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Do’s and Don’ts of Planning a Trip

How to Plan the Perfect Trip

Even as a frequent traveler, I somehow find myself making mistakes every time I start planning a trip. There are so many tools, apps and websites out there to supposedly help with planning a trip, and yet I’m easily overwhelmed with information overload.

And yet, when traveling through Germany on a last minute trip this past month, I downloaded the Triposo app (available on iOS). I used it to find recommendations on where to go and what to see, but I also used it as I used to use most print travel guides. I wanted to know a bit about the history of where I was visiting and get a sense of what the major tourist attractions were. The Triposo app worked really well for introducing me to some German cities in Saxony that I just didn’t know much about. The app has all sorts of cool features that work offline (you simply download where you’re going beforehand) such as a map, local facts & history, recommended activities, restaurants, nightlife and lots of tips!

I found the app really useful and so that’s why I was glad to partner with Triposo. Together, we’ve created this handy guide on how to plan the perfect trip—with many of my insider secrets as a frequent traveler! Illustrations by Clairikine.

Triposo - Google Play


How to Decide Where to Go

Wanderlust with Triposo

This is the fun part! Once you get caught with the wanderlust bug, it’s hard to lose it. Narrowing down your travel options can be tricky if you’re the type to want to see and do everything…

DO: Stay open-minded on where you want to go. It’s also helpful to do a bit of quick research on a destination first, such as local laws and safety issues (especially important for LGBTQ travelers). Look for inspiration everywhere—the movies, Pinterest, travel apps, where your friends have been, where your mom hasn’t been… There’s a lot to see!

DON’T: There’s not much to say for avoiding a particular destination. But know this: choosing where to travel can be a very personal decision, but it doesn’t always have to be. Sometimes there can be joy in just wandering for the sake of wandering. But it’s still very important to be mindful of regional laws and customs.

How to Book a Flight, Train or Bus

Choosing Where To Go

This is the hardest part of planning a trip. It’s the most difficult step because once you book the transportation, you’re committed. It’s the first step in planning a trip and once you do it, there’s a snowball effect.

DO: Start with one of the travel aggregators to search for routes – sites like work really well as a place to start with flight research.

DON’T: Don’t put so much pressure on yourself and just get through it. The feeling of relief once you book a plane ticket is going to be enormous – and, once that’s done, you get to start on the really fun stuff!

How to Find the Perfect Place to Stay

Finding the Perfect Place to Stay

When choosing where to stay, there are a number of things to consider: price, location, accessibility and wifi top my own personal list. But we each have our hotel preferences.

DO: Check “best of” lists and apps on travel sites (hey!). In the Triposo app, you can search and book both hotels and hostels. The search filters let you sort by the number of hotel stars, the location (with identifiers such as “near food and drink”) and even by themes such as design hotels or romantic hotels.

DON’T: Don’t leave booking the hotel to the last minute! If you end up in a less-than-amazing accommodation—whether it’s not convenient to the tourist things to see and do or outdated and rundown—the experience is certain to affect your overall impression of the trip. Sure, you don’t have to book a nice place to stay, but at least find one in the right area for the type of trip you’re planning. Anything less and you could end up with a disappointing holiday.

How to Plan a Travel Itinerary

Planning an Itinerary

After booking your transportation and place to stay, the next best thing to do is to start planning an itinerary. It can be time-consuming and stressful to build a travel itinerary, so make sure to take it slow to avoid overwhelming yourself. Use my travel tips below to build a perfect itinerary of the coolest and newest things to do.

DO: To find the newest, most popular things to do, you really have to use a site or app which pulls in from multiple sources. Local blogs are a great start to finding the coolest and newest things to do, but also make sure to use apps like Triposo which makes awesome travel guides using smart algorithms. Triposo’s free app pulls in data from open-source content such as World66, Wikivoyage, Wikipedia, Flickr and Open Street Maps to create local guides that work without internet. The app also features free City Walks which give you the freedom to explore the city at your own leisure with a self-guided tour. Create an itinerary in an app like Triposo and you’ll have it with you during the entire trip, plus a useful, offline map which will have all your planned destinations pinned.

