How to plan an amazing vacation: know your travel style

How to plan an amazing vacation: know your travel style

How do you plan an amazing vacation? To start, you have to know what makes a vacation amazing, right? It’s no surprise that the answer to that will vary from person to person, because we are all unique creatures with different ideas about that.

The thing to remember about vacations is that they are based on expectations, which are based on your own perception, ideas, and feelings. As you anticipate your vacation before departure, whether you realize it or not, you have some vision in your head about how you expect your vacation to be.

You imagine feeling a certain way. Maybe you look forward to taking a slower pace, or maybe you have this list of things that you want to see and do. You might expect a certain level of service and luxury. Perhaps you imagine meeting new people, or maybe you just want to enjoy being with your travel companions.

But tell me this: what happens if you don’t feel the way you expect to feel on your vacation? What happens if you have to miss out on that fun activity you were looking forward to? What happens if your lodging experience is way different than you envisioned? You don’t have an amazing vacation.

To plan an amazing vacation, we need to first and foremost understand what your expectations are about vacations.

I have created the foolproof solution to doing that: know your travel style.

A travel style is not whether you prefer to wear sweatpants or high heels on a plane ride, though that is a small part of it. It’s not just what you like to do on vacation either, even though that’s a biggie too. A travel style is information about how you prefer to travel, when it comes to planning, activities, confidence, and comforts. An easy way to think of it: it’s your travel personality.

Understanding your unique travel style is critical to planning an amazing vacation, because every vacation should be as unique as the person taking it. If it’s not personalized to you and your travel style, it will have a tough time being your definition of amazing.

Going on vacations that aren’t really your idea of a vacation is a chronic issue that I see, especially if you aren’t involved in planning the trip, or you don’t have someone that understands how you prefer to travel planning your vacation. Don’t plan activities you don’t enjoy, just because they are the Top 15 Things You Must Do in France list. Don’t stay at that super boutique hotel recommended to you by your aunt if you really to prefer to camp. Don’t follow a structured daily itinerary if you are a go-with-the-flow person.

By understanding your travel style, you can:

  • More easily cull through all of the suggestions of lodging and activities for your trip to hone in on what suits you best.
  • Choose how balanced your itinerary is between activities and relaxation.
  • Travel in a way that makes you feel confident and comfortable.

I’ve taken a deep dive into what makes each of us a little bit different in how we prefer to vacation and created my very own explanation of a personal travel style.

What is a travel style?

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My definition of a travel style is a combination of 4 different focus areas:

  1. Planning: How do you handle your trip logistics and itinerary?
  2. Excursions: What do you like to do on vacation?
  3. Confidence: How confident are you in unfamiliar situations?
  4. Style: What comforts are a requirement on your vacation?

Within these four focus areas, there is a spectrum of where you fall depending on your tendencies or preferences. I’m taking a deep dive into each below.

Planning: how do you handle your trip logistics and itinerary?

There is no getting around it: taking a vacation requires some amount of planning. Before you leave on vacation, you have to find a flight to get you there and a hotel to stay in. Once you arrive, you have to figure out what you want to do and see.

Understanding how much of the what, where, and when of your vacation that you like to plan in advance, as well as how structured or loose your daily itinerary is plays a big role in making sure that you’re going on a vacation that will meet your personal recharge needs and expectations.

Some people prefer to plan all of the details of their vacation ahead of time so that they can arrive and just start being on vacation. On the other end of the spectrum, some people prefer to go with the flow and discover things as they find them based on how they feel every day.

So in general, there’s two main types: those who prefer to have a plan and those who don’t want to have a plan; however, as humans we are by no means that black-and-white. In this focus area, there are four distinct planning travel styles.

Planners are the leaders of the trip who take charge of the travel plans and make sure all members of the trip party – usually Followers (see below) – are where they need to be. They prefer to have everything planned prior to departure, and usually have a set itinerary planned for each day, and it’s usually a pretty fast pace. They’ve done their research about a destination more than anyone else, and are the ones in the travel group with all of the answers about the what, where, and when.

