Do you want to plan a memorable vacation, but you aren’t sure where to start? Trying to organize all of the details of a successful trip for yourself can be intimidating, but practice makes perfect! Each time you plan and execute an adventure, you’ll learn some takeaways to make the process even smoother the next time.
As a travel enthusiast and blogger, I’ve planned my fair share of trips and have learned some lessons along the way. I put together this guide with my best tips to help you get started, maximize your time in a new destination, and keep track of your spending so you won’t be shocked or anxious when you get back home.
Here are 10 steps for planning a trip from a travel blogger.
1. Start with your dates and destination.
Whether your goal is to travel more frequently in general or to visit a specific bucket list destination, the first thing you need to nail down is where you’re going and when you’re going. This might seem obvious to more seasoned travelers, but I remember when I first graduated from college and eventually had a little bit of room in my budget to travel it was a bit overwhelming to know where to start.
If you’re struggling to choose a destination, make a list of all the places you’d love to visit and try to rank it as best you can. If you know you’re traveling with a partner or friends, factor their opinions into the equation. Then, quickly compare the basic prices of plane tickets and hotel rooms for your top five or so destinations to further narrow it down based on what your budget allows. Finally, if you’ve narrowed it down to two or three choices, search on Instagram for photos and videos of each location and determine which one is most important to you to visit first.
When deciding on your dates, there are a few different factors to consider: your work schedule, your children’s school schedule, the weather patterns in your destination, the crowd levels, and the fluctuating prices of plane tickets throughout the year. If you have lots of personal flexibility in the dates for your trip and your destination is somewhere you can enjoy any time of year, I definitely recommend booking plane tickets for dates during the “off season” to save some money. But if you want to participate in a seasonal activity like winter skiing or fall leaf peeping, you’ll obviously be much more limited in your schedule options.
Keep in mind that some popular locations and activities will be completely booked by ambitious travelers 6 months or even a year in advance. (For example, Washington D.C. in Cherry Blossom Season, Disney World at Christmas, or Salem on Halloween are so popular you will need to plan at least a year ahead.) Try to decide on your dates and destination as early as possible to have the best experience, and if your research tells you that you’ve struck out, move on to a different destination for the time being.
2. Consider using travel credit card points to save money.
This budget travel hack is not for everyone, but it can be a game changer for making your dream destination a more affordable reality. Many credit card companies offer cards that allow you to earn points that you can redeem for airline tickets, hotels, rental cars, and other experiences. The key is to use sign up bonuses on new cards, when you can quickly accumulate tens of thousands of points as a welcome gift without spending money.
For example, right now the Chase Sapphire Preferred card has a sign up bonus of 60,000 points after you use the card to make $4,000 in purchases within the first three months. If you use the card to pay for your regular household expenses like groceries, gas, clothes, etc and pay the balance off at the end of each month, you won’t have to do any extra spending whatsoever to obtain the bonus. Since $1 in purchases usually equates to 1-5 points, it would normally take years to accumulate 60,000 points. The sign up bonus is what makes the card appealing.
Remember: If you choose to use travel credit card points, it is crucial to pay off the balance on your card at the end of each month in full. I would never recommend taking on debt (especially debt that accrues interest at the standard rate) just to enjoy travel. Use the credit cards the same way you would use a debit card so you can rack up points, but keep the balance paid off so that you won’t lose track of what you spend.
3. Book flights, then hotel, then transportation.
Once you know when and where you’re going and you have worked out whether or not you want to use travel credit card points to help you get there, it’s time to start making your most important reservations.
Booking Flights
Personally, I find plane tickets to be the most expensive and inconsistently priced aspect of travel, so I usually base most of my decisions on booking those first. Here are my top tips for this.
- If your dates are a little bit flexible, you will usually save hundreds of dollars flying in and out of your destination in the middle of the week on a Tuesday, Wednesday, or Thursday.
- For obvious reasons, flights early in the morning or late at night are the least expensive. If you are on a really tight budget, I think it’s worth the inconvenience to lose some sleep in pursuit of travel and we did this frequently when we were young newlyweds. As I’ve gotten older (and better at using credit card points) I tend to prioritize reducing my stress over saving a little extra money this way and usually don’t book flights that involve arriving at the airport by 4:00 AM or leaving at midnight. Factor in what is most important to you and your experience!
