I love to plan travel.
Sitting down with books for inspiration or a computer and a cup of tea to plan a trip is my idea of a good time! I love finding hidden gems in new places, and the challenge of making all the logistics work. Of course, there are elements of planning travel that are frustrating, and travel itself can be uncertain.
Below I share exactly how to plan a trip (specifically how we plan adventure travel) with links to all the tools we use to help you plan your next amazing adventure. You can also see information below on how to save money while booking a trip and some of the tricks we use to make planning easier.
For more travel ideas check out: 100 Incredible Adventures with Kids: Have Amazing Family Travel Experiences Or for general information on how to plan a trip, visit our travel section.
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Quick Overview: Our Method of How to Plan a Trip
Over the years we’ve planned many different types of travel, from month-long US road trips through some of the most beautiful National Parks to a three-week trip to Thailand. We love diverse experiences and planning our own itineraries and trip details. This takes a range of trip planning methods.
Planning and packing for a trip becomes even more complicated when you are planning to include adventure travel as this takes special skills, gear, and logistics. You have to decide what you will do on your own (hiking) versus what you will do as a tour or trip (white water rafting)
Learning how to plan a family vacation is another thing entirely. It’s almost impossible to make everyone happy with every trip, and this makes family travel planning that much more complicated. We’ve traveled with babies, toddlers, kids, and now teenagers and have found every age has its own set of challenges (and of course rewards)!
Looking for more resources on how to plan a trip? Read more about Planning Adventure Travel with Teens.
I am sure there are countless other strategies for planning amazing family and adventure travel, but the information below walks you through our exact method and I will continue to update the article as our strategy changes over time.
If you are interested in planning for the next few years of adventure, you may want to check out our free planning guide: FIND YOUR ADVENTURE. This is free when you sign up for the Chasing ADVNTR monthly newsletter and is a 7-step plan to looking ahead and planning for a lifetime of adventure. You can learn more about the guide on the newsletter sign-up page.
Quick Trip Planning List
- Create a List of the Places you Want to Go
- Do Some Trip Research
- Create a General Travel Plan
- Double-check Health and Safety Resrictions
- Book your Transportation and Lodging
- Book Travel Insurance
- Create a More Detailed Trip Itinerary
- Book Some of Your Activities
- Double Check Your Documents
- Identify Anything you need to Purchase
- Revisit the Trip Details, Print Your Information, Pack Your Bags and Go!
How to Plan a Trip: The Exact Steps We Use
1. Create a List of the Places you Want to Go
This is really a pre-trip planning step. In my opinion, choosing a destination for your trip is the best part of planning. When you dive into trip planning, it is helpful to have a list of places you want to go. This can be a list you keep in your head, or you can actually write it down.
As a family, we discuss this often, so I have a good sense of the places everyone wants to go and I keep a long list of these places in a spreadsheet. From this long list, we try to keep a top 5 of the places that are at the top of the list. Not getting locked into a destination right away gives you more flexibility. It’s much easier to book a reasonably priced trip if you are flexible on your destination.
For example, we recently booked a trip to Hawaii. It is on our list of places we want to visit, but when I came across direct flights for an incredible deal, I couldn’t resist. This means we are visiting Hawaii in a few weeks for far less then if we insisted on visiting at a specific time.
There are so many places to find travel inspiration. I love to follow other travelers on Instagram or on blogs and we’ve bought several photo-based travel books over the years that sit on our coffee table. This has helped inspire our kids as they flip through the pages.
You can also see some suggestions of Destinations to Travel with Kids at Every Age.
The travel books on our coffee table right now (click the image to purchase them on Amazon – affiliate links)
Do Some Trip Research
Once you have some destinations in mind, it’s time to start planning your trip. The first step into trip research is where we spend the most time. If you already know exactly where and when you want to travel, you can skip down to the next step. There are generally 2 ways we approach this.
- Start with the date you want to travel
- Start with the destination you are hoping to go
Starting with the Travel Dates
If you are starting with the travel dates, you are likely working around school vacation or a specific event. For this type of planning, I start by writing down the dates that we have available to travel. Ideally, I start this research about 6 months in advance, but I’ve planned a trip this way in a month and also done longer trips a full 9 months in advance. I then keep in mind the top destinations on our list I always have a top 5 in mind.
