How to Plan a Trip: A Guide for Cultural Explorers

Shannon Whitney

“I have to go on this trip to Peru because I wouldn’t even know where to begin planning something like this. Tagging along with you is my only shot,” my sister told me over the phone. “Now walk me through which flights you bought; we’re coming.”

Of course, she and her husband, as well as my brother, joined my husband and me for a week in Peru last April. They all told me they were up for an adventure and wanted to see Machu Picchu, but had no idea where to start. I took the reins.

Another friend told me she was nervous to pull the trigger on a Eurotrip because she knew it was a chore to plan and she was afraid she wouldn’t be able to see it all. I told her she was right- seeing an entire continent in one trip is not realistic.

Deciding where to eat in my hometown, let alone another country, sometimes feels like a monumental decision, so I get that planning to go somewhere is never as much fun as actually being there. Is it crazy that I find a sick joy in all the preparation that leads up to takeoff? You’re reading a packing blog, so I’m guessing we might have that in common.

Somehow I’ve become the defacto travel agent for my family and friends.

How did I get here? I have no special training, except that I’ve had a bunch of practice.

I work a traditional full-time job. My vacation time is ok by American standards, but it’s by no means unlimited. My trips are usually somewhere between a long weekend and a week in length. I would love to spend months in one place, but that doesn’t work with my current gig.

This means I put extra pressure on myself to maximize the time I spend traveling. I seek the perfect balance: I want to return to work refreshed but, at the same time, I have no idea when I’ll be back to any destination so I want to see as much as I can.

Using a lot of trial and error, I devised a trip planning method that works for me. Here’s how to plan a trip that’s not crazy stressful, but still includes all the things YOU want. You don’t need a travel agent or months of legwork. You don’t even need seven new apps and a subscription to some janky online service. Let’s do this.

Decide Where

This is the biggest and sometimes scariest moment of planning anything, so let’s get it out of the way right now. Where are you going and when are you going there?

Take Into Account Weather & Peak Tourist Season

Figure out if it’s seasonally popular for a specific reason- it’s cheaper to go to Peru during the rainy season, but some of the famous trails are impassable… so not worth it. Other places, it’s awesome to go off season to get better deals and avoid crowds (shoutout to anything with Disney in the name and most of Europe).

Compare Flight Prices

Before making a final choice on dates, I always compare flight prices. Flying during the middle of the week is often significantly cheaper than leaving Friday after work. Shop for deals and compare on Google Flights, Expedia and Cheapoair.

If you decide to approach flights from a less traditional path, figure out when and how much time you have, then look at deal destinations. I love Airfare Watchdog and to get started.

Pulling the trigger on a flight is usually the hardest part for me. Often, it’s the most expensive part of the trip, plus it feels final. Once it’s done, the heat is on.

Research the Destination

Once you decide where and when you’re going, it’s time for my favorite phase: research. Dig into travel blogs, Trip Advisor, Viatour, Yelp, Foursquare and Google Reviews. Pick your friends’ brains asking for stuff to do and what to skip. Also, restaurants: always ask about food.

Use Blogs & Make a List

There are some blogs I love because they travel at my speed and have similar interests. Figure out which ones gel with your style and use the search bar to see if they’ve been to your desired destination. Add all of these points of interest to a list.

Full disclosure: I have a running Google Doc for each continent where I paste links to blog posts for this purpose. My own little archive cuts out some of the work when I actually pull the trigger and purchase a ticket. 

Sometimes I’ll check out a guide book at the library or bookstore for ideas too. I know, I know, but really there are some hidden gems.

Now you have a list of stuff to do, including food, tourist sights, museums, photo ops, hikes, and on, and on….

Dig Deeper

Using bullet points under each one, dig into the details. List the hours of operation and which days venues are open, or closed. Be sure to check out the official websites instead of trusting Google or Trip Advisor for the most up to date info. Include entrance fees and any tips to beat the lines. Jot down things you can’t miss (i.e. a specific painting or a drink to try). If it’s a hike, I try to include milage or landmarks used to find the access point.


Feel free to continue to add to your list as you go. Use Google Maps to build a map for each city you’re visiting ( > your places > MAPS> Create Map). Plot all the activities, neighborhoods, restaurants, bars and must-sees on your own map. Add airports, train stations or any other transportation you plan to use.

Organize Your Map

I recommend color-coding food and accommodations with separate symbols. I don’t generally plan where I’ll eat on each day, but it’s nice to be out and about and reference my map for nearby recommended chow. I also use another color to designate things I absolutely want to do versus things to do if there’s time.

When looking at your map, it’s easy to see which areas of the city are most important to your trip. The map is great for figuring out which destinations can be paired together and covered in the same day due to proximity. Luckily your map will allow you to visually group what’s each the neighborhood.

Plus, it’s helpful for getting an idea about routing your transportation. If some of the places you want to visit are particularly spread out, you may have to consider renting a car or shell out for a bus pass instead of single rides.


At this point in your planning you have a long list and a map covered in colorful markers. It’s beginning to feel overwhelming! How will I ever do everything I want? This is not the relaxing getaway I intended! Should I extend my trip by six weeks to accommodate it all? (The answer to that is always yes. If you can, you should absolutely take a longer trip, duh.)

Take some deep breaths. You’ve got this.

Now’s the time to spend some time with your travel companions, if you’re going with someone else. Decide on the non-negotiables. For example, I went to Rome this year and there was no way I was leaving without visiting the Vatican City. I’m an art history student and I knew I couldn’t live with the Catholic guilt if I skipped that. My husband was very adamant abouut seeing the Colosseum. We enjoyed St. Pete’s and seeing where the gladiators fought. We both we left Rome satisfied.

