How to Plan a Trip

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We’re just going to come out and say it, planning a trip can be hard.

There are so many moving parts — between picking the right destination, figuring out accommodations, transportation, staying on budget, and trying to cram everything into one perfect itinerary, it can be super overwhelming. We totally get it, because we’ve been there. That’s why we put together this step-by-step guide on how to plan a trip without losing your mind.

So if you’re staring at your computer or scrolling your phone wondering “Where do I even start?”, you’re in the right place. As your Passport Partners, we’ll walk you through every step.

1 Choose a Destination

In our experience, when you match your travel personality with the right kind of experience, everything else just sort of naturally starts to fall into place. So before you even open Google Flights, let’s figure out your travel vibe.

What Kind of Traveler Are You?

This quick check-in can help you figure out your style — and point you toward the right destination.

Are You the Adventurer?

Do you see yourself snorkeling the Silfra Fissure in Iceland, horseback riding on Mt. Vesuvius in Italy, or taking a paella class in Spain? If activities drive your destination selection, you’re an adventurer.

You’re not afraid to challenge yourself and step outside your comfort zone. Adventurers thrive on adrenaline-pumping activities and unique experiences that turn into the kinds of stories you tell for years.

Are You the Relaxer?

Do you find yourself drawn to vacations where you can unwind and recharge in a calm, scenic setting? Toes in the sand, crystal-clear water, and absolutely nothing on your calendar? You’re a relaxer, and Fiji or Turks and Caicos might be your dream haven.

Are You the Culture Seeker?

Are you a history buff or sightseer who wants to immerse yourself in local culture? If learning about other ways of life is what drives your trips, destinations like Greece, Peru, or Japan might be calling your name.

Are You the Foodie?

Is your mouth already watering thinking about your next meal? If food is the highlight of every trip, you can absolutely plan a vacation around eating. Italy, India, Spain, or Paris should all be near the top of your list.

Are You the Energizer Bunny?

If you’re the kind of traveler who wants to cram as much as humanly possible into one trip (This is very much our style) you’ll love Europe. Built for fast travel thanks to convenient trains and short flights between countries, this kind of travel is best when you have multiple weeks to explore.

Already Know Where You’re Headed?

Gold stars for you! Jump ahead to Step 2. But if you’re still figuring out the destination, that’s okay too. Your perfect trip begins with knowing what kind of traveler you are.

2 Set a Travel Budget

Creating a Budget

We have to be honest: budgeting is our least favorite part of how to plan a trip, but it’s arguably the most important.

Flights, tours, and even your morning coffee can all add up. The good news? A little research and prep on the front end can help you stretch your money further and enjoy your trip without the stress of unexpected expenses.

Here’s how to build a travel budget that works and stick to it without killing your vibe.

Knowing When to Travel

The time of year (peak season vs. shoulder season vs. off-season) directly impacts both the cost of your trip and the weather you’ll experience.

For example: do you want to visit the Amalfi Coast without spending a fortune? Try going in September or October. You’ll still get the stunning views, world-class food, and warm-ish weather without the sky-high prices of July and August.

Estimate Costs and Save Ahead of Time

Break your potential expenses down by category:

• Flights and local transportation — planes, trains, buses, Ubers, scooters, you name it
• Accommodations — hotels, hostels, Airbnbs, etc.
• Tours and experiences — day trips, museum tickets, wine tastings
• Meals and snacks — don’t forget coffee and gelato breaks
• Shopping and souvenirs — build in a little fun money
• Emergency fund — always have a buffer

Set aside money specifically for your trip, even if it’s just a little each paycheck. Open a dedicated travel savings account or use a money-saving app to build that fund over time.

Trust us, future you will thank you when it’s time to splurge on that bucket list meal or once-in-a-lifetime activity.

Don’t Forget Exchange Rates

If you’re traveling internationally, currency exchange rates can impact your budget. Rates fluctuate, so it’s smart to add a 5–10% buffer to cover unexpected shifts.

Plan for the “Just in Case” Stuff

We hope nothing goes wrong, but stuff happens. Flights get delayed, bags get lost, and occasionally someone eats the wrong street food. Set aside a little money for unexpected expenses like:

• Last-minute hotel bookings
• Medical visits or prescriptions
• Emergency transportation

You don’t need to obsess over every worst-case scenario, but having a backup plan makes you a savvy traveler.

Pick Your Non-Negotiables

When we travel, each of us picks one non-negotiable activity we want to do and we plan the rest of the trip around those. If you’re having trouble narrowing tours and attractions down, try a spreadsheet. Identify what fits into your budget and what makes the most sense in your itinerary. Just make sure you leave free days to explore. (We learned that one the hard way.)

Budgeting shouldn’t be painful. The more prepared you are, the more you’ll be able to actually enjoy your trip. Think of it as investing in peace of mind and future unforgettable moments.

