Five Things I Wish Every Traveler Knew Before Booking

After planning thousands of trips over the years, I've learned that the difference between a good vacation and a great one often comes down to a handful of decisions made long before you ever reach the airport.

Some of this advice might surprise you. Some of it goes against what you'll read in generic travel articles online. But all of it comes from real experience—watching what works, what doesn't, and what I wish I could tell every client before they start planning.

So here are the five pieces of important information before travel I find myself giving over and over again. The ones that actually make a difference.

1. Book Your Flights and Hotel Separately (Usually)

I know this sounds counterintuitive. Package deals are supposed to save you money, right? And sometimes they do. But here's what I've learned: packages are convenient, not always smart.

Last month, a couple came to me wanting to book a week in Punta Cana. They'd found a package deal online—flight plus resort for $2,400 per person. Seemed reasonable. We looked at it together.

Then I priced it out separately. Same flights, same resort, same dates. $1,650 per person.

That's $1,500 saved by spending an extra fifteen minutes comparing prices.

Package deals work great when airlines and hotels have unsold inventory they want to move. But when you're traveling during peak season to a popular destination, you're often better off booking separately. You get more flexibility with flight times, better room categories, and surprisingly often, a better price.

The exception: All-inclusive resorts in the Caribbean or Mexico often have genuine package savings. The tour operators have negotiated rates that are legitimately better than booking direct. But even then, I always check both ways.

Pro tip: Book your flights first, then your accommodation. Flight schedules change less frequently than hotel availability, and you want to make sure you're not stuck with an overnight connection just because the package told you to take it.

2. Travel Insurance Isn't Optional (Even If You Think It Is)

I already wrote an entire article about this, so I won't belabour the point. But I need to say it again because it's that important.

You know what's worse than spending $300 on insurance you don't use? Losing $8,000 on a trip you can't take because someone got sick, or spending $50,000 on a medical emergency abroad that your provincial health plan doesn't fully cover.

I've seen both scenarios. Multiple times. And every single person who declined insurance and then needed it has said the same thing: "I wish I'd listened to you."

Here's my rule: if you can't afford to lose the entire cost of your trip out of pocket, you can't afford to skip insurance. Full stop.

And before you tell me your credit card or workplace insurance has you covered, please—actually read the policy. The gaps in those coverages are real, and they're bigger than you think.

3. The "Best" Travel Dates Aren't When You Think They Are

Everyone wants to travel during spring break, Christmas week, and summer holidays. Which means everyone is competing for the same flights, same hotels, and same restaurant reservations.

Want to know the secret to better travel? Go one week earlier or one week later than everyone else.

The Martins wanted to go to Italy. Their kids' spring break was the second week of March. I suggested they pull the kids out of school for the week before spring break instead.

"Won't that be frowned upon?" Mrs. Martin asked.

Maybe. But they saved $1,800 on flights, got their first-choice hotel in Rome, and Venice wasn't shoulder-to-shoulder tourists. Their kids missed a few days of seventh grade. They gained a trip they'll remember for the rest of their lives.

I'm not saying skip school every year. But if you have flexibility, even one week can completely change your experience and your budget.

Off-season travel is underrated: Everyone thinks summer is the best time to visit Europe. You know what's better? September and early October. The weather's still beautiful, kids are back in school, and prices drop significantly. Same goes for Caribbean travel in May or early November.

4. Your Departure Airport Matters More Than You Realize

Torontonians, this one's for you. I know Pearson is convenient. But sometimes flying out of Buffalo or even Hamilton saves enough money to justify the extra drive.

I had a client trying to book a family of four to Orlando. Toronto to Orlando direct: $420 per person. Buffalo to Orlando direct: $180 per person. That's a $960 difference.

Yes, you have to drive to Buffalo. Yes, you need to factor in parking or a hotel if you're flying early. But even with those costs, they saved over $700.

But here's the flip side: Sometimes convenience is worth the premium. If you're traveling with young kids, elderly parents, or you're already stressed about the trip, maybe that extra $200 per person is worth it to leave from your home airport. Only you can decide that trade-off.

What I actually do: For any trip over $3,000, I price out at least three airport options. Toronto, Hamilton, Buffalo—sometimes even Detroit or Montreal if you're in Eastern Ontario. Then you can make an informed decision about whether the savings justify the extra effort.

5. Pay Attention to Entry Requirements Before You Book

This should be obvious, but you'd be shocked how many people book a trip without checking whether they need a visa, what documents their kids need, or whether their passport expires soon enough to be a problem.

Last year, I had a client book a cruise to Bermuda. Three weeks before departure, she called me in a panic. Her passport expired in four months. "That's fine, right? It's still valid."

