How to Plan a Trip: Tips from Two Crazy Travel Itinerary Planners

I am a planner. Not just a planner, but a CRAZY planner. I never go to the grocery store without a list, and I had my new apartment lined up three months before I needed to move in. So when it comes to traveling, I create super detailed itineraries, and thankfully, my best friend and travel partner is just as obsessed with itineraries as I am! So if you need help planning a trip, here is how to plan a trip and our top tips for creating a travel itinerary from two crazy planners! 🙂

How to plan a trip and create an itinerary

My travel itineraries vary depending on where I’m going and for how long. And I don’t always have a strict itinerary! If I have a lot of time in a place or if I’ve been there before, I’m fine with a more leisurely trip with little planning. On my last trip to Copenhagen, I had been to almost every main spot in the city before because I had studied abroad there, and I had two weeks there so I just made a list of things I wanted to see again and made decisions about what to do the day of. This worked out great because I didn’t want to climb the Christiansborg tower or the Round Tower on days with bad weather and not get good photos, so the flexibility of seeing what the weather was going to be like instead of having to stick to a rigid schedule worked out well.

On the other hand, I’ve had a lot of quick trips in new places that I’ve created VERY detailed itineraries for. I went to New Orleans recently for the first time and because I had scheduled three tours and had a long list of things I wanted to do, I made an itinerary so I could make time for everything.

On my recent trip to the Faroe Islands, Matt and I only had 3 days to see tons of things, we had to account for driving time, and we couldn’t miss scheduled ferries because there were so few of them, so you know I made a travel itinerary! Matt joked that I had planned out every second of our trip there, but it was no joke- I planned out every single minute of our trip AND I made alternate itineraries for back up! I know I’m crazy, don’t worry.

So thankfully, my bff and travel partner, Stephanie, is just as crazy as I am! We’ve traveled to Chincoteague Island, Italy, and New York City together, plus she’s come to visit me in Philadelphia a few times. And for each trip, we’ve created travel itineraries. So here our all our tips for creating a travel itinerary so you can be crazy planners like us!

First of all, why do you make itineraries and when did you start making them?

Stephanie: So a fun fact about me…I love lists. I keep lists & spreadsheets about all kinds of random things (favorite quotes, restaurants I want to try, etc.) and I love to stay organized. So naturally that carries over to staying organized for travel and making itineraries.

In high school, my church youth group spent our spring break in Charleston, SC every year. We spent the week helping out at food banks, building decks, or repairing roofs. At the very end of the week we’d spend our last day hanging out at the beach & then spending the evening in downtown Charleston. My freshmen year I didn’t really know what to expect and just went with the flow…it was a great evening but my friends and I definitely didn’t make the most of our time in such a beautiful & historic city. I wanted to explore the city & take in all I could. Every year after, I made sure to research the best restaurants to eat at, picturesque streets to stroll down, and cool places to visit. I learned that having a bit of background knowledge beforehand really helped in enjoying the city and this started my love of making itineraries for trips.

Julia: I plan literally everything in my life. I don’t go to the grocery store without a list, and I plan out my day in my business every day. So if I plan every part of my day, I definitely want to plan my travels to take advantage of every second I’m in a new place!

Growing up, I would go on long road trips with my family and my parents would plan everything, so I actually didn’t start planning my travels until I had made a few mistakes on my first solo trips. I studied abroad in Denmark during college, and I took a few trips around Europe during my semester. One of the first ones was to Estonia with a classmate, and I landed in Estonia with no Euros, maps, itinerary, or cell phone. We ended up getting separated with me on a bus going to who-knows-where, and long story short, we miraculously found each other again. And needless to say, I have learned my lesson and am always over prepared!

How far in advance do you start planning a trip?

Stephanie: As soon as I decide that I’m going on one! It’s never too early to start planning 😉 I try to nail down flights and accommodations as early as possible as those are the two most important pieces to me. They are usually the most expensive aspects of a trip so I want to book those before prices go up. Additionally, once those pieces are set, it is easier to plan the rest of my trip around them.

Julia: I do some general planning as soon as I get the plan tickets bought. Since I usually purchase tickets months in advance, I have plenty of time to get an itinerary together and will start doing more planning at least 2-3 months before my trip, especially if I’m going to be traveling to a few different places in a country or visiting multiple countries. I want to know where I’ll be going and for how long so I can book my Airbnb and transportation well in advance.

Have you ever gone on a trip without an itinerary?

Stephanie: Nope, never. There is always an itinerary, even if it is a loose one with just the basics mapped out.

Julia: Since learning my lesson in Estonia, nope! I do have looser itineraries if I’ve been to a place before or if I have a lot of time, but if I’m short on time, I will plan out literally every second of my trip (if you think I’m joking, ask Matt about our trip to the Faroe Islands). I’m going on my honeymoon in a few months, and since it’s going to be a more leisurely trip to relax after the wedding, I don’t have much of an itinerary planned other than when we take day trips into bigger cities.

What tools do you use to create an itinerary?

Stephanie: I LOVE Google Drive. There are a variety of tools within it (google docs, sheets, and maps to name a few). I keep everything organized on google drive & it is easily shareable with my travel buddies.

I especially love using Google Maps (and creating/saving my own map within Google Drive). It is great for organizing points of interest, transportation hubs, food, etc. You can easily see what is near what and plan a route. Planning around meals and opening/closing times of museums, parks, etc helps in determining my route or plan for the day.