3 Research and Book Transportation

You’ve chosen your destination and set your budget. Now it’s time to lock in your transportation and make this trip real. Whether you’re flying halfway across the globe, hopping on a scenic train, or planning an epic road trip, booking your transit early can help you save money and avoid last-minute stress.

There are usually three transportation decisions to make for any trip: how you’ll get to your destination (usually flights), how you’ll move between cities or regions if you’re doing more than one stop (often trains, buses, or short flights), and whether you need a rental car for any leg of the trip. Let’s break each one down.

Booking Flights

If you’re flying, having flexible travel dates (or even nearby airports) can help you score better deals. Start your search on flight comparison tools like:

• Skyscanner
• Google Flights
• Booking.com
• Going (formerly Scott’s Cheap Flights)

These tools let you compare multiple airlines at once, see flexible date options, and get a feel for pricing trends.

A few more pro tips worth knowing:

• Double-check baggage policies especially for budget airlines like Ryanair (speaking from experience).
• Book directly when possible to simplify cancellations or changes.
• Use a travel rewards credit card to earn points or miles for future trips. (More on those in Step 5.)

For more on finding cheap flights, read our full guide: 5 Smart Ways to Save Big on Travel.

Booking Trains, Buses, and Ground Transit

If you’re traveling within Europe, Asia, or any region with strong rail networks, trains often beat flights. They’re faster city-center to city-center, you skip airport security, and there are no baggage fees. We’ve taken trains from Amsterdam to Brussels, London to Paris, Pittsburgh to New York City, and through the Italian countryside, and we’d choose rail over a budget flight nine times out of ten.

For Europe specifically, here’s how to think about ground transportation:

• Short distances (under 4 hours) — Train almost always wins. You arrive in the city center, no airport transfer needed.
• Medium distances (4 to 8 hours) — Compare train vs. budget airline. Factor in airport transit time, baggage fees, and luggage hassle.
• Long distances (8+ hours) or remote regions — Flights usually make more sense unless you specifically want a scenic rail journey.

The booking site we recommend for European ground transport is Omio. It lets you search trains, buses, and short-haul flights all in one place across multiple countries, including operators that don’t show up on individual rail sites.

If you’re traveling in the US, Amtrak covers the East Coast well but is limited elsewhere. For longer US trips between cities, Greyhound or FlixBus are budget-friendly options worth pricing against flights.

Renting a Car

A rental car isn’t always necessary and in major cities, it’s usually a liability (parking is expensive, traffic is brutal, and most things are walkable or transit-accessible). But there are trips where a rental car genuinely transforms what’s possible:

• Road trips and scenic drives — Pacific Coast Highway, Iceland’s Ring Road, the Amalfi Coast
• Rural destinations — National parks, wine country, small towns without rail access
• Multi-stop regional trips — Tuscany, the Scottish Highlands, the American Southwest

A few things to know before you book:

• International Driving Permit (IDP) — Many countries require this in addition to your home license. It’s a $20 add-on through AAA in the US and takes about 15 minutes to get. Don’t skip this; some rental companies won’t hand over keys without one.
• Insurance — Rental car insurance is usually overpriced at the counter. Many travel rewards credit cards (including the Chase Sapphire Preferred and Capital One Venture mentioned in Step 5) include rental car coverage as a built-in benefit. Check your card’s coverage before you accept the upcharge.
• Manual vs. automatic — In Europe, manual transmission is standard and automatics often cost significantly more. If you can drive a manual, you’ll save real money.

4 Finalize Your Itinerary

History, culture, food, jaw-dropping scenery — these are just a few of the reasons we travel. But before you click “book” on your accommodations, take a moment to map out your must-see attractions and activities. This one step can make or break your travel flow.

The location of your stay should be influenced by what you plan to do. Booking accommodations in the heart of the action might save you hours of transit each day not to mention cab fare.

Start With Your Non-Negotiables

What are the things you absolutely cannot leave without doing? List them out your “non-negotiables.”

Once you have your must-do list, it’s time to book the experiences. We use both Viator and GetYourGuide depending on the destination — they often have overlapping inventory but slightly different pricing, so it’s worth checking both.

Prefer GetYourGuide? Their inventory of small-group experiences and skip-the-line tickets is especially strong in Europe.

Choose Where to Stay Based on What You’ll Do

Once your activities are picked, look for accommodations that cut down commute time and keep you close to the action. For example:

• Visiting lots of museums? Stay in the historic district.
• Chasing the great outdoors? Look for cabin options.
• Doing early morning tours? Stay within walking distance of departure points.

This keeps your days smoother and gives you more time exploring instead of stuck in traffic or changing train lines.

Where to Book Accommodations

Once you’ve narrowed down the area you want to stay in, it’s time to actually book. We use Booking.com for most hotel and apartment stays — they have the widest inventory, free cancellation on the majority of listings, and a Genius loyalty program that gets you 10–15% off after a few stays. For private rentals or longer stays (think a week or more), Airbnb is still our go-to. For budget travel, Hostelworld has the best filters for hostels with private rooms (which are often cheaper than budget hotels and a good middle ground for couples).

