15 Minute Read
We’re ready to share with you our expert guide on how to plan a vacation. Are you curious about how we find flight deals? Want to know more about how we choose what makes our itinerary and what doesn’t? Maybe you’re looking for the best travel, planning or organization apps? It’s all here. We’ve got you covered.
We booked our first flight for this journey in March 2017 and we’ve been planning trips back-to-back since then.
By the numbers, at five months into our adventure we’ve:
- Planned trips in more than five countries
- Made 13 travel itineraries
- Booked 17 flights
- Reserved or stayed in 27 Airbnb listings
- Rented four cars
- Downloaded and used 16 different travel-related apps
- Spent thousands of hours researching (we haven’t tracked this, but that’s got to be close right?)
And we aren’t even halfway through our entire trip yet!
So we’re taking everything we’ve learned from our own travels to help you find travel deals and book with confidence. We’ll break down the steps of planning your next vacation into each of the categories below for easy reference.
How to Plan a Vacation Categories:
Building Your Vacation Budget
We might argue that there is nothing more important than creating a budget for your trip.
“But, budgeting is so boring,” you say, “and I never really know how much anything is going to cost anyway.”
I know, I hear you. But if there is one thing we’ve learned from all this planning, I’d say it’s the importance of creating a budget before you go. And having a solid budget is critical when figuring out how to plan a vacation. We don’t go into debt to travel, so having a budget is the only way we know how much we need to save. It also helps control our spending while we traveling instead of making impulse purchases on things or experiences that are not essential.
What should be included in the vacation budget?
We find expenses typically fall into these categories:
- Transporation – Flights; car rentals and gas; bus, train or taxi fares, etc.
- Accommodations – The place(s) you’re staying.
- Food & Drink – We typically lump anything spent on food or drinks here, including grocery or liquor store purchases, visiting a winery, etc.
- Things to Do – Entertainment, tours, visiting attractions, etc
- Insurance & Health – We highly recommend getting travel insurance for your trip – especially if it’s international. Also included here: health insurance, vaccinations and medicine depending on your personal needs and preferences.
- Miscellaneous – A catch-all category that acts as a cushion. We normally recommend adding $20 for each day of your trip to the Misc fund.
Depending on the type of trip, you may also consider combining categories together. For example, if you’re going on an all-inclusive cruise you might pool together your accommodation and food/drink categories.
How can I accurately estimate expenses?
This requires time and research on your part – unless you’re working with a travel agent who can give you a good ballpark off the top of his or her head.
It also requires you to make several decisions. Before you can build an accurate budget, you need to determine:
- The location of your trip
- How many people are traveling
- Ideally where you would like to stay
- The must see attractions, tours, entertainment options, etc
- How often you plan to eat out for breakfast, lunch, dinner or dessert
We usually start with some basic Google searches on our desired location and then make a big list of things we’d like to do there using Evernote. Once we run through the steps outlined in the additional travel planning categories below, we can start to fill in our budget numbers with better accuracy.
How do I track my budget versus what I spent?
You need to use a tool that works for you. Some people prefer to write things down – if that’s you, get a notebook! Some people like using apps – we’ve heard Mint, Dollarbird, Fudget and GoodBudget are great. Your bank might even give you a way of tracking your budget through their online banking tools. It’s worth asking.
Personally, we use Google Sheets to track all of our spending. We like to list all of the categories with a budget and actual spending column so we can compare them side by side.
Once we’re on the trip, we fill in the actual spent by category in the appropriate column (these are the light gray cells).
We also add a note or comment to food, entertainment and misc cells with specific spending for those categories. We like to be able to look back and see that detail, but it’s up to you.
If you like how we use Google Sheets, we’ve created a free template for you to track your own travel or vacation expenses. Get it here.
Booking Flights & Finding Flight Deals
To be completely honest, I find booking airline flights to be one of the most stressful parts about how to plan a vacation. You too? Good to know I’m not alone.
I use a combination of different apps and online tools to help me track flight prices. From time to time, we also use a local travel agent in Winona to help us book flights too if she has better access to a flight deal. Something you might consider as well if you aren’t the “do-it-yourself” type.
The first thing I use for a preliminary flight search is Google Flights. It easy to use and will give me a good general idea what I can expect to pay for flight prices. You can easily use the filters at the top to find flights that match your preferences like the number of stops, airlines and departure time.
You’ll also notice that as you toggle through the calendar, flight prediction prices appear. This is a good way to estimate your flight price if you’re not planning to travel for a few months or even a year. I toggle through to find the month I plan to travel and look at the highest price listed in that time frame. That’s usually what I use for my budget and if necessary, I’ll add extra dollars for a checked baggage depending on the airline.
You can also turn on a flight tracker through Google Flights, but I prefer to use a couple different apps instead.
