How to Plan a Trip – An Easy Guide to Planning a Vacation

Half of the fun of creating a memorable vacation is actually planning a trip! As someone who excels at finding information online, we normally spend hours on the trip planning process in order to make sure our travels are near perfect. In fact, that’s a huge reason we started All World as a resourceful hub where we try to make traveling easier for other people. Planning a trip of any distance can be a cumbersome process, especially if you are looking for the best destinations to explore while staying within your budget. We’ve learned to embrace the unexpected, and roll with the punches. No matter how well we know how to plan a trip, we know that there could be speed bumps along the way, so having a “plan b” can be a big advantage.

Travel started with both of us at an early age. Michelle’s family, located in California, often explored Hawaii every year and took routine trips to Europe. Me, on the other hand, I was more of a stateside traveler until I reached college. (I’m four States shy of seeing every one!) Since then, we’ve racked up over 50 countries and are pushing hard to get to 100! Through these journeys we’ve become expert travel planners and probably could have been pretty good at running a travel agency if we took that career path earlier in life!

This guide to planning a trip is the result of many failures we’ve learned from over the years, and it is suited for travelers of all ages and tax brackets. We look forward to the travel planning process because when it goes as planned, it’s the same high that I personally get from building a successful business.

A “perfect trip” is the reward you get from taking vacation planning seriously. Dotting I’s, crossing T’s, and stopping at nothing to make sure you see and do exactly what each venue offers.

Whether you heard about a new destination from friends or family members, or saw it on Instagram, destinations are often the result of many factors that vary from person to person. Some people loathe for sun soaked beach vacations, while others are into adventure and prefer extreme skiing. Some folks look for the best deals, while others look for luxury accommodations. That’s the beauty of travel, there is something for every taste.

Enough travel inspiration, here’s our full proof guide on how to plan a trip that you’ll never forget!

Set a Travel Budget Before You Plan a Trip

Setting a Travel Budget

We review our financials every quarter and make sure we are on track to saving for retirement while also having investments, money for regular expenses, and of course – travel! For this reason we like to set a travel budget before we even start browsing our never-ending bucket list of trips. If a trip is in the USA, it’s typically easier for us, but as mentioned, we’ve pretty much moved on to the rest of the world so our expenses become a lot more these days as additional money is needed to travel abroad.

Budgeting is important because nobody wants to travel somewhere and get sticker shock or have to scale down their itinerary because of unexpected high prices. The best trips stay close to the budget and only go over if there was something that came up that you just had to experience. For us, that’s usually a restaurant we didn’t come across online that a local recommended.

Michelle and I are different in how we approach travel. I go “all out” and look for luxury experiences that make us feel like we have everything within arm’s reach. She’s more budget-conscious but will never turn down a trip to a luxury resort or spa. However, even when we go the luxury route, we always strive to find the best deals, which means traveling to places in the “off season” as well as being very active in rewards and loyalty programs. Everyone has different budgets, and as a guy who likes everything from dive bar to five star with the right people, I do my best to point out trip plans for people of all budgets so nobody is left behind.

The thing is, when budgeting, you need to look long and hard at what you want to get out of the trip. If it’s a great night’s sleep, perhaps the luxury resort is where you want to spend your money. If you value experiences and attractions, perhaps scale down your stay and use an AirBnb or hostel so you can allocate your budget to the things you’ll do outside of where you stay.

For me, my bucket list always includes Michelin Star restaurants if they are around, but I’ll never turn down a cheap local meal. Truth is, I’d rather eat than visit museums with Michelle! I’m not much into artifacts and history, but she sure is!

Whether you want to blow all your money in Orlando at theme parks or spend it at a five star hotel and eat from food trucks, these are decisions you need to make before you plan your trip.

What is a Good Vacation Planning Budget?

We’ve done it all over the years. From traveling with my college friend Jess who brought a hot plate with him on a ski trip and ate Kraft Mac & Cheese, to going to Antigua and spending crazy money on everything from airfare to food. There’s something for everyone and fun to be had no matter what your budget is.

You should think about your travel budget in terms of what’s going to be most expensive. For some people who only fly first class, that may be the airfare. For others who opt for a budget airlines, it could be food or attractions at the end destination.