I usually start by using Kayak. On this site, you can enter your starting destination, the dates you want to travel (or you can enter an entire month), and in the destination spot, type ‘anywhere’. This gives you a map with prices and flight options.
You can also do this type of search in Skyscanner, by searching ‘everywhere’ in the destination spot – I like to do both, but I always start with Kayak since I like their map. There are several other search engines you can use as well, and this gives you a sense of prices for the time you want to travel.
By using these search engines, you can get a sense of the flight prices when you want to travel. It’s important to do a search a few days before and after your trip dates (if you have any flexibility) – prices can drastically change in just a few days. Weekends are often more expensive (but not always).
Another strategy we use is to check other airport options nearby – what is the cheapest place to fly near your final destination? When we looked at flights to Europe for an upcoming trip, flights from Boston to Rome came in at $850/pp. Instead, we could fly from Boston to Lisbon for $400/pp and then book a separate flight to get from Lisbon to Rome. The benefit of these tickets is that it allows us to spend a day in Lisbon as a bonus.
After you start to narrow down which of your destinations make the most sense, you can check other airline carriers. If you have points or miles, you will want to check with the right carrier to see if these points apply.
Once you have one or two destinations that fit your budget during your travel dates, move down to the next step to create a general travel plan BEFORE you book your travel.
By searching different destinations and using different airports, we booked $450 flights to Thailand. It meant that we had to drive from NH to Newark (instead of leaving from Boston). Since there are 5 of us, this saved us money and we were able to fly directly to Japan and on to Bangkok.
Starting with a Destination
Another method when you are planning a trip is to start with a destination and choose when you want to travel to this destination. When you create your list of destinations you want to visit, some of those destinations likely have some time frame when they are best to visit.
If you are starting with a destination, take note of the general time you want to visit (let’s say you want to go to Iceland during the warm weather months). Using Skyscanner, enter the departure and arrival cities (I always click ‘add nearby airports’) – instead of entering the date, enter ‘whole month.’ You can either search the month you want to go or select the cheapest month to find out when is the cheapest time of year to travel to this destination. Google flights is another good tool.
You will get a calendar with the dates with the lowest airfare prices. This will give you a sense of which months and days are the least expensive. From here, I start to look at individual airlines and prices. Most carriers let you select ‘my dates are flexible,’ and this will give you a range of dates. I usually try to book tickets 3-6 months in advance, but I often start looking at prices for the destination and approximate dates even more in advance so I get a sense of the airfare trends.
Once you have a general date and destination, move on to the next step (don’t book anything yet).
Pro Tip: When you are planning more complicated travel, or want to book a layover, try using the multi-city function in Skyscanner. We've found that sometimes this is even cheaper than booking round trip.
Create a General Travel Plan (research the destination)
I often do this step simultaneously with the previous step.
Once I’ve narrowed it down to the approximate length of time we have to travel and one or two destinations, I create a very general trip itinerary. This involves researching the area we will be going to, reading blogs and trip reviews of the area, and creating a list of things to do.
I do this part of the planning in a spreadsheet. I usually get somewhat specific but don’t break it down into specific times unless there is part of the trip that involves specific logistics. I will likely make this more specific as I go along and will eventually mark down specific places I’ve booked and booking numbers.
By creating this basic plan, I will get a sense of whether I have enough time to visit a specific destination. We recently had a week to play with and were looking at going to Morrocco, but by the time I made a rough itinerary, I realized we needed at least a few more days to make the trip work and we decided to book something else.
This will help you narrow down your trip.
The next step is to look into lodging options. There are many excellent places to look for lodging options. As a family of 5, our favorite places to book lodging are through AirBNB and booking.com. We used to book mostly through AirBNB but have found the fees increasing and now prefer booking.com. I like that the lodging ranges from apartments and houses to hotel rooms.
You will also want to look into car rental or other transportation as this can sometimes be a limiting factor.
In addition to creating the itinerary listed above, I also make a rough budget to get a sense of the overall costs. If I am deciding on 2 different destinations, this often helps me decide where to go. I don’t get too detailed, but do note airfare, lodging, car rental (or other transportation costs), and an approximate cost for any activities.