Followers don’t necessarily need all of their ducks in a row to make a trip happen because they probably know a Planner who’s already on it! They enjoy following along with predetermined travel arrangements, but do not initiate or control them. They may not even know what all is planned for a trip, but they are usually agreeable to most things and along for the ride!

Laid-Back travelers don’t go out of their way to make too many plans ahead of time, but will have a general course of direction, such as where they are traveling to. After that, they prefer to explore and do things as they discover them in their destination.

Impromptu travelers are go-with-the-flow and don’t like to be tied down to travel plans. They are the ones to jump at the opportunity of a cheap flight to somewhere they hadn’t even considered visiting and can leave at a moment’s notice with little to no planning. Oh yeah, and a trip itinerary makes them want to vomit. Don’t expect Impromptu travelers to want to go on a vacation with a Planner – and vice versa.

Which category sounds most like you? As for me – considering I operate a travel planning business and specialize in vacation planning – I am most definitely the Planner.

Excursions – What do you like to do while on vacation?

When most people consider taking a vacation, a big factor to consider is what there is to do in the destination of choice. In general, there is usually a dominant theme in how people tend to like to spend their vacation time, though the specific activities can vary from vacation to vacation.

Some like to do a lot, some like to see a lot, and some like to eat or drink a lot. On the other hand, some enjoy doing “nothing”, according to their own expectations. This focus area hones in on the specific activities that will leave you feeling fulfilled from your vacation.

Active travelers prefer to do on vacation, meaning the more activities the better. They would prefer to hop around from city to city versus staying in one location, as sitting idly for too long can make them bored. They usually enjoy excursions that get their blood pumping, like hiking or some adrenaline activity. An all-inclusive resort is probably not where you would find these folks.

Sightseers are the bucket list travelers! They want to see and do all of those things that people post about and have their own pics to prove it. The recognize that the most beautiful and interesting places in the world have already been discovered, and there’s a reason people visit these places, so why stray too far from the beaten path?

Social travelers enjoy dining, drinking, and socializing while on vacation. Their vacation goal is usually to relax and have fun as much as possible. Social travelers will often travel in large groups of friends or family, because vacation is supposed to be a big party, right?

Introspective travelers strive to experience the true culture of another country. They tend to stray away from the tourist trail because they prefer to immerse themselves in traditional or custom activities that allow them to ponder the historical, political, and social part of the country.

Which category do you fall into? I am a blend between Active and Sightseer because I enjoy hiking and being out in nature, but also enjoy seeing the unique sites of a destination!

Confidence – How confident are you in unfamiliar situations?

Choosing vacation arrangements that are a match for your comfort level in unfamiliar territory is an important factor to making sure that your expectations are met. Experience will contribute some to the confidence level because the more you travel, the less uncertain and more familiar it becomes. Outside of experience, there are people that have a natural confidence towards uncertainty, and those that approach uncertainty with worry.

You might prefer to rely on the local experts in a destination to make sure that you are getting around to your activities safely and on-time. On the other hand, more experienced or independent travelers would rather travel around with their own personal group. This focus area takes a deeper look into how comfort and confidence contribute to your travel style.

Experienced travelers are the frequent flyers with the best travel rewards credit cards. Their confidence carries them through the airport process with a jet setter style and no stress. They know how to use their resources to find the best hotels, transportation, and flights, as well as planning and concierge services to ensure that their trip is a success. Basically, this ain’t their first rodeo.

Independent travelers prefer to DIY and like to venture out on their own versus joining a tour group or relying on anyone else. They are comfortable using public transportation or renting a car and navigating themselves. They may not be the most experienced, but have the confidence to make up for it.

Safe travelers can be nervous or worried about going to a new country regardless of how experienced they are. They prefer to rely on the experts and tour operators versus trying to figure it out on their own. You will often find them choosing an all-inclusive or guided tour so that they do not have to worry about travel logistics or find themselves all alone in a foreign country.

Eager travelers are not as experienced yet, so may be a bit clueless when it comes to travel logistics; however, they still see traveling through rose-colored glasses, causing their excitement to outweigh any uncertainties!

How confident are you traveling around in a new place? I fall somewhere between Experienced and Independent.

