5 Things I Always Do Before I Book Any Trip (to Save $$ and Stress)

5 Things I Always Do Before I Book Any Trip (to Save $$ and Stress)

You know that moment when you’re so excited to book a trip… but your brain suddenly fills with questions like: “Is this the best deal? Am I missing something? Is this going to be one of those bookings I regret?” Been there. More times than I care to admit.

Over time, I’ve built a simple pre-booking checklist that saves me from overpaying, overthinking, and (most importantly) showing up to a trip I wish I planned differently. Whether you book with me or DIY, these five steps will save you money, time, and stress.

1. Check Flight Flexibility Before Locking Anything In

Flights are often the biggest budget-buster—and the first thing I lock down. But I never book blindly. I use a mix of Google Flights, airline websites, and Hopper to see price trends and compare flexible dates. If I can shift my trip by even a day, I’ve saved $100+ per ticket (seriously). If your schedule is open, always look at Tuesday–Thursday departures or shoulder season dates first.

2. Compare Hotel Prices (the Right Way)

Those “lowest price guaranteed” pop-ups? Not always true. Before I book, I compare rates across at least three sources: the hotel’s own website, a major OTA (like Expedia), and my travel advisor portal (where I can often snag perks like free breakfast, resort credits, or upgrades for my clients). If the price is the same everywhere, booking direct or through an advisor gets you better benefits 99% of the time.

3. Factor in the Hidden Costs No One Tells You About

Here’s where trips can sneak up on you. Before I hit “confirm,” I make sure to factor in:

  • Resort or destination fees (common in the U.S. and Caribbean)
  • Transportation (airport transfers, ride shares, or rental cars)
  • Tipping (especially at all-inclusives)
  • Checked luggage fees and oversized baggage (for ski trips, etc.)

Knowing these costs ahead of time means no “surprise” charges eating into your fun money.

4. Read At Least 10 Recent Reviews (and Look for Patterns)

I don’t just look at star ratings. I dive into the most recent 10–15 reviews and scan for trends. Is everyone complaining about construction noise? Rude staff? Or are the only bad reviews from people upset about things like “the beach had sand” (yes, I’ve seen that)? Reviews tell you what you’re actually signing up for.

5. Ask Myself This One Question: “Will This Trip Feel Like a Treat?”

Even budget trips should feel good. I always ask myself if the accommodations, flights, and itinerary actually match the vibe I want. If something feels rushed, overpriced, or “meh,” I either tweak it or wait until I can make it right. No one wants to feel like they need a vacation after their vacation.

Need Help Doing All This Without Losing Hours of Your Life?

If you’re tired of comparing tabs and triple-checking rates, that’s literally what I do for clients every day. I can handle the flight tracking, hotel perks, and all those little extras so you can just show up and enjoy.

Click here to email me and I’ll build your next trip without the stress (and probably with some upgrades you didn’t know you could get).

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