The Ultimate Guide to planning for your next vacation


5 Steps to make your dream vacation a reality

Pull out that bucket list and get ready for some tips to make that dream vacation a reality! Take it from someone who is obsessively organized, this is your step by step guide to ensure your trip goes exactly as planned.

NOTICE: Please take all appropriate cautions when planning your trip during the COVID-19 Pandemic. However, even if it is not currently safe to travel, you can always PLAN your trip out - weeks, months, or even years in advance.

I’ve broken this guide down into 5 digestible steps: (1) What do you enjoy about travelling, (2) Duration, Budget, Destination, (3) Flesh out the big details, (4) Dig into the finer details, and (5) Make it official and prepare a checklist.

step one what do you enjoy about travelling

Step 1 - What do you enjoy about travelling?

This question is KEY and the first step to complete before even THINKING about when or where you want to go. Everyone travels for different reasons, and it is important to fully understand and recognize those reasons for every traveller in your party so that everyone can enjoy the trip. Don’t assume the things you like are the same for everyone else tagging along.

Here is a short list of the types of things I am talking about:

  • Trying new foods (or do you prefer familiar foods when out; what kinds of foods?)
  • Shopping (and if so - what kinds of shops)
  • Museums or general historical / cultural activities
  • Scenic walks (in the city or country?)
  • Local attractions/activities (such as putt-putt, zip lines, rock climbing, parks, etc…)
  • Hiking (how intense and for what purpose)
  • Taking photos
  • Relaxing in a nice hotel (such as reading a good book in a hot tub)

Of course there are more things to do while travelling, but that broadly covers things to do.

step two duration budget destination

Step 2 - Duration, Budget, Destination

Now that you know what kinds of things you are looking for, you can start to broadly plan the trip. I highly recommend starting with a “big picture” approach and then working your way into the finer details.


With the list of people coming and work schedules considered, how much time do you have available to be on a trip? At this stage you are not thinking about WHEN yet so much as generally how long the trip could be. This will help potentially narrow the scope of destinations as well (such as having only 3 days means you likely don’t want to fly anywhere but instead look in a 5 to 8 hour radius of you for interesting destinations).


This is just as essential as duration, as with these two pieces of information you can get a good sense of what you can do. Consider the number of people coming, and then costs for things such as your lodging, car rentals (if necessary), plane tickets (if necessary), gas, food, shopping, and activities. 

It may be difficult to get an accurate picture of these if this is your first trip, but based on Step 1 and your interests you can guesstimate. For example, I don’t tend to shop really much at ALL on my trips, as my interests are in food, hiking, and taking photos. So for me, my budget on shopping is extremely low (enough to cover that odd nick-nack or gift I get for a friend or family member).

You can think about the budget as a per day format (such as how much food per day might you spend) or a total (such as a plane ticket). I like to take the entire total and divide it by the number of days so I have a daily budget. This helps me then decide the quality of hotel and amount of restaurants versus grocery food I plan for.

Drive or fly?

You may go back to “budget” after this point, but maybe not. Your destination may require you to fly (such as overseas), or it may be somewhere you can drive but may not want to (such as from Indiana to Florida). 

The main reason to DRIVE if possible is to save on cost (no plane tickets or car rentals). 

The main reason to FLY is to save time.

So, depending on how long your trip is and your budget, you can decide on driving versus flying.

Pick your Destination

Now is the FUN part, where to go! Yes, I really do wait this far into the process to decide this. The decisions above will affect your options. Consider how much time you have for the trip and then how long you will spend travelling to/from, and that leaves you with how much time you have at your destination. 

Let's use an example of my trip to the Bahamas. We had a full 6 day trip planned; however, with the flights we basically lost the bookends in travel. That left us 4 full days of waking up and going to sleep at our destination. Now, of course, the bookend days of travel are still part of the trip and enjoyable, but not as much as having the entire day at your destination.

You may, at this stage, adjust your trip length if you are set on a certain destination.

PRO TIP - Try this hack out. Go to Entire in ONLY the airport you are departing from. Leave the destination and dates as they are ( it defaults to anywhere for a 1-week trip in the next 6 months). This will let you find the CHEAPEST flight options. You may start here first and that may influence your dates and destinations.

step three flesh out the big details

Step 3 - Flesh out the big details

At this point, you know where you are going. You know for how long. You know roughly your interests and budget. You are ready to go! WRONG! Far from it. Yes, you could leave on the fly up to this point, but you may end up being stressed by lack of the finer details to really enjoy your trip. You don’t want to be wasting precious and expensive vacation time with Google Searching what to do. Or worse, not having things to do when you get there and regretting your destination.

