Since I’ve had so many people ask me how I plan and book my trips, I’ve decided it’s time to finally write a blog post on it! While there is absolutely nothing wrong with using a travel agent, I personally prefer to do my own research and book everything myself. Mainly because, well, I LIKE reading about the places I’m traveling to, and also because it gives me a bit more sense of control. Some people prefer not to worry about any of that and let someone else handle it all, which is also perfectly fine! Figure out what works best for you and stick with it.
If you’re interested in learning about the steps I take to plan everything, keep reading! Hopefully you find some of this useful, and maybe you’ll even book your next trip all on your own! Buckle up and get comfy because this is going to be a long read.
WHO, WHEN, WHERE?
First thing is obviously figuring out WHERE you want to go. If you’re like me, you have a longgg list of travel destinations that you’re hoping to adventure to someday, so picking a location is one of the easier parts. But my destination usually depends on WHO I’m traveling WITH. For example, if I’m traveling with my dad, we are both scuba divers. So our trips usually involve somewhere with good diving, preferably in the ocean. We also both love history, so when we can combine the two (like when we went to Egypt!) it’s definitely a bonus. If I’m traveling with my husband, he is laid back and doesn’t want to be rushed around, but still likes to explore and do planned activities as long as we aren’t overdoing it. He also LOVES cruises. With my mom, she is very go-with-the-flow and will pretty much do anything and go anywhere within reason as long as I give her 2-3 days to relax, even if it means leaving her at the hotel and me going off by myself (although sometimes I do drag her out of her comfort zone…like the time I didn’t tell her we were hiking up an active volcano in Costa Rica until we were already on our way, lol). I also have a few friends who are sometimes up for traveling! So, when deciding where I’m going, I have to know who I’m going with!
When depends on where I’m going as well. When planning a trip somewhere, you need to find out the best time of year to go. Many people make this mistake. If you’re trying to go to a certain place during the “cheaper” time of the year, that’s one thing. I do that sometimes too, but it needs to be substantially cheaper for me to risk it, and this method obviously doesn’t work for everywhere. For example, let’s say you’re wanting to see the beautiful blue glacier-fed lakes in Banff, Canada. A quick Google search tells me that the best time to visit is July-September. Go too much earlier or too much later and the lakes will be frozen! You don’t want to go to Greece in December and be freezing, Egypt in the summer and be too hot, or Costa Rica in the rainy season, do you? So do your research! Who, when, and where are ALWAYS the first three things I start with when planning.
BOOKING FLIGHTS
If there’s anything I learned from the THREE international trips (brb, still crying over Germany, Canada, and Indonesia) that were cancelled during the very beginning of the pandemic, it’s this: Don’t use a third-party site such as Expedia, and if you’re in the US, do your best to avoid booking with international airlines.
The big reason you shouldn’t book with third party sites is that if you have issues with your flight and you call the airline, they’ll tell you to call Expedia. When you call Expedia, they’ll tell you to call the airline. It’s literally a never-ending cycle and it made getting refunds/credits and rebooking a NIGHTMARE. Ever since then, I decided I would never use them again! There’s nothing wrong with using these sites to search for flights though. In fact, I really like the app called Hopper because I can set “flight watches” with specific dates to tell me when the price drops, and it helps me find the cheapest day of the week to fly. But when it comes to booking, I now either book directly with the airline, OR I book directly through my credit card. If you’re new here, I have the Chase Sapphire Preferred card, which is excellent for traveling because it adds up points so quickly. I was able to use points to pay for all of one of our flights to Greece!
As for not using international airlines, that’s more of a personal preference that also started when my trips during the pandemic were cancelled. While this is not an all-or-nothing rule for me, I do tend to try to book with Delta, American, or Southwest when I can (they are my personal favorites). My reason is because when those 3 trips were cancelled, I was stuck with credits for American Airlines, AirCanada, SAS, and Qatar! And if you aren’t aware, the international ones don’t fly within the US, only to or from. I was basically stuck with credits that I couldn’t even use because of borders being shut, and was only able to use the AA one during our trip to Maine. Eventually, I did manage to get a refund from AirCanada and SAS, and with Qatar we switched locations and used our credits for Egypt instead of Indonesia before they expired. It was quite stressful though trying to figure it all out! So now, as long as the price difference isn’t insane, I’ll go with US airlines because in the event of borders shutting down again, I’m not quite as limited on where I can use the credits.
