How to Plan a Trip: A Guide for Beginners


How to Plan a Trip: A Guide for Beginners

Wondering how to plan a trip, and not sure where to start? You’re not alone!

For experienced travelers, booking flights and throwing together an itinerary is second nature. But I remember the first time I planned a trip all on my own, I was kiiiiind of a nervous wreck.

Sure, I was excited as hell for my first independent travel experience. But I had ZERO clue how to efficiently create an itinerary, search for flights, find places to stay, or figure out transportation. Needless to say, I second-guessed myself at every turn.

But, not anymore! All these years later, and I’m something of a trip-planning pro (…I did have a brief stint as a travel agent back in 2016, after all!)

I receive dozens and dozens of emails and messages from soon-to-be travelers, and I thought it would helpful to create a detailed guide for anxious first timers (or even experienced travelers who happen to love checklists and helpful tidbits – I like them too).

I crammed as much knowledge and as many resources as possible into this “How to Plan a Trip” guide. I hope you’ll find it helpful, but as always, drop any questions in the comments section and I’ll do my best to answer them!

(Short on time? You can find a condensed list of my favorite travel resources here.)

1. Pick a Destination

Researching and choosing a travel destination is by far one of the most exciting parts of planning a trip.

At this point in time, the whole world is your oyster. You can go anywhere, and do anything!

Then again, the world is a pretty damn big places, so it’s good to have a strategy for narrowing down your options.

Here are some methods for picking a travel destination:

  • Seek inspiration. One of my favorite resources for finding travel inspiration is The Travel Book by Lonely Planet. It features brief overviews of EVERY SINGLE COUNTRY in the world along with some seriously stunning photos. I’ve wasted away many hours flipping through this book! I also like browsing Pinterest and Reddit for travel photos and itineraries. And of course I follow many travel bloggers on Instagram and Bloglovin‘!
  • Choose the destination that’s cheapest to fly to. Open to going anywhere in the world? Save yourself some serious money by simply booking the least expensive flight you can find! Sign up for a service like Scott’s Cheap Flights, which sends you airfare deals from your local airports. You can also use the Explore tool on Kayak to shop around for cheap flights to anywhere.
  • Build a bucket list. Sometimes when I’m browsing online and stumble across a new destination or interesting attraction, I’ll jot it down in the notes section of my iPhone. I keep a “local” bucket list (filled with all sorts of destinations near where I live in California) as well as a global bucket list. It can be easy to forget what originally caught your eye about a city or country, so having some notes handy when it comes time to book a trip can help with your decision.

Pssst – I own all 3 of these coffee table books, and they’re amazing for finding travel inspiration!


2. Decide How Long Your Trip Should Be

Four days? A week? Two weeks? A month?

There’s no right or wrong answers when it comes to the length or your trip, but typically this decision will come down to a few factors:

  1. Vacation time. How much of it do you have? How much of it do you want to spend on this trip?
  2. Travel time to the destination. In general, the further away you’re traveling, the longer your trip should be. If your destination is only a three-hour flight away, you can definitely spend just a few days there and get your money’s worth. If you’re spending 20 hours on a plane, however, you’ll likely want a full week (better yet, two) at the minimum in order for the travel time to be worth it.
  3. Time needed to enjoy the destination. Countries come in all sizes, and the time needed to “properly” explore China vs. Costa Rica (for example) would be drastically different. It’s true that you’ll likely never see everything a country has to offer, no matter how much time you have. But if you’re visiting a large destination, or one that really fascinates you on a deep level, it’s smart to budget more time.
  4. Monetary budget. Generally speaking, the longer your trip, the more you’ll spend. Which brings us to…

3. Set Your Budget

Some people may prefer to set their budget earlier in the process; for example, even before deciding on the destination or length of trip. And this probably makes sense if you’re on a very strict or limited budget.

For example, if you know that you absolutely cannot spend more than $1,000 total, then it’s smart to make that decision first, and then look for destinations that fit into your budget (either because they have a low cost of living, or because they’re cheap to fly to).

