How to Plan a Trip: 10 Easy Steps To Independent Travel

Discover the art of independent travel with my comprehensive guide on how to plan a trip to any destination worldwide.

Embarking on a journey to unfamiliar destinations can often be daunting. From choosing where to stay to sifting through a sea of bookable tours and experiences– it’s clear why many opt to let travel agents handle their trip planning.

However, over the past five years of full-time travel, it’s safe to say that I’ve learned a thing or two. Below is my 10-step process that I use whenever I plan an international trip– whether it’s multiple months backpacking through Southeast Asia or week-long independent treks in the Himalayas.

In this useful guide, I’ll teach beginner travelers and backpackers the tricks and resources that I always use to research, plan, and book a DIY trip, without paying someone else to do it for you!

Olly GasparOlly Gaspar

I’m Olly, a full-time traveler for the past 5 years. I visit every destination I write about & handpick all recommendations.

The Quick Answer: My 10 Steps to Planning A Trip of a Lifetime

Admittedly, this is quite a long post. If you feel like you need a quick answer– here are the 10 steps laid out.

Remember, I expand on these with useful tips below.

Top Resources for Independent Travel

Here’s a list of essential online booking and travel resources that I use to plan and book all my trips and recommend throughout this blog post— from snagging the cheapest flights and best hotel deals to securing a local SIM card (even before I arrive).

Travel tip: Bookmark these resources so that you have them on hand when you go to plan your epic trip!

Step 0: Start With Why

I’m a big believer of Simon Sinek’s Start With Why philosophy. Before you even get into the logistics and trip planning, I recommend asking yourself why you want to travel.

Are you chasing of relaxation or an escape from your day job, or perhaps you feel the thrill of adventure missing from your life?

Travel is an experience after all– and asking yourself this fundamental question streamlines the entire trip planning process by carving out a trajectory tailored to the experiences you crave.

If you’re seeking historical depth, you might explore ancient ruins. If you want a challenge, perhaps you’ll book a trek in the Himalayas. Or if connection is your aim, choosing homestays over hotels can enrich your cultural experience.

So, before plotting points on a map, ask yourself why you’re drawn to the idea of travel. Your answer doesn’t just start your trip planning process– it becomes the driving force behind each chapter of your adventure, dictating the what, where, and how of your entire trip.

Trekking to Island PeakTrekking to Island Peak

Step 1: Pick Your Destination

With a world of options, choosing where to actually go is often the hardest part of planning a trip.

However, while some travel bloggers and travel agents recommend starting with a budget, I’m a firm believer in choosing a destination first– and then figuring out how to make it work financially.

If you’re truly dedicated to the adventure, money won’t stop you. For example, I drove around Iceland for less than $50 a day and spent weeks touring around New Zealand practically for free.

I’ll dive more into budgeting later. But for now, focus on picking a destination.

Longtail boat tour in ThailandLongtail boat tour in Thailand

Quick Tips to Help You Plan Your Destination

Here’s how I approach this pivotal stage of trip planning and what I recommend that you do to find the place you want to travel to:

  • Start with what you like: Okay, what are you yearning for? Hiking, beaches, waterfalls, culture, islands, or perhaps a mix? Plan how you picture your trip turning out and what you’ll be doing.
  • Use inspiration resources: Many travelers start with popular guidebooks & online resources like Lonely Planet, or even Instagram and YouTube for inspiration. Of course, there are plenty of great travel blogs like this one on the internet as well!
  • Watch shows & documentaries: Programs on networks like the Travel Channel or streaming services that showcase destinations in-depth are great for finding unique places to visit. I’ll admit it, I flew to Egypt after watching Graham Hancock’s Quest for a Lost Civilization.
  • Word of mouth: Talk to your friends and family and ask for recommendations. They know what you like best!
  • Unique twist: Don’t overlook podcasts dedicated to travel. They often feature interviews with locals or seasoned travelers as well as some inside stories on awesome places to visit. I have a lot of time for the Not Lost podcast for off-the-beaten-path travel.

Read guide travel guides: Shameless plug, I know. But seriously, I’ve spent the last five years documenting my non-stop adventures around the world and have visited over 50 countries across six continents. Check out my destinations page for a list of epic places I’ve visited. Otherwise, here are some location-specific resources that I’ll continue to build on.

