Booking Your First Trip Abroad

The first time we booked an international trip as a family, we did almost everything wrong. We booked the wrong type of accommodation for four people. We assumed our phones would just… work. We paid for tours we could have skipped. And we showed up to a hotel in Lisbon that looked nothing like the photos because we had ignored a dozen reviews warning us about exactly that.

That trip still happened. We still had an incredible time. But we left a few hundred euros on the table that we did not need to.

Since then, we have done these enough times that booking an international trip has become almost mechanical. Not boring, just efficient. These are the nine things we do every single time, and the four things we stopped doing after they burned us.

The mistakes that add $300 to a trip are almost always avoidable. They just look unavoidable until you have made them once.

The 9 Things We Always Do

1. Start on TripAdvisor, even before touching a booking site

Before we book anything; hotel, rental, tour, restaurant, we open TripAdvisor. Not to book. Just to read. The review culture on TripAdvisor is different from Google Reviews. People write actual paragraphs there. They mention the specific room with the noise problem. They warn you about the checkout process. They tell you which tour guide actually showed up on time.

We spend at least 30 minutes here before we commit to anything. It has saved us from bad hotels in three cities.

2. Book accommodation that has a kitchen

Once we were a family of four traveling internationally, hotels stopped making sense. The math is brutal: restaurant meals three times a day in a foreign city adds up faster than you think, especially with kids who have opinions about food. We use VRBO for almost every trip now. More space, a real kitchen, a living room where the kids can spread out. The cost difference over a week is usually significant and we actually eat better because we can shop at local markets.

We learned this in Barcelona, where four nights in a tiny hotel room with two kids almost ended the whole nomadic experiment.

3. Use Hotels.com when a rental is not the right call

Short layovers, city stopovers, or places where we genuinely want to be central — these are when a hotel makes sense. We use Hotels.com specifically because of the reward nights. After ten nights, you get one free. For the volume we travel, that adds up to a free hotel stay every few months. We have collected enough rewards to cover a full week in a good-quality hotel in Porto.

The key is to not split your hotel bookings across platforms. Pick one, stay consistent, and let the rewards compound.

4. Sort your data situation before you land

This one sound obvious until you land somewhere with no data, a crying toddler, and no idea where your rental is. We use Airalo for eSIMs. You buy the plan from your phone before you leave, it activates when you land, and you have data within minutes. No airport SIM kiosk, no roaming charges that show up on your bill three weeks later, no hunting for a local phone shop while carrying all your luggage.

We set everyone’s phones up the night before departure now. It is a five-minute job that has saved us from genuine chaos more than once.

5. Check the cancellation policy on everything

This became non-negotiable for us after a missed connection wiped out a non-refundable first night in a rental. We now filter for free cancellation until 48 hours before arrival on almost everything. The price difference is usually minor. The peace of mind is not.

6. Read the most recent reviews, not the average

A hotel with a 4.3 rating across 900 reviews over five years might currently have a staff problem that started eight months ago. Sort by most recent on TripAdvisor and read the last 20 reviews. The patterns reveal themselves quickly.

7. Book activities in advance for the things that actually matter

We do not pre-book everything. But the things that get sold out, popular restaurants, specific tours, timed-entry attractions we handle early using Get Your Guide. We have walked into cities in peak season where the one thing the kids were most excited about was booked for three weeks solid. Book those things. Leave everything else open.

8. Set up a fee-free bank account before your first international trip

Foreign transaction fees and ATM withdrawal charges are the most invisible expenses in travel. They happen in small amounts so you never notice them individually, but across a two-week trip they add up.

We switched to a Schwab checking account specifically because it reimburses ATM fees worldwide with no foreign transaction charges.

It is not exciting. It is just money we keep.

Most people don’t know how much they could have saved in the long run. You can check out the value you will get from switching to a Fee-Free ATM card service provider today.

9. Screenshot everything

Confirmation numbers, rental addresses, emergency contacts, airline booking references, the landlord’s phone number. All of it goes into a single Notes folder before we leave. No wifi? Does not matter. When our Lisbon rental had no name on the door and our data dropped, the offline screenshot of the host’s number was what saved us.

The 4 Things That Will Cost You

Don’t 1. Roam on your home carrier

We did this on our first trip. The bill arrived three weeks later. I won’t share the number because it still makes me feel slightly ill. Your carrier’s international roaming plan is not the same as actually having data. Get an eSIM through Airalo before you land. You will pay a fraction of what roaming costs, and it will work better.

Don’t 2. Book the cheapest option without reading why it is cheap

On TripAdvisor, the gap between a 3.8 and a 4.4 rating usually has a very specific reason. We have learned to find that reason before booking. A budget hotel that is cheap because it is genuinely great value is different from one that is cheap because the check-in staff are rude and the rooms smell like the previous decade.

Don’t 3. Assume a hotel room works for four people

A ‘family room’ at a hotel is not the same as a rental with two bedrooms, a living room, and a kitchen. After our Barcelona experience, we stopped assuming. For any trip longer than two nights with kids, we go straight to VRBO. The extra space changes the entire trip dynamic and not just for the kids.

Don’t 4. Split your hotel reward nights across platforms

We wasted two years of reward nights by booking across four different platforms depending on which had the cheapest nightly rate. The savings were marginal. The lost free nights were not. We consolidate onto our Hotels affiliations now and the loyalty math actually works in our favor.

One Last Thing

None of this is complicated once you have done it a few times. The first international trip is the most expensive because you are paying the tuition on mistakes you did not know you would make. This list exists so you can skip that tuition.

If you are also traveling with a dog which we do check out our dog travel packing checklist for what we bring on every trip with our four-legged third child.

More on how we handle data, accommodation, and money across borders in the posts coming this week. Start with the tools that work, and the rest gets easier.