A Pre-Trip Planning Guideline

It strikes me that my methods of researching and planning for a vacation might be of interest to someone out there who struggles to figure out what to do or how to find places to visit on their own vacation. I mean, I don’t know who would find this valuable but in the interest of being helpful to anyone, I’ve compiled my tried and tested means of trip planning that has never really failed me through multiple trips both near and far. With an upcoming holiday on the horizon, it was the perfect time to sit down and organize my thoughts. It’s been a long time since we’ve had a proper vacation together so I was a little rusty… but it all came back to me once I started getting excited.

I actually really do enjoy this part of a vacation. It’s all about possibilities and anticipation of what’s to come. And ultimately, what I’m trying to do here is maximize the amount of fun and relaxation time while minimizing potentially stressful decision-making or time wasting on picking where to go next. We only have a finite amount of time to enjoy our time off, why set ourselves up for disappointment or regret? So without further ado and in no particular order – although to be fair, there is a certain logic to these methods – my pre-trip planning guide.

City Subreddits

Reddit is a love-it-or-hate-it place but for region-specific information, it can be pretty darn useful. And not just for ideas on things to do or places to visit, but really useful information on things like current events or popular scams to watch out for. Opinions can be extreme and the place can be an echo chamber, but that said, and depending on the specific community itself and how well it is moderated, it can be a good source of ideas to investigate further. Always check for a FAQ/Wiki/Related Subreddits. The really good communities will have guides for people to check out so you don’t have to be subjected to using Reddit’s terrible search function.


Duh. But do take the SERP with a grain of salt and be prepared to do more digging. It’s overloaded with keyword-laden listicles that offer little to no actual substance or independent thought (yes, I know, the irony). Just be specific in what you’re searching for and learn how to parse the valuable information from the time-wasting links.

Google Maps

I will explore and study the area around our accommodation or things we want to do like a specific museum. Caf├ęs, Brewpubs, local shops, anything really. Finding things nearby cuts down on time wasted hoofing it across town to go somewhere when there are probably plenty of great options around us. It helps me strategically plan a rough itinerary for a day. I’ll read GMB reviews, look at photos users upload, check out Street View… In retrospect, I must be a bored person. But I genuinely do like to explore this way! I like to review menus before I ever step foot in a venue so I know what to expect and what dish I absolutely must order. I mean, if a restaurant has a 4.8 rating with 1000+ reviews… it might be worth a stop in. Maybe.

My Google Maps

Did you know you can create your own personal map on Google where you can pin landmarks? It’s a great tool to use when planning a trip. I categorize everything by type and color code it to keep it all organized and less chaotic. You can even add notes for pins so you can type in why you added it, or a special dish to remember. You can invite collaborators (e.g. anyone else joining you on your trip) to add their own pins. I’ll save all my maps of course and share them with friends and family if they reach out asking for ideas as well. I’m also pretty sure you can download to view offline which would be super handy if you aren’t on a data plan and relying on free WiFi.


This can really vary in quality and quantity of relevant and interesting content, but it can be an excellent resource to really get the vibe of a place. If you find a good YouTuber, you can find a whole cache of useful content that’s also entertaining. Win, win? Depending on how recent content was uploaded, it’s also a good gauge for what to expect or look forward to. I’m also a fan of walking videos, for example, Johnny Strides. There is something about it that’s relaxing. I’ll pop one on in the background while cleaning or folding laundry and just chill out casually watching random walking videos. It’s not for everyone, but at 76k+ subscribers, you can’t argue that it doesn’t have an audience.


I use Instagram as another search tool (TikTok is slowly edging its way in there). The platform really isn’t what it used to be in my opinion, but I still default to it to suss out the vibe or ambiance of a place. Oftentimes websites aren’t always the most up-to-date or reflective of a business. They may even have the barest of information to share. So if they are active on Instagram (for example), you might be able to find their most current menu (with prices) or special events, etc. Also, everyone loves a good food picture. I’ll check hashtags if relevant as well as posts from other users tagged at that location.

Personal Recommendations

Obviously. But again, I take everything with a grain of salt and I would of course do the above steps to learn more about the thing before I spend my time and money on the thing. What might be someone else’s idea of fun could be my idea of torture. Then again, you could hit the jackpot.

One final point to make which is pretty obvious, but I use all these methods to cross reference information. A girl needs confirmation.

This makes it seem as though I am the least spontaneous person on the planet… No comment. Ah, but seriously, I just enjoy learning as much as I can about new places, food, culture, and experiences. We have a limited amount of annual leave and budget, so why leave it all up in the air? I feel like I’d be setting ourselves up for disappointment and regret. Maximize the good memories, minimize the pain. And so far, this has worked for me.

Join the ConversationLeave a reply

Your email address will not be published. Required fields are marked *