- Make sure you think about everything that needs to happen before and after you arrive at the airport when planning the times for your flight. For example, you might need to allow time to grab a quick meal before or after you fly, you might have to pick up or drop off a rental car, or you might need to catch a train or metro by a certain time. I like to write down the timeline of these events and go over it carefully to help me make smart decisions when booking plane tickets.
Booking Hotels
With your arrival and departure locked in, you need to figure out where you’re going to stay. With so many different options, this might seem daunting. But I have a few tips to make it easier.
- Use discount websites like Booking.com, KAYAK, Travelocity, etc to research more quickly. This will save you so much time on checking to make sure hotels have certain amenities, comparing prices between very similar properties, and reading up-to-date and honest reviews from guest experiences. Compare prices between various websites and even the hotel’s main site to make sure you get the best deal available. Personally, I’ve had the best luck saving money so far with Booking.com.
- Investigate unique Airbnbs that can enhance your vacation experience. For example, you could stay inside a castle in the Scottish countryside or a treehouse in the Pacific Northwest wilderness instead of a run of the mill Marriott! Finding properties like these can make your trip extra memorable. Sometimes, we book discount accommodations for most of the trip but spend a night or two in a really special property and consider it part of the cultural experience of our vacation.
- On the other hand, in my personal experience, you won’t save as much money on budget Airbnb properties anymore compared to hotel rooms. The only exceptions to this rule are when you are traveling with a larger group who can split up the cost of an Airbnb, or you plan on cooking at home in the Airbnb kitchen for the vast majority of your meals. Some people still prefer the privacy or extra amenities of a vacation rental, which is totally valid. But if the only factor is your budget, I find the best deals on hotel rooms through Booking.com 9 times out of 10.
Booking Transportation
Unless you are up with meeting a friend who has a car or you’re going to Uber everywhere, you will probably have a few instances where you need to plan ahead for transportation. Don’t put this off until the last minute, or it can really mess up your trip!
- If you are picking up a rental car upon arrival, book it sooner rather than later. They are SO expensive these days, and they only get increasingly more expensive the closer it gets to your departure for vacation.
- Check out the reviews for the rental car kiosks for each specific brand at the airport where you’ll arrive: customer service by brand can differ widely by location! Don’t risk being stuck in line for an hour waiting to pick up your car when all you want to do is explore your destination. We have learned this lesson the hard way, and benefitted from doing more research!
- Find out ahead of time if your car insurance policy or travel credit card includes rental car insurance coverage. It usually does, and you can save about $100 by declining the extra coverage at the counter with no risk involved.
- Make sure you know what size car you really need for your party and luggage before you arrive, and don’t let anyone talk you into a bigger car than you actually need. We don’t pack light at all, and for two people we have never had a problem using an Economy size car.
- Be aware of some of the main roads you’ll be taking before you pick up your car, because usually the desk attendant will offer you the opportunity to purchase a toll road pass with a flat fee for each day of your rental. If you will rarely drive on any toll roads during your vacation, it is much cheaper to let the rental car company bill you for those toll charges after the fact. Realizing this saved us about $50-60 on our last vacation!
- If you need to take a train or some form of public transportation after your plane lands, make sure to purchase your ticket or metro pass beforehand if possible. Nobody wants to spend their first day of vacation standing around at an airport or train station all day.
4. Save ideas for your destination on Instagram and Pinterest.
Once you have the most important decisions and reservations out of the way, the real FUN of travel planning begins! Start saving posts on Instagram and Pinterest with ideas about the best places to eat or activities to do in your destination.
I like to check out the official tourism Instagram account for my destination as a great starting point. I also investigate to see whether any of my favorite travel bloggers have visited so I can check out their adventures and recommendations. I always search on the instagram explore page, especially when it comes to finding unique local restaurants in a particular area. And finally, I make a dedicated Pinterest board for my trip and save as many helpful pins as possible.
5. Read travel blogs and local reviews to make a short list of food and activities you want to try.
After accumulating lots of data and inspiration, I start combing through it to figure out which experiences are the biggest priority for me. It’s impossible to do everything your destination has to offer in one short trip, so it’s really important to decide ahead of time on which things you absolutely can’t miss so that you can ensure you carve out time for those first in your itinerary.
