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For me, planning a trip is almost as exciting as going on it. There’s just something about that dopamine hit from building the perfect itinerary, uncovering hidden gems, and watching it all come together. Over the years, I’ve developed a system that helps me plan fun, efficient, and stress-free travel, whether it’s a weekend road trip or a two-week international adventure.
Here’s how I personally like to plan travel, step-by-step:
1. Search and Save Travel Inspo
I start where most of us do on Instagram and TikTok. I save travel videos into organized folders (by destination) for future reference. If something looks good, I’ll just save it right then and go back to narrow down later.
2. Add Everything to Google Maps
All those saved spots? I add them to a custom Google Maps list. That way I can easily check reviews, hours, fees, and other important details. It also helps me visualize where everything is to plan smarter routes and days.
3. Research Best Travel Dates
I always look into the best time to visit. Off-season travel is my favorite because there are fewer crowds and generally better prices, but I also check if anything might be closed during that time. A quieter trip may not be worth it if everything you want to see is shut down.
4. Price Out Flights
Once I have a general timeframe, I dig into flight prices. Are you traveling during a peak holiday or can you shift your dates by a day or two to save some money? A flexible mindset here can make a big difference in your budget. Mid-week travel and flights can often be cheaper than weekend trips but that’s not always feasible in your schedule. If I am using points for flights I’ll try to prioritize using them for higher cost fligths.
5. Look Into Area Logistics
A place might look walkable, but two miles on a highway without sidewalks isn’t always ideal. I research public transportation, neighborhood safety, and even restaurant availability/times. Small town restaurants especially are often closed Monday/Tuesday and that’s important to know if you’re flying in! Bonus: I also check if there’s a local event that might impact traffic or accommodations. I recently switched up our European trip when I found out I was arriving by myself on King’s Day weekend in Amsterdam and didn’t feel like navigating the huge crowds when traveling alone.
6. Use ChatGPT to Build a Draft Itinerary
I did this for our most recent Scotland trip! I’ll input my must-see list and ask ChatGPT to help me organize it into a logical route or schedule. It’s a great way to spot things I missed, but always double-check opening hours, travel times, and routes. (Learned that when I put my travel schedule into google maps and realized one of the days Chat gave was off by a couple of hours in drive time)
7. Start Booking (But Shop Around!)
Before I hit book, I always compare prices across platforms and sites: official websites, third-party travel sites, even just a Google search. A quick promo code search or cashback extension can save you more than you’d think as well.
8. Prioritize Bucket List Activities
If there’s anything you don’t want to miss – book it early. Then, plan the rest of your days around those anchor experiences using your saved Google Maps list. I always try to group stops that are close to each other… though I still catch myself overpacking the day (every. time.).
9. Iron Out the Details
Once the big pieces are booked, I look at the finer details. What time will we arrive? Do we need a dinner reservation? Does our Airbnb have parking? If we check in early can we leave our bags somewhere? The little things make a big difference.
10. Recheck Everything Before You Go
About a week before the trip, I revisit all my bookings. Prices change! I’ve rebooked rental cars or flights last-minute and saved hundreds. This final sweep gives me peace of mind, and occasionally more money for food and souvenirs.
Final Thoughts
Trip-planning doesn’t have to be overwhelming. For me, it’s sort of like a treasure hunt; collecting ideas, solving the logistics puzzles, and crafting the perfect adventure for us. I promise, the more you practice this kind of intentional planning, the more fun it becomes. And if it doesn’t? There are always travel agents for that!
If you’re looking for even more tips or want to steal some of my itineraries, make sure to follow along here or on my socials!
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