A daily budget is something to consider as well, but it could mean some days you cook at home and relax on a beach (basically living off the land) while other days may be spent at theme parks and nice dinners.

Your budget will of course be tailored to your financial goals. I know people who are ultra savers and won’t travel until a certain amount of money is socked away, while others value experiences NOW versus waiting for their golden years. As they say “YOLO.” (You only live once.)

Truth is, I lived in Costa Rica as an exchange student and lived on less than $10 a day (minus tuition which covered room and board) but that was well before inflation got out of control.

I’ve also done trips where I’ve looked at my hotel folio and wanted to cry! Those drinks by the beach can add up in the Caribbean!

Traveling With Groups vs. Solo Travel

how to plan a group trip

There’s a lot to be gained from traveling with groups. A family will spend less money in an AirBnb where they get groceries and cook meals at home for the most part. Solo travel can be expensive as you bear all the costs of accommodations, which is why hostels are becoming all the rage lately.

Here’s some links with more tips on traveling solo:

The fact is, knowing how to plan a trip that will stay within your budget has a lot to do with who is going on this vacation. Choose your travel buddies carefully, because you don’t want to get into a trip where you are in disagreement about everything because your budgets are not aligned. I can’t stress this enough. I’ve been with people who just tried to save money while on vacation, and this makes the trip a major stress.

If you are traveling with friends, you need to discuss the budget and lay out a rough itinerary. This way the trip can be enjoyed and you won’t have to worry about getting into arguments while you are supposed to be having the time of your life!

Also know that some destinations will greatly alter your ability to do things as a group. For example, it’s really hard to stick together at a large theme park where everyone is different ages, but a couples trip to a remote island would be a perfect experience because everyone’s agenda will most likely be aligned.

Planning Different Types of Trips

how to plan a trip

The type of trip you plan will vary by your personal interests, the season, and of course, what’s going on in the world at that time. Some people are adventure travelers while others are beach bums. We are all built different, and that’s what makes us unique.

Our recent trip to Costa Rica for our wedding was a prime example of this in action. We were married at the Springs Resort and Spa in Arenal, Costa Rica, and had about 60 guests. We had some that soaked in the swim up bars in the hot springs for 99% of their trip. We had others who were into the outdoor activities and took advantage of white water rafting, hanging bridges, a volcano tour, ATV tours, hiking, and more. They wanted to do new things and get outside of their comfort zone, which I totally respect. I usually gravitate towards the middle of this mix, as I love some R & R and adult beverages, but I’ll never turn down an excursion, as long as it’s not to a boring museum! (Sorry, wifey.)

If you are at ground zero with trip planning, you’ll want to decide things like:

Are you looking for sun, snow, or another type of climate?

Are you looking to relax, or be moving around the whole time?

Are you looking to stay in your country, or travel the world?

We often struggle when planning long trips to unknown places because we don’t love public transportation and although I love to road trip and have no problems in rental cars, we like to hit the ground running and start enjoying our time away.

You can get trip ideas online as many travel blogs, including ours, offer itinerary ideas for just about everywhere you could imagine.

Decide on the Length of Your Trip

Trip Planning Tips

After you set a budget for your trip, figure out what exactly you want to do on your trip, and finalize who will be traveling, you now need to figure out how long you will be traveling for. This may come up during conversations if you decide to travel with others, of course, but it’s crucial to figure out how much time you’ll be at your destination. Whether it’s a long weekend getaway, a Spring Break type of trip where its about a week, or a multi-week trip to travel to new areas, you’ll need to get an idea of how long of a trip you can take.

One thing I want to emphasize is that time should never be the sole reason for not visiting a new place. Of course, you’ll need enough time to travel to and from your destination and to spend some time there. However, I often hear people say they don’t want to visit certain destinations unless they have a specific number of days or weeks to spend there. While I understand this perspective, I’d like to challenge it. If you plan to have a job with limited vacation days for the foreseeable future, will there ever be an ideal time that perfectly fits your needs? Do you really want to wait until retirement to visit that destination, or risk missing out altogether? Just something to consider!

Choose a Travel Destination

planning for a trip
Santorini is on our bucket list!

