miles away from all the action.

The Sources I Use to Plan My Trip

  • Instagram – I do this 2 ways. Look at locations or hashtags for the place I’m visiting or go to my saved folders to see if I have anything already saved
  • Blogs – I read lots of blogs to make sure I get a balanced view
  • Pinterest – This is new but I recently started using Pinterest for trip planning and I love it! I’ll save pins onto boards and read as I plan
  • Ask around – I chat with people who have been to places I am planning to visit. My favorite source is my good friend Rajeev who is well traveled and a wealth of knowledge! I always consult him about my itinerary when I am going to Europe and he always has the best advice and suggestions. He owns a travel agency called Tourama will be happy to help you too. You can reach him HERE on his website or on his Facebook page

Plan and Book Internal Travel for the Trip

Once you have an idea of what places you want to visit, book trains, buses, and internal flights. Keep in mind that sometimes, trains are not always faster than buses due to connections. They can also be more expensive than planes. For example it was cheaper for me to fly from London to Edinburgh than to take the train. Research the best time to book as well as this changes depending on the season or mode.

Furthermore, have a plan for how you are getting from the airport to your accommodation. The last thing you need after a plane ride is to figure out your transfer.

Plan Your Trip Using an Excel Sheet

All my planning translates in to an excel sheet that keeps me organized both before and during a trip. There are many ways to do this but excel is my favorite!

Buy Travel Insurance

Travel insurance is super affordable and offers that ease of mind during your travels.

Put Together a Packing List

In addition to clothes, there are certain things I never travel without. Click HERE to find out more!

How to plan a trip

Research Money Matters

What’s the best way to exchange money once you get there? Is it through an ATM or a money changer? This really depends on the country.

If you don’t have one already, get a credit card with no foreign transaction fees. This will save you from racking up unwanted exchange fees during your trip. Also, don’t forget to get a pin for your card if you don’t have one already and inform your bank of your travels. I do this the minute I book my flight so I don’t forget.

Time Off from Work

The one travel question I always get asked is how I manage to take so much time off for vacation. The truth is that I don’t! I work for a corporate office of a major retailer and only get 6 public holidays (the bare minimum) plus the American standard for paid vacation. So how do I do it? I plan to go on my trip almost exclusively during these public holidays (Thanksgiving, Christmas, New Years, Independence day etc). I head out on a Friday afternoon, which means, I’ll land in most places Saturday morning or afternoon and take an evening flight back home the following Sunday, if I am traveling in the direction of time. This way I get 9 days at a place but only need to take 4 days off work!

Want to know more travel tips especially once you get to your destination? Check out my travel tips post HERE.

Are you a solo traveler? I am too (most of the time!) and have an extensive list of tips! Check out my solo travel tips HERE.

Did you find this post useful? Please let me know by liking/commenting below or sharing this post on social media! Thank you!!

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About Me

Welcome to my blog and thank you for visiting! Believe it or not this blog is not my full time job! I work 8-5 in Supply Chain and run this blog after work!  I’ve dreamed of traveling the world since I was a child and at 44 countries and counting, I am so grateful to get to live that dream.

To say travel is my passion is truly an understatement! What I love most about travel is that I get to connect with locals and meet with fellow travelers from around the world. In addition, travel also enables all my other interests like photography, architecture, art, music and food! Please feel free to share any posts or leave me feedback on how I can improve. Thank you and happy travels!


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