How to Plan a Trip: 5 Steps to Planning the Perfect Vacation

I LOVE PLANNING VACATIONS!

Which is why I became a travel agent. But as a travel agent, I realized most people don’t share my enthusiasm for travel planning. I get it. There are a lot of decisions to be made, especially concerning your wallet. But the overwhelming feeling usually comes from people not knowing what to look for and where to find it.

I’m not going to lie and say planning a vacation is quick and easy. It can be, but this is an occurrence that happens less often. I plan every vacation (for myself and clients) using the same method and enjoy the planning process every step of the way. As with life, a change of mentality can make a world of a difference (as well as following my method)!

With just 5 steps, planning a vacation, IMO, can be so much fun. Granted, this is the opinion of a travel planner.

Travel is my life and is on my mind 24/7. Not everyone has this luxury (or wants it). Don’t worry! You definitely don’t have to be a travelholic to plan amazing experiences.

The more you use this travel planning guide, the easier (and faster) travel planning will become.

When you come across an amazing video on YouTube and you can’t wait to experience that yourself, put it on your list. When you see the most amazing pictures on Instagram, add the location to your list. When you keep adding these places to your list, the next time an opportunity for a vacation comes up, you already have a list of places you want to go.

I can’t tell you how many times I’ve come across places, tried to remember it for later, and then ended up completely forgetting where the hell it was. So now I keep a list on my phone (which is always on me) and update the file on my USB periodically. I’m extra. I know.

When deciding where to go on vacation, you can refine your options by asking yourself why you’re going and when you’re going.

You can ask a dozen people why they’d want to take a vacation and you’d get a dozen different answers. But it all boils down to people wanting an experience.

When it comes to travel experiences, I like to think of the acronym L.A.T.E.R. People are traveling for love/romance, adventure, tourism, eating/food, and/or relaxation. Food didn’t really fit, so I went with “eating” instead. LOL.

Anyway, these are the 5 most common experiences people want when they travel. Of course, they are often intertwined and there are numerous extensions of these categories, but the central reason typically falls into one of these categories.

When you know the “why” to your travels, it makes the first part of planning easy.

If you really don’t want to be bothered with creating your own list, check out mine! I’m constantly updating it with new places I want to experience!

If I’m in the mood for looooove, I’ve got several locations on my list that would be great romantic spots. The same goes for if I’m in the mood for an adventure, or just relaxing on a beach, or eating my heart out. Check your list. Always.

Having a list is also great for conducting streamlined research when planning your trip. Googling “couples-only resorts in Mallorca” will yield far better results (and less time digging) than, “romantic vacation spots”. While the latter is great for building a list, it will be quite time-consuming to go through numerous articles searching for a destination that speaks to you.

So, we have the “where”, the “why”…how about the “when”?

This is another question that is either answered right away or requires a great deal of thought. Sometimes the reason for travel is date specific (a birthday trip, anniversary/honeymoon, events, etc.), while other times it’s just for the helluvit. And it’s the “helluvit” that’s a whole lot harder to plan around.

Choosing when to travel can also greatly affect the cost of your trip. How far out you book a trip can manipulate pricing as well.

Not to mention, we have work, school, families, finances, and other responsibilities to work around. So, how the heck are you supposed to figure it out?

That brings me to step 2.

2. How to Get There

If you haven’t heard of my best friend, allow me to introduce you to them: Google Flights!

Ten times out of ten when I am planning a trip, I start with Google Flights. Their calendar tool is great for gauging when prices are lowest for the destination you are considering.

I use Google Flights when I’m actively planning a trip, or during downtime when I’m just browsing.

Which brings me to my next travel tip:

TRAVEL TIP #2: Flights are typically cheapest four to twelve weeks ahead of departure.