But personally, I tend to already have a dream destination in mind, and then build my budget around the airfare and average destination costs.

Street food = cheap!

For example, if I’ve picked Mexico (which is a short flight away, as well as a relatively cheap destination) I will set a much lower budget than if I had picked Germany, which costs more money to fly to, on top of being a more expensive country.

Again, if you know that you have a limited budget, it makes sense to rule out unaffordable destinations right off the bat. But if you have a bit of wiggle room, it makes sense to be flexible in your budgeting based on the location.

But how do you actually set your travel budget?

Essentially, you just figure out how much you’re able to comfortably spend, and then force your expenses to fit into that budget. Easy, right?

It can be helpful to think in terms of dollars per day; for instance, if you have $2,000 available to spend (not including flight costs) and want to travel for 10 days, you know that you can spend $200 per day on accommodations + food + activities, etc.

Having this estimate handy can help you make decisions about hotels and activities later in the planning process.

4. Start Researching Flights & Dates

Super important rule: flights should ALWAYS be the first thing you book. 


Airline prices and availability are much more volatile than hotel or activity prices and availability.

If you a book a flight, and then discover that the hotel room you liked is no longer available, there’s still a good chance you can find someplace to stay that will meet your needs and fall within your budget.

But what if you already booked your hotels, only to find that the flight you were looking at has doubled in price? Or is no longer available at all? Or is significantly cheaper the day before or after you had planned to start your trip?

You’ll also need to know your arrival and departure schedule in order to build your itinerary.

For instance, factors such as whether your flight arrives in the morning or evening may determine how much time you spend in your arrival city before moving on to the next destination.

Here are some variables to consider while researching dates and flight routes:

  • When can you comfortably take time away from work or school?
  • What season do you want to travel in? What will the weather be like in your destination at that time?
  • Do you want to travel during high season (typically the best weather, but most expensive prices) or low season (fewer tourists and lower costs, but may have poor weather or other inconveniences)?

I personally like using Kayak to search for flights, but I always book directly with the airline. Why? If something happens (like a delay, cancellation, or missed flight) third party vendors will be less equipped to help you than the actual airline.

Once you’ve locked down your dates and identified a flight you’re happy with, I still recommend creating a rough itinerary before actually booking your flights. Which brings us to…

5. Create Your Itinerary

At this stage, I like to make a list of all potential cities, sights, and activities within my destination that interest me. A Word document or the notes section on your phone is a good place to make this list. I’ve even used PowerPoint if I want to include images in my notes.

…this list is usually WAY too long.

If you have a week to explore a country, you’re not going to fit visits to 5 different cities in. You’re just not! Narrow down your list to the 2 cities that interest you the most.

If your trip is longer, scale up the number of destinations accordingly; for instance, in 2 weeks you could reasonably visit 4 (or possibly 5) cities.

Some personal rules of thumb:

  • 2 days per city at an absolute minimum
  • For major cities (like Paris), double that number
  • 3 days is my sweet spot for most mid-sized cities
  • Avoid single-night stays…even for small towns. It’s just too much of a hassle with checking in and out of hotels; no time to actually relax!

Factors to help you narrow down your list and choose which cities to visit:

  • Travel accessibility and time between cities (if one city is a 9-hour bus ride away, and another city is a 1-hour shuttle ride, I’d almost always pick the second city)
  • Things to do in each city; what interests you the most?
  • Accommodation availability in each city

And here’s something most guide books probably won’t tell you: there is no such thing as a must-see city or attraction.

Seriously! It’s all relative.

If your dream is to bicycle around the French countryside exploring small villages and tasting local wines, and the thought of walking through city streets and touring art museums sounds like hell, why would you spend any of your precious time in Paris during your week in France?

I know, it sounds like a sin to skip a city as great as Paris…but honestly, I believe it’s worse to skip those destinations that set your imagination on fire and fill you with excitement, in favor of someone else’s “must see.”

I mean…Paris IS pretty great though!

