Over the years, I have learned that there are generally two types of travelers – the planners and the spontaneous. I am a planner – I love the thrill that goes into finding the perfect place to eat or that hidden gem. How to plan a trip is something that I love to teach people. During this hunt, planning can easily turn to stress, confusion, and being overwhelmed. There are so many things to plan and think about when it. If only you had a fairy travel-blogger to help you out (oh, wait – that’s me!). From Pinterest boards to excel spreadsheets, planning a trip is one of my favorite hobbies. That’s why I wanted to write this post to help you plan your next trip with zero stress.
Whether you’re planning a group trip with family and friends or heading out on a solo travel adventure, these steps will help you plan the ultimate trip!
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Step One: Get Comfortable
That’s right. It’s not going to be easy. So get into those comfy pants, bring over some snacks, and a drink. It’s a marathon, not a sprint. Breaks are required. Depending on the length of the trip and how detailed you want to get in your itinerary, you may not want to plan every second of every day – leave room for spontaneous adventures.
Step Two: The Budget
The easiest and hardest part of planning a trip at the same time. Figuring out how much you want to spend on the trip can be overwhelming. You probably want to figure out your budget before picking a destination. In fact, your budget is probably the most important step.
A few questions to think about for setting your budget:
- What money do you have set aside?
- How much will the trip you want really set you back?
- Are you planning on opening a credit card for rewards? Sometimes these take a few months to get the rewards – and be careful about carrying a balance.
I recommend maintaining an ongoing savings plan for travel. The travel bug can bite – and the only thing that satisfies it is more travel. Check out my 8 ways to save for travel so you can have the trip you want! Saving habits are important so you can plan a trip which achieves all of your travel goals!
To plan a trip, there are a lot to consider other than flights and hotel for the cost of your trip. (If you’re using Excel, be sure to have a budget tab). Flights, hotels, tours, meals, transportation, and daily activities are the most common. Don’t forget about souvenirs, spontaneous spending (that afternoon coffee can add up on a two-week trip), and tipping!
Bonus Tip: Always add a buffer to your budget. You never know when you’ll have the opportunity to do something amazing – or when you might need some emergency cash. It’s better to overestimate than to be living on bread and water.
Step Three: The Outline
Breaking down any huge goal or task into manageable steps is important. Sizeable chunks that all come together to make an epic overall plan. This is also the step where you’ll want to figure out how you’re organizing your information. I love Pinterest boards for organization and inspiration, Google Sheets (or Excel) for hotels and tours, and Google My Maps for putting destinations on maps – which can then be downloaded to use offline when you’re on your trip!
It’s also time to pick a few destinations. This is a bit more complicated than throwing a dart at the map (also, 70% of the world is water, so chances are you’ll end up in an ocean anyway).
A few questions to think about:
- What style of trip do you want? (cruising, staying in one place for a longer time, or moving around?)
- Do you prefer adventure or relaxing?
- Do you prefer cities more or prefer to be surrounded by nature?
All of these preferences will impact your destination (and how you plan a trip)!
Bonus Tip: Using Group boards on Pinterest and Google Drive can help organize group trips. My family of 11 used Google My Maps to plan a trip to Scotland – we all added where we’d like to go so we can organize it by region!
Step Four: Find Cheap Flights
Flights are typically a huge chunk of the trip budget, but they don’t have to be. Knowing what to look for, being flexible with dates and destinations can help! We found $150 round trip tickets to Panama because our dates were flexible. Plan a trip around destinations and time of year for the best deal
You can do this in conjunction with selecting a destination (I know that sounds weird). You can use Skyscanner to have an “open destination” which allows you to see destinations from your chosen airport. Check out my tips for finding cheap flights for more details!
Bonus Tip: When searching for a trip, be sure to at least look +/- 3 days to see if one day can make a difference. Some search engines can even look at a month at a time so you can really check prices.
Once you find a cheap flight, research the destination a bit before heading there. Just because you found a cheap flight to Reykjavik, doesn’t mean that the expensive food is in your budget. Be sure to research average prices for hotels, food, and some things you’d like to do (be sure to put these general prices on your organization from Step 2!).
Step Five (Part 1): Are you moving around or staying put?