If you’re not traveling for a specific event, BEFORE YOU EVEN START YOUR GOOGLE RESEARCH, take to Google Flights. I recommend researching flights first because you’ll be able to see what airfare is like for the destination you have in mind. If the airfare looks a bit pricey, the calendar gives a great overview of when prices are lower. If that doesn’t seem to be within a suitable time frame for you, move on to your next destination option on your handy dandy travel list. Another issue that is sometimes overlooked is flight times. Some destinations have crazy flight times on certain days, and more manageable flights on other days. Always double, triple, and quadruple-check flight time information before booking a flight (and I strongly urge against booking flights with a layover of 2 hours or less; you don’t want to miss your connecting flight if your initial flight gets delayed). If you look at airfare before you start researching your destination, no time will be wasted if you end up changing your destination (a few times).

If you’re still struggling with choosing where to go, Google Flights also has an “Explore” feature that allows you to select your departure city and leave your dates flexible and it will show you the lowest airfare for cities all around the world. If the cost is your primary focus, this is a great tool to see what your most affordable options are.

Airfare is a large part of travel expenses, but it is also where the price is most flexible. The earlier you start looking into a trip, the more time you have to be flexible.

I always plan my trips around the cheapest days to fly. For example, I may have wanted to travel from September 14-20, but Google Flights may show me that September 17-23 is cheaper. Many airlines also have this tool on their site, but Google Flights allows you to compare prices between dozens of domestic and international airlines in one place.

Another tool I use from time to time is Hopper. But I’m definitely a Google Flights girl.

While flying is the most popular mode of transportation (and sometimes the only choice), it can also be the most expensive.

When the budget doesn’t quite stretch for airfare, but your destination is within reach, DRIVE THERE!

I love road trips. Big or small. I just love driving.

If your car is in good condition (have your car checked out before ANY road trip), fill her up and hit the road. Yes, you’re sacrificing time for money, but depending on your budget, it may definitely be worth it. And sometimes, it’s not the most cost-effective option, but the journey can be definitely worth it.

When deciding between driving and flying to a destination, here are a few things to consider:

how much will gas, car rental/maintenance, and overnight stays cost compared to airfare
how much time will driving (and resting) eat into vacation time
is the time/cost trade-off worth it?

3. What to Do While You're There

This is my favoritest favorite part of travel planning!

Alright! We’ve decided on a place, a time to visit, and a way to get there. Now, what are we doing while we’re there? Search it out! This is the fun part. The hours of getting excited and jotting places down and screenshotting and saying “Oh, that’s dope as #$@%.”

Now, if you’re more of the laissez-faire type, I totally get it. Treat each day with new interest and curiosity.

As for me, I like to think of myself as someone who plans to go with the flow.

I need to know all my options: the price, the hours of operation, the distance, etc. BUT, we can decide when we get there. (Or not. Please not. Plan it now! Please!)

Being unprepared on a vacation can be a costly mistake. You can waste time and money. As I mentioned, there’s nothing wrong with wanting to take each day in stride, but certain aspects to a trip require careful planning and research. My advisement is no matter what type of trip, always research transportation info (bus, taxis, ferries, trains, etc.), and ticket information for tourist attractions. Even if you don’t want to research in the weeks before your trip, at least look it up a few days before the trip. Often times, there are discounts for tickets purchased online as well as “skip-the-line” benefits compared to tickets purchased on-site.

I promise, I do know how to just kick back and relax, but that’s usually reserved for my beachside vacations. Going back to vacation experiences, I’m usually on a tourism or adventure-type vacation. I’m usually going to see landmarks or join tours that require planning and reservations.

Mini tip: This step doesn’t have to be done right away or all at once. Take your time and have fun with it.

When it comes to planning this part of a trip, I 100% of the time start with my best friend, Google, and my handy dandy activities planner.

Search: “What to do in…[DESTINATION]”.

Google provides a great overview of the most popular attractions and things to do in a specific location.

For every single trip I plan, I start with Google. Even when I have specific activities in mind, I still like to Google other attractions in case there are other great experiences to be found.

After starting my activities list with Google, I then go to Instagram. The Explore/Search page is great for searching places and hashtags to find activities for your trip (and inspiration for future trips).

