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How to Plan a Trip: The Order We Use After 23 Countries

By Mariya & Sam · November 1, 2026 · 6 min read

We’ve planned trips to 23 countries, and the early ones were a mess. On one of them, we flew to Bali, took a ferry to Gili T, and loaded every bag we owned onto a horse and carriage. The carriage pulled up to an Airbnb that hadn’t been open since before COVID.

Good trip planning comes down to a few decisions made in the right order. Below is the order we use now, from picking dates to packing, with the tools and official checklists we lean on at each step.

Start with a Budget and a Flexible Date Window

Before you choose a place, decide roughly what you can spend and which weeks you could leave. A loose window gives you room to wait for a better fare, and we have moved trips by a few days more than once because the price dropped.

Google Flights lets you track prices for a route, either on set travel dates or on any date. It emails you when the price changes significantly, so turn tracking on as soon as you have two or three places in mind.

Work Out a Rough Trip Budget

Rough numbers keep the rest of your travel planning honest. Split it into flights, places to sleep, food, and things to do, then add about 10% as a cushion for the taxi you didn’t expect.

Here’s an illustrative example for two people spending a week somewhere affordable. Round-trip flights at $600 each come to $1,200 for two. Six nights in a mid-range hotel room or vacation rental at $90 a night add $540, and food at $50 a day for both of you adds $350. Budget $300 for tours and dives on top of that. A 10% cushion of about $240 brings the week to roughly $2,630.

Check how you’ll pay before you leave, too. Some credit cards charge a foreign transaction fee on every purchase abroad, and on a two-week trip those small charges turn into a real line in your budget.

Choose the Place around What You Want to Do

A destination is easier to pick once you know what the trip is for. For us it was diving, so for about two years we went wherever the reefs were best that season, and everything else fit around the dive schedule.

Write down the one or two things from your bucket list that would make the trip worth it, like a hike you’ve wanted to do for years. Then look up when that thing is at its best, since a great place in the wrong month can feel like a different trip.

The same order works for a weekend getaway or a road trip. You’ll move through it in a few evenings instead of a few weeks, but skipping a step still costs you later.

Check Entry Rules, Safety, and Health Before You Book

Entry rules are easy to skip while you plan, and they can end a trip at the check-in desk. If you’re a U.S. citizen traveling within the United States, the visa questions disappear, though your ID still has to meet airport rules.

U.S. travelers can start with the State Department’s International Travel Checklist, which walks through five steps, beginning with your destination’s travel advisory and local requirements. Pick your country on that page for specific travel information and tips from the U.S. embassy. Look at your passport’s expiration date at the same time. Schengen visa applicants, for example, need a passport valid at least three months after they leave.

For vaccines and health notices, the CDC keeps a page for every destination. Look yours up a few weeks before you fly, so there’s time to see a doctor if you need to.

Book Flights and the First Nights, Then Stop Booking

We search Kayak’s Explore page first to see which places on our list are cheap to reach, then check Kiwi for specials on those routes. A cheap layover city can double as a bonus stop, and flying San Diego to Roatán through Miami once saved us more than $200.

Once the flight is set, book only your first few nights. Arriving with a bed sorted takes the stress out of landing, and leaving the rest open lets you stay longer in the place you love.

Read recent reviews before you book any stay. After Gili T, we only book rentals with reviews from the last few months, and we ask hosts for an internet speed test before we commit.

Build a Day-by-Day Plan with Room to Breathe

Give each day one anchor, like a dive or a dinner reservation, and group everything else by neighborhood around it. Grouping by area keeps you from crossing the same city three times.

Book the anchors that can sell out before you go. We learned that in Italy, when we tried to stumble upon dinner in Turin and every restaurant we walked into required a reservation.

Leave at least one loose afternoon every few days, because travel days run long and you’ll want time to recover or follow a tip from someone you met. Our guide on how to make a travel itinerary walks through the format we use.

Choose a Trip Planner That Fits Your Travel Style

You don’t need a fancy planning tool to plan a trip well. A Google Maps list of every place you want to see, plus one shared document for bookings, covers what a typical trip needs.

Travel apps work too, as long as you pick one and keep everything in it, since bookings go missing when plans are split across three apps. A detailed trip planner suits people who like every hour mapped out. Looser travel styles only need anchors, addresses, and confirmation numbers.

Start a Packing List the Week You Book

Packing goes faster when the list exists well ahead of the night before you leave. Start it the week you book, and add to it whenever something comes to mind, like a plug adapter for your destination or a warm layer for an overnight bus.

Save digital copies of your passport, bookings, and travel insurance somewhere you can open without a signal. Your phone can die, and a copy in your email won’t help if the Wi-Fi is down too.

Sort Out Your Phone and Money

Plan how you’ll stay connected before you land. In Italy we bought a Vodafone SIM card for about €60 with 50 GB of data. We kept the little card it came in, since the phone asked for its PIN every time it restarted.

Bring a second way to pay and keep it in a different bag from your main card. If one goes missing, the trip keeps going while you sort out the other.

Enroll in STEP and Pack Your Carry-On

Enrolling in the Smart Traveler Enrollment Program, the State Department’s free service for U.S. citizens heading abroad, is another step on its checklist, along with reviewing travel insurance.

Carry-on liquids have to fit the TSA’s rule: travel-size containers of 3.4 ounces (100 milliliters) or less, all in one quart-size bag. Anything larger than that has to go in your checked bag.

Or Buy an Itinerary Someone Already Tested

If you’d rather skip most of the research, you can buy a day-by-day itinerary from someone who took the trip. Every plan in our marketplace is checked by our team before it goes on sale, and you can ask other travelers questions in the Heist Network.