I don’t believe in skipping touristic sights just for the sake of going off the beaten path (truthfully, popular sights are usually popular for a good reason) but if they truly don’t speak to you, follow your heart.

…Sorry, that was a bit of tangent! But here’s where I’m going with that: I know it’s hard fitting everything you want to see into your itinerary. For me, it’s usually more than hard – it’s impossible!

My advice: Accept the fact that you can’t see it all, choose the places that excite you or interest you the most, and trust that you’ll have such an amazing time visiting those places, that you won’t even think about the places you had to cut.

It’s the truth, I promise.

6. Start Booking!

Once you’ve settled on an itinerary you’re happy with, it’s time to lock it all into place by finally booking your flights, accommodations, activities, and any other transportation.

Book Your Flights

Boom! Done.

This is always a super exciting moment for me, because no matter what happens next…there’s no turning back now, you’re going on your trip!

Book Your Accommodation

After securing flights, accommodation is always the next thing I book.

Where to Stay in San Miguel de Allende
My amazing Airbnb in San Miguel de Allende, Mexico!

More often than not, I end up booking a place to stay via Airbnb. I find that you can get some really amazing value from Airbnb, for the same cost or lower than what you’d find at a hotel. A lot of the homes I’ve rented have amazing views or amenities, and are usually in great locations.

(Psst – get $40 off your first Airbnb stay!)

When I’m not staying in an Airbnb, I like to search for hotel rooms on

Not only is it a useful search engine for finding available rooms, you can also view photos, read user reviews, and see ratings of features like location, cleanliness, and overall value.

(function(d, sc, u) {
var s = d.createElement(sc), p = d.getElementsByTagName(sc)[0];
s.type = ‘text/javascript’;
s.async = true;
s.src = u + ‘?v=’ + (+new Date());
})(document, ‘script’, ‘//’);

Unlike with flights (which I prefer to book direct with the airlines), I’m happy to book hotels through third party vendors like Booking. You can sometimes find better deals than what you’ll see on the hotel website, such as free breakfast or flexible booking.

That said, I always recommend shopping around to see where you can find the lowest price!

When I’m traveling on a budget, HostelWorld is my go-to source for finding dorm rooms, or even private rooms in hostels.

If you’ve never stayed in a hostel before, my advice is this: don’t knock it ’til you’ve tried it! They can be great for traveling cheaply and meeting likeminded travelers.

Whichever service I’m using to book my accommodation, these are a few things I always look for:

  • Location, location, location. No matter how stunning or unique a hotel is, it’s hard to pass up accommodation that’s perfectly located. You can save so much time and stress by picking someplace that’s walking distance to the city center, major sights, good food and nightlife, etc.
  • Character/charm. Why book a cookie cutter room when there are so many quirky hostels, boutique hotels, family-owned guesthouses, or beautifully decorated Airbnbs to choose from?
  • Views. Not a must-have, but I take ’em where I can get ’em!

Plan/Book Other Transportation

How will you travel between the various cities you’re visiting? How about any day trips or excursions?

Booking transportation may not be something you need to do in advance, but it is something you should definitely research and plan for.

  • If you’re renting a car, I highly recommend reserving in advance.
  • If you’re traveling by train, it may depend on the destination whether or not you need to book in advance. Look up train schedules to see how frequently they depart for your destination, and browse forums like Reddit or TripAdvisor to see what other travelers say about booking in advance vs. after you’ve arrived.
  • If you’re traveling by bus, you most likely don’t need to book before you arrive…but again, it doesn’t hurt to double check.

Plan/Book Activities

This part is always a lot of fun!

Much like you did while selecting which cities to visit, I recommend compiling a big master list of all the possible activities and sights you’re interested in: walking tours, day trips, museums, architectural or historic sites, food tours, bar crawls, hikes, snorkeling, etc.

Tulum Travel Guide
Swimming in a cenote…definitely a worthwhile activity!