Travel tip: Once you know where you want to go, tell your friends, family, and coworkers (and probably your boss too). This gives you a concrete plan that is easier to commit to and of course, a trip that is easier to plan.

Step 2: Decide When & How Long You Plan to Travel

Determining the duration and timing of your trip is the next critical step that can influence everything from costs to what you pack.

Here’s how I tackle this. I first establish the dates that I can travel. For digital nomads, this might be any time of the year, but for most, you’ll have a set block of dates free on your calendar.

When?

After spending a month on a small remote Thai island during the monsoon season, I know how important it is to pick the right time of year to travel to your chosen destination.

While seasons will be a huge dictator of what you do, how crowded it might be– and ultimately how much fun you have, here are some more considerations.

  • Seasonality: Research your destination’s seasons and any events that may influence your stay. High season typically means better weather but also higher prices and crowds. For this reason, visiting during shoulder season can offer an excellent balance of reasonable costs and good weather.
  • Cultural events & festivals: Look into local events, festivals, or local holidays that could be a highlight of your trip or, conversely, a time you’d prefer to avoid due to crowds and increased prices. For example I traveled around Malta during the festi season and this made my visit!
  • Flight & accommodation prices: Monitor price trends for flights and hotels using the links I provided above. Prices can fluctuate dramatically based on the time of year and this may make or break your budget.
  • Length of daylight: Consider the amount of daylight you may have at your destination based on the season. For example I cycled across Norway during summer and didn’t even see a dark night for six weeks!
Patan Durbar Square in Kathmandu, NepalPatan Durbar Square in Kathmandu, Nepal

How Long?

Great, you know where and when you’re going. You’re now deep in the trip-planning process. But wait, another consideration is how long you will be traveling for.

Here are a few things to think about:

  • Work & personal commitments: Align your travel plans with your work schedule and personal life to determine how much time you can realistically take off. I always advocate for considering remote work options to maximize travel opportunities, if possible!
  • Budget: Your budget might have a significant impact on how long you can afford to travel. But trust me, longer trips don’t necessarily mean spending more, especially if you’re willing to consider budget accommodations or off-peak travel.
  • Visa regulations: Check the visa requirements for your destination. Some countries may only grant you a short stay, while others might offer longer visas for tourists. Only rely on official government sources for this information.
  • Logistics: Boring… but yeah, you have to consider the travel time to and from your destination. If you’re spending a significant amount of time in transit, you may want to extend your trip to make the most of it.

Tip for flexible travelers: SkyScanner’s “search by whole month” feature lets you find the cheapest days to fly and can also open up some cheap layovers to extend your trip.

Step 3: Decide on a Travel Budget

Okay, you might be wondering why I decided on the order of these steps.

Wouldn’t it make more sense to start with a budget?… What if I can’t afford to travel to the places I want during the time I want to go?…

As Mike Corey puts it in the short video below, our concept of travel is broken.

Trust me, I’ve traveled around the globe working with five-star hotels and tourism boards who have put me up in some of the most luxurious resorts in the world. Yet, it’s the raw adventures from tracking chimpanzees in Uganda, to driving around Sri Lanka in a tuk-tuk with friends that have left the deepest impressions, far surpassing any luxury stay.

And while I’m grateful for it all, I want to stress that travel should be about experience– and often the best experiences are free.

So, once you know where you want to go and when you want to go, work out how much you are willing to spend to make this trip happen.

travelerwashing clothes in the shower in asiatravelerwashing clothes in the shower in asia
The early days: doing what you have to do to keep the trips rolling…

Not Sure How Much You Will Spend?

While it’s very easy to blow your travel budget, it helps a lot to plan ahead.

The biggest costs when it comes to planning and going on a trip are accommodation, flights and transport, food, and entertainment (yes, that includes booze).

The good news is that if you’re using my recommended booking sites above, you can already budget for your accommodation, flights, and even your entertainment if you book your tours in advance.

I recommend browsing your available options on these sites and then allocating a set budget for food and other entertainment for your trip.

Olly Gaspar at Milford SoundOlly Gaspar at Milford Sound

Tips to Help You Travel for Longer

Traveling longer doesn’t necessarily mean spending more; it’s about smart trip planning and being open to new experiences.

Here are tips to extend your journey without blowing your budget.

