How to Plan a Trip

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Welcome! If you found your way here, you’re probably dreaming about a trip and have no idea where to actually begin. We’ve been right there, twelve tabs deep at 11pm. So this is the page we wish we’d had, everything we do to plan a trip, from picking a destination to landing with working phone service, in the order we actually do it. Not sure where to start? Take the quiz below to find your travel type. Already know where you’re headed? Skip to Step 2.

Real Talk Before You Start Planning

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 get overwhelming fast. 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 naturally starts to fall into place. So before you even open Google Flights, let’s figure out your travel vibe.

What is Your Travel Style?

Before you open Google Flights, it helps to know what actually makes a trip feel worth it to you. Take the quiz below and we’ll match you to one of five travel types, then send you a guide built for the kind of trip you’ll love. Take it with your partner and compare. We’re a Bucket Lister married to a Foodie, and it explains a lot about our itineraries.

Are You the Bucket Lister?

Do you picture yourself snorkeling the Silfra Fissure in Iceland, riding horseback on Mt. Vesuvius, or jumping off a cliff into the Adriatic? If one big experience is the reason you book the whole trip, you’re a Bucket Lister. You build the itinerary around the thing you’ll still be talking about in ten years and let everything else fall into place around it.

Are You the Recharger?

Are you drawn to the trips where the whole point is to do nothing at all? Toes in the sand, crystal-clear water, and absolutely nothing on your calendar? You’re a Recharger, and Fiji or Turks and Caicos might be your dream haven. You travel to actually rest, so the move is to pick one place you won’t want to leave and protect your downtime like it’s a booked excursion.

Are You the Old Soul?

Are you the one reading every plaque and booking the walking tour before anything else? If you travel to understand a place rather than just photograph it, you’re an Old Soul. Greece, Peru, and Japan are calling your name, and you’re happy to sort out where to eat and sleep in the gaps between the history.

Are You the Foodie?

Is your mouth already watering thinking about your next meal? If the itinerary is really a meal plan in disguise, you’re a Foodie, and honestly, respect. Italy, Spain, India, and Paris belong near the top of your list, and you can absolutely plan a whole trip around eating.

Are You the Maximizer?

Do you want to see everything and refuse to apologize for it? If you cram as much as humanly possible into a single trip (very much our style), you’re a Maximizer. Europe was basically built for you, with short flights and fast trains between countries, so you can string together cities most people would split into three separate trips. 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

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

Flights, tours, and even your morning coffee can all add up. The good news is that 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, including planes, trains, buses, Ubers, and scooters
• Accommodations like hotels, hostels, and Airbnbs
• Tours and experiences like day trips, museum tickets, and wine tastings
• Meals and snacks, and don’t forget the coffee and gelato breaks
• Shopping and souvenirs, so build in a little fun money
• An emergency fund, because you always want 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 to 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. There’s 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:

• For short distances under 4 hours, the train almost always wins, since you arrive right in the city center with no airport transfer needed.
• For medium distances of 4 to 8 hours, compare the train against a budget airline, and factor in airport transit time, baggage fees, and luggage hassle.
• For long distances over 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 like the Pacific Coast Highway, Iceland’s Ring Road, and the Amalfi Coast
• Rural destinations like national parks, wine country, and small towns without rail access
• Multi-stop regional trips like Tuscany, the Scottish Highlands, and 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, so don’t skip it, because some rental companies won’t hand over the 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, so check your card before you accept the upcharge.
• Manual vs. automatic. In Europe, manual transmission is standard and automatics often cost significantly more, so if you can drive a stick, you’ll save real money.

4 Finalize Your Itinerary

History, culture, food, and jaw-dropping scenery 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 as 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 to 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, while 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 to 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, and 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, a solid travel rewards card with built-in trip protection
• Capital One Venture, with flexible miles you can redeem against any travel purchase

And always keep a backup form of payment, like a small amount of local currency or a second 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. It’s a special memory and a great conversation piece when guests come over.

Frequently Asked Questions