All The Best Tips & Apps For How To Plan An Epic Trip

That’s how the epic adventure starts. Like a tiny blob of a tadpole that grows its legs and then leaps from its lily home to the great beyond, so too can you leap off your couch into the trip of a lifetime. (Say that in a Morgan Freeman voice, and we’ve begun).

In this blog post I’m going to give you a few steps that will make your dream vacay further from a dream, and waaay closer to reality.

A little background for perspective…… I invited a friend to join me last minute on a trip that I had planned (2+ weeks around Scotland’s Highlands), when my original travel mate could no longer go. My new travel buddy was shocked at all the reservations I had made and all the research I had done, and told me he’d never planned as much on all the 50+ country trips in his entire life combined, as I had for this one.

So, why do I plan? Well, I can’t afford not to. Literally. I mean, I’m a single mom, who runs her own business, and I’m certainly not rolling in it. So, if I’m going to take a trip, and fly halfway across the globe (which is pretty much any destination from my home in Hawaii), then I’m gonna be damn well sure I make it count! I want to see, taste, and experience as much as I can…. and within my budget. And that, takes some ahead-of-time research and planning. (Can you get last minute deals? Sure, sometimes. But usually, the earlier bird gets the coolest bookings before it sells out.) To my friend’s credit, he’s a single guy with no kids, and has a job that he can do remotely. So, while spinning the globe and jumping on a plane to the first place his finger lands (without any plans for accommodation or what to see), is an incredibly sexy notion, I’ll leave that to my no-plan Stan, and I’ll stick to my research and reservations.

Now, this isn’t to say that once I get to a destination, I can’t be flexible or spontaneous, changing up the plans, or veering off the main road. I actually love doing that and have happened across some of my favorite places that way. But there’s also something to be said about booking a fairytale accommodation (that no one really knows about because its usually booked for special events), because you’ve contacted the place far in advance and planned your itinerary around that one epic stay.

Case in point: The private treehouse in Scotland that stands in its own shrouded forrest on the grounds of the Ackergill Castle-transformed-hotel (and the largest treehouse in Europe, that Prince Charles himself stayed at). I managed to book it, and even my travel buddy was immensely impressed at how unbelievably awesome it was. Which I think won me the argument of plan vs no-plan (at least for that evening!)

So, plan, I will continue to do! There’s also a great pride I take in being able to fit in so many things— visiting incredible vistas, enjoying the local the culture, eating delectable food, and most especially finding magical hidden spots with no one else there— that I feel I might miss out on without some forethought and planning.

For me, planning a trip is a super fun part of the trip itself. Some people dread it as much as they dread tooth extraction without drugs, but I’m here to tell you that it can be a fun process, if you let it. It builds anticipation, which builds excitement, which I’m pretty sure releases dopamine, which is the reason why people on ecstasy are so happy. And which is why you will be too, as you plan this trip. No drugs needed!

1. My blog (if I have a post about the place you want to visit- read that!!! Or if you’re not sure where you want to go, scroll through my blogs to see if anything captures your eye. Disclaimer: I only go on epic trips ;), so if you pick any of the places I have traveled to, you pretty much cannot go wrong.)
2. Pinterest (trust me)
3. Instagram (no, you are not too old for this. It’s not Snapchat)
4. Maps.me (I never travel anywhere without this specific app)
5. Booking.com (Love this site! More info on that soon)
6. Skyscanner.com and Kayak.com (More helpful tools)
7. Extra Dirty martini (Nuff said)

Those are in order of how I do it. But if you start with #7, you may give yourself a better shot at enjoying the whole process and also feeling like a badass, take-names, get-‘er-done vacation vigilante, while you do it.

#2 – Why Pinterest? Isn’t that for bake-sale moms who wear way too high jeans and have nothing better to do than create tongue depressor photo frames? Nooooooooo. Pinterest is amazing. In fact, I have turned twentysomething guy friends onto Pinterest (who would never admit it), but love it for trip planning in particular.

Pinterest has everything. It is a compilation of incredible advice, blog posts, snippets of most important travel info, and photos of anything or from anywhere you want. And the beauty of it is that you can ‘pin’ only what you truly want, to boards that you create. Example: create a board called ‘Bali’. Do a search for ‘best restaurants in bali’, and you will find lists, reviews, descriptions, etc. Type in ‘must see in Bali’ and scroll down the photos to see what appeals to you and what you’d like to see, and pin that to your board. They also have great posts with specific day itineraries. So if you can only take a week from work, you can see what others have suggested for ‘one week in Bali’. You can create boards for each trip, or even each city. I create boards for all my trips, pinning only the things that interest me. Makes actual planning way easier. And the photos are eye candy, with zero calories!