  1. Slow travel: Staying longer in one place can reduce costs significantly. I used to hop around a lot, but these days I find it much cheaper and more enjoyable to get to know a place.
  2. Volunteering: Volunteering is a great way to travel for free. Check websites like Workaway or WWOOF to connect with hosts from around the world. You’ll usually get food and board in exchange for some work.
  3. Accommodation: Do you really need to stay in an all-inclusive resort? Consider guest houses or AirBnB for a more local experience, or stay in a hostel dorm to meet other travelers. Couchsurfing is also another way to get accommodation for free!
  4. Work Remotely: If your job permits, consider bringing your laptop and working remotely. This way, you can earn while you travel.
  5. Local SIM Cards: Seriously, don’t use roaming EVER. I’ve always found it cheaper to buy a local SIM card at the airport or using the Airalo App.
  6. Pack smart: Avoid checked luggage fees by packing light and using carry-on luggage only, if possible.
  7. Focus on free activities: Take advantage of free activities like local city walking tours, public museums, and hikes.
  8. Off-Peak travel: I mentioned this before but it’s surprising just how much cheaper it is to travel during the off-peak times. Everything from flights to accommodations will usually be cheaper.
  9. Take local transport: Use local transport like buses and ferries, or even hitchhike if you’re up for it.
HITCH HIKING TO PETTIGALA ROCK SRI LANKAHITCH HIKING TO PETTIGALA ROCK SRI LANKA
Out of cash? Stick a thumb out…

Step 4: Plan an Itinerary (Or Keep it Flexible)

The next step in my trip planning process is choosing what you’d like to do during your travels. Searching for terms like “things to do in…” will help you find a wealth of free travel resources from travel blogs which is my favorite way to find new hidden gems to add to my itinerary.

These days, I usually keep things fairly flexible and only tend to book my accommodation and the must-do experiences in each destination before I arrive. Then, once I’m on the ground I like to speak to other travelers and locals for tips and advice on great places to visit and unique experiences.

Still don’t know where to start? GetYourGuide and Viator are my go-to resource for finding must-do experiences & tours in every destination.

Prebooked vs. Flexible Travel

If you’re the type of person who would like to plan an entire itinerary before you fly, then kudos to you (it’s hard, and even harder to stick to).

A firm itinerary will help you stay organized and means that you can spend lest time planning once you arrive, and just enjoying the travel.

However, I usually recommend not to be too rigid with your travel itinerary. Travel is full of surprises. By not over-scheduling, you leave room for those spontaneous moments that often become the highlight of a trip.

Maybe it’s a local festival you didn’t know about, an invitation to a family dinner, or a new trail that leads to an amazing view.

Either way, I believe that the best way to plan your travel itinerary is to note down or book the unmissable experiences, for example snorkeling on the Great Barrier Reef, or a Northern Light’s bus tour in Iceland and then leaving space open for new activities, or just to relax.

SCUBA DIVING ON THE GREAT BARRIER REEF TOUR CAIRNSSCUBA DIVING ON THE GREAT BARRIER REEF TOUR CAIRNS

Step 5: Book Flights & Transport

You know where and when you want to go and you’ve formed a rough budget and itinerary.

In my experience, the hardest part about planning a trip are the first four steps. But now that you’ve got your plan laid out now– let’s book!

Remember, you want to use SkyScanner or Google Flights.

These websites compile all of the available flight routes and offerings across the web so that you can compare the price. If you look at my screenshot below, you’ll see that I use

  • To: “Everywhere”
  • Travel period: “Flexible dates”
Skyscanner website finding cheap flightSkyscanner website finding cheap flight
Using Skycanner’s flexible travel features to find the cheapest flights

This will pull up the cheapest flights to any destination from your city, for the entire month that you seek to travel. This allows for the most flexible itineraries and you can also find some great layovers.

Tip: I sometimes also find good deals on CheapOAir, another good flight comparison website. However, lately, Skyscanner and Google Flights have been better for me. Google also has the option of filtering for airline alliance networks to leverage your loyalty or frequent flyer bonuses (I use One World).

Step 6: Book Your Accommodation

After booking flights, I usually rush in and secure some cheap hotel deals. In my experience, this process usually takes a little longer than finding flights, since there are so many hotels and booking sites to troll through.

To save time, I usually stick to Booking.com and Expedia to start with, since they have the best maps for finding a place to stay. If I’m traveling solo, I usually like to stay in a hostel that I find on Hostelworld.

