While the below list and tips may seem daunting at first, they’ll help you become an expert on your upcoming location. Depending on the trip, I’ll use a variety of the below to set a game plan, gauge pricing and manage travel logistics. Hopefully you’ll learn a new tip or two and I’d love to hear how you plan your travels. Any tips on spontaneity are also welcome…
step one: research & find inspiration
Whether you’ve selected your destination(s) or you’re still looking for the right spot to visit, you can use the following resources to inspire your trip. (For the sake of this exercise, I’ll use Tulum since the photos are so dreamy…)
While I haven’t used Pinterest to update my boards in years, it’s my number one resource for finding in-depth details on neighborhoods and restaurants, activities when traveling to a new location. Travel bloggers and other influencers will pin their travel guides with key words and phrases, making it so easy to search a location and find tons of travel guides.
While the search feature on Instagram will show you images taken in your desired location, you’re at the mercy of how much information that user has decided to share or which hashtags they’ve used. It’s still a great place for inspiration and I like to use it in the planning and scheduling step to help pick one restaurant/bar over another. (Side note: If you’re not currently planning any trips, file away anything that catches your eye or might be a spot you want to see one day. Screenshot and save to a travel inspiration folder in your Photos.)
Not only is the regular search feature helpful on Google for tracking down great locations, try searching images to see a variety of photography from the location you’re interested in. You might even find a few travel guides this way, but searches like “What to do in ____” will give you a lot of links to review websites instead of niche travel blogs.
Crowd-Source
Put out some feelers. More often than not, you’ll know someone (or a lot of people) that have gone to the location you’re traveling to and will have some great recommendations.
step two: plan & schedule
Based on how Type-A you are, you can take all of these steps, or just the first one to gain a better feel for the location. (I’ll use Charleston as an example as I used it to influence this itinerary.)
Make a List
When I’ve finally selected a location, I go through the above four steps, making a master list of every restaurant, bar, neighborhood, hotel/Airbnb, activity etc., and highlighting the ones I’m really excited about visiting so I don’t forget about them. Sometimes my lists will have 50+ restaurants for a three-day stay, so don’t feel like you need to be picky here, but also don’t throw a restaurant onto the list for no reason. I’ll also cross-reference locations on Instagram, Google image search and Yelp to gain a little more insight into each spot, learn any inside tips and of course, read the reviews.
Map It Out
Once my list is in a good place, I’ll start mapping out all of the locations to gain some geographical awareness of the city/area. PowerPoint (can you tell I work in marketing?) makes it really easy to put everything on a few pages and compare. First, I’ll screenshot a map in Google Maps and insert it into a slide, using shapes and text boxes to draw from a location and create a label, making sure to include addresses as well. I’ll usually create three map pages, one each for restaurants, bars and activities, changing the color for my top picks so they’re not forgotten about. If possible, I like completing this step before booking my hotel/Airbnb so I can be in walking distance to what’s important on my list.
Schedule Itineraries Based on Location and Timing
Once you have your mapped-out pages, start grouping things together based on location and the time of day you’d complete them. This can be tricky, so make sure you’re taking note of restaurant hours, closures, ticket times, etc. so you can make the most of your time. Once I’ve got a rough itinerary mapped out back in my Word document, I’ll start adding in times as a guide, making sure to include travel times and important details like when a breakfast spot opens in case we’re up earlier than expected (usually not a problem!)
For group or couple trips, I like creating a very detailed, designed itinerary with images of each location (to get the people i’m traveling with excited) in addition to the maps.
The map slides will help you make last minute adjustments based on what’s around you. This tip led us to a rooftop bar in Paris, which ended up being one of my favorite memories, all because I had it on my map and we just happened to be two blocks away, needing a break from all the walking.
I’ll save the PDFs on my phone and add the written itineraries to my calendar so I can access the info without wifi or scrolling through my email. I’ve heard Google Trips is great for this as well, I just need to practice with it.
step three: purchase & book
Now comes the part where your wallet starts to hurt from the airfare and accommodations. Just remember you’ll be spending even more money once you arrive at your destination, so be frugal on this part if/when you can.
Book Your Hotel & Other Accommodations
Remember that most hotels are refundable (and most Airbnbs have a small cancelation fee), while flights are a little more strict. Make sure you book your accommodations well in advance to stay exactly where you want. Like I said earlier, location is important to your experience, so make sure your hotel isn’t far from the things you want to do and see.
Purchase Flights
I like to use Google Flights or Sky Scanner as the user experience is super easy and the tracker feature is helpful if you’re bad at remembering you still need to purchase that flight. Getting your flight at the lowest price is always a gamble, so if you know when and where you’re going, book as early as possible or keep an eye on flight prices with an app like Hopper. (Disclaimer: My mom is an international flight attendant, so there are some trips where I take advantage of a buddy pass. But now that I’m older, the buddy pass fee is so close to a full-fare fee for most locations, so I end up purchasing to have control over when I arrive.)
Make Dinner Reservations
If you completed each item in Step Two, you’ll already know where you want to eat. If it’s a hard-to-get-in place, make sure you book your reservation well in advance. Another thing that’s easy to cancel, but hard to reserve if you forgot until you arrive.
Set Alerts
Are you crazy enough to plan your trip 6+ months in advance? Then you’ll probably have a few things that need to be reserved, but aren’t available yet. Be sure to set alerts so you don’t miss out. Whether it’s an adventure tour, an international ferry boat or a lunch reservation you’re too embarrassed to make six months in advance, you don’t want to miss out on the day/time you had originally planned for.
step four: prep & pack
Gradually Make Purchases
If you know your destination well in advance, you can start picking up things for your trip. Going hiking? Do some research on hiking boots, clothing and bug/bear sprays. Beach vacation? Purchase your swim suits/resort wear during the Christmas season to get a better deal. With more time to plan, you’ll be less likely to spend a ton of money on one large haul and can pick the specialty items that will keep you excited for your trip.
Plan Ahead
Traveling internationally? Make sure your passport is where you think it is and not expired. Don’t want to check a bag? Make sure you have all the necessary travel sizes to pack your toiletries in advance and reduce stress. I love traveling with my Away “bigger carry-on” and it makes carrying on luggage a little more fun.