How to Plan Your Trip: 8 Easy Steps for Unforgettable Adventures

Before you pack your bags and head off on an awesome adventure overseas, the most critical (yet boring) step is to plan things out. I know, I know – researching places to stay, figuring out a budget, and designing an itinerary sounds about as fun as joining a company meeting on Friday at 5 PM.

But putting in that work ahead of time is what takes a trip from chaotic, stressful, and messy to smooth, affordable, and unforgettable (in a good way). Speaking from plenty of travel mishaps in our years of nomading around the globe, believe me when I say that solid trip planning pays off big time.

So, in this article, we want to walk you through exactly how we plan out our travels from start to finish in 8 key steps. We’ll share the exact process we use, what tools we can’t live without, and all the little tricks we’ve learned from our mistakes over the years. Getting these basics locked down might not be glamorous, but it lays the foundation for adventure – so let’s dive in!

Step 1: Set Your Budget

Passport, money, and camera

The first key step is setting your total budget realistically by considering how much you can spend on your upcoming trip. We like to start by building a rough itinerary based on "backpacker prices" in cheaper regions like Southeast Asia. Then, we scale up if we may have more funds available later while planning.

If you don’t have much past travel experience to guide budgeting, we recommend using cost comparison sites like Numbeo. You enter your desired destination, and it provides an estimate of the expected costs of lodging, meals, transportation, fun activities, and more. This gives a decent idea of what the average daily spend could be. We also track what money we currently have available to save using a simple free expense tracking on Google Sheets (you can make a copy of our tracker for free here). This quickly illustrates where your money goes so you can shift more towards travel savings!

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Step 2: Pick Your Destinations

Pins on paper map

Once we've set our total trip budget, the fun part comes next – picking some incredible destinations! When researching locations and comparing living costs between places worldwide, we love using YouTube or travel blogs. This tool allows you to evaluate countries and cities based on real-life experiences from other travelers who have been in that location and know exactly what to expect regarding budget range, safety, internet speeds, weather, and other factors.

We'll typically do a Google search based on keywords like "best places for digital nomads in Europe" or "top destinations for budget travelers'' to create our wishlist. We order locations from cheapest daily costs to most expensive average spends. This allows us to stretch our budget as far as possible if we plan routing wisely!

Step 3: Make Your Accommodation Arrangements

Digital noamds entering accommodation

For 1-2 week trips, we’ll browse the usual rental platforms like and Tripadvisor to find relatively affordable lodging options pretty much everywhere around the world, while for Southeast Asian destinations, we use Agoda.

But if you are a digital nomad like us and tend to travel full-time for extended periods (we are talking for months or even years), our favorite is subscription living services like Flataway. This game-changing platform allows you to pay a fixed monthly rent to pay a fixed monthly rent and live in multiple destinations worldwide. that are also fully equipped with unlimited wi-fi, laptop-friendly space, a kitchen, and a washer.

Flataway subscription living hero section
Flataway subscription living "How It Works"

They offer 2 main services: Subscription plans, which offer the ultimate flexibility to pick destinations month-by-month. With listings in more than 90+ global destinations, you can finally travel long-term without worrying about fluctuating rents from country to country. And the Travel Bundles that feature premade itineraries (or bundles) with stays ranging from 2-8 weeks per destination. You can also build your own custom bundle with a minimum of 2 weeks per place. In both cases, you’ll pay a fixed monthly rent no matter where in the world you’re, and you’ll secure all those destinations with 1 booking process.

Flataway subscription living options

Step 4: Book Flights & Transportation

Swiss airline airplance at dusk

The next step is searching for the most affordable flights using sites like Skyscanner. We look for budget airlines like Ryanair or Easyjet for trips around Europe to get the best fares. We like to use Going (Formerly Scott’s Cheap Flights) for the US, which is also great for finding airline fare deals and save money worldwide.

For overland travel, we’ll browse options like trains, buses, and rideshares. Sites like Trainline allow you to easily compare routes, times, and prices across multiple providers, while Rome2Rio and Google Maps are awesome apps when it comes to understanding the walkability of a destination, as well as learning how to reach point A to point B and whether we need to rent a car, a bike or simply use public transports.

