Planning For A Trip

It might be the type-A in me, but planning for a trip is always one of my favorite parts about taking trips. I love heading off on a trip absolutely relaxed because I’ve planned out the entire trip to a T. If you’re anything like me, then hey, high five! If you’re not, keep reading to see my plan of action for making my vacations as seamless as possible.

First things first, I always start by planning how I’m going to get there. The only real debate here for me is car vs plane. Once I’ve figured that out, the next thing I do is find the best route or deal. Finding the best route is usually as easy as getting directions via Google Maps, but if I have the time, I try to find the prettiest route to take. It is my vacation after all. If I’m flying and my dates are flexible, I always try to use a site that offers suggestions for cheaper travel days, like Google Flights. It’ll compare flight prices from a ton of airlines so that I get the best deal possible. (Pro tip: clear your history and cookies before booking! It’s likely that whatever host site you’re using is tracking how many times you come to the site and is raising the prices each time you come back.)

Once I’ve figured out what dates I’m traveling, the next thing I do is try to figure out where I’m staying. If I can, I always try to book an Airbnb. They just provide a comfier and homier feel, and they have the added bonus of usually being cheaper than hotels. Personally, I like booking my Airbnb’s or hotels that are both in safe neighborhoods and close by some form of public transportation that runs late at night. I never know how long I’ll be out for the day, so I like to make sure that the subway/metro/tube/bus will be running later at night and stopping right near where I’m staying.

After booking my place to stay, I immediately start the deeper dive of the research process. This is when I really start to figure out what I want to do while I’m there. Museums, tours, attractions, places to eat, and of course, a nice little park or path to walk around. The first part of this phase is going to a bookstore and combing through the travel section for a guidebook and a map. Guidebooks are the best way to find some hidden gems, and since I’m directionally challenged, I always need to have a map handy. I have a tendency to pack as much as possible into every single day, so I’m trying to get better at actually giving myself some downtime. Does anyone else have this problem? Just me? Okay, cool. But seriously, it’s during the second part of the research phase with my guidebook and my map that I see when certain places are open, when is the best time to visit them, and how close they are to other things so that I can get the most out of my day and not be spending a ton of money on transportation.

When I finish planning out my itinerary and the date of the trip gets a little closer, I start tracking the weather. This is super important because it helps me realize if I need to change any part of my itinerary. If it’s set to rain, I want to make sure I’m not planning a day of walking around from place to place or hanging out at attractions that aren’t completely inside. Tracking the weather also helps me start thinking about what I need to be packing. For some more intense packing tips, you can read my other blog post, Packing For A Trip, by clicking here, but the short and sweet of it is to always pack layers, a raincoat, and an umbrella small enough to fit into your purse. (My secret tip? I always search for locations on Instagram to see what kind of outfits people are wearing – it’s a great indication of how the weather is actually feeling.)

The last thing I do right before I head out of town is make sure that all my bases are covered at work. Are all the loose ends tied up on my projects? Who’s going to be the point of contact for my clients when I leave? Do I have my team prepped for what to do in emergencies? Have I set my “out-of-pocket-and-on-vacation” automatic email reply? Do I have my laptop and charger packed just in case? Since I have a hard time letting go unless I feel that things at work are completely taken care of, this step is so important to my sanity while on vacation. Because if I’m worried about work, I won’t possibly be able to enjoy my time off.

I hope these little tips and tricks helped a little bit if you’re beginning to plan for a trip!




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