How to Plan a Trip: An Easy Travel Planning Guide
April 24, 2022
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There are few things that I love more in life than planning a trip, except actually taking said trip of course. That said, I recognize that planning a trip, especially an international one, can be extremely overwhelming. There are just so many details, especially these days with all of the new rules. You want to make sure you’re getting the best deals, seeing the best places, and fitting everything into your pre-determined schedule and budget. And then of course, you’ll need everything to go smoothly. All of these details go into the art of how to plan a trip, the perfect trip.
Over the years I’ve been fortunate enough to travel to over 70 different countries around the world. Throughout these travels I’ve become quite an expert on everything you need to know about how to plan the best trip for any budget or travel style. Trust me, there have been many mistakes over the years.
This easy travel planning guide will break down the step-by-step details on how to plan a trip. I personally love the planning process and find it very similar to completing a complicated puzzle. You need to fit all of the little pieces together until you complete the perfect full picture.
Although it may surprise you, picking where you are going to travel to is not the first step in the travel planning process. In fact, if you’re an open-minded traveler, you’ll find that picking the destination should actually come along pretty far in the process, after you’ve determined a number of other factors.
Determine your travel budget for the trip
The very first thing you should determine, and the first step in planning any trip, is how much money you have to spend. Depending on how far away your trip is, you may still need or plan to save some additional money. Or you may be in a situation where you already know how much disposable income you have to spare for this trip. Either way, the rough cost of a trip should never be a surprise. Even if you just have a rough estimate of how much you’d like to, or can afford to, spend, it will allow you to plan a perfect trip that fits that budget.
While I do occasionally splurge on some luxury travel, especially as I start to get a bit older, I am a budget traveler at heart. I am always looking for the best deals and ways to stretch my money as far as possible when traveling. What is important is to determine what your top spending priorities are, as these will be different for everyone.
For example, would you rather spend your money on a super fancy hotel or stay at a basic hotel and save your money on activities in the country? What does great food look like to you? Are you looking to dine at top Michelin star restaurants? Or does great food mean street food and local restaurants to you? All of these little details go into how to plan a trip.
What is a good travel budget?
I truly believe that you can travel on just about any budget if you are strategic. There are two different ways that you can think about your travel budget. You can break it down into buckets by how much you want to spend on each large item (transportation, food, accommodation, etc), or you can determine a daily budget. There isn’t really much of a difference, it is more about personal preference on how you like to conceptualize your budget.
I’ve taken trips where my budget was as little as $20 per day (inclusive of flights), and trips where I’ve spent a few hundred dollars a day. Typically I find that the longer that you’re planning to travel, the easier it is to spend less money day-to-day. This is because you’re typically moving around less, trying to cram less into your days, and perhaps you’re being a bit more frugal with your spending on things like dining out and therefore saving money.
Who will you travel with? Solo or with someone else?
You’ll want to figure out who you are planning to travel with. If you are planning to travel solo then you will likely have a lot more freedom to make travel decisions, but of course there will be other factors to consider as well. Of the 70+ countries I’ve visited, I’ve traveled to at least 25 of them as a solo traveler and have plenty of resources on my blog that you can check out. I personally love solo traveling and think that it is an experience that everyone should have at least once in their life.
However, this might not be your time for a solo trip. In which case, you’ll need to determine who you are taking this trip with. Is this a trip with family? A significant other? One friend or a group of friends?
Figuring out who is coming on the trip is super important because it could play a huge role in the budget we were just discussing. I have found over the years that one of the biggest stressors of traveling with others is money. I find that it is best to be super open and transparent about money and budget from the get go so that everyone can comfortably enjoy the trip.
The number of people you are traveling with will also determine the type of trip that you want to take, which we’ll get more into next. Some types of travel and travel activities are better suited for larger groups, while you may want something a bit more romantic for a couples trip.
What type of trip are you planning?
The next thing you will want to figure out is the type of trip you want to plan, what you’re craving at the moment so to speak. I’ve been told many times over the years that I don’t know how to vacation. As relaxing as it may be, a trip that requires nothing more than laying on a sandy beach is not typically what I gravitate towards. I love myself some quality beach time, but when planning a trip I usually seek out destinations that also offer outdoor adventures, usually hiking, and excellent food. The more street food the better for me! I travel to experience something different from what I can experience at home, so I look for destinations that challenge me and push me outside of my comfort zone.
So you can start narrowing down your list with options like city or countryside? Perhaps a mix of both? Beach or mountains? Domestic or international? These are just a few thought starters to get your wheels turning.
Decide the length of your trip
Okay, so you’ve figured out how much money you have to spend, the type of trip that you want to take, and have an idea of who you want to take it with. Before you can comfortably pick out a destination to visit, you need to understand how much time you have for this trip. Where you are able to travel to is going to differ greatly if you have a 3 day weekend versus 3 weeks to travel. I personally find that if you are able to take 6-7 days off of work, utilizing two full weekends, you can visit pretty much anywhere!
