Restless Pursuits

Helping adventurous families with older kids and teens explore beautiful destinations while avoiding the crowds

Easy Step-by-Step Guide: Travel Planning For The Best Family Trip

I have planned a lot of trips in my life and really enjoy it. I get excited when finding new activities. That moment when my itinerary comes together makes me thrilled to get on the plane. Because I have done it so often, I have built out a step-by-step guide on travel planning so you can have the best family vacation. Here is the simplified version, but keep reading for plenty of helpful insider tips! 

Step 1 – Do the research

Step 2 – Book flights

Step 3 – Reserve your lodging

Step 4 – Book rental car (if needed)

Step 5 – Create detailed-ish itinerary

Step 6 – Make reservations

Step 7 – Request time off work 

Step 8 – Make home arrangements 

Step 9 – Create a packing list 

Travel Planning Checklist

Preview of Restless Pursuits's travel planning checklist

Step 1 – Do The Research

Picking a location could be as easy as looking at your bucket list and choosing the spot you want to visit next. If your travel goal is more broad, say a relaxing beach vacation, you have some options.

Playa Bluff - Panama
Playa Bluff – Bocas del Toro, Panama

Consider Your Budget While Researching Locations

How much do you want to spend on your flights, lodging, meals and activities? Research all of these items since they are the biggest travel expenses. For example, it might cost a big chunk of your budget to fly to Sri Lanka, but once you are there, your money can go a long way. OR maybe you can fly to Norway fairly inexpensively but everything else will blow your budget. Alternatively, you might be able to drive to Disney World, but the park will cost you a pretty penny. 

Tips to save money: 

  • Use credit card miles or points to fly or stay in a hotel! If you don’t have a travel credit card, consider one looking into a few options. We like Chase Sapphire and Capital One Venture X.
  • If you don’t have airline points and you want to find a cheap flight, do a search on Kiwi.com. You can put it in your local airport and “anywhere” in the destination box. See what the cheapest options are that pop up and if they meet your travel goal. For more money saving strategies for finding cheap flights, check out: 7 Simple Ways to Discover Cheap Flights and Save Money

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Some of the links on this post are affiliate links. When clicking on the links and booking travel, I receive a small commission with no extra costs for you. Please note, I only recommend brands I actually use and trust. Please see full disclosure here.

Think About Activities And Transportation

Researching what you want to do will help tremendously in the travel planning process. Are you someone that likes to plan unique activities and be on your own, do you prefer to be more hands off and go on a tour, or do you want to fly in and be pampered at an all-inclusive resort?

Isaac at the base of the Quilotoa Crater, Ecuador
Quilotoa Crater, Ecuador

For me, I am usually not a an all-inclusive person. I like to wander and explore off the beaten path locations. However, tours and all-inclusive resorts can save you a lot of travel planning time. Usually you can gain more historical and cultural knowledge about a place if you are with a tour guide as well. 

Also, another bonus to a tour is that it can provide transportation. For example, when we were in Quito, we wanted to visit a few places outside of the city, Quilotoa Crater and Cotopaxi. (Read about our adventures by clicking the links.) We didn’t have a car and didn’t really want to drive at the time, so we booked a small group tour. It was great because it wasn’t too crowded, they drove us everywhere and we learned so much. Also, the price was right! Here’s a link to the Quilotoa Tour and the Cotopaxi Tour!

The family in Cotopaxi National Park, Ecuador
Cotopaxi National Park – Cotopaxi is hiding in the clouds behind us

Google Maps For Travel Planning

If you are planning it all on your own, I would suggest using Google Maps to organize yourself. Find the attractions you want to see and save them on Google maps. Then figure out a very rough itinerary to see how long you would need to stay in each of the areas to see all of the sights. 

Bonus Tip: Make separate categories and choose a different emoji for each category. That way when you look at the map you can clearly see the difference between a restaurant or a tourist attraction.

Lately, I have been researching our summer trip. We have a few things in our life that are up in the air. This makes it a little hard for me to book the trip, but it doesn’t stop me from doing research. I know that I will be taking most of the summer to travel, but depending on our housing, Mike’s job situation and the kids’ summer activities, they may be joining me for part of the time or the whole time. 

Because of the uncertainty, I have two itineraries that I have considered. The first one would be if the whole family joins for the full 5-6 weeks, the other would be if it’s just me for the majority of it and they join for a part of the time.

What is the difference you may ask? A couple of things. First, I don’t really want to drive in another country. I could do it, but it’s not my cup of tea. So, I have planned areas where I can take the train or a bus. Second factor is that, while I enjoy a big city, my kids do not. So if they are going to be there, it will be mostly outdoor activities and wide open spaces. 

Step 2, 3 And 4 – Book Flights, Hotel And Rental Car

After doing your research, you should have a fairly good idea of where you want to go, for how long, and how you are going to get there and around. Next step is the exciting part. Book the trip!

I usually book flights first, lodging and then lastly a rental car (if needed). 

Flight Tips For Travel Planning

You will have less options for flights, so buying the one that works best is essential to do first. Find flights that work with your schedule. If traveling with little kids that nap, consider a flight during their nap time or an overnight flight. If you are traveling with older kids, don’t make the flight too early. Remember you have to be at the airport a couple hours in advance. Older kids get cranky when they don’t have enough sleep and they won’t nap (unless they are teenagers 🙂). 

Bonus Tip: Consider a long layover in a city you haven’t explored and take some time to look around!