For me, the most effective way to do this is by reading tons of travel blogs and making a big list of everything that stands out to me: food, attractions, museums, nature, etc. Then, I go through the items on the list and look at pictures and reviews of them to eliminate anything that seems overhyped or like a bad use of my limited money and time. This leaves me with a personalized list of restaurants and activities so that I have the best chance of enjoying myself when I get there.
6. Use Google maps to plan your itinerary based on locations.
I know having a daily itinerary for your vacation is not everyone’s style, but I swear by it for several reasons. First and foremost, lots of activities have limited hours of operation or require advanced tickets, and if you don’t plan ahead you will miss out altogether. And secondly, if you aren’t familiar with your destination it is easy to underestimate how much time it will take to get from one activity to another even within the same state or city. Miscalculating that based on your personal experiences where you live can end in a travel disaster.
When I make an itinerary for a trip, I use the list of experiences I made from research online and look up the locations of each item with Google maps. Then, I group the activities by their proximity to each other within my destination. This drastically cuts down on the time spent going from place to place so that you can enjoy more experiences for longer periods of time within your limited days of vacation.
As you put restaurants and activities into their respective time slots in your itinerary with this method, make sure to factor in things like business hours, timed tickets, and sunset that might impact multiple activities on the same day.
7. Make reservations for food and activities in advance.
Now that your itinerary is planned, you can confidently purchase online tickets for experiences and make dining reservations without worrying that you will run out of time for something you know you want to do. Planning this out ahead of time leaves you with so much less to think about while you’re actually enjoying your trip! In my opinion, there is nothing worse than wasting a day of PTO wandering around a city without any plans or trying to decide where to eat.
8. Save copies of all of your bookings on your phone and in a physical folder.
One your flights, hotel, transportation, food, and activities are all reserved, save all of this information somewhere in your phone so that it is easy to find it right when you need it. Make a note file or Google Doc with links and confirmation numbers or make a special folder in your email account. If you really want to go the extra mile towards having peace of mind, print out physical copies of your confirmation and booking info and slide it into a folder that you can keep in your backpack or carry on. I like to do this to ensure that even if I can’t connect to the internet, my phone battery dies, or my phone gets lost or stolen, I can still board flights and check in to hotels while I figure it out. It’s probably just my anxiety speaking, but I’d rather be safe than sorry.
9. Make a list of what clothes, toiletries, and other supplies you’ll need to pack.
Even when my trip is still several weeks away and I won’t be packing a bag any time soon, I like to go ahead and make a list of everything I need and plan to bring. This way, if there’s something I need to order or pick up before the trip, I won’t find myself scrambling around the day before when I have actual packing to get done.
I start with clothes for different weather scenarios (and I plan this out down to the outfit in a Google Doc, but that’s optional and probably sounds crazy to some). Then I make a list of toiletries, technology, and any other miscellaneous items I’ll need. I order the basics online a week or two before my trip to make sure everything has time to arrive before I leave. Don’t feel pressure to do this, but for me it reduces stress and prevents me from overspending in a panic if I’m missing something.
10. Keep track of your planned expenses and budget for your variable expenses.
Last but certainly not least, do at least a little bit of documentation on your planned spending for the vacation. Make a simple Google Doc or Sheet that lists the costs for your big ticket items like flights, hotels, and rental cars. If you purchase tickets for experiences beforehand, go ahead and include that info too as you book. Use your itinerary to estimate how much you think you’ll spend on food, activities, and souvenirs.
It doesn’t have to be perfect, but getting as close as you can will help you ensure your budget allows for all of the different aspects of your trip before you leave so you won’t have a terrible shock when you check your bank account after you get home.
Travel: If you fail to plan, you plan to fail.
This motto might seem silly, but in my personal experience I’ve had much more fulfilling travels when I was better prepared and things could go smoothly. Even if you don’t implement all of these steps for planning a trip, I hope the advice helps you get started and leaves you with memories that will last a lifetime. Happy travels!
If you want to learn more details about some of our favorite trips, check out our Blog. If you’re looking for more travel inspo and photography, follow along on our Instagram page.