There’s a Million Ways to Do It. How I Plan for Trips

A mind that is stretched by a new experience can never go back to its old dimensions.

Oliver Wendell Holmes

Planning trips is like pulling teeth for some people, but I’m a weirdo and love it. It’s part of the travel experience and it always gets me pumped up for an upcoming trip. For those of you who hate planning, this post is for you. For those of you who love to plan, but also love to creep on how other people do it to get more ideas, please creep on this post.

Step 1: Set a Budget

It’s boring. It’s sometimes terrifying, but it’s the necessary first step in going on vacation. If you can afford to go to your backyard and not across the planet, you need to choose a trip that fits in your CURRENT budget without making you flat-out broke.

Choose a destination known for being less expensive if money is tight. Find cheaper accommodations like a hostel, fly economy, or opt for an all-inclusive deal. Once you have your budget, it’s easy to eliminate destinations that won’t fit in that. Those destinations are for the future and give you more motivation to save for a more decadent getaway in the future.

Step 2: Pick Your Destination

What place do you keep talking about, Googling, and drooling over pictures on Instagram most often? What are the top places you’ve been wanting to visit? Narrowing down where you want to go is exciting, but with the entire world as your oyster, it can be hard to choose. Luckily, you’ve narrowed it down with your budgetary constraints.

Make this as fun as possible for yourself. Decide whether you want an adventure-filled weekend, a lazy week by the beach, or something in between or all of the above. It’s your vacation, make it as wonderful as possible. One of my favorite ways of choosing a vacation is by spicing it up with adventure. Spinning a globe is one of my favorites, but it’s not always helpful when I’m on a major budget. Check out my fun ways to choose a destination here.

If in doubt, pick 5 places. Write the names down on separate pieces of paper and choose one from a hat.

Step 3: Research the Location, Sites, and Must-Sees

SO many people choose a destination and immediately book their flight and accommodations. From experience, this is an easy mistake (sometimes) to make. Hear me out. I’ve been to places thinking I booked a hostel or hotel really close to everything I wanted to see to later find out (after arriving) that I’m miles away from everything I was looking forward to seeing.

This is why I ALWAYS make a list of all the sites, attractions, and sometimes restaurants I want to see/try and put them on a map before I even buy my flight. I put them on a map using either Google or Sygic so I can see exactly where everything is in relation to each other. This makes it easier to plan your days based on what’s close to another site and allows you to see where potential hotels or other accommodations are in relation to where you’ll be spending most of your day.

Step 4: Investigate Transportation Methods

Are you in a rural area where you’ll need to rent a car? Are you in a city with fantastic public transportation? Can you walk everywhere? Once you know what you want to do, you can start to figure out how to get there. You need to know what options are available to you before you choose a hotel. If you don’t want to rent a car, but you’re staying in the middle of nowhere, you need to be able to move around.

Use what’s available as an opportunity to make traveling more fun and immersive in local culture. Research what the locals do and use. It’s probably your best option as well. However, you can make it more unique by renting bikes or even sail. Your possibilities are endless.

Step 5: Choose Your Accommodation(s)

You’ve got your budget, your list of sites to see, and researched how the heck you could get to all of them. Now it’s time to choose your accommodations. Since my room is usually where I spend the least amount of time, I usually opt for a place that’s central to everything I want to see and use it as a base to spring from.

Some people would rather stay on the outskirts of the action for a quiet night of restful sleep. Others want the full hustle and bustle. There’s an accommodation for everyone. Hostels tend to be the cheapest option, especially when outside of the main tourist area. Hotels can be pricey, but good deals can be found online and the further you go from the center of town.

When searching, always look at multiple websites and different accommodation types you’re willing to use. Some hotels even list their rooms on sites like Airbnb for much cheaper prices than can be found on their own websites. Assess how much time you want to spend in your room and factor that into the type of place you want to stay in, especially if your budget isn’t crazy high.

Step 6: Book Everything

This is the step where your brain says YES, but your wallet say OOF. If you’ve stuck to your budget and kept money aside for expenses like food, adventures, admissions, and drinks you will be completely fine. You prepared for this! Now that you’ve booked your hotel, flight, rental car, bus tickets, you name it you can sit back and celebrate.

Don’t forget to book tours and entries into more popular sites ahead of time if possible. Sometimes attractions can have weeks or months-long waiting lists, so don’t miss out by not booking as much as possible ahead of time.

Step 7: Make a Loose Itinerary

Your plans are going to change daily as you walk by new, exciting places you want to try out but didn’t plan for. Plan your itinerary loosely. Allow for more time than is necessary so you have the flexibility to try new things and spend more time in places you’re loving without feeling like you will miss out on several other stops.

Pro tip: Plan your days in clusters. Since you’ve already made a map of your must-see attractions and tours, try to do as much as possible in one area each day. Lots of destinations have tons to see and do in one area and then another. They aren’t typically evenly spaced out. I like to go to the furthest attraction at the start of the day and get closer to my hotel towards the end. That ensures I’ll have the energy to do everything without worrying about having the energy to make a long trek back to home base.

If you’ve ever been on a vacation, you know that shit happens. Sometimes it hits the fan and splatters all over your beautiful itinerary. That’s okay. It’s also why we need to be flexible. Give yourself a break and remember you’re on vacation. Experience what you can, when you can and enjoy being in the moment. There’s always next time.

Step 8: Happy Dance Celebrations

You’re all set! Go break out some music and do a happy dance. You’re going on vacation!

Need more tips and tricks about travel planning? You’re in luck. I did a post two years ago on that very subject! Let me know if these tips helped you and if you have any suggestions. I love learning from fellow travelers and swapping stories!


7 thoughts on “There’s a Million Ways to Do It. How I Plan for Trips

  1. Sounds like we have similar travel-planning styles. My favorite part of planning is putting everything in Google Maps, narrowing down a neighborhood, and then going on the hunt for the perfect accommodation! Much more fun than buying travel insurance or booking a rental car!

    Liked by 1 person

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