Double-check Health and Safety Restrictions
The last few years have taught us many things, but one important thing is that travel restriction may alter your travel plans. You should do a search for relevant travel restrictions or cautions to the area you are planning to travel. This includes any shots you may need as well as any safety concerns.
At this point you’ve confirmed your destination, the time you hope to travel and whether you can actually travel to this destination.
Book your Transportation and Lodging
It’s time to book your transportation and lodging. Once I have confirmed everything, I do a once over and then usually book the major transportation and lodging all at once. This ensures that prices don’t go up on one of these items. It is no fun to book your flights only to learn in a few weeks that your lodging options are no longer available.
You should also book any rental car or other major transportation parts of your trip.
Book Travel Insurance
Once your main trip is set, it’s time to buy insurance. There are so many reasons to buy insurance. It’s worth checking that you don’t already have it through your credit card or another service. We like to book through World Nomads or search for options at Visitor’s Coverage. Quick note that we often book non-refundable flights and book travel insurance. Read your travel insurance carefully as it often doesn’t cover everything.
Create a More Detailed Trip Itinerary
After doing the hardest work, I will go ahead and create a more detailed itinerary using the rough itinerary I’ve already started that includes suggestions for activities, backup ideas, notes about what I’ve booked and reservation numbers. Since I’m going to print this and bring it with me, I try to include any information that will be helpful on my spreadsheet.
I never create my itinerary down to the hour (although this is just personal preference). I usually try to plan about 2/3 and leave about 1/3 of the time flexible. This gives us a chance to stop at something that looks interesting or stay longer at something we love, but doesn’t mean we arrive to a place with no plan.
It also means that if my kids (or us parents) don’t sleep well one night, we can sleep in or take a nap if we need to.
As you go through the itinerary, it’s a good time to note any challenges you might encounter (like opening hours, backup plans for rain, etc).
I love to create a Google My Map to help create my itinerary – you can see more on exactly how I do this in the article: 5 Easy Steps for Exactly How to Plan a Road Trip With Google Maps.
Book Some of Your Activities
Some of your activities may need to be booked in advance while some of your activities you can book after you arrive. If there is a bucket list activity that is part of the reason you are going to this destination, I say book it in advance.
Another thing to book in advance is permits for hikes or camping, or entry times to National Parks. Make sure to note these details on your spreadsheet in case you don’t have access to email. One of my favorite places to look for different activities is Viator.
When planning adventure travel, it is helpful to read first hand reports of other people’s experience. For hiking, I love to read personal blogs or All Trails.
Double Check Your Documents
This includes checking your passport or other documents you will need for your travel (remember your passport needs to be valid for at least 6 month for many places). Do you need vaccinations? Do you need special medication? If you are traveling without your kid’s other parent, do you have a letter from that parent?
Get all your paperwork in order so you aren’t scrambling at the last minute.
Looking at Your Itinerary, Identify Anything you need to Purchase
Your trip is planned! Give yourself a break and a pat on the back!
Then take a good look at your itinerary and decide if you will need anything else for your travels? Do you need sleeping bags liners? Does one of your kids need a new bathing suit? Are last year’s hiking boots leaking?
Especially if you are traveling somewhere warm in the winter, or somewhere cold in the summer, you will want to get on top of your packing list so you have plenty of time to find everything you need.
Another housekeeping task before you leave is to decide whether you need a house or pet sitter or decide if you will be travelling with your pet.
1 Week Prior to Your Trip: Revisit the Trip Details, Print Your Information, Pack Your Bags and Go!
About 1 week before the trip, I start getting ready (really just a few days, but one week is something to aspire to)!
This means printing or sharing your packing list, checking in, collecting paperwork, snapping some photos of your travel documents on your phone, and packing your bag! We always try to give our kids as much responsibility as possible with packing. I give them a list and they pack it. I have one child that I do double-check, since I don’t want to have to buy a new coast just because someone forgot a coat for our hike.
Additional Travel Resources
In addition to the resources I’ve shared above, I also like to follow blogs, Instagram, and several travel facebook groups. These resources are all incredibly helpful when planning travel for different reason. Some offer inspiration, some are more practice and some give me a better sense of where other folks are going.
What are your travel planning strategies? Please feel free to share your thoughts in the comments on how to plan a trip!