Once I know which hotel or hostel I want to book, I double-check prices on Agoda and sometimes Hotels.com just to make sure I’m not missing out on any specific deals.

Screenshot of map search feature on Booking.comScreenshot of map search feature on Booking.com
Using Booking.com’s map feature to find good hotels close to main attractions.

Resources for Finding Where to Stay

I get it, how are you supposed to know where to stay in a destination before you’ve even been there? Trust me, booking a hotel far from town can really suck—suddenly, you’re spending more time commuting than exploring, missing out on spontaneous local encounters, and facing the hassle of coordinating transport late at night.

I’ve written hundreds of accommodation guides on my blog to help you avoid that (and find awesome deals and unique hotels). Below are some of my comprehensive guides to epic destinations around the world.

Otherwise, if you want to do some independent research yourself, read my tips below.

Seychelles AccommodationSeychelles Accommodation

Tips for Booking Accommodation

Here is what I look for when choosing a hotel, resort, hostel, guest house, or homestay.

  1. Location: I always prioritize location above amenities. I do this by finding all the places I want to visit in a town or city, then try to find accommodation deals close to those attractions or public transport routes to them.
  2. Reviews: I scour through reviews critically. Other traveler’s opinions are worth so much more than marketing and pretty pictures.
  3. Amenities that matter: I pinpoint my must-haves. Usually, I just look for decent Wi-Fi, a good breakfast, and a fitness center is also a nice plus. Then I use them as my filter on the booking sites I mentioned. Identify what is important to you.
  4. Check for Hidden Fees: Before booking, verify if there are additional charges for services like parking, resort fees, or Wi-Fi. It’s always better to know the full cost upfront.
  5. Book flexible rates: Life is unpredictable, and so are travel plans. Plans can change, and I prefer rates that allow for that without penalizing me. That’s why I always like to stick with sites like Booking.com over contacting a hotel directly (I’m still waiting on my Covid-era refunds from a hotel).

My advice: At the end of the day, I think people put too much emphasis on the hotel or resort. Yeah, luxury amenities are nice but travel is about the experience. Save your budget for adventures, sights, and connections—that’s what truly makes a trip!

Tree house in Bali, IndonesiaTree house in Bali, Indonesia

Step 7: Plan & Book Your Activities in Advance

Alright, this step is technically optional, but I do recommend booking some activities or experiences in advance. Especially if they are a huge bucket list item for you like a hot air balloon in Cappadocia or stepping inside the Great Pyramid.

Booking activities and tours in advance will help you secure those experiences, which is essential if traveling in the peak season. Plus, there’s nothing that will get you as excited for your trip as having that dream bucket list experience booked and locked in!

Remember, you can find great deals for your planned activities on GetYourGuide or Viator, including skip-the-line entry tickets.

If you’ve planned yourself an independent travel itinerary, then you may want to rent a car. I always use DiscoverCars to compare vehicle prices across all the dealerships in the destination I’m flying to. For other transport options, check 12Go, Bookaway, or BusBud, as well as any local transport options that you may be able to book in advance.

Girl at the Great Shinx of GizaGirl at the Great Shinx of Giza

Step 8: Purchase Travel Insurance

As a general rule of thumb, I NEVER travel without travel insurance. I’ve had my entire bag (everything I own) stolen in Barcelona and dropped my DSLR off a cliff in Queensland.

Safe to say, travel insurance has saved my skin more times than I care to admit.

These days, I use and recommend HeyMondo as they have great coverage, decent prices, excellent claims teams (essential), and a really easy to use app to manage your policy and your claims.

Alternatively, long-term travelers can also consider Safetywing, which I have been using on-and-off for the past three years.

For mountaineering and adventure insurance without altitude caps, read my guide to trekking travel insurance.

Update: HeyMondo now offers long-stay travel insurance at a really affordable rate too.

Man riding Moped on the beachMan riding Moped on the beach

Step 9: Pack Your Bags

The last step before you actually hit the road is packing your bags! Every destination is different, I recommend reading my packing guides for destinations all around the world.

No matter where you go, here are a few essentials that I recommend every traveler brings.

If you haven’t got everything you need, consider asking for a unique travel gift from your friends and family!

Backpack or Suitcase?

I lived out of a backpack for several years and love the freedom of being able to pick up your kit and hike it through a cobblestone street or along a white sand beach with ease. This is the best option if you are planning to move around a lot and explore different regions.

