How To: Over Plan a Vacation and Be Uber Organized When You Get There

I always love it when bloggers share their tips on how to pack for trips. I've gotten some great tips over the years on ways to save space and bought handy products that were recommended in the posts.

But you know what I never seem to see? Blog posts on how to actually plan the trips, and even more importantly, tips on how to be organized when you're on the trip. Maybe nobody cares about this, but whatever, I'm going to share it anyway! :)

It's no secret that I love to plan trips. LOVE. It's like, 40% of the fun of travel for me! And while I've shared some sample trip itineraries with budget breakdowns, I thought I'd dive a little deeper and walk through how I actually plan out trips. These days, anyone can be their own travel agent, it's all just a matter of doing a bit lot of research, keeping things organized, and having the tools you need when you get there.

So here are the steps I go through every time we go somewhere:


Step 1: Pick a destination

This may or may not be easy. Most of the time I know I will decide I want to go somewhere, but not really know that much about the destination. Or I'll want to go somewhere to do a certain activity. Maybe I just know I want to go somewhere tropical, for example. Narrowing down the destination is always the first step though, since you can't plan a trip to nowhere. Usually this isn't an issue for me, since I've got such a long list of places I want to visit, but if you're unsure, Google Images is sometimes a good place to start. Try searching for, say, "Caribbean" and see if there are any images that stand out to you. You can then click through to find out where they were taken, and bam! There's your next vacation destination.

Step 2: Make a list of some fun things you might like to do at your destination

I like to start with reading the "Things To Do" page on Trip Advisor for my initial ideas list. And it's important to keep it organized, with links to where you found your info, and notes to yourself. A column for the location, as well as the activity cost can be really useful too. Sometimes trip planning can take weeks, or even months, and you don't want to have to try to remember where you saw that review about the best beach to visit, or have to search again to check the cost of a tour.

I do the same with listing out potential restaurants we might want to eat at, and maybe hotels to stay at, although I usually prioritize hotels last, since I prefer to have our activities and things we want to do dictate where we stay, so we're in close proximity to the action.

Step 3: Check reviews, to find the best tour companies/restaurants/hotels



This step goes hand in hand with step two, but takes things a little further. Once you've determined you want to do a snorkel tour, for example, dig deeper to see which tour companies have the best reviews, and make sure to read at least a couple pages of the reviews. Just because something has a high rating, doesn't always mean it's exactly what you're looking for. This will also help you determine if the cost of the tour/restaurant/hotel is a good value or not. I also like to cross check places in the travel forums on Trip Advisor. Often times people will write 'trip reports' that have even more details and tips than just the regular reviews.

Ok, those tips were pretty no-brainers. But now it's time for the organization to really come in handy!

Step 4: Do some initial mapping out of where your potential activities, restaurants and hotels are, to help you in beginning to build an itinerary

Once you've got your list of what companies you'll be doing tours with, what activities you want to do (and you've saved links, so it's easy to pull up the addresses), where you want to eat and where you might want to stay, you can start building out an itinerary.

I like to do this in a couple of steps. The first one is to map out where everything is. This may or may not be necessary though, depending on the scope of your trip. If you're just mainly staying on a resort, and doing a couple of off-resort activities, probably not a big deal to skip this part. But if you're planning a multiple-hotel stays with a rental car trip, or especially a road trip, it's a huge help in making an itinerary.

Once you've located everything on the map, you can start to get a feel for proximity, which in turn, allows you to go to the next step...

Step 5: Planning what days to do which activities and eat at which restaurants

Again, the depth you need to go really depends on the kind of trip you're planning. But in the example I'm using for our Florida Keys trip I'm putting together, we are flying in to Ft. Lauderdale, renting a car, working our way down the Keys to Key West, then back up and to the Everglades, over the course of 5 days. So while both a gator show and Duval Street are on my list of things I want to do, I can't really do them both the same day, since they're about 3.5-4 hours drive from each other. But that's where the mapping of things from the last step comes in handy.

Once I know where everything is, I can start grouping things together by days. This step usually involves some playing around and shifting activities until they're appropriately spread out so we have enough time to actually do them, while keeping things grouped by proximity to each other. And that brings us to the next step, timing.

Step 6: Add times to your itinerary

Once you've got your itinerary built out by the days you'll do the activities, working with your maps from step 4, you can begin to finalize your itinerary with the times. Go ahead and pull up that snorkel trip link you saved to verify the trip start time options. Check how far it is to drive from point A to point B. What time is sunset, and do you want to be at a waterfront restaurant to watch it? Consider all of these factors, and add the times to your itinerary. This might mean you still need to do some shuffling around of the activities, to make sure you have enough time for it all, or even remove some stuff from the list if you just can't squeeze it in. But this step will ensure that you get to where you need to be, have time to enjoy doing it, and don't miss out on anything because you didn't consider how long something would take.