Now, we’ve arrived at arguably the most exciting part of this trip planning guide: deciding where to go.

Personally, I have an endless list of cities and countries I’d love to visit. However, I’ve come to realize that this isn’t the case for most people. In fact, one of the most common questions I get asked is how I discover so many cool destinations, especially those that are off the beaten path. For instance, some people commented on our Instagram and asked what led us to Anguilla. The answer was easy, our friends had a destination wedding there and we happily accepted their invite. There’s nothing better than exploring a new destination when you are forced to go there for a wedding! We would have probably never had that one on our list, so it was a blessing to get that invite and we thoroughly enjoyed it!

How to Find New Travel Destinations

It’s not every day we’ll get an invite to an exotic location like Anguilla to celebrate a friend’s wedding! Here’s where we get our travel inspirations from for the most part.

  • Instagram – not a day goes by where I don’t see some amazing pics on this social media platform! I typically like to follow big travel accounts. When they post something really interesting, I add it to my notepad of “bucket list destinations to look into.”
  • Pinterest is also a solid place to look for travel destinations.
  • Of course, you can peruse the various sections of our website and see where our team has traveled and get detailed reports and even itineraries that will help you plan your trip. We like to answer questions and help others, which takes place quite often in our community forum.
  • Friends, family, and co-workers. When people travel, and have a good experience, they are usually on that “travel high” for many weeks after it. When people rave about a destination, we typically like to get together for dinner or drinks and let them show us all their amazing photos and hear them elaborate about their adventures.
  • YouTube is great to watch videos about various destinations. There are many creators, including ourselves, who love to edit and curate their trips in short and long videos, giving the in’s and outs about their travels, and showing it all on video.

Researching Flights in Advance of Your Trip

I find that between flight prices and routes, this is usually the factor that comes into play that decides if we can make a trip happen – or not. We live in South Florida, and navigating to the Caribbean, Central and South America, is a breeze. These are usually direct flights with daily routes. However, getting to many parts of Europe can be a challenge, as our trip to Wroclaw, Poland had us connect twice and led to some very hectic travel days.

I find that Google Flights does a great job of curating the various routes and prices when trying to research flights. From there, they give you a great list of options and you can simply click a link to lead to the airlines website to book directly with them.

Note: I know many people recommend Orbitz, Expedia, and other booking engines for flights. I avoid these at all costs!

Here’s why…..

When you book at a third party engine you usually do so in order to get a travel package. This could be air and hotel, or air plus a rental car all in one stop. However, what happens when a problem arises?

This happened to me once, as a flight was cancelled. I called the airline, which was American Airlines, and they referred me to Expedia. They refused to help me since I booked elsewhere. I called Expedia, and they have very limited options in terms of accommodating a flight change. To boot, they have to negotiate with the airlines and try to keep their profit tidy, which means you’ll experience long hold times and potentially bad travel options. This is just too much to deal with as travel is stressful enough!

Booking directly with an airline means that when there’s a problem with the flight, you have one company to call and they have to make it right. They also have locations in the airport where you can speak to a human in person and solve the issue. That’s a lot more easy to handle versus hoping to get through to a third party call center at a booking engine. I know this is an unpopular opinion and some people swear by third party booking engines for flights, but when you’ve experienced the misery of having some changes in your flights, you’ll quickly see why I book flights this way.

I also suggest you visit places in the off-season. You may find less flight options and less volume in daily flights, but you’ll get way better rates. One example I can cite is Costa Rica, which is our home away from home. We typically visit in the Costa Rican Rainy Season, which is very low in tourism and has way less people in the streets. (May – October is the best time to visit for low tourism in Costa Rica.) Yes, we’ll experience that evening rain, and we are fine with that. There are just too many people in the high season and rates skyrocket around the country for air, hotel, and everything else.

Pre-Trip Research Checklist

How to Plan a Vacation

Now that we’ve decided on some possible destinations, carefully selected who we are traveling with, have an amount of time in mind, and finalized our budget, there’s still a little more to do in the trip planning phase to make sure it goes off without any issues.

At this point, I do a few web searches (and hopefully we have helped solve some of this with our blog articles, but we know the world is huge and we haven’t covered every nook and cranny – yet) to see if there is any reason to NOT visit any of the places on our list.