As for picking flights, I usually also base it on which airport is cheaper/easier to fly from. For instance, we use St. Louis Lambert most of the time for domestic, but Chicago O’Hare is usually way cheaper for international. If you’re in a location with multiple airports to choose from, make sure you price flights through all of them.
You also need to closely look at flight times, because picking flights should also largely be based on that. For instance, on long-haul international flights, like Italy, I would rather fly out in the evening that way I can hopefully sleep on the plane and arrive in the morning. If it’s a shorter international flight or a domestic flight, I prefer to leave in the morning so that I’m not wasting as much time and get to enjoy part of the day once we get there. Just keep in mind wherever you are going though that morning flights are the least likely to be cancelled and also the most likely to be running on time. I also prefer flights with no layover OR one layover that is >2 hours, so that there is less room for errors (lost luggage, missing a flight, etc).
BOOKING ACCOMODATIONS
This can be kind of controversial because everyone has their preference, but I am personally fine with staying in a hotel OR Airbnb, it doesn’t matter to me. This is also largely based on other factors such as location, what I’m going to be doing, if I’m renting a car, etc. If I’m going diving, we have found that finding hotels without carpet in the rooms works best because we have a lot of gear that obviously gets wet, so this makes cleanup the easiest. Other trips where I’m doing more exploring and relaxing, such as Greece and Italy, I mainly used Airbnb.
One thing to watch for with Airbnb is the price. It used to be much cheaper to stay in one, but with the way the market is saturated nowadays, hotels can actually sometimes be cheaper, so it’s a great idea to compare before you decide. A lot of the times Airbnb’s will charge a hefty cleaning fee while also leaving you a “chore list”, such as washing towels before you leave or taking out the trash, so make sure to read the rules before booking if those aren’t things you’re willing to do.
If I’m looking for a hotel, my favorite site to use is definitely Booking.com. It is extremely user friendly and I have had great luck with it so far! I also feel like it tends to have better prices and more options than other sites.
No matter where you decide to stay, it’s also important to utilize the map tools on these sites to make sure the location is appropriate, especially if you don’t have a car or it’s somewhere that doesn’t have many taxis or Ubers. Otherwise, you may accidentally book someplace really inconveniently far away! Like in Rome, I made sure to research neighborhoods so that I booked an apartment close to everything, since we walked everywhere.
If you’re brave and want to try solo travel, I have heard hostels are a lot of fun and a great way to meet new people! I have never personally stayed in one but have heard they are very affordable, so I wanted to at least mention them. There are usually options for private rooms or dormitories.
HOW TO PLAN WHAT YOU’RE GOING TO DO
Now that we’ve got the who, when, where, flights, and accommodations covered, it’s time to get to the FUN stuff; what are you going to do?!
This is where reading blogs (like mine!) come in very handy, because you’re reading someone’s ACTUAL experience about what they did! If you’ve been around for a while, you know I’m pretty honest, and if I don’t feel like an activity or restaurant is worth it, I’ll tell you.
My favorite tool for finding blogs about locations is Pinterest! I can do a quick search of something as simple as “Charleston, South Carolina” and it’ll pull up sooooo many different options for me to read! I can usually tell if a blog is actually going to be worth my time as soon as I open it, because I personally prefer reading blogs similar to my own. Things I look for in a blog include…
• A blogger who writes about their personal experience. If I feel like they are making a generic list of “things to do” that they probably copied from a Google search, that tells me that maybe they didn’t even actually do those things or go there, so how will I know if they are worth it or not? I want to know how hard they thought a hike was, if a tour company was good or not, where they bought tickets, etc.
• Pictures of them or ones they obviously took. A huge red flag for me is using stock photos that they found on the internet. For one thing, that’s stealing. And for another, as I mentioned above, how do I know if they actually went there?! TBH, I could write a bull s*** blog post about a place I’ve never been to just by reading about it, but what good would that do for you? I want to see a picture of them in front of the Eiffel Tower, not a random Google stock photo!
• Links! Or at least names of companies to point me in the right direction. I never would have found the shared shuttle we used in Italy if it weren’t for reading a blog that had a link to the website they used. Trust me, I had done multiple searches on my own to find transportation, and I don’t remember seeing the website they used pop up. It also helped because it told me it was a legitimate company and not a scam, because they talked about their experience!