After Google and Instagram is my other favorite: Pinterest.

Pinterest has tons of destination listicles, itineraries, and travel guides to just about anywhere. I constantly find myself on Pinterest looking for travel guides and recommendations on certain locations.

If you’re not a fan of crowded places or tourist traps, search for “unique experiences in [DESTINATION]”.

Now, my not-so-favorite part about planning what to do is refining the giant list you’ve comprised.

I know, I know, please don’t hate me.

Realistically speaking, you won’t see everything on your list. You can try, but it just won’t happen. And quite frankly, it shouldn’t happen!

TRAVEL TIP #3: FOR EVERY 3 DAYS OF ACTIVITIES, ALLOW 1 DAY FOR RELAXATION/RECOOPERATION. You’ll thank me later.

I can’t tell you how many times I’ve overestimated myself and only ended up disappointed.

In my younger years (pre-COVID times), I always had FOMO when planning my trips, so I tried to squeeze in as much as I could.

DON’T DO THAT.

You’ll only exhaust yourself and that’s not the goal here.

I like to follow this “model” when planning my trips:

Day 1: Arrival/Relaxation/Low-key meal

Day 2: 1-2 attractions

Day 3: 2-3 attractions or day/half-day tours

Day 4: Relaxation (beach/pool)/shopping/local tourism

Day 5: 2-3 attractions or day/half-day tours

Day 6: 1-2 attractions/low-key day (maybe a nice dinner reservation)/pack

Day 7: Departure

Depending on the length (and purpose) of your vacation, the order of things may look a little different. The main points I like to follow are:

1. Don’t plan big activities on arrival days (if that can be avoided)

2. If a trip is 5-7 days, I like to plan a relaxation/low-key day in the middle and/or the day before departure. 7+ days get a relaxation/low-key day every 3-4 days.

3. Be mindful of your departure time when planning activities on your second to last day. Try not to exhaust yourself if you have an early start the next day. You don’t want to miss that flight home! Try your best to avoid packing on your day of departure unless you have an afternoon/evening flight.

It’s important to schedule some R&R time because, at the end of the day, that’s what a vacation is really about, right? Plus, you may not realize it because of the excitement, but your body is going to be supporting you through a lot (plane rides, car rides, hours of walking/sitting/hiking, early mornings/late nights, etc.), so it’s nice to reward it.

Another itinerary-building tip I implore you to use is: prioritize your must-sees and attractions that require reservations.

Example: when I visited to London in 2019, two things I was keen on doing were going to Stonehenge and eating at Coppa Club near Tower Bridge. Coppa Club required a reservation for their igloo seating, so I booked with them first. The reservation ended up being on our second day there, so I planned everything else around it. I took that day slow (Buckingham Palace, rode Big Bus London, and walked about the city) and then had dinner at Coppa Club, followed by a lovely boat tour (courtesy of our Big Bus London tickets). In the days after, we went to Stonehenge, Windsor Castle, Oxford University, more Big Bus London touring, shopping, and walking. Stonehenge, Windsor, and Oxford was a full-day tour, which we planned on our third (of five) day of the trip.

Planning where to go on a trip may seem daunting to some, but it is exciting to me. It’s where all your efforts into making it a memorable experience go. BUT, no matter how much you plan, life happens. Go with the flow and be amicable to adjustments. Sometimes the unexpected creates (for better or worse) an unforgettable experience.

4. What to Bring/Wear

This section is so difficult to write because there is such a HUGE umbrella when it comes to packing. In fact, I’m probably the worst person to ask on this subject.

But I’m getting better!! I still hold the title of “Queen of Overpacking”, but I improve greatly with each trip I take.