Plan for Local Transportation

Determine how you’ll get around. Depending on your destination, you might use:

• Public transit (metro, buses, trams)
• Rideshare like Uber, Lyft, or FreeNow
• Taxis or private drivers
• Bikes or scooters in urban areas
• Rental cars (best for rural or off-the-beaten-path trips)

Look up whether you’ll need a transit card, ride app, or parking options, and make a rough plan.

Build (But Don’t Overbuild) Your Daily Plan

Create a Google Doc, Google Sheet, or note in your phone with each day’s plans. Include:

• Your must-see activities
• Estimated time needed for each attraction
• Travel time between activities
• Breaks for food and rest

5 Pre-Departure Preparations

You’ve done the fun part, now it’s time to make sure everything behind the scenes is squared away so your trip can run smoothly from takeoff to touchdown. These final steps will save you headaches later and help you travel with confidence.

Check Your Passport, Visa Requirements, and Digital Entry

First things first: is your passport valid? Many countries require it to be valid for at least six months beyond your return date, so double-check yours well in advance.

If you’re traveling to a country that requires a visa, research the process early. Some are quick online applications; others take weeks or even require an embassy visit. Don’t let paperwork delay your dream trip.

Set Up International Data Before You Go

Nothing kills a smooth arrival like landing in a foreign country with no internet, no maps, and no way to call your Airbnb host. You have three options for staying connected abroad, and the best one has changed a lot in the last few years.

1. Use your existing carrier’s international plan. Verizon, T-Mobile, and AT&T all offer international day passes ($10–15/day) or month-long packages. T-Mobile’s higher-tier plans include free international data in 200+ countries (slow but workable). Easy, but expensive on longer trips.
2. Buy a physical SIM card at the airport. Cheap, but you have to swap your SIM, deal with a foreign phone number, and find the right kiosk on arrival when you’re jet-lagged. We don’t recommend this anymore.
3. eSIM (what we use now). An eSIM is a digital SIM you download to your phone before you leave. No physical card swap, no airport kiosks, no carrier roaming fees. You buy a data plan for your destination, install it through the app, and switch it on when you land.

We use Airalo for almost every international trip now. You can buy a country-specific plan (like 5GB in Spain for around $11) or a regional plan (Europe-wide on one plan), download it before you fly, and have data the second your plane touches the ground.

Do You Need Travel Insurance?

You’ve invested time, money, and excitement into this trip, whether you insure it is up to you. Travel insurance can cover canceled or delayed flights, lost baggage, medical emergencies abroad, and trip interruptions.

Our honest take: While travel insurance is meant to bring peace of mind, we don’t typically buy it. We’ve not had much success in recouping costs through insurance claims. Instead, we travel smarter by booking with companies that build flexibility in upfront:

• Tour platforms like Viator and GetYourGuide offer free cancellation and pay-later options
• Airbnb offers strict and flexible cancellation policies depending on the host
• Airlines like United and Southwest have flexible booking policies built in
• A travel rewards credit card (like the ones below) often includes built-in trip protection

If you’re booking expensive non-refundable items (cruises, multi-stop international flights, big tour packages), insurance might be worth it. For most flexible bookings, you can travel uninsured if you book smart.

Take Health Precautions

Make sure you’re up to date on routine vaccines and check if your destination requires specific shots (like Yellow Fever or Typhoid). Consult your doctor or visit a travel health clinic for personalized advice.

Pack any prescription medications you’ll need, plus a mini first-aid kit just in case.

Alert Your Bank and Plan for Payments

Before you leave, notify your bank and credit card companies about your travel dates and destinations to avoid fraud alerts or frozen cards abroad. Not all banks require this, but better safe than sorry.

You’ll also want to bring a credit card with no foreign transaction fees. Great options include:

• Chase Sapphire Preferred — solid travel rewards card with built-in trip protection
• Capital One Venture — flexible miles you can redeem against any travel purchase

And always keep a backup form of payment — a small amount of local currency or another card — just in case.

Pack Smart (and Light!)

Make a packing list and stick to the essentials:

• Comfortable clothes and shoes
• Toiletries and meds
• Chargers and travel adapters
• Copies of important documents (passport, visas, bookings)

Leave some room for souvenirs (because we know you’ll find something you can’t resist).

Souvenir idea: If you’re looking for a small, affordable souvenir, grab a flag from each destination. Every time we travel somewhere new, we grab one and add it to a vase in our kitchen. Special memory + great conversation piece when guests come over.

Frequently Asked Questions

Ready to Start Planning?

Now that you know how to plan a trip from start to finish, the only thing left is to pick a date and start booking. Don’t let the logistics scare you off. Try breaking it into the five steps above, take it one piece at a time, and you’ll be on your way.

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• Travel Tips FAQ: Common Travel Questions Answered
• 6 Ways to Travel as a Couple Without Losing Your Mind
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• 5-Day Paris Itinerary and Guide