While reading these blogs, I start planning out my “itinerary”. I like to open a fresh page on Microsoft Word, and start making a list of things I want to do. Sometimes if I find a really helpful blog, I will even save it on Pinterest or just save the link to the website so that I can go back and refresh my memory later if need be. I will also save links to tour companies if the activity is something I need to book in advance.
Eventually, I will start planning out the trip day-by-day as I decide what we are going to do. Below is an example of my itinerary for Italy. A lot of people think I’m weird for doing this, but it really helps me stay organized! And my itineraries are also not strict at all. I’m a big fan of leaving room in the day for exploring or rest, or even leaving a full day open. For example, we didn’t follow this exact itinerary because our boat day got cancelled and moved to our second beach day due to weather, so we ended up having two beach days in a row! I wouldn’t have been able to do that if I had already planned an activity for that day.
Another reason I am a big believer in planning/booking in advance is because believe it or not, in busier season, sometimes things sell out VERY quickly. I can’t tell you how many times I have witnessed people be unable to do an activity on a trip that they were really looking forward to because they waited too long and it was already sold out. You need to have a good mix of spontaneity and plans!
STAYING ORGANIZED
Speaking of doing all this booking…remember, you’re doing it yourself, not through a travel agent. That means that you are the responsible one!
I think this is what stresses people out and deters them from planning their own trips. As I said before, there is nothing wrong with using an agent. Most of them are no extra cost to you. I have just found that I thoroughly enjoy the process of planning, so I prefer to do it myself. If you have no interest, then by all means use an agent!
You could also always do a mixture of both, too. Use an agent to book your flights & accommodations, and then book all the activities yourself. Just an idea! Especially if you’re wanting to start doing some of it on your own, that would be a great way to begin.
One thing that has really helped me be more organized for trips is printing off allllll my confirmation e-mails, and then organizing them in a folder that I bring on the trip with me. I will even highlight important information such as times, addresses, phone numbers, etc. We all rely on technology way too much so I love having physical copies of everything! I have personally had my phone stolen on a vacation before and it really bothered me how helpless that I felt, so this relieves some of that anxiety. It is even great practice to carry copies of important documents such as your I.D. or passport in case they are stolen/lost/ruined.
TRAVEL REQUIREMENTS
I feel like some people are not aware that some countries have entry requirements, so I wanted to mention this. It may be something like a PCR Covid test or proof of vaccination (Not just for Covid, either! Many places require other vaccinations!), or it may be something a bit more in-depth, like a Visa.
No, I’m not talking about a credit card. I’m talking about a tourist Visa. Believe it or not, your passport is actually *not* enough to just waltz into every single country. Some require Visa approval before entry, some require it on arrival, some don’t require it at all. So it’s very important to look into this! For example, you can’t go to Egypt without a Visa, either obtained prior to arrival or once you arrive. You will NOT get through without one, and I watched multiple people get sent over to the Visa kiosk and have to wait in line alllll over again. If you aren’t sure, just Google it! Most countries have websites that list all of their entry requirements.
If you’re going on a multi-country trip, or even just a long trip, do your research on that as well. For example, a lot of European countries are considered part of the Schengen zone. You can only stay for a maximum of 90 days. After staying for 90 days, you must be gone for 90 days before you can enter again. Some countries will also restrict entrance to people who have criminal charges or if you’ve been in a certain country recently that they don’t have good relations with. Canada is a good example of this; apparently you will literally be told to turn around and go home if you have a DUI on your record!
IN SUMMARY…
No, planning a trip is not easy. Truthfully, I have had lots of people message me and ask me to do it for them, and I always have to politely tell them no, because I don’t think they realize how much time and effort I put into it. Kudos to travel agents because I definitely couldn’t handle managing that many people’s vacations!
I really hope this blog has not only encouraged some people to plan their own trips, but also given some helpful insight on what to do & what not do to. Travel is so important to me and I want your adventures to be successful! I also hope that this will open some people’s eyes to see that my trips aren’t just all pretty pictures and fun times, and that I really put a lot of work into them. I’ve never had a trip go absolutely perfectly but that’s ok, I manage to roll with it and still have fun and that’s what matters! If something doesn’t work out, it is just a lesson learned.
Thank you for reading if you’ve made it this far! Please feel free to reach out if you have any questions. Happy planning!