Here’s where I like to search for things to do and see while traveling:

  • Travel blogs (like this one 😉 )
  • Pinterest
  • TripAdvisor
  • Rough Guides (I love their “Things Not to Miss” sections)
  • Lonely Planet
  • WikiTravel
  • Reddit

Once you have a good idea of your possible options, go back to your list and narrow down your choices to your personal “must do’s.” When deciding which activities to cut, consider factors like length of time, cost, location, and – most importantly – how much each attraction or activity interests you.

Here’s another tip: you don’t need a minute-by-minute itinerary for every single day of your trip.

Everyone has different travel styles; some prefer to leave their plans wide open and make decisions on the fly, while others like to plan and pre-book as much as possible.

Either way, I recommend leaving some amount of wiggle room in your daily itineraries.

My personal preference is to 1) make a list of all the activities, attractions, and restaurants I definitely want to try, and then 2) loosely “assign” them to various days. This tactic allows me to ensure that I can fit everything I want into my schedule, while still keeping it flexible.

Remember: travel should be fun! Don’t force yourself into anything just because it was originally on your itinerary; if you’re not feeling it anymore once you’re in the destination, or you think you’d rather experience it on another day, it’s no biggie!

7. Make a Detailed Arrival Plan

Arriving for the first time in a foreign country always leaves me with butterflies in my stomach…and not just the good kind of butterflies.

What if I get lost? What if I get scammed? What if, what if…

These are all perfectly normal thoughts, but making a detailed arrival plan can help alleviate some of these anxieties.

Plan for factors such as:

  • What’s the best way to get to your hotel/hostel/Airbnb? How much should it cost? How should you deal with taxi drivers who try to overcharge you? (Tip: refuse to accept a ride unless they turn the meter on)
  • Where/how will you acquire the local currency? (An airport ATM is usually a good option)

I also like to screenshot the name and address of my hotel (in the local language if possible) as well as my booking confirmations. That way if there’s an issue with connecting to WiFi, I still have everything I need to get checked into my room, which is the most important thing on Day One.

8. Plan for These Not-Very-Fun-But-Super-Important Steps

Visas – Do you need a visa to visit your destination? For Americans visiting most countries, the answer will usually be no. But it’s always smart to double check visa requirements, as well as passport validity requirements (note: most countries will require your passport to be valid for at least six months after your return date).

Vaccines – On the CDC website, there is a section where travelers can input their destination and find recommended vaccinations, as well as health risks.

Travel Insurance – You should never travel without proper travel insurance! We would all like to assume the worst will never happen to us while traveling abroad…but the truth is, none of us can plan for these things.

If you’re seriously injured or become sick abroad, having insurance can make a world of difference to ensuring you get the care you need. Especially when it comes to major illnesses and emergencies! World Nomads is a favorite among experienced travelers; you can pop your travel details into the tool below to see a pricing estimate:


Tell Your Credit Card Companies Your Travel Plans – Typically, if your bank sees a sudden influx of charges on your credit card coming from a foreign country, what are they going to do…? Flag the charges as potentially fraudulent and freeze your card, perhaps?

This would be considered great service most of the time, but could become a nightmare situation for someone traveling abroad. ALWAYS let your bank know about your travel plans; almost all banks allow you to input this information online nowadays. If not, just give them a call.

9. Have the Time of Your Life!

Planning a trip definitely takes work, but it’s one of those things that gets easier and far less stress-inducing the more you do it. And hey, the effort definitely pays off – you’re going to have a blast!

Enjoy your trip – eat all the food, see all the sights, soak in all the culture, and take all the photos. Happy travels!

Discovering Gorgeous Guanajuato

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Travel Planning Resources

Are you in the process of planning a trip to somewhere amazing? What questions do you still have about how to plan a trip? I can do my best to answer them in the comments!

Note: This post contains several affiliate links. If you make a purchase using one of these links, I will earn a small commission at no additional cost to you. My affiliate income helps offset the cost of running this blog, and allows me to keep this site free of ads and sponsored posts. So, thank you!! 

The post How to Plan a Trip: A Guide for Beginners appeared first on The Wandering Blonde.


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