Are you planning on spending a week in Dublin or are you more interested in staying in different places in Ireland? It’s going to have an impact on flights too (you can fly into one city and fly out of another) as well as your budget for transportation. If you’re moving around you may want to switch up accommodation as well – a nicer hotel on the first night and hostels the rest? Or are you visiting somewhere remote that only has one type of accommodation? All of these answers are essential when you plan a trip!
Step Five (Part 2): Figuring out where you want to stay
Okay, if you haven’t taken a break yet – now is the time to do it. This is the most overwhelming, confusing, and frustrating part of trip planning. It’s also sparked a few fights debates in our household.
Hopefully, in figuring out the budget for the trip, you have some idea of the kind of accommodation you’re looking for. Do you prefer hostels, rentals by owners (such as Airbnb), or a luxury hotel? Some of these depend on location – you won’t see any hostels on safari in Kenya – and the room options are a bit limited on cruise ships.
Hostels: They tend to be the cheapest option and you’re more likely to meet new people here than in a hotel. They tend to be centrally located. However, many hostels are dorm-like, meaning that you may have to share a room (unless you opt for a private room).
Bed & Breakfasts: I separated this from hotels because they have a different ambiance. It’s usually in a person’s home and includes breakfast! Typically not in center city – but perfect for trips like a road trip around Ireland!
Rentals by Owner: Most people think of this as an Airbnb, but there are plenty of options – my favorite is Vacation Rental By Owner (VRBO). You get the whole place to yourself, which is awesome, but sometimes they include cleaning and service fees (not so awesome) – these fees may make it equal to a hotel room. However, you can find small gems like this cabin in Pennsylvania!
Hotel: By far the most common and varied accommodation option out there. If you’re booking a hotel, it’s important to think about what is included. Some hotels offer complimentary breakfasts (which can vary from a huge buffet to a bagel or muffin), turn down service and room cleanings. Some hotels include a fridge and microwave, others don’t. I love using booking.com to compare deals and hotels.
Step Six: Figuring out how long to travel
Now that you have a better idea of flight and accommodation costs, you can pinpoint the length of time you want to stay. This is relatively easy compared to the previous two steps. You’ll have an idea about the flight times (do you need 2 days of travel time?) and cost of accommodation (can your budget last two weeks or five days for a place to say?)
Step Seven: Transportation
Sure, flights are the biggest transportation issue you have. You still need to think about how you’ll get around once there. If you’re moving around a lot (especially in Europe) it may be better to fly domestic flights on your travels. Some countries, like Japan, it’s better to take the train or bus. Or, you may want to rent a car instead of using public transportation. You can also do a mixture of transportation, like we did on our road trip through Italy.
Travel Tip: If you’re going somewhere that you don’t speak the language, then you might want to learn how to get around there. Sometimes splurging for a guide with transportation is worth it.
Step Eight: Activities and Tours
Time for another break! This is another step that can be overwhelming (especially if you’re traveling with other people). I tend to have FOMO (Fear of Missing Out) and I want to do all the tours with limited free time – but that’s not very fun, to be honest. You don’t want to over plan a trip – leave some time for rest and exploring on your own.
Few hours/Half-day trips: Usually a few hours specific to a topic (food tour or walking tour) or location (castle tour)
Day Trips: Typically lasts around 8-10 hours and includes transportation.
Overnight Trips: A 24-hour trip that includes an overnight in a new destination – giving you more time to visit and explore.
Multi-Day Trip: A more extensive visit to new places. Typically these are added to the middle or ends of trips to lessen the stress of trip planning.
Over time you’ll realize the types of tours YOU like. For me, I love the few hour tours – food tours especially! Some people prefer day trips so they don’t have to worry about transportation and can just relax. The beautiful thing is, it’s your experience – make it your own!
Final Thoughts on How to Plan a Trip
Once you put these 8 steps together, you should have one epic trip! I don’t recommend doing all this is one sit down – it’s a lot and you’ll probably not have fun doing it. Be sure to start organized – it’s a lot harder to organize information once you get started. Pinterest is a great place to store ideas and inspiration.
Read more Travel Tips
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18 Tips for Saving Money on Accommodation
Long-Haul Flight Survival Guide
Pin “How to Plan a Trip” for Later
Recently, my sister and I decided to organize a trip for our whole family. We’re relieved you talked about planning a trip in a few steps to ensure we find the best transportation for our family, so we’ll use your guide to help us plan the best trip. Thank you for the information on the different types of transportation options we’d choose from for our trip.
That’s awesome! Feel free to reach out if you have any questions along the way!