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Hotel And Airbnb Tips

Pick a hotel or vacation rental that is within walking distance of all the major attractions or near public transportation if you don’t have a car. If you do have a car, double check that there is a parking option. 

Another thing to consider is the cancellation policy. Of course you never WANT to cancel a trip, but sometimes life happens. It’s nice to know you can cancel without penalties up to a certain point.

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Rental Car Travel Planning Tips

When booking a rental car, we check for a few different important features. 

One, we haven’t driven (and when I say we, it’s Mike that drives our rental cars 😀) a manual in a while and he prefers an automatic. In many countries you can save money if you select a manual transmission, but if you can’t or don’t want to drive one, be sure you choose the automatic option. 

Space! Cars are not as big if you are renting them outside of the U.S. Even the smaller American car options are big in comparison to some over here in Europe. On the rental car site, check the amount of luggage and people that can fit in the car to be sure it will be comfortable for you and your family. 

Be sure that you are also looking at the cancellation policy for the rental car.

Bonus Tip: Check the pricing in the weeks leading up to your trip. You might save some money if the price drops. Book your new rental car and cancel the old one if the price is less! 

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Step 5 and 6 – Travel Planning For Activities And Reservations

Be Flexible 

Now that you have the important parts booked, it’s time to make your detailed-ish itinerary. When you are traveling with kids, it’s important to keep things flexible and to not overbook! Factor in getting snacks at the store, taking naps, going to the playground, resting tired legs, ice cream breaks etc… 

I usually break up my travel days by planning activities that are nearby each other. If everything is close together, you can just have a wish list of activities that you’d like to do while you are there and see how everyone is feeling on that day. 

Book Tours

The exception to having a flexible schedule would be if you need to book a tour or if attractions are only open on certain days and times. Always be sure to check times and dates! Especially if you are traveling off peak season. 

Isaac driving the boat during our Amsterdam Canal tour

If you need a ticket for a popular attraction, make that reservation in advance online. For example, The Anne Frank House in Amsterdam releases tickets 6 weeks in advance and they are timed entry. During the busy season, you need to book these tickets early to get a time slot you want. You won’t be able to show up and buy a ticket at the door. 

If you are looking into tours, I would suggest looking at Viator or Get Your Guide. I like Viator and Get Your Guide because they have many interesting options and most of their tours you can cancel up to 48 hours in advance for free. They are very similar but I like to check both since they offer different options.

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Reserve A Table

S'mores in Antwerp

Other reservations to consider are restaurants. If you are looking to eat at a nice restaurant for lunch or dinner, I would recommend booking a table. Not only are you guaranteed a spot at that restaurant but it also makes it less stressful when everyone is hungry, and you are frantically trying to search up a place to eat. 

Step 7 And 8 – Home Considerations

There are a few things to remember to arrange when you are going on a trip that are closer to home. First one is making sure you request time off at your job! Other important considerations are: 

  • Arranging a sitter for your pets (or your kids! – Couple trips are great too!)
  • Mail
  • Snow removal
  • Mowing your lawn
  • Watering your plants
  • etc… 

Many of these factors depend on where you live and for how long you will be gone. 

International Trip Considerations

  • Call your bank or credit card company and tell them if you are leaving the country. Some banks or credit cards don’t require it, but you should double check. You don’t want them to shut down your access to money!
  • Check your passport and make sure it isn’t expired or won’t be expiring within 6 months of your trip. If it is, you will most likely need to renew it before you go. If you would like a simple explanation on how to do this, I have written a post about it here. Simplified Steps to Apply for or Renew a U.S. Passport
  • Check if the country you are visiting requires a visa. Learn more about what countries are visa-free for Americans here and how to find out what to do if a country does require a visa. 
  • Research cultural differences: tipping, a few phrases in the language, dress codes, currency exchange rate and other customs
  • Get travel health insurance – Check out Visitors Coverage.
  • Make sure your cell phone data will work. You can either get an international plan through your cell phone company or for a much cheaper option, you can get an e-sim. I would recommend using Airlo. You can purchase as much data as you need and it is much more affordable than what Verizon is going to offer you. Need to make a call? Use wifi or data by calling through Whatsapp or Facetime. 

Step 9 – Make A Packing List 

When making a packing list, I look at the amount of days we are traveling, access to laundry, and factor in space. We normally like to travel with carry-ons only. That limits the amount of items we can bring. 

Bonus Tip: Don’t pack things you can buy in other countries if you are running out of space! Plan a little time to go to the store upon arrival and pick up diapers, laundry sheets, shampoo, etc…

Packing App For Travel Planning

Another tip I just recently learned about is that there are tons of apps that help you make your packing list. I looked through a few of the options, and I prefer PackPoint. Here’s why:

  1. Easy to Use – The interface is really easy to navigate and it walks you through the questions in a simple way. 
  2. It’s smart – When creating a packing list, you add in where you are going, when, for how long, and if it is for business or leisure. Then you select your activities. You will need different items if you are going swimming versus skiing. This makes it easy for the app to figure out what accessories to recommend. It even asks if you will have access to laundry or not. Genius!
  3. It factors in the weather – After selecting your activities, your list is created. Easy peasy. At the top is the basic info about your trip and the average weather for when you will be there. 
  4. Different categories and easily customizable – The list is separated into different categories based on the activities you selected. Sometimes this means that there are repeat items or accessories that you might not need to bring. You can delete items on the list easily or make a note that you want to bring more than one. 

It’s available on Android and IOS.

Don’t forget to download a simplified version of this blog post as a printable travel planning checklist. Click the link or send me a quick email at [email protected], and I will send you one for free!

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