I’m someone who likes options when it comes to getting dressed. Rarely do I know what I’m wearing out until it is time to get dressed. I have to see what I’m in the mood to wear. I can’t plan for Thursday on Tuesday because Tuesday, my stomach is flat, my face is clear, and my confidence is dialed to 11. Thursday, I’m bloated, my face is irritated, I’m self-conscious, and want to wear a sack. You may think I’m exaggerating, but I’m not. I can’t plan an outfit too far ahead.

I don’t just have trouble packing clothes, though. I’m also a makeup and tech junkie, especially as a content creator.

I have to bring ALL my palettes, lip colors, and brushes, and my tech list is a mile long.

But the more I have traveled, the more I’ve learned to reduce. 😭

This section is less about the specific items to pack, and more about how to plan to pack.

HERE IS MY ULTIMATE PACKING LIST PRINTABLE

ALWAYS, check seasonal/weather information BEFORE booking a trip. You may think you’re headed to an Australian winter when you’ll be there in the dead of summer (the Northern and Southern hemispheres have opposing seasons).

I like to add my destination to the weather app on my phone after booking a new destination. Every now and then, I’ll check the weather of my future destination. When it gets closer to the trip, about 1-2 weeks before, I start to check daily or every other day. I like to check to see the weather trend, and depending on location, any storms or systems that may be incoming.

When I went to Europe in 2019, I encountered chilly/windy weather, overcast/wet weather, and HOT AS $#!% weather. I (proudly) packed 3 weeks of clothes, for 4 different cities in a check-on suitcase (and a duffel bag). Still proud.

Most of us use vacations as a time to wear our best clothing. There’s nothing wrong with this, but there is a right way to do it.

Think of packing as a pyramid. Starting at the top, the smallest section, you’ll find your shoes. Then you move to the middle for your bottoms and/or dresses/formal wear. At the bottom, the largest section, you’ll find your tops and outerwear.

When you plan an outfit first, and then find the shoes to match, you can end up with too many shoes. I typically aim to bring 3-4 pairs of shoes per trip (depending on how long and where I’m going). Sometimes I’m able to get the number lower, but I always need at least 2 pairs. I usually bring a pair of trainers (most likely what I wear to the airport), slippers/sandals (for wearing around the hotel, to the pool, or wherever casual), 2 pairs of heels (because, of course), and then 1 or 2 miscellaneous. For Europe, that was a waterproof heeled boot. In my opinion, shoes shape the outfit more than anything. This brings me to tip number 4:

TRAVEL TIP #4: PICK YOUR SHOES FIRST. THE REST WILL FOLLOW

When you know what shoes you’ll be bringing, it’ll be easier to pick the bottoms that go best with them, which makes choosing tops and dresses easier too. See? It all works out.

If you’re going on a unique experience, make sure to do research on specific clothing/equipment that may be needed. It can be as small as needing water shoes for waterfall climbing, or more intensive like hiking/camping equipment. Luggage expenses can be a factor that some people overlook, but it can get very pricey very fast. So do your due diligence with researching the activities you’ll be participating in.

If you have medical conditions, a medical bag is probably not something you’d overlook, but for many others, it is. No matter the type of trip, it’s always best to carry pain meds, allergy meds, motion sickness (if needed), and vitamin C. Personally, I use EmergenC.

We may no longer be in the middle of a pandemic, but it is still a good practice to carry masks, hand sanitizer, and hand/disinfectant wipes.

5. What to Know Before You Go

After all that planning and Googling, I’m sure Googling some more is the last thing you’d want to do. Yet, here we are.

Since COVID-19, so much has changed. It’s always important to check travel advisories to make sure a country or state is allowing entry, what their quarantine or testing requirements are, as well as any other potentially harmful activities (crime, medical, etc.) going on in the area.

But there are also a few things to research after you’ve booked.

· Weather/natural disasters

· Time difference

· Cultural/tourist information

Weather is something that is pretty much checked throughout the entire trip-planning process. But don’t forget to keep checking after you’ve booked the trip.

