Planning a trip can be overwhelming and stressful at times, especially larger trips. The planning process can take time depending on where you’re planning to go. I always recommended planning early if possible to relieve stress and give yourself plenty of time to make reservations and develop a plan for your trip. If planning in advance isn’t a strength of yours, I’m hoping this guide gives you some ideas to make it a little less stressful!

Where to Start When Planning a Trip

📍Pick your desired destination, the fun part! Sometimes this is easy but if you aren’t sure where you’d like to go, consider what types of activities you’d like to do, if you’d rather relax or adventure, and how far you’re willing to fly or drive to reach your destination.

⏰ Determine timeframe. I like to start the planning process with a general idea of when I’ll be going on a trip. This may be depend on the area you’re visiting and whether there’s a better time to visit or it may be based on your availability. I usually gravitate towards traveling in the summer or fall months, the weather is usually better and there’s more opportunity for activities.

🚐 Decide whether driving or flying makes the most sense. Driving can take more time but it saves you the hassle of having to find a rental car or other means of transportation at your destination. Plus, there’s no limit to what you can bring, if you’re an over packer like me!

🎟 If you have/want to fly, I’d book flight tickets pretty soon after deciding on dates. Similarly, if you decide to drive, plan out any reservations you’ll need for accommodations or tickets needed for various activities.

How to Develop an Itinerary

• Once you have a general timeframe decided, know where you’ll be going, and choosen whether to drive or fly, it’s time to start forming an itinerary.
• I typically create my itineraries in Notion but any word doc, excel sheet, or even hand written will work fine!
• An itinerary can be as detailed as you want it to be! If you feel more confident with a detailed plan of activities and sites to see while on a trip, a list of several things may be better for you. Or, if you’d rather go with the flow on your trip but still resort to a list of ideas of what to do some days, a lighter itinerary may work better. Reflect and be realistic with what will work for you! It is vacation after all so nothing with an itinerary has to be set in stone, it’s really just to have something to guide you, especially if it’s a new destination you’ll be visiting.
• I like to list out all the days I know I’ll be on a trip and include:
  • Where we are sleeping that day
  • Any “must sees” if it’s a specific area
  • How much drive time is required between sites
  • Resturants to try
  • A collection of hikes, sites, or other attractions I want to visit that given day
• On the itinerary, I also include reminders for myself if I need to reserve tickets for an activity or if I should check the weather before committing to a particular activity on a given day, etc.

How to Find Things to Do

• I usually always start by browsing on Pinterest to find blog posts or other online sources that others have shared from visiting the area. I love hearing about other’s experiences and gaining a visual of what the area I’ll be visiting looks like. It really inspires me and excites me while planning a trip!
• Social media will be your friend. Similarly to Pinterest, I’ll browse instagram, youtube or TikTok to gain video sources of what others did in the area I’ll be visiting to give me ideas.
• I also recommend making a list of what you find through research. This will help you keep organized on things you’d like to do and see throughout your trip and then add to the itinerary later.

Tips

• Be flexible with plans! Things can change so easily while traveling so even with an itinerary, it’s important to have an expectation that things may not go according to plan and that’s ok! Whenever I’ve gone on a larger trip, there are always changes to plans that happen just depending on weather, crowds, fatigue, etc. In my experience, because I had a list of so many places and activities I wanted to see for a trip, I would sometimes switch days or plans around if needed while on the trip which worked so well and gave me alternate ideas if I needed to be flexible.
• I always recommended planning at least 3-6 months in advance, more for ease of mind that things are booked and there’s a plan in place.
• Start a check list of packing necessities you’ll need to bring, especially if it’s a big trip. This is so helpful to ensure you don’t forget anything!
• If you’re a visual person, I’d recommend adding photos of certain spots you’re excited to see on the trip to your itinerary or planner. I do this and it always helps to see what I’lll be doing and makes me even more excited for the trip to come!