Read the Reviews

And take them with a grain of salt. What do people recommend? What does the internet say is overhyped, or ok from the outside? While the people of the interwebs can be whiney or frustrating, they are sometimes helpful in figuring out if popular places are worth the trip, if a museum is child-friendly, or how to avoid the very worst dish on the menu at the restaurant with the world’s worst service.

From here you can narrow down which sites are worth swinging by if you have time. Hopefully you’ll get a rough idea of how long you’d like to spend at each one- is this a full day hike, or just a morning out and back? More importantly, should I bring a sandwich for lunch?


Now that you know where you’re going and what to do, book a couple of things. For starters, accommodations are important. By comparing your map to the ones on booking sites, you can find a rental, hotel or hostel near your points of interest.


Keep an open mind with accommodations. If you’re a Hilton person and you have a heap of Hilton points, go for it. If you’re paying for this in cash, compare Airbnb, VBRO and HomeAway. I love playing house in someone’s apartment. I walk around saying, “I could totally see myself living here.”

Don’t forget about hostels too, HostelWorld and HostelBookers have some crazy deals, plus reviews. All of these sites have a map feature you can bring up alongside your map to find a convenient bed. If you’re a hotel person (and that’s ok!), I love the Blind Booking tool on Expedia and Priceline.

Now you have a place to sleep.

Book the Big Activities

While I always make a pretty extensive list, I don’t like a strict itinerary packed full of activities. Generally, I assign one activity or area of the city to each day. Sometimes that’s a tour, or a hike, or a museum, or a neighborhood full of shops and galleries. Make yours as busy or as open as you’d like. If you need to schedule naps, by all means. If you want to go to six museums in one day- best of luck, my friend! Book anything that requires it in advance.

Sync Up!

I sync my map and my research doc to my phone, and enjoy the flexibility without feeling like I’m missing out or I need to look up the next thing instead of enjoying my mojito. I know I have all the info right in my pocket. If there’s time to spare, I have ideas about what’s open in the area. If we’re hungry, I know a couple of nearby places to check out. I’m prepared, but not working off a packed cruise ship-style schedule.

The best part is, if I stumble upon something great, or a tour guide recommends a lunch spot, I say yes! I’m not committed to tons of reservations or plans.

Personally, I work off Google Docs and Google Maps. Google also has a trip planner- Google Trips. TripIt and TripCase are popular itinerary apps for our team, as well as Evernote to keep all the info in one convenient place. Even if you’re a paper person and you want to print this out, I recommend having one local copy saved on your phone for easy reference.


Things are getting fun, right? Even if you’re still a couple of months or weeks out from your trip, start making a list. Figure out the best bag, may I recommend a backpack?

If backpacking feels extreme, or something for the likes of free spirits and broke college kids, you have not seen our packs. The Outbreaker travel backpacks are made specifically for cultural explorers like you. They are as sleek and spacious as a suitcase, but easier to maneuver in a crowded airport or bus.

Outbreaker Travel Backpack

The generously sized 45L travel backpack is the maximum allowable size for a carry on for most airlines. The 35L is better for smaller torsos and more restrictive budget airlines.

Since these are carry on bags, there’s no chance that the airline will lose your luggage and mess up your trip. The harness system is robust, like a hiking pack, so the weight is smoothly transferred to your hips for a comfortable carry experience. The interior design with six pockets in the main part of the bag keeps everything nicely organized. The computer sleeve is tucked close to your back to increase comfort and security. And, of course, it’s made out of waterproof sailcloth, so that downpour as you leave the train station won’t ruin your trip, or the contents of your bag!

Add a set of packing cubes to maximize interior organization and make packing and unpacking a breeze.

Since you know how long you’ll be gone and what you’re doing, you can commit to carry on travel! Those weird “just in case” items can be paired down thanks to all your destination research. You know what to pack and checking a bag isn’t necessary.

Decide whether you need any special equipment or if the climate calls for a heavy down coat that you don’t have. Is your passport valid for at least six months after the end of your trip? Please check. Right now.

Packsmith is packed- pun intended- with packing lists for countries all over the globe. I always search this site for my destination for both packing and trip recommendations. Add this step to your planning process to avoid running to Target six times the week before you leave for one last thing.

Final Prep

The trip is coming together swimmingly. This is the point at which I get very excited.

Find out if you need any shots or meds just in case. Double check whether the country you’re visiting requires a visa or any specific paperwork.

Spend the last couple of weeks (or days) reading books set in your destination’s location. Watch a movie. Google commonly used phrases to get ready to barter in the market. Read up on cultural nuances or local fashion trends. Skim regional news. Figure out the city’s sports teams.

Be sure to save the area for your destination as an Offline Map in Google Maps so you can use it with or without data. Save your Google Doc (or Evernote or whatever you use to list) locally too so you’re not waiting on the internet every time you need to reference it.


Now get out there and see the sights, eat the food, take the selfies! The tough stuff is tackled and you have a detailed list and a colorful map to show for it. You should be feeling confident about all the cool stuff you’ll see as opposed to overwhelmed by the need to do 1,000 things in 10 days.

No, you won’t see everything. But now you know what you want and you have a plan.


Planning a trip to somewhere new can be intimidating, but anyone can do it! Plan an encompassing, yet flexible trip with these steps:

  • Decide- where and when are you going
  • Research- find stuff to do
  • Map- plot it all on Google Maps to visualize
  • Prioritize- figure out what you must see/do/eat and what’s less important
  • Book- make reservations and loose plans
  • Pack- research what to bring
  • Prep- get pumped with fun cultural research
  • Go- see ya!

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