I love traveling. I don’t suppose I am unique in that. The part of what I love about traveling that perhaps is a bit more unique, is the planning for it. I’ve read that a large part of the joy in experiences comes from the anticipation of said experiences, and planning helps me indulge in that. Perhaps it could be called, dare I say, travel foreplay?!

If I hadn’t traveled with friends in several occasions over the last few years, I wouldn’t know that my approach is slightly out-of-the-norm. That saving places to Yelp and Google Maps is unusual. I wouldn’t fathom that someone WOULDN’T have a general agenda in a google doc, with links to websites and pinned locations. I do that stuff. And I love it. But apparently it is not super normal.

If you are the “free bird” type, and even reading that gives you anxiety, don’t give up on this post just yet. I’ve found that doing your research beforehand and saving spots to a google map can allow you to wander with more confidence, because you can be somewhat assured that no matter what part of town you find yourself in, you’ll have some favorites in the vicinity saved, and you won’t have to make in-the-moment decisions about where to go to get coffee or a bite to eat. Sometimes having to pick those things while out and about can create decision fatigue during your trip. (NO ONE wants decision fatigue when on a fab vacay, yaknowhatimean?)

The way I see it, is that I only have so much time. So many meals. So much energy. Why not increase my odds of hitting the best places and making the most of my trip?

Picking your trip.

Not always an option. Sometimes you’ll just know you are going somewhere due to outside circumstances. That’s where the wedding is. That’s where your parents retired to. That’s where the group has decided to go.

But – if you have the option of choosing where you want to vacation, here are some steps:

  • Poll everyone involved on what their interests are, including:
    • Specific destinations
    • Activities of interest (Nature? Art? Shopping? Pampering?)
    • Other considerations (is it winter and everyone really wants warmer weather?)
  • Do some relevant web searches, like:
    • “Most affordable US vacations in winter”
    • “Family-friendly vacation options”
    • “Top foodie cities in Europe”
    • “Best hikes”
  • Put out social media feelers with you network for vacation recommendations – “Hey guys – I don’t know where to go on vacation. I want something low-key and relaxing, close to the water. Advice?”
  • Make your final choice:
    • Group trip: Narrow the list down, and let people vote
    • Couples trip: Narrow the list down, and then, just make decisions the way you usually make decisions together (don’t know what else to say here because every couple is so different)
    • Solo trip: Narrow the list down, visualize yourself in each destination and then decide what feels best

Getting the best deals.

There’s a lot of options here. A lot of competition in the “travel deals” space. I’ll weigh in here with a few thoughts, but wouldn’t consider myself a subject matter expert. In fact, if you ARE a subject matter expert and want to weigh in, I’d love the comments for me to use in future travels.

Flights – I recently discovered Hopper, an app that allows you to select your desired destination and dates, and give you price options. That isn’t unique, but it tells you whether you should buy now or wait, based on historical data. That’s helpful. Plus, you can save your trips of interest and “watch” them. (I just enable push notifications and let it remind me periodically about a trip I was thinking about with tips on whether I should be buying or waiting.) Recently I was deciding between Los Angeles, Miami, and San Diego, so I just set up alerts to watch all three, so the decision stayed top of mind and I could monitor what was going on with flight prices for each.

Lodging – In instances where I want to stay in a hotel or hostel, I’ll start with a google search like “Best economy hotels in Phoenix” – especially if I am traveling to a large city that likely has write-ups. That can help you make a short list to start with. I don’t know if that is an absolutely necessary step, but I tend to do it just to be thorough. Then I hit one of the big deal providers like travelocity or hotels.com, or whatever, and check ratings, availability, location, etc. In instances where I want to stay in an AirBNB, I tend to search for best neighborhoods to stay in first, and then go to the app for choices, knowing what neighborhoods to look for. AirBNB sometimes has slightly less flexible cancellation policies, but not always. And, I once found myself in a situation where I had to cancel a booking due to an emergency situation, and even though I had passed my official cancellation date, I wrote the host, explained the situation, and she refunded everything but the AirBNB fee, which she technically couldn’t cancel.

Activities – I run searches on this too, like “Best things to do in Washington DC on a budget.” And, if I have my heart set on particular museums or attractions, I’ll check to see if they offer discounted admission on certain days. (Caution – that can mean a more chaotic experience and longer waits – so be sure to weigh the cost-saving advantages against the experience disadvantages.) Unexpectedly, I’ve found that Pinterest has been a helpful search device for this. Google is still awesome, of course, but Pinterest can serve up some different options. I also like to create a private Pinterest board and save all of the links that I’m finding to helpful articles and such. Pocket is another app that offers the ability to save web links into a central repository that you can come back to. Both options are nice because they have websites AND mobile apps so you can be doing research on your phone and/or your computer and still be set.

