Travel Planning

How I Plan My Trips

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When it comes to planning trips, some cringe at the thought while others relish the opportunity.

I happen to fall into the second category myself, which I suppose comes with the territory of being a classic Type A personality. I’ve always been detail-oriented by nature, so the idea of researching, planning, and putting all the little pieces of a trip together sort of excites me.

So whether you’re a planner like me or are wildly spontaneous but perhaps looking to get more organized, here’s a look at how I plan my trips to help you arrange your next adventure.

Determine the Purpose of the Trip

Before I plan a trip, I like to set my intention for it beforehand. While the point of every trip is obviously to travel and see more of the world, there’s quite a bit more that goes into the pre-planning stages for me.

In its simplest form, I look at each trip as one of these two things:

  1. A work trip
  2. An actual vacation

I’ll admit, with my semi-addiction to Instagram, I feel like I’ve forgotten what it truly means to be on vacation. In other words, I’ve lost touch with what it feels like to actually relax, enjoy, and take in my surroundings without the compulsion to document every second of it.

Then again, considering that Instagram is so inextricably linked with my working life at this point, it’s easy to see why there’s a great deal of overlap.

So until I’m officially solo traveling and truly running the show, I’ve found it’s best to inform whomever I’m traveling with (husband, family member, friend, etc.) whether or not I’ll be spending the majority of the trip working.

So how would I define “working”?

Working can be anything from literally collaborating with a hotel (in exchange for coverage on my blog and/or social channels) to documenting most of the trip for personal content purposes but without an official partnership.

Realistically, this translates into shooting anywhere from hundreds to thousands of photos, taking video footage, creating Instagram Stories, editing photos, and brainstorming/writing new blogs.

Obviously it’s quite different than the experience of chilling in a beach cabana with a piña colada, but hey, without the hustle, I wouldn’t be traveling.

However, if/when I do allow myself to enjoy a true vacay again, there will be less planning and more spontaneity.

In any case, once I decide the type of trip I’m taking, it’s time to consider that big ol’ bucket list.

Consider My Bucket List

Ahh, the bucket list. The list that seems to keep on growing no matter how many things I tick off. Personally, that’s part of the fun for me. I love setting goals, but I especially love crushing them.

So when I’m figuring out where to travel to next, I start by returning to this list.

Now I’ll admit, I don’t have a full-fledged list written down anywhere, but I’d say there’s at least 30-50 mental bucket list items constantly swirling around in my mind.

Fortunately, to keep things simple, most of them involve traveling to Europe. Realistically, my big hairy goal is to visit every country in Europe eventually.

What can I say? I binge watch Rick Steves. I cried twice in Santorini – once when I arrived and then again when I left.

Every European country I visit – whether I love it or not – feeds my curiosity and makes me hungry for more. The people, the food, the architecture, the work culture, the landscapes, the climate, I find all of it absolutely intoxicating.

So I think it’s safe to say I have a continent covered for the next good while. After that, it just comes down to narrowing my focus and selecting my countries.

Seek Inspiration

One of the perks of essentially living on Instagram is that it’s incessantly stimulating. Never will you ever hear me say I’ve run out of travel inspiration or places to see (and if you do, promptly smack me).

In fact, I think it’s safe to say that since starting an Instagram, I’m now aware of about twice as many cities and towns as I was before. Wild, right?!

The Carry-On Chronicles on Instagram
The Carry-On Chronicles on Instagram

So when it comes to selecting my next destination, I find this platform is a great place to start. I can search destinations, hashtags, influencers I admire, or look at the accounts of people I follow.

I typically look for anything that inspires me, which generally means its jaw-dropping architecture. Magnificent castles, unique doors, beautiful tiling, charming storybook villages, I’ll never get my fill!

Once I’ve narrowed down some areas I’m interested in, I’ll take my search over to Pinterest for a deeper dive.

The Carry-On Chronicles on Pinterest

Like Google, Pinterest is an incredible search engine, and I actually prefer researching travel destinations through here versus a standard Google search. Pinterest is filled with tons of first-hand accounts, so I can read about what a desired destination is actually like, as opposed to going directly to a tourism site.