However, one thing I will say is that time should never be the reason to not visit a new place. Obviously you will quite literally need enough time to actually travel to and from your destination and actually spend some time there. But I hear time and again from people that they don’t want to visit specific destinations until they have x amount of days or x amount of weeks to spend there. And while I completely understand that way of thinking, I want to challenge it a bit. If you plan on working in Corporate America with limited vacation days for the next 30 or 40 years, will there realistically be a time that fits your needs. Do you really want to wait until you’re retired to visit that destination? Or pass on the opportunity of visiting at all? Just some food for thought!
Pick a travel destination
Okay, we’ve reached what is arguably the best part of this “how to plan a trip guide”: the part where you actually decide where to visit.
I am personally the type of person who has an endless list of cities and countries that I would love to visit. But over the years I’ve realized more and more that that isn’t the case for most people. In fact, one of the most common questions that I get asked is how I find out about many of the cool destinations that I visit. Especially the destinations that are a bit more off-the-beaten path so to speak. I got that question a ton when my boyfriend and I decided to spend a week in the amazing country of Georgia last year, a trip that was actually inspired by an amazing bottle of wine from my local NYC wine shop. And honestly some of my trips really do come to be just like that!
How to find new travel destinations
But it is not always a bottle of wine that sparks my need to travel to a new destination. Here are a few of the places that you can look to for travel inspiration:
- Friends and family
- Social Media (Instagram and TikTok)
- The many destination guides on my blog
Friends and family
If you have friends, family members or even coworkers who have taken a trip, that is a great way to get inspiration for your own adventures. I know I am personally so influenced by any trips that the people around me take, and am always guilty of immediately looking up flights to the destination. It’s always a great way to find new trip ideas because you know them personally and can get the inside scoop on any must-do’s or general recommendations. This is of course if you trust their travel advice!
Pinterest is the number one platform that I use for my trip planning. I usually use it more in the travel research phase, that we will dive into more below, but it is also a great platform to find inspiration. If there is one thing you learn about how to plan a trip it is that Pinterest will be your best friend. Unlike traditional social media platforms, Pinterest is really just a visual search engine. In the same way that you might use Google, you can instead use Pinterest. You can search some general travel terms and trip types to get some inspiration. This might look like “summer european destinations” or “best hikes in the US”.
We live in such a social media focused world, and I can’t complain because I am just as much a part of the “problem” with my various social platforms. But I would argue that social media has made discovering new destinations so much easier. If you’re looking for general travel destination ideas, I would recommend following travel influencers or content creators that fit your travel style. Not all travel creators are the same. Some focus on luxury travel while others are long-term budget backpackers. Some look at travel as relaxation only: beach-front properties and infinity pools, while others will provide you with all of the best adventure or outdoor destinations tips.
And of course I’ve got to plug my own blog here, although you’ve already ended up on my website so that is a start! I’ve got tons of detailed destination guides, as well as some comprehensive roundup destination lists.
Once you have an idea of where you want to visit, you’ll want to first check flight prices. This is not the flight booking step yet, but the research phase. If you’re planning a road trip, you can skip this step! Unless of course your road trip requires you to fly in to the starting point.
If possible, I always recommend visiting destinations during shoulder seasons. You may get one or two less than ideal weather days (maybe), but prices for both flights and accommodations tend to be much more reasonable.
I would recommend picking out a few destinations you are interested in visiting and comparing initial flight prices for each based on the dates you have available. If you have a number of destinations in Europe on your bucket list, for example, you may want to consider looking more broadly at all of Europe rather than a specific city.
I use Google Flights to search for my flights and you can search for all flights to Europe or to Asia, for example, to see if there are any deals. For example, a direct flight from NYC to Rome might be $800, while a direct flight from NYC to Lisbon (one of my favorite cities in the world) is only $350. And this doesn’t mean that you can’t also visit Rome. You’ll find that within Europe it is extremely cheap to travel between countries on low-cost carriers. Scott’s Cheap Flights is another amazing resource for finding amazing flight deals, especially if you’re open to new destinations and want to save money.
Another thing to consider is the cost of the destination versus the cost of the flight. Using Portugal as an example again, you might find a flight to Iceland for $350 and a flight to Portugal for $450 and be tempted to choose Iceland as the cheaper option. Now, while I’m by no means telling you not to visit Iceland because it is an amazing country, it will definitely not be the cheaper trip, even if you are saving a hundred, or even a couple of hundred dollars on the flight. When thinking about the cost of the trip it is so important to look at it holistically and not just the cost of the flight.