If you're traveling to Europe, a good idea could be to look into transport passes like the Eurail pass, which offers hop-on, hop-off access across Europe’s train network and can mean big savings depending on our itinerary!

Step 5: Arrange Travel Insurance

Passport, airplane model, and stethoscope

To protect against any unforeseen incidents on the road, arranging travel insurance is always a must for us. We always compare different travel insurance providers and look at coverage details around emergency medical, trip cancellation, lost baggage, and other key benefits.

Most cards like Revolut provide some basic coverage, but we prefer supplemental insurance for extensive trips abroad for multiple weeks or longer. Our top choices are SafetyWing and Genki for their budget-friendly monthly policies, ease of extending coverage as you go, and strong digital nomad focus.

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Step 6: Check Your Passport and Visa Requirements

USA passport

Then comes the part that gives us more anxiety: gathering paperwork. To ensure we have proper documentation for entering each country, we first compile all visa rules and application specifics using super useful tools like VisaList. Rules vary drastically depending on where you’re headed - some spots easily offer visas upon arrival, while others involve lengthy applications way in advance. We determine what documents, invitation letters, onward travel bookings, or other items we might need to prepare as part of our visa application.

Of course, we also always verify that our passport meets any validity rules for the destinations we’re traveling to. Many countries require that passports be valid for at least 6 months after your planned departure date. If ours expires before then, we renew it early to sidestep any headaches. And if we are staying long-term in one location as a digital nomad, we also look into special remote worker or digital nomad visas that make residency much smoother.

By giving our paperwork plenty of lead time and staying uber-organized, we set ourselves up for smooth travels from the moment we depart. No one wants to risk missing a flight over an expired document!

Step 7: Pack Smartly and Efficiently

Digital noamd carrying backpack

Once you have all these boxes checked, it's time to pack! Checking in luggage is expensive, slow, and risks losing belongings, so we only carry on travel backpacks when traveling. To fit everything into a backpack, choosing versatile, lightweight clothing that layers, mixes & matches is essential.

Learn more about the best backpacks here:

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We follow a minimalist packing approach: laying out only essentials, then cutting that in half to reduce further. Having fewer things and washing frequently is better than overpacking! Plus it leaves room for shopping abroad. We stick to neutral colors that disguise dirt and stains between washes. Breathable tech fabrics, merino wool t-shirts, and versatile shoes like AllBirds transition seamlessly between adventures like hiking or nights out. To keep items compact, we use packing cubes, vacuum seal bags, and fold using the KonMari technique.

The exact items we bring differ based on climate, trip length, and planned activities. But our core principles of packing light, utilizing versatile gear, and rolling vs. folding clothes hold strong no matter where we jet off to!

Step 8: Research Local Customs

Bali indigenous population

But before heading somewhere totally new, we always want to brush up on local cultural norms and etiquette to avoid accidentally offending anyone! Cultural nuances range from hand gestures to tone of voice to appropriate clothing, depending on the destination.

Even regional differences that impact local norms exist within the same country. The pace of life in NYC vastly differs from small towns in Montana, for example. So, whenever possible, we seek very localized guidance tailored to the specific area we’re visiting.

To ensure we follow the right customs and cultural norms, we scour blogs and YouTube videos created by locals to find insider tips.

The key for us is striking the right balance between observing local etiquette yet still staying true to our personality and comfort levels. Educating ourselves upfront means we travel thoughtfully and respectfully.

BONUS TIP: Use Travel Bundles Instead

Flataway travel bundles hero section

If going through the full travel planning process sounds daunting or you just tend to travel for months and want to get the stress out of this process, companies like Flataway offer premade "Travel Bundles". These fixed-price packages are great because they cover accommodations, bills, and amenities so you can enjoy stress-free home-hopping between destinations. They also feature pet-friendly options and remote worker-focused amenities like reliable WiFi and laptop-friendly workstations.

Getting these travel bundles is easy, you have just to:

  1. Browse bundle itineraries with set start dates, stay lengths, built-in check-ins/outs, and more
  2. Select extras like airport transfers, cleaning service or coworking spaces
  3. Secure your spot with the first payment

Then Flataway handles the rest - all your subscription living details will be visible in your profile, so you can start preparing for an awesome adventure without the stress of always planning the next trip!

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Ready to Plan Your Next Trip?

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We'll see you there, Freaking Nomads!

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