Here, I’ve curated a separate travel inspiration board for each country I’m interested in visiting. These boards are chock-full of travel tips, destination guides, must-see sights, restaurants of choice, most Instagrammable places, and more.

Belgium Inspo on Pinterest

When I become infatuated with a new country, I simply create a new board and pin my little heart out. In fact, it’s usually pretty easy to tell which place I’m visiting next by the sheer the number of pins that board has. For example, if you take a look at my France board, you’ll see it has a whopping 390 pins at the moment!

Similar to bookmarking a page, I love the fact that I can pin something whenever I want and essentially forget about it until it’s time to plan my next trip. I simply refer back and everything I had saved is ready and waiting for me!

Pitch to Hotels

As I’m moving toward becoming a full-time travel blogger, I’m now starting to collaborate with hotels. I actually have some collaborations coming up later this month in France and Belgium and I couldn’t be more excited!

If you’re not familiar with the idea of a blogger collaboration, it’s when bloggers/influencers provide exposure for a hotel through their blogs and/or social media platforms in exchange for a stay.

The process of researching, pitching, and then landing these opportunities is worth a dedicated blog post unto itself, so I’ll definitely go into more explicit details on that in a later post.

For now, I’ll just say that if I’m doing a work trip as opposed to a vacation somewhere, I’ll pitch hotels within my niche in the hopes of working with them during my stay.

Book Flights as Cheaply as Possible

Once hotels have been sorted out (whether collaborations or otherwise), I’ll start researching flights. Now that I’ve been booking flights for some time, I’ve picked up some money-saving strategies along the way that I’ll briefly share with you.

Again, there’s enough information here to fill an entirely separate post, so I will just outline the main points for the time being.

  • Search for flights on “incognito” mode – A fellow traveler friend of mine taught me how to do this, and it’s a simple and effective way to save some cash on your trips. Essentially, going “incognito” means that the search engine you’re using will perceive you as a completely new visitor.

    Therefore, you won’t be targeted with rates that are “tailored” to you based on any previous searches. In other words, you’ll see a more accurate picture of what flight are actually worth as opposed to receiving inflated rates based on your search history.

  • Rack up Flight Miles – Another way I save on flights is by using my Capital One Venture card. I am not in any way sponsored by them (although I probably should be at some point). While this card is not aligned with one specific airline or hotel chain (as some are), I prefer the flexibility this one offers. I earn two miles per dollar on every purchase that I can use toward a flight, hotel stay, etc.

    There are a number of travel cards on the market, so if this is something you’re interested in, I recommend comparing the rates and features and finding the card that best meets your needs.

  • Travel Off-Season – I’ve discussed the benefits of off-season travel in a previous post for The Vacation Times. Booking flights in the off-season (such as my upcoming Euro-trip this month, for example) is one of the best ways to enjoy deeply discounted flights (and often less crowded planes, as well)!

Plan the Itinerary

Once everything is booked, it’s time for one of my favorite parts of the travel process: planning the itinerary! This is where my Type A personality really kicks in as I revisit those Pinterest boards and quite literally map out my trip.

While I don’t like to plan out the details of each day (I prefer to build in some flexibility for things that may pop up), I do like to keep a running list of the hotels where I’ll be staying, must-see sites, photo shoot opportunities, and ideas for future blogs.

That said, this whole planning process is a ton of work, and it’s further complicated by the fact that I’ll now be collaborating with hotels and keeping track of various deliverables and timelines.

So, in order to keep everything organized in one place, simplify the travel planning process, and avoid the stress of multiple lists scribbled in various notebooks, I’ve designed my very own Travel Planner. This planner is ideal for travel bloggers, influencers, and frequent jet setters who need to keep track of travel information on the-go.

But it’s more than just a place to organize travel information. It’s also a place to dream, to plan, and to collect inspiration.

In it, I create the space for you to map out your yearly travel goals and wishes, plan the details of your trips, keep track of your collaboration deliverables, record the experiences of your hotel stays, plan out the best photo shoot locations, take note of must-see activities, jot down inspiration for blog posts, and more.

You can purchase your very own 2019 Travel Planner here or by clicking below.

Here’s to setting some amazing globetrotting goals and enjoying more stress-free travels in 2019!

Did you find this post useful? Don’t forget to pin it to your boards!

How I Plan My Trips

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