Search for:

“Best time to visit xyz destination.”

This will help you find out if there are any reasons you should NOT visit said destination during your proposed dates.

“Events in xyz destination (add the month you are looking to travel.)”

This will help you determine if there is something you wouldn’t think about normally that could really change your trip. For example, we traveled one year to Nicaragua to find out there was a political rally the day of our arrival in Managua. This meant chaos in the streets and added hours to our commute to the beach.

“Holidays in xyz destination (add the month you are looking to travel.)”

Holidays will change the scope of what is open, including national parks, restaurants, and more. In Latin America, “Semana Santa” is “Easter Week” and everything shuts down and alcohol is limited.

“Road closures in xyz destination.”

Imagine arriving somewhere with an hour drive to the beach, BUT, during that time they decided to upgrade the highway and you had to deter four hours around to make it to the same destination. Five minutes of research could have saved you this headache.

Planning a Multi City Or Country Trip

Repeat the above searches for anywhere you may be traveling to during your journey. Make sure that everything is accessible, without any major events that would alter your itinerary, and make sure to the best of your knowledge any routes you would take will be open.

Booking Flights Like an Expert Traveler

flight booking tips

So you’ve done all of the above, and it’s now time to book your flights!

Let’s make sure you handle this like an expert traveler.

Again, the cheapest flight isn’t always the best way to go. You can use sites like FlightAware to check out the actual on time percentage of the flight you are looking into. I use this frequently to make sure the flight times I’m looking at get there on time, take off on time, and have a low cancellation percentage. We used this essentially bump up our arrival for our wedding an entire day because of the amount of times the flight showed up late. With so much to do and prepare for ahead of the wedding, we didn’t want to risk even a small delay and eat into our precious time for our special celebration.

Also, we like to use major airlines whenever possible, even if that means paying more. Sure, flying an off brand airline that has a huge discount could sound amazing, but often times they have only one flight per day and if that flight has an issue, your entire vacation will be kicked back a day, or more. Using a major airline like American or Delta means multiple flight options and the ability to re-route to other hubs in case there are issues with your plane. In short, it’s hedging your bet on getting there on schedule with the least amount of potential headaches. Yes, you can save money choosing lesser known airlines, but would you rather save money or have the peace of mind knowing you gave yourself the best chance to not suffer a miserable travel day or have your vacation cut short because of an issue?

A good travel planner is better than any travel agent who simply looks for solid prices that work for your travel dates. I also visit other travel websites that speak of my destination and if they have any community forum, I ask questions about getting there. People are usually happy to share their stories, whether they are good, bad, or ugly.

How to Plan a Vacation – The Itinerary!

how to create a travel itinerary

With most of the tedious nitty gritty out of the way, we get to the fun part: building an itinerary of what to do, eat, and see! To me, this is the pinnacle of planning the trip!

I’m again going to double down on my recommendation to use social media, especially Instagram, YouTube, and Pinterest, to your advantage. Use these engines to search for your destination and you’ll run into countless images, videos, and even blog posts that will help you make a list of things you should experience. Think of social media as a travel agent that you don’t have to pay! Some will even have discount codes you can use to save money, and who doesn’t like to do that?

There are also many blogs (like ours) that drill down on certain parts of the world. From there you can get first hand experiences from personalities that you may be similar to (always read their bio) and set yourself up for a memorable vacation.

Once I get a solid idea of places to see, do, and of course being a foodie – eat – I like to see if those venues have their own social media pages. For example, if someone says the lobster was good at this local seafood place in Spain, see if they have an Instagram page. If they do, you can count on them showcasing it for the world to see and determine if that’s something you are going to add to your itinerary. The same goes for national parks, which will announce any closings or weather changes as well so you can know ahead of time. And bars? Some of the best bars I’ve been to showcase their craft cocktails online and that really gets my blood pumping!

If you really want to nerd out and be organized like I do, add them to a custom list on Google Maps. This gives you a central place to see all of the things you’ve got planned in one easily accessible location. You can share with your travel buddies as well and let them know you are the alpha dog when it comes to directing the trip!