#3 – Once I read several blogs and lists about things and places multiple people say not to miss, then I check multiple photos and posts of those places on Instagram to see if it is really something worth my time, specifically. A picture paints a thousand words, and I am a very visual person. And I can admit it, I’m a bit of an Instagram junkie. There are a lot of closet instajunkies out there, who secretly troll and never comment or like anything, but I’m out in the open. C’mon though, what’s not to love? Constant and never-disappointing snippets of faraway lands and visions of paradises to satiate your daydream fantasies ….all delivered to you in a 2×2 inch compact frame that you can carry in your pocket and whip out whenever your bosses aren’t looking. It’s brilliance, really. A daily dose of inspiration at your fingertips. And entirely customizable. I mean, that’s why I love it. I look forward to the few minutes I have each day to gaze upon images of new places that will undoubtedly fall immediately into my never-ending bucket list of ‘OMGs I’ve GOT to see that!’

So, on to the planning part – I do a search on Instagram for the hashtags using that town’s name (or hotel, attraction, etc), and I scroll through the photos to see what I think. If I know it is something I want to see, I bookmark it and save it to its own folder on instagram for that location. I can then always go back to those photos when I am building my driving itinerary to remember how much (or not so much) I want to go there.

#4 – I then open up my Maps.me app, download the map of the country/city/area I plan to travel to (when I am connected to WiFi), and do a search for the location of that attraction, restaurant, location, hotel that I now want to include in my itinerary because of the epic photos and posts I’ve seen about it. I want to see its exact location to see where it is in relation to other things (airport, city center, etc), and to see if it makes sense to got there, or whether I’ll have time to fit it into my itinerary. I click on the spot and ‘save’ it with a star bookmark. I can then go in and edit the bookmark, by changing the name, or adding more descriptive info. I also change the color of the star based on whether it is an attraction (red), hotel (blue), restaurant (yellow), hike (green), transportation (brown), etc etc. These are just my color codes that I use for every country I travel to, but you can do whatever floats your boat! It is very helpful though when you ultimately get to your trip location, to see the colored starts, so you’ll know right by looking at the greater map, whether there are restaurants, hotels, gas stations, etc. near you. And the best thing about this app, is the the map and GPS and turn by turn audio navigation is available ENTIRELY offline, even if you have zero service at all, because the map and all its info was downloaded directly to your phone. I have used this map in the most remote regions of Iceland, where no service exists, and never once got lost. It’s an amazing app. It is also connected to Booking.com and other apps, so sometimes, if you are doing a search for a hotel, to see where it’s located, you may be able to click right through to book it.

#5 Which brings me to Booking.com – I always try to use this website/app for booking any accommodations anywhere! It is the first place I go, because it is so easy to navigate, it is very easy to use, they offer discounts to ‘genius’ (regular) users, and on most properties they offer a full-refund cancellation policy up until a few days before your trip. This is incredibly helpful and offers peace of mind, in case you need to cancel or change your reservation for any reason, or if you just find a more appealing place to stay. Plus they offer an awesome rating system & terrific reviews. They also keep track of all of your upcoming trips and send you reminder emails or texts about info you need, the location, the check in time, etc etc. Booking.com has never led me wrong in all my years of travel & booking through them. (If Booking.com does not house the accommodations I want to stay at, I try AirBnB and then I also look direct to the property’s website).

#6 – Skyskanner – I often use Kayak.com to book my trips, but I have found that Skyscanner can be a great tool as well, and allows you to compare and toggle results between the cheapest flights & the fastest (that will get you to your destination in the least amount of time, which can often be entirely worth the extra cost!). You can set up price alerts on both Kayak & Skyscanner if you think prices may go down. Kayak also has a great tool, called ‘Explore’. You can find it under the ‘More…’ tab at the bottom of the app. You can put your originating airport and then choose a month, duration of trip, budget, and see where you can fly to in that month for the amount you’d like to spend. So if you are open to locations for your vacation, this could be a great way to choose the spot! I found a roundtrip flight to Melbourne, Australia from Honolulu, HI for $425 during the month I wanted to travel. Usually, flights there are over $1000. So, if you have some flexibility- try it out!

Happy Planning!!