Nope. Many countries require your passport to be valid for at least six months beyond your travel dates. Bermuda requires six months. She had to do a rush passport renewal—$300 extra—and the stress nearly ruined the trip before it started.

Here's what to check every single time:

Passport validity: Most countries want six months. Some require three. The U.S. only requires your passport be valid for the duration of your stay, but your airline might have stricter rules. Check before you book.

Visa requirements: Canadians have it pretty good, but we still need visas for countries like China, India, Vietnam, Australia, and many others. Some can be done electronically (like the U.S. ESTA or Australian ETA), but some require applications weeks in advance.

Children's documentation: If you're traveling with kids and only one parent is going, many countries require a consent letter from the non-traveling parent. Even traveling within North America. It's a pain, but border agents take it seriously.

COVID and health requirements: As of late 2025, most countries have dropped COVID entry restrictions, but some still require proof of vaccination for certain destinations. And things can change quickly. Always check current requirements a few weeks before departure.

I keep a checklist I run through with every client during booking. It's boring and takes five minutes, but it's saved countless trips from last-minute disasters.

The Advice I Give That Nobody Wants to Hear

Here's the thing about travel advice: the best tips are rarely the fun ones.

Nobody wants to hear "book insurance." They want to hear about hidden beaches and secret restaurants. Nobody wants to check passport expiry dates. They want to daydream about their vacation.

But you know what kills travel dreams faster than anything? Preventable disasters.

The couple who lost $12,000 because they didn't have insurance and someone got sick.

The family who missed their flight because they didn't realize they needed a visa.

The travelers who paid $800 more than they needed to because they didn't shop around for airports.

I'm not trying to be a downer. I love travel. I love helping people create amazing experiences. But I've been doing this long enough to know that the best trips are the ones where you get the boring stuff right first.

What Makes a Great Trip (Beyond the Basics)

Once you've got the practical stuff sorted—flights booked, insurance purchased, documents checked—then you get to focus on the fun part.

And here's what I've learned about that: the best trips aren't about ticking off every tourist attraction. They're about having enough time to actually experience where you are.

Two weeks in Europe hitting eight cities sounds exciting. But you'll spend half your time packing, unpacking, and sitting on trains. Three cities in two weeks? Now you're actually traveling instead of just moving luggage around.

Build in buffer time. Don't land in Rome at noon and try to see the Colosseum that afternoon. You'll be jet-lagged and cranky. Land, check in, have a nice dinner, get some sleep. Start fresh the next day.

Make restaurant reservations before you leave. The best restaurants in popular destinations book up weeks or months in advance. If there's somewhere you really want to eat, reserve it when you book your trip. Then you can be spontaneous with everything else.

Don't schedule every hour. Some of my best travel memories are from afternoons where we had nothing planned and just wandered. Leave room for spontaneity.

The Real Reason I'm Telling You All This

I could write a completely generic blog post about travel tips. "Pack light! Arrive early at the airport! Bring hand sanitizer!"

But that's not helpful. You already know that stuff.

What I'm sharing here is what actually matters based on years of watching travelers succeed and struggle. The passport thing? I've seen it cause problems at least a dozen times. The package deal advice? That's from pricing thousands of trips both ways. The travel insurance lecture? That's from too many heartbreaking phone calls with clients who found out the hard way.

My job isn't just to book your trip. It's to make sure you're set up for success from the moment you decide to travel to the moment you walk back through your front door with nothing but great memories and photos.

Some of that is choosing the right resort or finding the perfect flight times. But a lot of it is making sure you avoid the preventable disasters that turn dream vacations into stressful nightmares.

What to Do Next

If you're planning a trip, start with the basics:

Check your passport expiry dates. Yes, right now. I'll wait.

Research what entry requirements exist for where you want to go.

Price out different airport options if you're flexible on departure points.

Consider whether booking flights and hotels separately might save you money.

And please, for the love of stress-free travel, factor in travel insurance from the beginning. It's not optional.

Once you've got those pieces sorted, then comes the fun part—choosing destinations, planning activities, getting excited about your trip.

That's where we come in. Because while I can give you practical advice in a blog post, the real magic happens when we sit down together and plan something perfectly suited to you. Your budget. Your travel style. Your definition of a great vacation.

Maybe that's a week at an all-inclusive in Mexico where you don't think about anything. Maybe it's a two-week adventure through Southeast Asia hitting temples and night markets. Maybe it's a cruise where you unpack once and wake up in a new port every morning.

Whatever it is, we'll make sure you've got the boring stuff handled so you can focus on the exciting stuff.

Because that's what travel should be. Exciting. Not stressful.

Ready to start planning your next adventure? Contact us and let's turn your travel dreams into real plans—with all the details handled right...the first time.