How I Plan My Travel Itineraries (AKA How to Find the Best Bookstores & BBQ Joints)

As a full time travel blogger, I plan a LOT of trips. Trips that I go on, trips I decide not to go on, trips that end up getting cancelled, dream trips. My greatest form of procrastination is actually planning trips that I have absolutely no intention of taking. It was always a hobby really and I ended up finding a way to make it my job. 

All of this to say that I’ve developed a process for planning a travel itinerary. 

Obviously planning an itinerary for a city trip is different from a road trip which is different from a big destination trip like Hawaii. But here’s generally how I do it:

Is It a Trip or a Vacation?

First things first, this is always good to know. Not all trips are vacations and that’s ok, but it’s good for everyone in your travel group to be on the same page. If you’re planning a great vacation, you’re probably not going for much of an itinerary. Pick the best place to stay, plan a couple of don’t miss activities and spend most of the time relaxing around where you’re staying and eating some good food. 

Now, if it’s really a “trip” then you’re probably going to want to have more of a daily itinerary scheduled. Besides where you’ll be staying on what days (if it’s a road trip or a multi-city/destination trip) you’ll also want to nail down all the things you want to do, reservations, where to eat, etc. 

Figure Out Your System

When I’m laying out a trip, I’m usually a pen and paper gal. I’ll sit down with a stack of blank computer paper and some markers and start making lists and then organizing all the info I have until it starts to take shape. I do like to use Google Maps though to check locations and distances between places to see what makes sense and what’s doable. 

If you’re more tech inclined, you can even plan your whole trip with Google Maps. This is especially helpful if you’re dealing with a large area or a road trip so you don’t spend much time crisscrossing and backtracking. Plot all of your locations on a Google Map and then not only can you see what’s near each other to start planning your days that way, but you can create layers for different days or different types of activities and sites and organize things that way.

How I Find Things to Do, Restaurants, etc. 

So once you have your system, how do you find the best things to do? Where do you get the best restaurant recommendations or even find where you want to stay?

Okay, this is my favorite part. If I’m planning a trip (or trying to decide if I want to plan a trip) to a place and I only have a vague idea of what I want to do there, or I’m looking for more suggestions to round my trip out, here’s what I do:

Google Search the Destination: Actually, unless I know NOTHING about a place this isn’t usually my first search. Search “things to do in Nashville” or “things to do in Palm Springs” and you’re going to find hundreds of cookie cutter blog posts all mentioning the exact same things. It’s like they’re not even written by a person who’s actually been to the place ; ) Like I said, if you know absolutely nothing about a place it will give you a start, but don’t ever end your research with a search like this. 

Google Search the Destination + a Publication You Like: This is my secret tip and it’s how I’ve been planning quite a few trips lately. My go to is searching “Southern Living Dallas” or “Southern Living Nashville” and it will bring up all of the posts and articles that Southern Living Magazine has on that destination. Now I’m using Southern Living as an example because I happen to really like their travel section and most of the region that they cover is within driving distance to where I live. But depending on where you’re based or where you’re going, it might be another magazine or website. I also search “Conde Nast Traveler” and “Travel & Leisure” plus the destination quite a bit. It gives you a well curated guide to that destination that’s usually a lot better quality than a generic “things to do in ___” that ranks on the front page of Google. 

So if you like my blog and think I give good recommendations, you can Google “Hulaland Marco Island” or “Hulaland Maui” or wherever to see if I have any posts about that place. 

Pinterest: If you don’t have a list of bloggers or publications whose opinions you trust, try doing a Pinterest search for the destination. If you search for a place on Pinterest, 99% of the pins will lead you to a blog post about that destination. It’s a great way to find curated information about a place from smaller bloggers who actually travel to the places they right about. 

TripAdvisor: There’s no better place for reading reviews than TripAdvisor. It’ll give you lists of the best places to stay, restaurants, and activities ranked by real life reviews. It’s a super useful resource, but you’ve got to take everything with a grain of salt. I don’t necessarily trust their rankings all that much because there’s so many variables at play (including how many people review each place), but I do like to read specific reviews for things and pay attention to see if things that matter to me (or don’t) are mentioned. 

Search for What Interests YOU: Most lists and guides mention things that will appeal to the majority of people, but if you have specific interests then definitely search for those. You’ll be surprised by how many truly great things you’ll find to do that aren’t really mentioned most places on the internet unless you go looking for them. Some things that I usually search for when I’m planning a trip: bookstores, amazing boutique hotels, bbq joints, local historical sites and museums, places with interesting architecture and design (I love a good architecture walking tour), and good vintage and antique stores. 

Follow Local Instagram Accounts: So much of the best (and most “in the moment”) info on the Internet is actually on social media now. If I’m looking for recommendations for a specific city, I’ll usually search to see what accounts I can find on Instagram and use the related accounts feature. It’s an absolute rabbit hole, but you can find some amazing stuff. It’s especially a good way to find restaurants and shops that sometimes have a higher turnover rate and don’t always make it to the mainstream internet super fast. 

Come up with a Game Plan, but Don’t Overplan! 

Mmmkay, now that you’ve got your list…if I could only give you one piece of advice about planning a trip, this would be it. Here’s how I always lay out my trips:

As I’m researching my destination (yes, I do a LOT of research), I keep a running list of things I want to do, places I want to visit, restaurants I want to eat at, shops I want to go to, etc. From my main list, I break it down into three categories:

A “don’t miss” list: These are the things that you ABSOLUTELY have to see/do or you’ll return home heartbroken. Okay, that’s a little dramatic, but you get my point. 

A “nice to see” list: These are things that you really want to see and experience, but they might be a little more minor.

An “if there’s time” list: I think you can guess what this list is for. Things that you’d like to see or do if there’s time, but won’t be upset about if you miss.

As you lay out each day, plan ONE thing from your “don’t miss” list each day. Combine it with one or two things from your “nice to see” list, and a smattering of things from your “if there’s time” list. Prioritize your “don’t miss” item every day (whether it’s doing it first thing or making sure you have a reservation for it) and fill in the rest of the day with things from the other categories.

Be Flexible

I think this tip is the secret to making a good vacation great!  It’s so simple, yet key to really having the best experience…anywhere. I think that a good plan is essential, but you have to know when it’s time to go to plan B. Or do something else entirely. You may have to be flexible about weather, time, what kind of a mood you’re in, etc. Or you may stumble across something that you didn’t plan for but seems too good to pass up!