vacation planning process 101

The trip planning process is unique for everyone. I absolutely love the planning process however it can be viewed as tedious, confusing, and stressful for new travelers or for people that flat out don’t enjoy planning in general. This weeks post is your one-stop shop for all of your trip planning needs!

It All Starts With A Little Inspiration

For us, the process always begins with a seedling of an idea. I keep a list in my phone of bucket list places and am constantly on the lookout for new (to me) places that spark interest.

At the start of a new year, I like to map out at a high level what our plans look like. This includes weddings, events, etc. so then I can see what our pockets of opportunity are. This year we added on additional travel days to a wedding in Milwaukee and also realized we had quite a few pockets with no plans at all which immediately put my planning gears into motion.

After identifying our available times (based on paid-time-off and available funds also) I refer back to the places that spark interest and look at what’s feasible. Yes, I’d love to go to Europe every year but for us, that isn’t realistic. We went to Europe in 2018 and knew that we’d go again in 2020, so 2019 was our year of domestic travel and more manageable trips.

We also like to think through the type of trip we want. Are we craving exploration, experiencing other cultures, warmth, or relaxation? Through our conversations is when I’ll start to notice patterns with places that we’re interested in. For us, this year our list included Montauk, Chicago, Washington D.C., Vermont, Florida, and Grand Cayman.

You Can Always Trust A Book

Once we hone in on a few places that sound great, I immediately turn to books! The Internet can be confusing with influencers trying to sell you on different places and Google searches that turn up thousands of results.

First, I recommend finding the official city/town/state/country site of the place you’re considering visiting. Most offer free visitor guides that they’ll mail you. These guides will have helpful tips (costs of parking for example) and details on where to eat, and what to do and will generally get you excited at the thought of your potential visit. Here are a few examples that I used for recent trips:

  1. Visit Colorado
  2. Visit Milwaukee
  3. Visit Tampa

In addition to the visitor guides, I LOVE the Lonely Planet guides. These books are the ultimate guide to any country or city you want to explore and I use them for every international trip I plan. They include endless options of where to stay, details about the culture, and inside secrets. After pouring through these books, I not only have a better idea of the place but can clearly tell if it’s somewhere I want to travel to or if I’ll put the trip idea on hold.

I also recently got this beautiful book by The New York Times called 36 Hours Europe (pictured above) which will surely inspire anyone during in the planning process.

Getting There and Where To Stay

After you’ve decided where you want to go it can be really exciting and you want to book your flight and accommodations right then and there! I could do an entire post on flights alone because the art of getting the perfect flight is a tricky one. The best thing you can do though it wait until the airline tickets are at an ideal cost. This will depend on how far out you are from when you’d like to travel, the airlines you want to fly, and where you’re flying to and from.

We almost always fly budget airlines and during off times of the week to save money. We also use tools like Hopper to map prices and Google Flights to track whether or not we’re booking at an expensive time or not. Also, always search for flights in Incognito mode within your browser. The airlines are able to track if you’re interested in a flight and you’ll see the cost slowly increase the more you search for it.

We also have the luxury of scheduling flexibility with our jobs and easy planning since we don’t have children. Knowing that we want to go to Italy in 2020 is really the only planning parameter we have. We will want to go when the weather is nice, when tourist crowds are low, and flights are affordable. This could mean we’re going in the middle of April, or early September. If you don’t have this flexibility in travel dates, then really rely on the budget airlines and flight tracking tools to know when to pull the trigger.

For tips on accommodations read my post here!

What Can You Not Live Without

One of the best pieces of travel advice I ever got was mapping out ahead of time the things that you absolutely want to do while you’re at your destination. What are those things that if you don’t get to do, you’ll be devastated? I like to come up with 1-3 of my own and also for Phil since these items are usually different between us both.

Then, I prioritize weaving these things into our plan first. Going to the Anne Frank House in Amsterdam was one of those items for me. Based on ticket availability, timing, distance, weather, etc. you’ll start to see your plans get some structure as you’re mapping out those must-do elements. After I’ve organized our must do’s, I move onto filling in the second tier of things that would be nice to do.

This is also usually around the time I also ask friends who live in the area or have visited for feedback and advice. Although I don’t take all that they offer, you’re bound to hear of something new that sparks interest and from who better than people you trust!

Go With The Flow Vs. Plan Every Detail

I try to balance our trips with set activities that are planned ahead of time with time set-aside for exploring, talking to locals once we’re there to get recommendations, and just seeing how we feel. This balance will be different for everyone! I’ve found for us we like to have at least one set activity/plan per day to anchor us otherwise, it can turn into “where should we go?” “what should we do?” and then it feels like we’re wasting time trying to decide.

I also always map out restaurants and places to eat since good food is always a travel highlight for me. Even though I’ll find dozens of places ahead of time knowing we can’t hit all of them, it’s nice knowing we have some well thought out options. I will also make a few different reservations for throughout the trip knowing that we’ll likely cancel a few while we’re there to accommodate a change in plans or how we’re feeling that day.

For example, in Chicago on our last night, we had dinner plans to eat in the sky-high Handcock tower which overlooks the city. Not only were we exhausted, but it was so foggy we wouldn’t have been able to see the view of the city we had planned on. Instead, we canceled the reservation and ordered deep dish pizza and ate it in our hotel room which ended up being glorious.

Keeping Yourself Organized

I’ve used the same Excel document for every trip we’ve done for a few years now and it works perfectly. I map out each day individually to include transportation details, lodging, the planned activity (even if that activity is just “exploring no set plans”), reservation details, and notable meals. This is where I get into the real details of the trip. I use Google Maps to check on the distance of the places we’re visiting to bake in travel time, I store my confirmation numbers and key addresses. For international travel, I always include a tab with the U.S. Embassy information and what number to call in case of an emergency.

Planning Excel Doc

Final Touches

Now as the trip is finally taking shape, you’re almost ready to go! Here are some other helpful planning posts I’ve done:

  1. Packing Organizers 
  2. Beach Vacation Must-Haves
  3. Finding Something Special While Traveling
  4. Museum Review Around The World

What are some of your travel planning must-dos? I’d love to know in the comments below!

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