Style – What comforts are a requirement on your vacation?

The amenities that you prefer to have available on a vacation is an equally important consideration to a travel style. Speaking about more than just your wardrobe, we are talking about the type of lodging and modern luxuries, that you require, or don’t require, on your vacation. Since vacations are a chance to treat yourself to experiences that you don’t normally get, this focus area needs it’s own focus.

If you’re someone who goes on vacation to enjoy the finer things, then paying extra attention to the details of your hotel selection is a big priority. You may opt to spend more on small-batch luxury experiences or comfortable transportation because those things will make you feel the way you expect to feel. On the other hand, if you require only clean, comfortable, and safe accommodations, then you may not care about fancy hotels or luxury experiences. In fact, you might feel uncomfortable or like you’re unnecessarily splurging if it’s not a match for you how you envisioned.

Comfortable travelers are not ashamed to admit that they came on vacation to enjoy the finer things. Modern, boutique, and luxury hotels or resorts with top-notch services and amenities is a must. Comfortable travelers tend to pack lots of clothes – probably too many – and are sure to bring along every single toiletry item that they might need.

Classic travelers will tell you that they just want to stay in a place that is “clean and safe.” You will often find these travelers in some of the familiar, well-known hotel chains or a guesthouse where they have many of the amenities from home. They don’t require luxury services or amenities, but do expect normal comforts like a hot shower and are sure to pack most everything that they might need.

Minimalist travelers know how to pack only the essentials and are comfortable in modest lodging like a hostel or culturally immersive accommodations. They likely seek out lodging experiences that are off-the-beaten path and make less of an imprint on the environment.

Rugged travelers are most at home when they can be surrounded by nature and away from hoards of other travelers. Cabins, tent camping, or other lodging experiences in the wild that allow them to have a close and personal view with nature from their back porch is what they seek. Depending

What are the comforts of home that you can’t live without on vacation? I fall between the Comfortable and Classic traveler.

What is your travel style?

So there you have it: the behind-the-scenes look at my personal methodology of defining a travel style. I’ve taken it a step further by grouping different combinations of the four focus areas and have consolidated these groupings into 8 unique travel styles.

Which one are you? Keep reading and see if you can self-identify.


You are the seeker of the wild! Your vacations are typically spent hiking, camping, or road-tripping – anything that allows you to see as much jaw-dropping nature as you can. You strive to summit mountains, meander through valleys, nap by lakes, and see wildlife of all kinds. Adventurers typically prefer to have their travel plans mapped out before departure and come prepared with all of the gear and equipment that they would need on a rugged vacation. When you pass other travelers, they likely see you as someone who looks like they know what they’re doing!

You should visit: Canada, Tanzania


You are the traveler that wants to do it all! You are an experienced traveler that knows the most efficient way to get around to see and do as much as you can. Your vacations are spent hopping around to multiple places within a country checking sights, excursions, and restaurants off your list on a tight schedule. Bucket-Listers will typically have the majority of their trip planned before departure and will already know what their plans are for each day. Because of all of the activities that they will be doing in their jam-packed day, they prefer nice accommodations with a hot shower and some added luxuries to rejuvenate themselves before their next big day.

You should visit: Peru, Iceland


You are the sightseer! You travel to see bucket-list sights and experience new cultures, but from a distance and at a rapid pace. Your vacations are spent following the paved tourist trail because you realize that certain destinations are popular for a reason. Tourists typically will have the majority of their trip planned before departure, often times in the form of an organized tour group, so that they do not have to worry about the logistics of getting from place to place and can maximize how much they can see in a short amount of time.

You should visit: England, Costa Rica


You are the traveler that wants to get away from everyday life and take a break! Your vacations are a balance between fun and total relaxation. Escapists prefer luxury accommodations that offer dining and activities as part of or in close proximity to their room because they don’t want the hassle of traveling much once they arrive. Though they will have their hotel and airport transport sorted out before departure, they prefer to be laid-back when it comes to the daily activities on their vacation.