Finding Where to Stay for Your Vacation

Now that you’ve mapped out where you want to go, it’s time to find somewhere close to those venues.

If your places you wish to visit are all in a particular area, you may want to get accommodations near that area. For that, I use this booking engine, which will let you type in the general area you wish to stay and a highly curated list of options will populate.

I’m always one to explore a new area on foot, but if you want to rent a car or rely on public transportation, of course, you can always stay further away from the places on your travel itinerary. It’s worth noting that if you use Uber, do a quick Google search to see if it’s available in the area you are visiting.

For rental cars, I always suggest using this service. I cover the reasons why on this page, so I won’t get into that here, but know it’s a one stop shop when it comes to renting vehicles and getting the best prices from global brands and local agencies.

Get Travel Insurance

I don’t always get travel insurance, but for those week or more trips across the world, it’s something I don’t think twice about. Travel insurance saved my parents over one million dollars back in 2019 (I tell the story here) and you never know when the unexpected will happen.

Especially if your trip includes adventure travel, it’s something that you’ll want to get in case any issues surface during your travels. I use Safety Wing and found them to offer the best protection for health care and all other items that you’d need. No matter where you go, they’ve got you covered.

Fortunately I’ve only had to use the insurance once, but it saved me over $4,500 in Costa Rica hospital expenses, so it was WELL worth it in all my days traveling.

Consider a Travel Credit Card And Earn Free Travel

This is something most people overlook, but if you travel from time to time this can really help cut down on costs and earn you some free travel or at the least, some potential upgrades. For full disclosure I have travel credit cards with American Airlines, Delta, and Marriott Bonvoy through Chase Bank.

My Top Rated Credit Card for Hotel Stays
Marriott Bonvoy Credit Card

Why Should You Get the Bonvoy credit Card?

  • Earn up to 17X total points for every $1 spent at hotels participating in Marriott Bonvoy®
  • Earn 6X points with Marriott Bonvoy Boundless® Credit Card
  • Earn up to 10X points from Marriott Bonvoy® for being a loyalty member
  • Earn 3 points per $1 on the first $6,000 spent in combined purchases each year on gas stations, grocery stores, and dining
  • Earn 2X points per $1 spent on other travel purchases
  • Receive 15 Elite Night Credits per calendar year
  • Enjoy a Free Night Award every year after your account anniversary, valid for a one-night hotel stay at a property with a redemption level up to 35,000 points. Certain hotels have resort fees

And Much More! Points never expire. This is the card I use to earn free stays, upgrades, and status at Marriott Hotel brands.

I’d like to think I’m an expert on using travel credit cards, and I won’t get into a huge rant about them, but if you find yourself using a certain airline or brand, consider getting a credit card that earns you rewards there. For example, you get MORE points when you use an American Airlines card when booking on, and same goes for Delta. Marriott gives you 6 points for every dollar you spend at a Marriott umbrella brand when you use their credit card, plus free breakfast or bonus points depending on your status, and that comes in very handy when you spend big money on a hotel room in a luxurious area like say the Ritz in Grand Cayman. (We spent over $4,000 there last trip, and that equated to 24,000+ points which can be used for a free room at a basic Marriott. It beats the alternative to get nothing in return.)

>> Learn More About How I Use My Marriott Card

Consider getting a credit card ahead of your next trip. We discuss this topic in our forum, so feel free to ask questions there if you need help on picking a rewards card.


That’s it! My complete guide to planning a trip for beginners all the way to expert travelers. Whether you are in the planning stages for your next trip, or are simply going to use these tips to compare prices for your next great vacation, generally speaking, these tips will help you avoid tourist traps, book flights like a boss, and make sure your travel bookings are done to make your next vacation hassle free, cost efficient, and without stress. If I can ever assist you in planning a trip, simply comment here, contact us, or ask questions in our travel forum.


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Tim Schmidt is a 20+ year Entrepreneur and Digital Marketer. A Fort Lauderdale-based "Digital Nomad," he enjoys traveling as much as possible with family and friends. AllWorld is his escape to document all of his adventures, including being a hardcore "foodie." He has property in Costa Rica and visits several times each year and is happy to offer his expert advice for planning your trip.

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