Hopper is the main app I use to track flight prices and learn when to book. It’s completely free and super easy to use. Once you open the app, you can enter your to/from locations and pick your departure date. Hopper will then tell you if you should book your flight now, based on the current flight prices, or wait. You can scroll down to see more specific recommendations, including when flight prices are expected to climb.
From here, I press the Watch This Trip button and Hopper will notify me when the flight prices change. If there is a sharp price decrease, the app will send me a push notification to book my flight now. Once I receive the push notification to book now, I like to confirm flight prices through one or two more apps and then I usually go straight to the airline site to book.
Kayak and Skyscanner
These two apps also offer flight trackers like Hopper, but they don’t provide the recommendations on when to book. I do like using Kayak and SkyScanner in conjunction with Hopper to make sure I’m getting the best flight deal possible. You can set up flight tracking just as easily through both of these apps and they are also free. Plus, they also give you the ability to look up hotel and car rental information, which you cannot get through Hopper. One thing I do think is important to note…Kayak only offers flight price tracking through their app – not their website. You’ll want to make sure you download this app on your device if you want this functionality.
The best place to look for flight deals – especially internationally – is kiwi.com. I found out about this website from fellow travel bloggers and it is a gem. With Kiwi, you can research flight combinations across different airlines, which can add up to a ton of savings. Their map view also helps you see price comparisons to other nearby destinations. If you’re flexible with your locations, you can sometimes save even more by flying somewhere nearby your destination instead.
Before you book a flight, I would highly recommend checking flight prices on Kiwi first. It’s gotten us some great information on flight deals in the past few months and it’s also great to use in combination with the Hopper app. Once you’re ready to book, we’d recommend booking directly through the airline carrier website as the pricing should match what you find on Kiwi.
The Best of Hotels, Resorts, Rentals & More
In a previous post, we talked a lot about why Airbnb has been our accommodation option of choice on this trip. But when it comes to figuring out how to plan a vacation, there are a lot of options to choose from. We haven’t ruled out hotels and resorts yet though, and we are actually actively researching options right now for Southeast Asia and the Mediterranean.
Read the Reviews
My biggest piece of advice when booking any accommodation is to read other traveler reviews. This is the number one indicator we use to weed out where to stay. If the place we are considering has less than four stars (out of five) and a couple of bad reviews, we take it off the list. Anytime someone mentions the manager, owner, staff or rental host were difficult to communicate with, we take it off the list. When you’re on vacation you want to stay somewhere you’re going to be taken care of, so when we see a red flag in a traveler’s review, we pay attention.
Know Your Must Haves
We also have a list of must-have amenities. This can be helpful if you’re trying to choose between several accommodation options. Feel free to use our list as a starting point and tweak it to make it your own.
- Wi-Fi – Most places should include free, unlimited wi-fi at this point…but, it’s always good to double check.
- Laundry – When we traveling we like to pack light, which is much easier if we have access to a washing machine.
- Personal Bathroom – Through Airbnb, you can rent shared spaces which have included a shared bathroom with the house owner. Simply put, we’ve learned we prefer a private bathroom. You might have other preferences like a bathtub and a shower or two bathrooms. It’s important to keep this in mind when searching for an accommodation.
- Location, Location, Location – Are you going to have a car? Are you okay with public transportation? All of these things are important to consider when you start looking at where places are located.
- Kitchen – We like to cook a lot of our meals, and it saves us a lot of money, so a kitchen is a must for us. You might simply want to make sure your accommodation has a small fridge to store your leftovers. Whatever suits your plans, make sure to include it in your accommodation research.
Research Your Options
We read traveler reviews and look up accommodation pricing through several different sites. Check these to get a good overall picture of your accommodation options:
- Airbnb or VRBO for vacation rentals by owner
- Tripadvisor.com for top rated hotel and resort recommendations from other travelers
- Booking.com for more of the same from Trip Advisor, but also flash sales and deals
- Groupon.com for special discounts and deals on hotel stays (especially good if you’re going to a big city)
After you’ve dug into the details, you should be able to plug in a good estimate in your vacation budget.
Finding Things to Do, Entertainment & Attractions
This all comes down to personal preference. Your travel itinerary can be as light or full as you want it to be – it’s all up to you. This is one of the most overwhelming aspects of how to plan a vacation. You have so many options to choose from. We’d like to remind you though, that (for the most part) your vacation should feel stress-free. It’s never a good idea to try and cram too much in at the expense of wearing yourself out.
That’s why we recommend taking a “slow down day” for every two days of your trip. If you’ve been sightseeing or on the go for a couple of days, spend the next day doing something relaxing. It could be reading, going for a spa day or having a movie marathon. Do it and don’t feel guilty for it.
So how do we find things to fill up our travel itineraries? We use a combination of resources to find things that interest us. Generally, we gravitate towards anything free, outdoors, involves history or showcases the local culture.
Here’s where we’d recommend you start:
- Pinterest – This is one of the best places to find travel blog posts. We use search phrases like “best things to do in (insert city name),” “free things to do in (city name)” or “(city name) like a local” to pull up good results.