DON’T: Don’t simply just trust your guidebook. Printed guidebooks are often written and published the year before, so while they’re good for finding the tourist hotspot basics, they’re going to lack the newest, trendiest options. Don’t just stick to the top tourist attractions, either. The beauty of travel in this digital age is the ability to see and do more, to experience both new things and the same things you have back home—but with a different cultural understanding.


Use Triposo to plan a customized itinerary!

Cherry pick your favorite hotels, sights, activities and restaurants and add them to your bucket list. And then book your hotel, tours, activities and transportation seamlessly through the app so that your entire trip is planned in one place!


How to Pack

How to Pack

I’m notorious for leaving the packing until the very last minute. It’s a bad habit, but I’ve got a secret to make it easier!

DO: First (and very important!), check the weather before you leave! You don’t want to be that guy who lands abroad only to be totally unprepared. That’s how you end up spending your first few days in a new place either stuck inside or shopping for new clothes.

DON’T: Don’t leave the packing until the last minute! It’s helpful to keep a drawer in your house with all your travel necessities. Keep things like a toothbrush, pocket tissues, travel-sized liquids, power adapters, condoms and spare headphones in a ‘travel drawer.’ That way you won’t forget to bring what you end up needing for every trip. Also: don’t bother exchanging money before you go, but have some backup cash just in case. ATMs almost always offer the best rates if your debit card will work abroad and there’ll be one in the airport or train station when you arrive.

And then? …Go!

Go Travel!

If you’re anything like me, the real rush of travel excitement starts when you’re on the way to the airport or the station. There’s an adrenaline when you’re starting a new adventure. Let it flow and stay flexible with your plans—that’s where the best travel memories come from. Get cash and a SIM card (if you’re addicted to Instagram like me) when you arrive and remember to stay flexible with the plans. Trip planning doesn’t end when you arrive.

DO: Spend a bit of time on your flight getting acquainted with your destination. The Triposo app (which works offline) includes articles on the history and culture of their 50,000+ destinations so you can do a bit of light reading to learn a bit more than what’s on the surface. When you arrive, remember to stay flexible with your itinerary. Again, Triposo includes offline maps of each destination so you can feel comfortable with getting lost and still knowing how and where to find your hotel if you wander too far.

DON’T: Don’t sweat the small stuff. Things rarely go to plan when traveling, but if you’re prepared and have a smartphone loaded up with all the necessary information you might need (offline maps, free travel guides, attractions and tour lists…), you’ll be 10 times more prepared than any other traveler. You don’t have to use all the tools that you might have with you, but it can’t hurt to have them available…just in case.

Have more travel tips for planning the perfect holiday? Share them below!

  1. Good post! The do’s and the don’ts curated so well that even a novice trip planner would take the most out of this post.
    By the way, I landed here after I saw your post in NomadicMatt :)
    I loved the post on you reminiscing your 5 years of travel.
    Impressive blog. Keep going! Good luck :)

  2. Maria says:

    Awesome tips and hacks! Thanks Adam <3

  3. Diane says:

    Hey! I was just curious if you can link Triposo with previous accommodations made through (since the platforms are linked)?

  4. Besides what to pack and where to go, we try to do as little planning as possible. We booked a trip to India for two months and didn’t plan a single thing besides our first night in the city we landed in. Other than that we figured it out.

    We prefer not planning and find the spontaneous way of travel the best for our liking. We really do love the adventure of it, and when you over plan, that can just cause frustrations when things don’t turn out as planned.

  5. Tara Molloy says:

    I love travel apps. Never used Triposo before. Thanks for the tip!

    I like to go to top 10 sites too. Especially when looking for places to eat. But sometimes I find that when you get there… they no longer exist!

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