This might be my favorite part of the planning. What can I say, logistics planning is my jam! It's like a puzzle, to fit everything together, and at the end your reward is an amazing trip.

Step 7: Get the buy-in from your travel companion(s)

I'm sure it's not surprising that I'm the main travel planner in our household. My husband just likes to show up, which is fine by me. But it's his vacation too, so I always want to make sure he's happy with what I'm planning. So once I've got the itinerary laid out (but nothing is booked yet), I present it to him to make sure he's cool with everything. I've found over the years that he doesn't really care about the exact times we'll do stuff, where we'll eat, etc. He just wants an overview, and reassurance that there will be some downtime for relaxing, and beers. So I like to put together a little collage along with the itinerary (or sometimes even a whole PowerPoint!), which just makes things more fun to look at anyway. :) And you'll notice notes about beer, like "Sail, Snorkel and Kayak trip with beer." Ha!

Step 8: Book flights, hotels and activities, in that order

Once you've got the seal of approval from your travel buddies, it's finally time to book everything you've painstakingly researched and planned out. Flights first, since your whole trip can be thrown off if you don't arrive and depart when you were expecting to. Hotels second, since you're not going to get to participate in the activities you've planned unless you have a place to stay. And finally, book your activities. Often times tours and such will have multiple trips per day, so if one time is booked by that point, it's usually not too hard to shuffle your itinerary around to do another time. But if the hotel is full or there's no seats on your flight, you might be out of luck if you've booked your activities first.

Step 9: Save everything with a label in Gmail for easy organizing of your bookings. This also makes it easy pull up your reservations on your phone while traveling

Do you use labels in Gmail? If you don't, you are really missing out on a great organizational tool. You can even set up auto filters that will automatically apply the label to any email you receive with a specific word, or from a specific email address. And not only is this really useful to find all of your reservations when you've booked a trip far in advance, it ensures you can easily find the reservations on your phone while you're traveling, just in case you lose your hard copy.

Which brings me to the next step.

Step 10: Make hard copies of everything related to your travel plans

Your itinerary, flight and car rental confirmations, hotel reservations, pre-booked activity confirmations and maps should all be printed out before you leave. Print double sided to conserve paper, but I feel this is a really important step. Just because you saved everything so you could pull it up easily on your phone in the last step, doesn't mean you'll have cell service when you get there. Or maybe you have phone reception, but your GPS isn't getting a signal. Trust me, it's happened, so if I'm doing any driving while on vacation, I always have my directions printed out.

Optional things you might want to also print are any tips on activities you might be doing, and menus for the restaurants you'll be eating at. If you're traveling internationally, you might want to print out a copy of your passport too. It's also optional, but you get a gold star if you make dividers for the different sections and a cover sheet and put it all into a report binder. :)

You know you're a type-A planner if this makes you smile. Organization FTW!

Step 11: If doing a road trip or traveling by car, send yourself an email with all of the destinations maps links

Yes, I know I can email myself directions from Google Maps. However, my experience has been when you have a map with multiple stops, when I click on the Google Maps-generated email to pull up the map in my GPS, it only will direct me to the last stop, and skips over the other stops. I have no idea why this is, if it's an Android issue, or just on my phone with my Google Maps GPS. So to cover my bases, I manually insert the map links to each destination in an email to myself. It's about 10 minutes of extra work (since I already have the addresses saved in my Excel sheet), but just makes things a lot easier. And having back ups to my printed out maps is just extra piece of mind!

Step 12: Make a business card sized pocket itinerary

This is especially useful for days when you'll be walking a lot, or don't want to carry your travel packet around with you in your purse, but still want a reference to what time you need to be where, or need to see what's on the agenda for the next day. I usually make one for myself and one for my husband. Call me anal (I am!), but this little card is just more piece of mind while traveling, and has often come in handy. Plus, I think it's cute, and so easy just to slip in your wallet or pocket.

So, those are my tips on how to (over) plan a vacation and how I stay organized when we're traveling. I know some of you will think this is overkill. It is, but what can I say, I really, really like to be prepared! Plus, I always assume when traveling that this will be my one and only opportunity to visit a destination, so I want to take the time to find the best of the best things to do and stuff to see, in case I never make it back again. Life is too short to miss out on an amazing activity or awesome restaurant, just because I didn't do any research to find out about it. Luckily I've got my more laid back husband to keep me grounded, and to make me always add in some relaxation time on our vacations, and a night or two of just wandering around to find a yummy looking restaurant.

Do you have any other tips on how to be organized when you travel? And do you usually do uber-prepared and researched vacations, or the more laid back, see what you find when you get there vacations?