You should visit: Turks & Caicos, French Polynesia


You are the traveler that wants to shop by day and dance by night! You travel to experience the fine cuisine, drinks, and modern finds of another country. Your vacations are spent with a group of friends wining and dining your way through the country as you find the best restaurants, nightlife and parties. Socialites typically don’t plan their vacations much outside of choosing a great hotel close to a hip part of town and making some dinner reservations.

You should visit: Israel, Greece

Soul Searcher

You are the traveler seeking to find something within yourself or the world. You travel to experience the true culture of another country. Your vacations are spent immersing yourself in traditional customs and cultural activities that allow you to ponder social and religious beliefs. Your eyes are wide with eagerness to learn about the world. You prefer culturally immersive lodging over a standard hotel because you know that it will open your eyes to so much more. You plan some of your vacation, but also rely on those you meet along the way to guide you on what to do and where to go next.

You should visit: Papua New Guinea, Sri Lanka


You are the traveler with the free spirit! You travel with no set plan or sense of time commitment and go where the wind takes you, as you feel this is the best way to truly experience a country. Your vacations are spent walking, hitchhiking, or taking a bus from city to village, existing alongside the locals in their daily lives. You are an independent traveler carrying only the essentials on your back who doesn’t require much in terms of comforts and would be comfortable in simple accommodations like a hostel or a new friend’s couch.

You should visit: Chile, Vietnam

Thrill Seeker

You are the traveler addicted to thrills! You travel to push your limits and do things most people wouldn’t dare to – and of course document this on YouTube or Insta! Your vacations are typically spent hopping from place to place in search of that one epic excursion after another. Thrill-seekers typically don’t plan their vacations much and prefer to go along for the ride once they arrive. You don’t require much in terms of comforts and would be comfortable in simple accommodations like a hostel.

You should visit: New Zealand, Morocco

Traveling with different travel styles

Since everyone has their own personal travel style, you might not be able to plan a trip that is exactly tailored to every person if there are different travel styles in the group, which means compromise will have to happen. But if you understand your own travel style and those of your travel buddies, you will have a much better chance at designing a trip that you all can consider a success.

For example, within the Planning focus area, Planners and Followers travel really well together because they prefer to approach their vacation days the same way: with a plan. Their personalities complement each other because there is the proactive, take-charge person and the easygoing person that’s happy to be along for the ride.

However, if you have a lot of Planners in your travel group, there’s a chance for conflict because there are too many people trying to take charge. Likewise, if you have a travel group full of only Followers, there’s a chance for frustration that they’re wasting time on vacation if no one steps up to initiate the plans.

Just like Planners and Followers, Laid Back and Impromptu travelers tend to travel well together because they prefer to approach their vacation days the same way: they like to wake up in a leisurely manner and take on each day as it comes and discover things naturally. However, the extreme last-minute tendency of the Impromptu travelers may not totally jive with a Laid Back traveler, who feels comfort in having at least the basics sorted out before arriving in a destination.

When I plan custom vacations for my clients, my top priority is understanding the travel style of every member of the travel group. Planning vacations that are a match for the various travel styles in a group is a challenge that I love taking on, because I can serve as the objective third-party who makes sure that everyone will be happy with the vacation.

Travel styles can change

You should know that travel styles can and will change and evolve as you do in your seasons of life. You can even have a different travel style depending on the type of vacation that you are seeking.

I used to plan multi-city, intensive itineraries because I enjoyed hopping from place to place to see as much as possible. I liked touring cities aimlessly, but also planned some excursions. Beer was usually on the menu at night, along with not very much sleep.

With age, I’ve chilled out a bit and appreciate that some scheduled relaxation time is a necessity for me. I enjoy seeing beautiful landscapes and being in nature with animals. It’s icing on the cake to be immersed in the culture and chat with locals. While I still prefer to be mostly active on vacation, I will plan a relaxing vacation every now and then.

Are you looking for a custom travel advisor to plan your next vacation? Get a taste for what it’s like to work one-on-one with me by signing up for a free consultation where I help you take the first steps in making your vacation a reality. I help you understand how you want to feel on your next vacation and recommend vacation experiences that are a perfect match for your travel style and budget.

Get to know Angela from Wild Hair Travels.