Finding the gems.

For years, as soon as a trip has been decided upon, I’ve quickly pulled up Design Sponge and checked whether that particular city has a City Guide. More and more bloggers are writing them, and I’ve found that if I already like the blogger who has published the guide, then I’ll likely love their recommendations. I used this tactic heavily for LA, because there are so many bloggers I follow that live there. (Design Love Fest, SF Girl By BayEmily Henderson, etc etc.)

And, in case you are interested, I’ve done my own city guide. Just one so far. To Asheville.

But, because I can so rarely take just one person’s word on anything, I’ll cross-reference. And I love using Yelp for it. I look up the spot (be it restaurant, music venue, thrift store, etc.), and check for:

  • Whether it is still open. Learned this the hard way. Sometimes blogger guides are a couple years old and places have gone out of business.
  • Ratings and reviews
  • Photos (sure – something can have great reviews, but will I enjoy being in the space? This certainly won’t matter to everyone, but it matters to me.)

Outside of this, put feelers out on social media again. Recommendations from friends are so helpful. They know you! They know what you’ll like.

Getting organized.

I’ve found myself in situations where I zig zag the city FAR too much because I haven’t really plotted out where everything is. Then I discovered Google Maps. Actually – I was shown Google Maps from my thoughtful ex-husband who planned a trip for us, and would give me a little card with a bit.ly URL on it every morning, which, when keyed in, would have plotted out points of where/what we would be going/doing. I forgot about it for a while (I was using favorites in Yelp), but then used it for a recent trip to NYC and found it to be incredibly helpful. It assists you in visualizing what attractions of interest are in the vicinity of one another and can save you time, money, and gas. Usually, I complete this step before attempting to think about what I’ll be doing each day. Very important – create a map for your trip that you can save locations to. Rather than typing out all of the technical instructions on how to do this, here’s a helpful resource. You can simply pin all your desired destinations on the map, or you can go as far as creating layers on the map, or selecting specific icons/colors for types of attractions… what I’m saying is that you can get REAL GEEKY with it if you want.

Then, planning out the days has taken various forms. I always think about it – what I want each day to consist of. Sometimes it’s just the theme of the day: “Thriting.” “Museums.” “Nature.” Other times I just decide what parts of the city I want to hit on various days, and that dictates what I’ll be doing based on chosen neighborhoods and my saved attractions. Or, agendas have been driven by what is open/available on specific days. Either way, usually something is documented somewhere. It’s been as simple as scrawled out thoughts in a notebook, and as complex as a multi-tabbed (by day) Google sheet with columns for (I kid you not):

  • Name (with website link)
  • Type (“Museum,” “Boutique” “Park” etc.)
  • Cost (this is especially important if you need to adhere to a strict budget)
  • General time frame
  • Location
  • Notes

Sometimes I cannot believe the behaviors I am admitting to in this public arena. 

Other things.

Save all of your important things to your phone (or write them down) in a place that doesn’t require internet or network connection. Because – you just never know when you might have access issues and be stuck trying to find a confirmation number that you just. can’t. get. to.

Let people know where you’ll be, especially if you are traveling alone. It allows people to reach you if an emergency situation comes up and they can’t get to you on your cell. Which, is pretty old-fashioned, but I learned it from my parents and grandparents and it just stuck.

For your OWN emergency situations, if you happen to be traveling alone, here is a fantastic instructions article on how to set up medical ID for Emergency on your iPhone. It allows someone to access essential information about you (name, medical conditions, emergency contacts, etc.) while your phone is locked. The only drawback of it, is that is requires whoever might need to provide you help in an urgent situation to know about the function, but that probably isn’t the thing to worry about. Control what you can control, you know?

Don’t be so married to your agenda that you stress yourself out, but also don’t wimp out too early. Tired from walking? Take a little rest instead of deciding to retire back to your hotel. I tend to push myself a little harder on trips than I normally do, in order to capture as many experiences as I can. But, this really is a personal preference. For some, that would be the opposite of relaxing. I push myself on trips because I get to relax at home, and I know many people are in the exact opposite situation.

Any tips or tricks that you guys know and love? Would appreciate hearing them!



One thought on “Trip Awesomeness Maximization (Otherwise known as “Planning”)

  1. Yes to everything you said! If I don’t plan it causes me stress and great experiences can be missed!

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