Julia: I also love Google Drive! I like that you can organize things in different folders and that you can see everything on your phone, even when you don’t have service. I can easily share my itinerary with my travel partners and with my parents so they’ll know where I’ll be. I also like that you can upload things like tickets or information packets to a Google Drive folder to keep every single thing you need for your trip in one place.

What websites or resources do you use for research for your trips?

Stephanie: I use so many! Pinterest & Instagram are great for inspiration and Tripadvisor is great for reviews. Travel guide sites like Lonely Planet, Fodor’s, USA Today, Conde Nast Traveler, and Thrillist are also great because they have tons of “best of” lists. I’ll also look for travel blogs that has articles featuring the country or city that I’m traveling to. And then, of course, the country or city’s travel/tourism website which has a wealth of information.

Julia: I exclusively use Pinterest to find travel blogs! I like finding resources from people who have similar interests to me, and you can find all kinds of specific information like the best spots to take photos, hidden gems, and small towns you wouldn’t know to look for on Google. I also upload all of my travel posts on Pinterest, so you can follow me and check them out if you’re looking to plan a trip 🙂

If you’ve made any mistakes with your trip planning, how did you take care of it?

Stephanie: I don’t really encounter mistakes per say, but rather stumbling blocks or interruptions to plans. One example that comes to mind is from a labor day weekend trip to Charleston, SC for a friend’s bachelorette weekend. We wanted to eat lunch at a certain popular restaurant while we were exploring the downtown area. We tried making reservations online the night before which didn’t work as the restaurant didn’t have a system set up for that. The next morning while exploring the downtown area we tried calling the restaurant to set up reservations only to get their voice mail! Trying again later we finally got someone on the phone who told us that they didn’t take reservations for lunch and we would just have to show up and wait 1-1.5 hours for a table to open up.

We quickly vetoed that idea as we only had half a day in the city and didn’t want to waste part of it parked outside a restaurant. By this time it was noon and with it being a holiday weekend we feared we’d have trouble making reservations elsewhere. Me being me, I had a short list of restaurants grouped by location within the downtown area and I called a few to see who took reservations and had an opening for us. In 5 minutes we had a table booked for 1 p.m. and we changed up our route/order of stops to explore a different section which perfectly timed us to arrive at the restaurant for lunch. And it ended up being the cutest spot where we ate on the porch and had amazing food and service.

My advice is to just be flexible & have back up plans and resources to fix the issue or change course.

Julia: I always make backup plans. During my trip to the Faroe Islands, I had rented a hotspot and was told that it would work there, but it didn’t! So I didn’t have service at all unless I was connected to Wifi. Which typically wouldn’t be a big deal, but we were driving all over the islands to remote villages where we didn’t see a single person. So if we got lost, we could be in big trouble. Thankfully, I had planned ahead and had printed out maps with directions to every single spot we were driving to AND I had uploaded all the maps to my Google Drive folder. So we didn’t get lost!

I’ve also had issues with transportation, which is out of my control. During my trip to Hamburg, there was a crazy lightning storm that messed up all the trains and delayed my trip to Luneburg. So I just swapped my day around and did the things in Hamburg I was planning on doing later in the day so I could still see as much as I wanted. So just be a little flexible and go with the flow if you have to.

Do your travel buddies usually like having a strict itinerary?

Stephanie: Some do and some don’t…everyone has a different travel and vacation style, so for those who want something more leisurely, I try to plan in breaks and down time.

Julia: It probably drives Matt a little crazy (especially when I planned every single second of our Faroe Islands trip), but I think he’s gotten used to it! Stephanie is ok with it, of course, and she might plan even more than I do.

I have traveled with some people who aren’t crazy planners like me, and I think it helps to let them know far in advance what your travel style is. If they’re not planners like you, I would budget in extra time for things in case they want to be spontaneous and see something that catches their eye. And definitely ask them about things they want to see before you start planning so they don’t get bored with your itinerary.

What has been the best trip you’ve planned well?

Stephanie: Italy!! In 10 days my friends and I visited 12 cities/islands and traveled over 1,000 miles! Italy is just such a beautiful and amazing country with so much to see and do. I knew that we’d have to be strategic in how we visited the country for everyone in the group to have the best time and see/do all that we each wanted.

Julia: I keep bringing up the Faroe Islands, but I am very proud of how I planned that trip, especially with how few resources there are on the Faroe Islands compared to most other places! We had a jam packed trip and got to see so many amazing places. The Faroe Islands is a place that would be hard to just wing it, and I was pretty happy with how the trip turned out. I was over prepared with maps and food (most towns don’t have restaurants or grocery stores) and budgeted extra time in case we got lost, and everything went off without a hitch.

What’s your #1 tip for planning a trip?

Stephanie: Have fun! Discover what matters most to you & focus on that.

Julia: I recommend having at least a loose backup plan! You can’t control the weather or train schedules, so you want to have some flexibility if it pours all day and you can’t walk around a city like you planned. If you have some backup plans in your itinerary, you’ll still be able to make the most of your time instead of wasting time trying to figure out what to do with your day if your train is delayed or the weather is bad.

I hope Stephanie and I have given you some ideas for how to plan a trip! If you want some itinerary inspiration, I’ve created itineraries for three days in the Faroe Islands, one day in Copenhagen, ten days in Italy, four days in Philadelphia, three days in Hamburg. Happy planning! 🙂

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