How I Actually Plan My Trips (So You Don’t Have To Stress About Yours)

Let’s be honest: planning a trip is a whole emotional rollercoaster.
One second you’re picturing yourself in a flowy dress on some rooftop with a cocktail… and the next you’re 17 tabs deep, comparing hotels that all look “fine but maybe not that fine,” flight prices that clearly lost their minds, and reviews written by people who sound like they’ve never left their house. I’ve been there too many times.

That’s why I created my Plan Your Trip page: because if you’re anything like me, you want the good stuff fast. The reliable tools, the shortcuts, the “I’ve already done the homework, babe, here you go” kind of help.

And because I travel often (and plan obsessively), I’ve tested everything: apps, booking platforms, flight tools, tour sites… all of it. Some were great, some were dramatic flops. So I gathered the ones that I use for my own trips and organized them neatly for you.

Now let me show you exactly how I plan every trip, step by step.

Step 1: Pick the Dates & Destination (The Mood-Based Method)

I don’t start with “Where is cheap right now?” I start with: What kind of escape do I need? City energy? Ocean breeze? Food coma trip? A little romance? A little chaos? Once the vibe is clear, I narrow down the destination and dates. Then I move to the fun part: flights.

Step 2: The Flight Hunt

The internet is basically a jungle of “unbelievable deals,” and some of those online travel agents… let’s just say they promise more than they deliver. I’ve seen:

Prices that jump the second you click “book.”
Companies are adding mystery fees like they’re decorating a Christmas tree.
Customer service that evaporates into thin air.
And in the worst cases, full-on fraudulent platforms. Yes, cheap is cute, but losing your money definitely isn’t.

Because of that, I stick to flight search tools that show real prices, honest results, and no disappearing bookings. If a platform makes me feel like I need to pray before clicking “confirm,” it’s not for me, or for you.

Here’s how to spot sketchy OTAs:

If the price looks “too good”… it probably is.
Check their reputation and history online.
If recent reviews mention refunds taking months - nope.
If the company has no real support channels - big red flag.
Besides, if your gut says “hmm”… trust it. Expensive instincts save money.

I linked the tools I use to book my flights on my Plan Your Trip page.

And once your flights are booked, don’t forget the one thing that saves you from airport Wi-Fi misery and surprise roaming fees: GigSky. That’s how I stay connected wherever I land: reliable, fast, and no drama.

Step 3: Finding a Hotel That Actually Deserves You

I love resorts and hotels. Boutique ones, design ones, places with personality. Give me a stylish lobby, stunning room views, a comfy bed, and at least one corner that looks good in photos, and I’m happy. What am I not? An Airbnb person.

Don’t get me wrong, Airbnb has its charm for some people. Not because it’s “bad,” but because half the time you don’t actually know what you’re walking into (that was my experience). And you end up shopping for basics, cooking, cleaning, and suddenly you’re doing domestic chores on your holiday. No thanks.

And let’s talk about the navigation dance: finding the apartment, finding the key box, finding the host’s “very simple instructions” that somehow read like a treasure map. It’s too much admin for someone who just got off a flight. I travel to enjoy, not to play house. I want comfort. I want zero guesswork.

So I stick to two hotel platforms I trust; both curated, both consistent, both with options that match the way I like to travel: chic, comfortable, and stress-free. One usually wins depending on the city, but both give me solid choices without the roulette-wheel energy of private rentals.

I’ve linked only the ones actually worth your time on the Plan Your Trip page.

**Manawa** - Outdoor Adventures for Every Thrill Level! Kayaking, canyoning, skydiving, a luxury private catamaran… Manawa has 6,700 activities worldwide, promising unforgettable experiences tailored to you.

Step 4: Booking Experiences Without Chaos

You know what I refuse to do? Stand in line on vacation. I’d rather queue at immigration than queue outside the Colosseum like a tourist on punishment. That’s why, depending on the destination, I use two tours & experiences platforms; skip-the-lines, clear timings, and great rates.

Also on the Plan Your Trip page because it’s one of my must-haves.

Step 5: Prep, Packing & The Essentials

The only packing rule I live by: options. Even on vacation.
Pro Girl Tip: Build 3 outfits around one hero piece. One piece, three ways, it’s a packing game-changer!
For the essential side of things (SIM cards, car rental, airport transfers, etc.), I rely on a handful of tools that have never failed me. They’re simple, efficient, and crucially stress-reducing.

You’ll find those on the Plan Your Trip page too. I use them on every trip.

Quick Wins - Here are the shortcuts I swear by:

Book flights on weekdays - weekends are for amateurs.
Hotels: look at the map first, photos second.
Plan your “musts,” leave space for spontaneity. Overpacked itineraries lead to meltdowns, not magic.
Always book one “treat yourself” activity. Life is short, and no, lunch with a view doesn’t count as “too much.”
Carry one outfit that makes you feel unstoppable. You never know when the moment calls for it.

Planning a Trip Soon? Start Here

Book a flight and accommodations. Stay connected without roaming charges with GigSky international eSIMs, book your flights, trains, and buses in one clean sweep, and sort your wheels with DiscoverCars or QEEQ (because no one has time for rental roulette). Glide from airport to hotel with i’way or Welcome Pickups, island-hop with Ferryscanner, and claim a private pool day through Swimmy because balance matters. Skip the queues worldwide with Tiqets or Get Your Guide, and when your appetite decides to lead the way, EatWith has you tasting cities the right way.

And the gear? Reismonkey is where I grab the things that actually survive real travel, not the cute-everything-but-functional nonsense.

Packing cubes? A game-changer.
Cable organizer? Sanity-saver.
Laundry bag? Because real life happens.
Waterproof phone pouch? Content queen protection.
Luggage scale + tags? No surprises at check-in.
Backpack, travel wallet, and universal plug? Sorted.

🎁 USE MY CODE FOR 10% OFF! You’ll thank me later.

Explore them all here:
👉 Plan Your Trip

💬 P.S. Some links are affiliate, which means I earn a small commission at no extra cost to you, and all the perks still apply. It helps keep this trail blazing🙂
See you on the next trail!
With love,
Diti | My Trendy Trail 💋✈️

Planning Your Next Escape? Quick Wins - The Shortcuts I Swear By!

Quick Wins - Here are the shortcuts I swear by:

Planning a Trip Soon? Start Here

Explore them all here: 👉 Plan Your Trip

Explore them all here:
👉 Plan Your Trip