However, a backpack is limited in the amount of gear you can carry. After such a long time on the road, I’ve recently swapped to wheeled duffel bags, which are pretty much a backpack and suitcase hybrid, with more room for overpackers like me.

Still, a suitcase is much easier to drag through the airport. And, if you’re planning to stay in one spot on your vacation, then a suitcase is fine!

Island Peak Expedition GroupIsland Peak Expedition Group

Step 10: Last-Minute Preparation

So, with nine steps done, you’ve got yourself a pretty awesome trip planned! See, I told you it was easy.

Before you fly out for the adventure of your dreams, here is my last-minute to-do list.

  • Check travel documents: Ensure passports, visas, and IDs are valid.
  • Confirm bookings: Double-check flight times, accommodation, and activity reservations so that they line up with your planned itinerary.
  • Get an e-Sim: If your device supports it, I recommend downloading the Airalo app and getting an e-sim for your country before you arrive. That way, you’ll stay connected the whole time, making planning your trip on the go so much easier!
  • Rental cars: If you haven’t already, checking for last-minute rental car deals might secure you a good price. I use DiscoverCars.
  • Notify banks: I always notify my bank that I’m going overseas to avoid them closing my accounts.
  • Emergency info: It’s a good idea to have your emergency contacts and addresses written down and to know the emergency numbers in the country you’re visiting.
  • Travel insurance: I always travel with travel insurance. I recommend reading your PDS or policy information schedule to ensure that you’re covered for everything you need.

And there we have it– 10 easy steps on how to plan a trip independently. See, it wasn’t that hard, was it?

Wall in IndiaWall in India

My Top Tips for Planning Independent Travel

Now that you have a solid framework for planning, booking, and arranging independent travel, here are some of my top tips to make the process of actually traveling go a bit smoother.

Download the Best Travel Apps

Your phone is your best friend, travel agent, and personal trip planner. Seriosuly, can you imagine traveling without one? Here are some apps that I use all the time when on the road.

Map reading class at HMI DarjeelingMap reading class at HMI Darjeeling

Get Internet & Data Abroad

These days, hotel and hostel Wi-Fi is standard almost everywhere on Earth. I’ve even found decent Wi-Fi in a small tea house in the Himalayas!

However, as soon as you leave the hotel, you’re pretty much on your own. That’s why I’ve recommended Airalo so many times in this travel planning guide because it really is that useful.

However, the downsides are that not every device supports e-sims (yet), and sometimes it can be cheaper to buy a local, physical SIM card. There’s a guy called Tom from Travel Tom Tom who has written sim card guides to almost every country on Earth, it’s a great resource!

Travel Blogger working in the mountainsTravel Blogger working in the mountains

Learn a Few Phrases

Taking the time to learn a few key phrases in the local language has opened doors to richer interactions and experiences. It also helps to avoid those embarrassing gringo moments.

Here’s how I go about it:

  • Essential phrases: I focus on greetings, thank you, please, and help. These basics go a long way in showing respect for the culture.
  • Pronunciation practice: I use language apps to hear native pronunciation and practice until I feel confident enough to try it on my own.
  • Carry a Cheat Sheet: I keep a small list of phrases on my phone and in a notebook when I travel. I find it really helps to remember certain words or phrases when written down.
  • Local Interaction: I try out my new language skills with locals, who often appreciate the effort and are usually happy to help me improve. Although numbers in the millions got a bit hard for me in Colombia, everyone I spoke to appreciated the effort.
Olly speaking to a local in Sri LankaOlly speaking to a local in Sri Lanka

Join Travel Communities

Keen to share your stoke with the world? Before you go, look for online travel communities, either for the destination you’re about to travel to, or global ones. Facebook Groups and Hostelworld’s “who’s going” feature are great.

If you’re looking for an active community of adventure travelers, check out the We Seek Travel Facebook Community for great inspiration and a wealth of useful travel information.

We Seek Travel CommunityWe Seek Travel Community

More Useful Travel Planning Resources

And that’s a wrap for my ultimate travel planning resource. Now that you know how to plan a trip, get out there and get it done! There’s a wealth of experiences out there, don’t leave it too long.

I always keep this travel resource updated with the latest resources and advice. However, if you find any new resources that you think I should add to my list, please let me know in the comments, or shoot me an email at [email protected]!

Below is a list of more useful travel resources for your trip.