- Trip Advisor – We’ll check out Trip Adviser to see what they’re showing as the top 10 things to do in a given area. You can also find top ten lists for specific categories like outdoors, arts, etc.
- Atlas Obscura – A website dedicated to all the weird, wacky, and unique features of a city/area. Where else can you find recommendations for the Sewer Museum in France or a death mask in Melbourne?
- Google – No surprise that we’d recommend checking Google. I try to dig through the results and find local publications or other travel blogs. They tend to have more detailed and varied recommendations compared to most tourism agency websites I visit.
- Ask Others – Taking roll call from people who’ve been to your location destination can help a lot when deciding what to do. Just put out a Facebook post and see how many responses you get – and these recommendations often align with Trip Advisor. A word of caution: Be aware that people love to tell you where to go and what to do, which can become overwhelming. Above all else, make sure you do what you want to do, not what other people tell you to do to make them happy.
Some Unique Suggestions
Movie Filming Locations: Some of the longest lasting trip memories come from the unorthodox sightseeing adventures. When considering what to do in a city, check to see which movies have been filmed there. We couldn’t leave San Francisco without checking out the Full House house and the Dragon Gate from Big Trouble in Little China. A quick photo in front of one of your favorite movie monuments will bring you joy for years – plus on the next watching of that film you can say “I was there!”
Local Markets: One of our favorite things to do is visit a local farmer’s market. You can get a taste of local cuisine (usually at a better price) and visit with local vendors, makers, and businesses. Markets are typically free too, which is all the better for that budget you’re building.
Free Tours of Government Buildings: If you’re visiting a town with a government entity, it’s usually worth looking into tour options. We’ve learned some of the most fascinating things on our free tours of the New Zealand Supreme Court and Victoria Parliament buildings. It’s also an easy and cheap way to learn about a location’s history from a local. Plus, if you find the weather isn’t cooperating with you on a certain day, going on one of these tours is a great option.
Keeping Your Ideas Organized
You might feel like your “things to see” list is getting to be a mile long. How are you supposed to keep track of it all? I used to create Pinterest boards for trips, which isn’t a bad way to stay organized. My latest and favorite tool for keeping track of it all is Evernote. I make a new note for each location and include a list of things I’d like to do. I also make sure to include links to any websites to help me remember specifics about certain attractions. From there, I ask Scott to review the list and add things he would like to do or delete anything that doesn’t interest him (this can actually all be done within Evernote just by sharing the note with the person you’d like to review it – super easy!).
After we’ve narrowed the list down, I spend more time researching potential costs and can then provide an accurate estimate for our budget. I also start to plug plans into a trip itinerary to see what we will have time to see and do based on the number of days we’ll be in a certain location. You can see an example of our Sydney, Australia itinerary in progress by clicking here.
One of the best parts about figuring out how to plan a vacation is the food you get to eat! We use a lot of the same websites listed above to research dining options. One of our favorite things to find are lists from other bloggers of the must-try foods for a particular destination. Trust us – your mouth will be watering in no time.
Another website and app you’ve probably heard of is Yelp. With Yelp you can see ranked dining recommendations along with customer reviews to help you find the best places. We like to use the filters on Yelp to narrow down our results based on where we’ll be staying, the type of cuisine and our budget.
One thing we discovered while traveling abroad is that Yelp is not the go-to app for all countries when it comes to restaurant ratings. For example, New Zealand and Australia prefer to use a website called Zomato. Just keep this tip in mind in case you’re attempting to use Yelp and aren’t getting a lot of results. In this case, you might be better off using Google and reading Google Reviews or looking for a more used restaurant ranking website for your destination.
Cutting Food Costs & Finding Deals
Your food budget can add up quickly, so here are a few things you can do to save money.
- Try lunch instead of dinner – We’ve saved sometimes up to half by going to a restaurant for lunch instead of dinner, especially if it’s a nice (read: fancy) one. You should be able to find menus online and compare prices. Plus, places are usually less busy during lunch so you can spend more time soaking up the atmosphere.
- Filter your results by budget – As mentioned above, most restaurant ranking websites should allow you to filter your search results by budget. You’ll find prices are broken down normally from one to four dollar signs. The website should also give a definition of what a dollar sign means, for example, $20 or less. To filter your results, just click on the number of dollar signs you are comfortable spending to only see restaurants that will cost you that much.
- Check Facebook and Instagram for specials – Lots of restaurants have happy hour specials and other discounts that aren’t advertised on their regular website. I like to review the restaurant’s Facebook and Instagram posts for possible deals.
What’s Next? Share Your Tips
Well folks, now that you’ve picked our brain, hopefully you have a better idea about how to plan a vacation. We hope you found this guide useful and would love to hear your feedback. If you have a travel app you can’t live without, let us know. Got questions about something we mentioned? Leave it in the comments.
…and don’t forget to access our FREE travel budget template!