It might be the type-A in me, but actually planning for a trip is always one of my favorite parts about taking a trip. I find that it makes my trips more enjoyable when I feel like everything is sorted before I’ve even left. And since I’ve been doing a ton of traveling this year (with more trips to come!) I thought I would share my go-to tips for how I prepare and plan for my trips! 

1. Transportation: The first thing I always do after deciding when I’m going on my trip is figuring out how I’m getting there. Most of the time, it’s just a decision between flying or driving, but sometimes if I’m going to more than one place, I’ll also like to plan how I’m getting from one city to the next. Of course finding a deal on airlines can always be tricky, but I’ve learned that if you have flexible dates, sometimes the rates can be cheaper the days before or after you initially were planning for. Certain sites like Google Flights or Kayak, are great for this. (Pro tip: clear your history, cache, 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.)

2. Home Base: Once I know how I’m getting somewhere, my next order of business is always figuring out where I’m going to stay. My options for my home base while I’m on a trip are usually either a hotel or an Airbnb. Hotels are great because you know you’ll be looked after, you’ll usually get breakfast included, and you know you’ll be in a safe building. But there’s something I love just a little more about an Airbnb. They feel a bit cozier to me than a hotel and it makes the whole stay feel a little more authentic too – almost like you’re living there for a while. Wherever I end up staying though, I always do a little research to make sure it’s in a safe part of town and near some sort of public transportation that runs late into the night. I never know how long I’ll be out for the day, so making sure that there is a subway, metro, tube, bus station, etc. to get me back to where I’m staying safely is always a must for me.

3. What To See: Now the really fun part begins – planning the itinerary! I absolutely love planning out my days for a trip. I do a ton of research to figure out all of the things that I want to see and do while I’m on my trip. I like to plan out days by location. It makes no sense to be running back and forth and every which way across a city daily when you could just take it on neighborhood by neighborhood. So when I’m looking up my museums, tours, attractions, places to eat, parks, and more, I make sure that they all have a location in common when dividing up my days. (Pro tip: Also sort your “must-see” places into a list with what you want to see the most at the top and what you could live without towards the bottom. Then if you have to cut things out, you know where to start!) Guidebooks are a huge help to me when I am trying to figure out all of the things I should absolutely do on trips. Recently I used a Rick Steve’s guidebook to plan my upcoming trip and loved it, so he’s my top recommendation for you guys. Once you’ve sorted out what you’re going to try and do on what days, the next step is figuring out what days certain things are open, what hours they are open (pay attention to summer hours vs. off-season hours!) and when the best time to visit them is.

4. Packing: The key to packing the right clothes every time? Becoming best friends with your weather app. In the days leading up to my trips, I check my weather app religiously. I look at the expected temperatures, precipitation chances, humidity, everything. If it’s ever predicted to rain, I make sure to pack a good raincoat, an umbrella, and a sturdy pair of shoes that won’t be ruined if they get wet. As far as my day-to-day clothing I tend to pack, I always stick to packing in layers. I’d much rather pack a tee and denim jacket that I could tie around my waist than a single sweater and be left sweating all day since I can’t take it off. My secret tip is searching for locations on Instagram though. It’s such a great indication of what people in that city or town are actually wearing though and can really help you differentiate between a cold 70º and a hot 70º.

5. Work Prep: The last thing I do before I head out of town is make sure I have all my bases covered at work. This boils down to making sure loose ends are tied up, my accounts are in the hands of the right people on my team, my clients know I’ll be out-of-pocket, and I’ve set up my auto-reply email. Because while I never go anywhere without my laptop, I definitely won’t be checking my email unless it’s an emergency. Making sure all of my ducks are in a row before I leave for my trips is a huge help in being able to actually disconnect, be present and enjoy my trip while I’m on it.

If you’re planning a trip, or thinking of taking one soon, I hope these little tips and tricks help make the process easier for you! And if you have any tips or tricks of your own, be sure to leave them in the comments below – I’d love to hear them before I jet off again in 2 weeks! 

xx,

lovelyingrey