How to Plan Your First Big Trip

Want to start traveling but don’t know where to start? Feeling overwhelmed?

That’s normal! Planning a trip doesn’t have to feel like climbing Mount Everest (unless that’s where you’re going). With a few tips, strategies, and tools you can get out of your armchair and onto your next great adventure. So let’s break it down into bite-sized steps.

Planning & Research

This will take up a large chunk of your time and for good reason. Planning should equal success and for the most part, it does. You can over plan and over research which is where many people get stuck and never actually get their trip off the ground.

Don’t Over Research. You can do all the research, blog reading, travel show watching, Pinteresting and Instagramming you want, but the reality is you can overwhelm yourself with that…real quick. All the research in the world will not prepare you for being in a new place so once you’ve landed on a location(s) throw together a Pinterest board, a list of bookmarks, or however you prefer to keep track of the best websites you’ve cultivated and get ready for step two. Check out my Pinterest page for boards for my recent and future trips. Maybe I can save you some work!
Plan. Once you’ve got a general idea. Lay out a list of “Must Sees” and “Would Like to Sees” and prioritize accordingly. Realistically, you’re not going to get to everything in a few days but this also doesn’t have to be your one and only trip to a place. I don’t like to think of it as I’ll never come back since that permanence just doesn’t sit right with me. I get my “must sees” down first and if I find time, I’ll sprinkle in the “would like to” along the way. After you’ve done this, lay out a physical calendar with what makes the most sense and ALWAYS considering time, distance, budget, etc. I like to sit down with pencil and paper at this point and map it all out.
Be Reasonable. Some museums will literally take all day, other sites you can get through in an hour. It’s good to get ideas from other travelers on how long certain sites will take. Your “must sees” should get more time devoted to them. If you spend all day at one location because you want to, then do it! That time isn’t wasted when you’re doing what you’ve come all that way to see. However, it’s important that you be reasonable in your expectations of what can be done in a day. I’m famous for over-planning and over-packing into a single day. I’ve planned to do 4 or 5 things in a day when 2 was much more realistic. Don’t fall into that trap!

Budgeting

Ahh….the (all important) buzzkill. It can be done on any budget! I planned a trip on a shoestring to Europe for two people and made it 2 weeks on $3000. Where there’s a will, there’s a plan…I mean a way! You just need to be strategic about it. At this point, you’ll have a general idea of where you want to go and what you want to do, now you just need to find a way to make it work. I always start with the two big budget suckers, (usually air) travel and hotel. After you’ve figured these out, the rest is just a game of financial Tetris. Here are my tips for getting that travel budget under control:

Start with flights and be flexible. Using tools like Hopper and Skycanner can help you track and pin down the best flight options for you. Be open to flying out of or flying into an airport that isn’t exactly what you were thinking. For example, I live in Tampa which has an airport that flies internationally however, Orlando is about 1.5 hours drive from my house and has way more flights and options daily, bringing down the overall cost of the trip. Sometimes the money in gas works out to fly out of Orlando, sometimes it doesn’t. Do the math and weigh it out. On the destination side for example, I choose to fly into Manchester instead of London and take the train to the city. This meant a few more hours travel time on the back end of my arrival but money in my pocket for a nice dinner out. Which brings me to…
Balance. Planning your trip on a budget is all about balance. 16 hour flight to Asia? You might want to spring for first class. 8 hours to Europe? Maybe you can suck it up for those 8 hours and save that money for an excursion once you get there. Want to stay in nice hotel? How much time do you plan to stay in the hotel? If you’re only there to sleep, why not save the money on something a little less opulent and spend it on some delicious local eats? It’s all about knowing your comfort level and where you draw the line. Remember, no two trips are the same so where you rest your head at the end of the day may vary from place to place and trip to trip.
Accommodations. Once you’ve got your flights nailed down, now you can fiddle around with your accommodations with the same flexible mindset as with your flights. First, decide on how you want to stay in your new city. Are Airbnbs available? Would you rather a chain type hotel? Maybe hostels are more in your wheelhouse because you want to save money and you don’t plan on being there much. These are all questions you need to ask yourself BEFORE you start searching. From there you can choose by price range and location. I have an accommodation guide all about figuring out your comfort level, budget and what you want out of your stay that helps to narrow things down if the options out there seem too overwhelming. If possible, I always try to stay near a public transit route if I’m not budgeting a rental car. It also doesn’t hurt to do a little research on the neighborhood you’re staying in. Safety is always factor but so is ambiance. My dad always likes to be in the center of the action, so he’ll book a nice hotel room in Times Square in NYC, whereas I want to be in the funky, local neighborhoods so you’ll find me in an Airbnb in Greenwich Village or on the Lower East Side.
Put it all Together. Once you’ve nailed these major expenses down, now you can figure out how to plug in all the things you want to see and do since you know where your starting and ending locations are (your accommodations) and how much time traveling will be spent to and from that location. This is where I’ll take my physical calendar, pencil and paper, and literally write and erase until I can make it all realistically fit. Just remember to leave some space for down time because the longer your trip, the more you will need.
1. Two things I’ve learned about all this:
  1. You’ll likely need a day off about every 3-4 days. So take it! Lay around, watch a movie or go out to one, go to the beach or the pool, just RELAX. If you go-go-go the entire trip, you’ll eventually burn out.
  2. You need a MINIMUM of 4 days in a city to feel like you’ve really seen it. If that makes sense. It takes me at least a day or two just to get my bearings, then another to get everything in I can. 3 days is pushing it and, in my opinion, any less and you’d better plan to just come back and do half of your list this trip to avoid burnout and disappointment.

Tools & Resources

There is a plethora of tools and resources out there to help you plan your trip. The problem is that there are just so many and not all in one spot. I’ve done the work for you and created and entire list of my fav tried and true tools and resources that I’ve used myself to plan my trips. I have pretty concise lists of different tools and resources in this post that you are more than welcome to peruse and use what you need!

Rip the Band-Aid & GO!

Okay, now you have no excuse. You can do this! In the words of FDR, the only thing you have to fear, is fear itself! And that’s just a little thing. Planning a trip yourself is completely doable and attainable! Even better, YOU get to control what you get to see and do and at what cost. Sure, a tour company can do it for you but you’ll give up your freedom and a lot of that authentic travel experience! Still need somewhere to organize your trip dreams? Download my workbook for planning out your trip!