Traveling to an Unknown Destination

More often than not, traveling is preceded by months of planning and preparation. You know where you’re going, what you’re doing, and where you’re staying. If you ever fall into a situation where that isn’t true, I understand your pain. So how is it even possible to prepare for an unknown destination? It’s easier than it sounds, and I hope I can convince you of that. In fact, this form of traveling can be more thrilling and exciting than your standard pre-planned itinerary.

Recently, I had the most wonderful getaway with my boyfriend in Puerto Rico. I am so lucky with every opportunity I have to see the world, so I try not to complain or let myself see faults. But wow it’s hard not to stress out about how to properly prepare. After this experience, I have to admit it wasn’t nearly as bad as I made it out to be. From my experience traveling to an unknown destination, here is what I’ve learned.

Traveling to an Unknown Destination


The most important thing, and also the only thing you can prepare for well in advance! Above all else, I recommend packing carry-on luggage. This is not practical or doable for everyone, but I really believe checking in luggage should be avoided if possible.

I packed a flimsy duffel bag from TJ Maxx and a backpack. I ended up overpacking my duffel bag and not needing a lot of the items I brought, but my motto is “it’s better to not need something instead of wish you brought it!”

When deciding what to pack, the most important thing is to consider the climate options. To make things easier, let’s hope your travel options all have similar climates. I packed with Puerto Rico, Florida, and California in mind. This definitely helped make things easier, as these three locations would mean packing similar items.

But what if you don’t even have a similar climate to base your attire on? What if you literally have zero clue? Packing a mix of outfits isn’t fun when you might not even touch them, but see the above motto. Here’s an idea of what I’d pack for clothes if I could end up in Alaska just as easily as Florida.

  • Mix of tops — Some that can be dressed up with jewelry, workout tops for hiking, comfy tops for traveling.
  • A pair of jeans — Jeans can be worn multiple times with multiple outfits!
  • Leggings — I love traveling in leggings because they’re comfy. Plus, if you’re in a cold climate, layer leggings under jeans for extra warmth!
  • Rain jacket/Rain poncho — Rain jackets can usually be rolled up tightly to save space and are the perfect “in-between” for a more cool or rainy climate.
  • Down Jacket — These jackets are SO warm, lightweight, and many can be rolled up to fit in pouches or even your pocket!
  • Swim suit — Because nothing is worse than ending up on a beach without a swim suit.
  • Tennis shoes — Rain, cold, or shine, these are shoes you can wear no matter what.


Figuring out what to do at this unknown destination is a little bit trickier than packing, as there’s usually not a whole lot of planning you can do until last minute. When my boyfriend and I found out we officially had seats on a flight to San Juan, there was an initial scramble to figure out how we would spend our short time in Puerto Rico.

There are three apps that I used the most frequently to build a spontaneous itinerary.

1. Yelp

This app is a great resource no matter if you’re at home or traveling. It’s especially useful for dining and hotels, though they do have reviews on museums, nightlife, parks, and more. While traveling, I mainly use it to find eating establishments. Most of the time you can see a menu and pictures of food to decide whether to eat there or not. This also makes it convenient to compare to other food options.

In Puerto Rico, we used this app to decide on where we’d eat breakfast. There were tons of reviews on a particular diner that made wonderful mallorcas. It seemed that this diner was a very special place that would be a sin to pass up. And Yelp was right–it was just as delicious as everyone raved!

2. TripAdvisor

This is one of my favorite resources to use! It is full of highly rated attractions and must-see destinations. This app was a lifesaver when it came time to cram as many outings as we could into a short span of time. This is also a great app for finding hotels and places to eat.

3. GoGoBot

This app is just as great as TripAdvisor, and sometimes even has attractions that TripAdvisor is missing. This is the same concept as TripAdvisor, but doesn’t have quite as many users. However, it’s a great to still use this app to make sure you aren’t missing anything.

Besides using these three apps, I had a lot of success scouring through Google searches. Not quite as time efficient, but it proved to be worth it. We found directions to an off-the-grid waterfall that wasn’t mentioned on any of the apps!

Above all else, it’s important to not forget about your greatest resource–locals. Whether this is your server, hotel staff, or friendly people you run into. They know their home better than anyone, and often give great recommendations that aren’t as popular. While TripAdvisor and GoGoBot are great apps, they can sometimes lead you to tourist traps. If that’s not your thing, asking locals is your best bet to finding hidden treasures.


Arguably the most stressful part of this whole scenario is figuring out where you’re going to sleep. The second day in Puerto Rico, we were deep in the rainforest and had ZERO cell service. So much for booking a hotel. I was preparing for the possibility that we’d have to sleep in the rental car. Luckily for us, our dream place to stay with only 17 rooms still had a vacancy by the time we called at 4pm!

Part of that luck was traveling during the low season, and I wouldn’t recommend waiting until 4pm to reserve a hotel room. If it all possible, I would highly suggest that this is one of the first things on your to-do list once you arrive.

As previously mentioned, TripAdvisor and GoGoBot are great resources for finding funky, off-the-wall places to stay. While there are probably Hyatt and Marriott’s to fall back on, I think it’s more fun to stay in a smaller, locally owned hotel. There are usually plenty of pictures on either app to give you an idea of what to expect, and most places allow online booking. So book your hotel online, and then spend your day exploring worry-free!

And that’s it! The hard stuff is out of the way.

What are your favorite travel resources? Have you ever traveled and not known where you would end up?

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