Do your initial research
Okay, so we have an idea of where we want to go, who we want to go with, and when and for how long this trip will take place. Now it’s time for some preliminary research. This is your time to check for any red flags so to speak. Here are a few things that we’re going to want to check during this phase:
- Best times to visit destinations, specifically if there are any rainy seasons to avoid
- Any large festivals or events that might make it more difficult or expensive to secure flights and hotels
- Any holidays that might restrict activities that you are able to partake in during your visit
- Necessary visas or country entry travel requirements
- Ongoing conflict in the country (this may seem obvious but I have found in the past that we are often very sheltered in the US from much of the conflict going on in the world)
- If you’re visiting a National Park or popular attraction, make sure it is open and entry is possible during the time period that you plan to visit
Create a skeleton itinerary
Before just jumping to book flights (unless they were such a good deal that you couldn’t resist), it is important to put together a skeleton itinerary. If you’re just traveling to one destination (and by that I mean just one city) then you are probably fine to skip this step and go ahead with booking those flights.
But if you’re planning on incorporating a number of cities and/or countries into this trip, having a skeleton itinerary is super important. For example, you’ll want to understand which airports you’re flying into, and at what times. If you’re transferring to trains or ferries, you’ll want to make sure that everything lines up so there are no surprises later in the trip planning process. This is what I mean when I say that my view on how to plan a trip is like a puzzle.
Book your flights (or other transportation)
Booking flights is seriously an artform in itself. Flight prices have fluctuated a lot over the past few years, and many of those changes are out of our control. However, I usually find that there are always ways to find a deal!
If you have flexibility to leave midweek instead of over the weekend, you can usually save quite a bit of money. I also encourage you to be open to layovers. If you’re limited on time this may not be an option, but if you have time this can be a great opportunity to add an additional destination to your itinerary. Look for long layovers that give you as much as a day or two in a secondary destination! Of course, you’ll want to make sure that there aren’t any additional visa requirements that could add on unnecessary costs!
I will likely write an entire guide to booking the best flights but there are a few things that I’ll mention here to keep top of mind. The cheapest price is not always the best or cheapest option. What I mean by that is that for example the early morning flight might be $25 cheaper than the flight in the middle of the day, but if the flight is so early that you’re required to spend $50 on a taxi because the public transportation options aren’t running yet, you won’t actually be saving any money. This also applies for smaller, less convenient airports that may not have public transportation options!
Research the best things to do, places to eat, and more (the best part of how to plan a trip)
Remember when I mentioned that Pinterest would be your best friend? This is where is comes into play. I use Pinterest for all of my trip planning and travel research. Simply use it to search for your destination and you’ll be directed to a number of blog posts written on the topic. I love using blogs for research because I find them much more informative than outdated platforms like TripAdvisor.
What I love about blogs is that you can actually see and understand who the tips are coming from. One way that I like to check the quality of a travel blog is by reading articles that they’ve written about cities that I have already visited, or even my own city. If I trust those recommendations, then I can assume that I can trust their recommendations for the new destination that I’m visiting.
Similar to compiling travel inspiration, friends/family as well as social media are also great places to look for recommendations. On both Instagram and TikTok you can look up popular hashtags for the destination, as well as look up location geotags.
I like to compile all of these recommendations and add them to a custom list on Google Maps. Not only will this allow me to have all of these recommendations in one place, but it also gives you a better sense of where everything is located. This will come in handy when you’re deciding where to stay.
Pick out where you want to stay
Remember that Google Maps list that you made? This is going to come in handy when deciding where you want to stay. If you see that most of the places you want to visit, whether that be activities or restaurants, are all in one area, that is likely a good place to look to stay. Of course, that might not always be an option due to budget or preference. But having everything mapped out will allow you to get a sense of distance and transportation options.
Personally, I usually find that it is more beneficial to stay closer to where you want to be at night. During the day it is easier to get around, there are more public transportation options, etc. At night however, it is nice to stay close to where you’ll be eating or drinking, as you may not want to walk home late at night depending on the destination, and taxi and rideshare prices might be more expensive.
Secure travel insurance
I am guilty of avoiding travel insurance over the years, but if you are planning any sort of adventure trip, I highly recommend booking travel insurance through World Nomads. This will ensure that you are covered in the event that any issues arrive during your travels. And unfortunately, issues do arise! I’ve been to hospitals in 8 different countries around the world throughout my travels.
Sign up for a Travel Credit Card
I am adding this step in here as a bonus step because obviously credit card usage is a more personal topic, and I won’t pretend to be the expert on this (yet). But if you have decent credit and use credit cards responsibly then signing up for a travel credit card is a great way to save money on travel. Not only do most cards have excellent sign on bonuses that can help pay for a large chunk of your trip, but you’ll be able to keep earning points towards more travel as you go!
Plus, most travel credit cards don’t have any additional fees when using them internationally. It’s worth also looking at your debit card and switching to one without atm fees if you plan to travel often. Some also have perks such as travel insurance or car insurance when renting cards abroad.
Need a little inspiration? Here are a few articles to some of my favorite destinations around the world:
- The Ultimate Tulum Itinerary
- San Miguel de Allende Weekend Guide
- Planning a Road Trip in the Dolomites
- 10 Days in Thailand