

For most of us, we have two or three weeks of vacation a year. Precious weeks that we dream about and savor like the last few bites of a really fantastic cheesecake. So how do you maximize those priceless days? With these five simple steps to plan a vacation:
Step 1 – Decide Where You Want to Go
If you’re like most people, you have a bucket list. It’s filled with places you aspire to go to and things you hope to do. Have you started checking some of those off? Have you even taken the time to write them down? Each year I pull out my own bucket list and find two or three things I want to check off (usually revolving around travel.)
I pay particularly close attention to locations that are near each other so I can see even more. This is especially easy to do in Europe, where other countries are an effortless train ride or short flight away. For instance, when I was in Poland I was able to get to Copenhagen (an hour flight away) for only $28! In addition to knocking one more thing off my bucket list, it enabled me to fly home for $1,000 less than I would have from Krakow. Jackpot!

Step 2 – Find Your Flights and Accommodations
There are a lot of travel sites out there, so it can be hard to determine which are best to score amazingly low prices. I’ve narrowed them down for you here so you can put that extra money to work while you’re on vacation. After all, what better way to celebrate a great flight deal than using that extra cash on a fancy dinner! If you’re not a do it yourself’er though, consider using a travel agent to help plan these details for you.
Insider Tip: If you’re searching for the cheapest way to get somewhere, it’s often more cost effective to fly into a major hub near where you want to go, rather than flying directly there. (Even better, choose two or three major airlines that are reasonably priced with large footprints and try to always fly those. It’s a great way to rack up frequent flyer miles for additional discounts!) Once at a major hub, transportation to your final destination by train, car, or puddle jumper are fairly inexpensive.
Step 3 – Decide What You Want to See and Do
So you’ve decided where you’re going, how you’re getting there, and where you’re going to stay. Now comes the fun part – deciding what you’re going to see and do when you get there! Two apps I use all the time when planning my itineraries are Google Maps and Visit A City.
Google Maps has a great feature where you can star different locations and landmarks for future reference. Any time I see a photo of a really amazing place, I find it on Google Maps and star it. Then, when I’m going on a trip, I pull up where I’m headed and reference those places so I don’t miss anything. It’s also a fantastic way to plan when you’ll see things. You can group things together by area, rather than bouncing back and forth all over the place (wasting precious time.)
You can also use services that offer tours. For instance, if I’m planning a Panama City to San Blas day trip, I’ll use a local travel service to plan a tour so I can see all the best sites in Panama. It’s a great way to easily experience it all!
Visit A City is one of my favorite apps. You can pull up suggested itineraries for different places around the world. These suggestions are based on the length of your visit and what you’re most interested in (museums, food & wine, relaxation, family fun, etc.)
For more great travel apps to help you plan your next vacation click here.
Step 4 – Get Packin’!
Now you’re planned, prepped, and ready to pack! I know how tempting it is to bring everything you own on vacation, but you’re not traveling to the moon. Repeat after me – less is always more.
I’m a huge proponent of never checking baggage, even on long trips. Not only does this save my suitcase from being destroyed, but it also saves me time and headaches while traveling. No waiting in baggage claim or losing my suitcase (the worst!) Think it’s impossible to pack enough in a small bag for your next vacation? Try the seven simple steps I use to ensure I always carry-on during my own travels.

Step 5 – Protect Yourself and Your Belongings
I’m all about not spending more than I need to on vacation, so travel insurance always seemed like a total waste of money. Kind of like the warranties companies are always trying to sell you (who buys those things?!?) But the more I travel the more I realize travel insurance is a must for any vacation (especially ones outside the country!)
I personally use World Nomads for their comprehensive coverage and reasonable pricing. That way I can enjoy my trip without worrying about what would happen if I got hurt or sick, lost my luggage, or had my belongings stolen (in addition to a number of other things).
The amount I pay for my policies is a fraction of what it would cost me if something went wrong on a trip. Worth it!
BONUS – Capture the Moment
If a picture is worth a thousand words, then I come back from every trip with a mouthful. As an obsessive shutterbug, I never leave for a trip without my camera. For me, finding the perfect moment or landscape to photograph is one of the best parts of travel! But even if you’re not quite as passionate about photography as I am, it’s still important to capture a few images on your next adventure. Pictures help you re-live those magical moments, remind you of everything you did (because after a little wine, things can get fuzzy), and they’re great for photo albums and holiday cards!
With advances in smartphone cameras these days you don’t even need expensive equipment to capture some great shots. With the help of a few photo apps, you can take great pictures with your smartphone! So whether you bring photography equipment or simply your phone, make sure pictures make their way into your planning. After all, how else will you make your friends and family jealous? Wink wink.
And just like that, you’re all set for your next vacation! With these five simple steps to plan a vacation, I have no doubt you’ll be able to organize the trip of your dreams!
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Thanks for the tip to remember that less is more as we begin the process of planning a vacation. My husband and I want to book a stay at a mountain lodge soon because we’ve both been really stressed from our jobs and need some time away from it all. I’m glad I read your article so I can keep your tips in mind as we start prepping for the trip!
I’m so glad you found it helpful! Using the tips in my packing post, I was able to bring all my belongings for a two week trip to Antarctica in a carry on. Trust me, it can be done! And, your back will thank you for it. 🙂
Hope you enjoy your much needed time away!
Thanks for pointing out that before you go on a vacation it’s important to find your flights and accommodations early so that you can find the best prices. I think that it would be smart to look into what kind of accommodations you want on your holiday pretty early on since that’s going to be your home base while you’re there. I also think it would be nice to look into staying at a place that has things for you to do or is by the sea or something so that if you just want to stay there and hang out you still have options for what to do.
Absolutely! The earlier you can plan ahead, the more likely you can see and do exactly what you want. A little foresight can go a long way! 😉