Yes, the website said cloudless skies 350 days a year. Well, keep checking because you may just end up going during the 15 cloudy days, and you’ll want to pack accordingly. Additionally, especially when traveling to the Caribbean during hurricane season, keep checking the weather for any possible storms headed that way. Things can change in an instant and completely alter your plans.

The time difference is something that can be researched just before you go on a trip because, regardless of the time difference, you’re still going on that trip. Jet lag is probably going to hit either way. You’re really only looking it up to see how your sleep pattern will change. Personally, I like to book my flights for morning/afternoon arrivals and take a small nap during the day.

Looking up cultural and tourist information is one of my favorite parts of planning a trip. I enjoy learning about the people and environment I’ll be immersing myself in. I love learning the differences and similarities between my life and theirs. This research is also important to learn what may be considered offensive in a different country than yours, and what is considered acceptable which may be a bit strange back home. It’s also fun to learn a little history about the places you’ll be visiting.

Knowledge is key, especially when traveling. Researching before a trip is essential because nothing feels worse than a charlie foxtrot in unfamiliar territory.

Speaking of charlie foxtrots:

TRAVEL TIP #5: ALWAYS KEEP A DIGITAL AND PHYSICAL COPY OF YOUR PASSPORT AND I.D. AND DISPERSE YOUR CASH.

I have yet to be grateful for this tip, but it’s like insurance. You’re only grateful when you have to use it.

God forbid you to lose your credentials while traveling, having a picture of your identification can go a long way in getting help (contact your country’s embassy immediately if you lose your passport). Additionally, if you lose your wallet and/or your phone, having cash saved in your luggage can come in handy during emergencies.

If you made it here, CONGRATULATIONS! You are determined to be an efficient vacation planner! A lot of information was thrown at you, but you persevered!

Let’s recap!

Where to go
If you haven’t started a bucket list, start now. You may already have a destination in mind, but if you don’t, focus on the experience you wish to have and let that guide you when selecting your destination. If staying within budget is key, let Google Flights’ Explore tool lead you to the destinations with the lowest airfare.
How to get there
Airplanes are not the only way to get around. Road trips are a super fun way to get to your destination. This is when the journey becomes equally if not more important than the destination. Trains, too! Decide on your priority (time vs. money) before committing to your commute. Google Flights is a great tool to compare airfare and price trends.
What to do
If you weren’t tired of Google before, you might be by this point. Google “What to do in [DESTINATION] and you’ll get all the major highlights of your destination. However, these activities are probably quite touristy. Pinterest is another great tool to find tons of listicles about your destination. You’ll probably find more hidden gems and unique experiences here.
What to pack
Make a packing list before you start packing. This will help you keep a focused mind when building outfits so you don’t overpack. Packing cubes are your best friend. Trust me. When participating in tours/excursions, pay attention to any special gear you may need to bring. Build your outfits around your shoes. Decide on the shoes you NEED to bring that can be worn with multiple outfits.
What to know
Make sure to check for passport/visa, vaccination, or quarantine requirements. When traveling abroad, familiarize yourself with your country’s embassy, hospitals, and police stations. Knowing how to call “911” locally is also useful. Respect local customs and traditions and don’t forget to exchange currency.

It may seem like a daunting task to plan a vacation, but it can be done! Take your time and break each step down. There’s nothing like the feeling of being able to completely disconnect from home life and truly enjoy the moment. And there’s an extra jolt of joy when you remember, “I made this happen”.

If you need a helping organizational hand, use my Ultimate Travel Itinerary to arrange the details of your upcoming vacation!

How to Plan a Trip: 5 Steps to Planning the Perfect Vacation

TABLE OF CONTENTS

STEP 1: WHERE TO GO

STEP 2: HOW TO GET THERE

STEP 3: WHAT TO DO WHILE YOU’RE THERE

STEP 4: WHAT TO BRING/WEAR

STEP 5: WHAT TO KNOW BEFORE YOU GO

CLIFFNOTES VERSION

1. Where to Go

TRAVEL TIP #1: Keep an ever-growing bucket list.

Download my bucket list template here