Research the big activities

Start researching the area you are visiting and making notes of places you want to go. Focus on the BIG activities that are essential. That may fill your itinerary, or you may research further into smaller activities. It is better to have more than you can do in case something falls through (such as being closed or too busy).

You can also note any particular hotels or lodgings you are interested in, depending on how important that aspect of your trip is.

When are you going?

You are in a good position to decide WHEN you want to go. Think about potential obstacles such as:

  • Weather - I like to Google annual weather trends for my destination and pick a time of year that has the type of weather I want.
  • Nature events - Make sure there are no particular concerns, such as forest fires or closures at parks you want to see.
  • Slow season - You may see when is most popular and consider avoiding that if you want to avoid crowds. This MAY conflict with your weather goals, and you have to balance that. For the Bahamas, we found the holiday season was the most popular and the best weather, but we pushed our trip back a month and found much less traffic but still very nice weather. Great compromise!

Now, your trip is really starting to feel fleshed out!

step four dig into the finer details

Step 4 - Dig into the finer details

With the plan nicely fleshed out, now go through and browse in the gaps (such as if you have an 8 hour drive from destination A to B and finding what is halfway that would serve as a good break).

Make an official list

You can start deciding very officially what hotel to stay at for which days (you may have many hotels if you are doing more of a road trip format). Consider having BACKUP hotels as well to be safe.

You can start making a list of local restaurants you want to try, or again, look at food options in between destinations. 

Check reviews and photos

Be sure to look at reviews and photos of everywhere you are going so that your expectations are met when you are there. I cannot emphasize this enough - That amazing photo/video you saw on social media or Google Images does NOT reflect very well at all what you will experience. Often, my wishlist is based on these images I find, but I find it best to dig much deeper into the reviews and photos online to see if I really want to go there.

Google Maps is your friend

I’m going to let you in on my newest obsession - Planning a trip in Google Maps. Start “saving” each destination in a list on Google Maps (or even multiple lists). I have one for restaurants, hotels, and activities. 

As you start getting everything “pinned” down (pun intended), you can get a better idea of what a good order is to complete the activities. You might find some go well together. This will help you plan each day out much more efficiently.

Last, I love using Google Maps to really find points of interest I would have NEVER found otherwise. That may mean searching “chinese food” in that area and really exploring all the options to find one you didn’t know about.

It may mean searching “Parks” to dig into each and every option and potentially find a great hike not on your list. 

Sometimes the best part of a trip is something off the main road that no one seems to talk about as much. This has happened to me on a trip to Michigan, where I discovered Canyon Falls. It was not on my list from lack of research, but simply a roadside park we found on our way. Because of that, there wasn’t as much time to spend there as I would have liked, which resulted in a second trip later that spent dedicated time around that park (nothing wrong with that either).

From that note, keep in mind that you can make a list of all these places but do NOT put pressure on yourselves to go to every single place on your list. 

Repeat after me - “This is a vacation, not work.” 

Accept that you won’t go to everything on your list. Think of it, in fact, as GOOD news when that happens. That means you have a reason to visit this destination again and it is now already planned!

step five make it official and prepare a checklist

Step 5 - Make it official and prepare a checklist

Alright, you made it! You know the why, where, and when! Now you can make it official!

Start booking

Confirm the when with all going, making sure work is all sorted out for you being away. Put it on the calendar and call. It. Official!

Do the fun process of officially booking hotels, flights, and car rentals. I advise doing these all at once so if there are ANY hiccups you can make adjustments if necessary. These 3 things above are the most important items to ensure a reservation.

Make a Travel Checklist!

This part, I know surprisingly, I love. I have a travel checklist of things to pack or to DO before leaving. Mine is broken down into three sections:

Items to Pack

This list is very helpful and I use the SAME list for all trips, so it is constantly changing/improving over time to be more inclusive. Every time I have a trip and think “man I should have brought that”, ON the list it goes. Think clothing (casual, fine, coats, swim trunks, spare socks, etc…), bathroom supplies (shower, toothpaste, sunscreen…), technology (laptops, chargers…), trip information (itinerary, tickets, reservations…), safety (especially if hiking; bandaids, bear spray perhaps, those magical water straws in case you run out of water…), and odds and ends (one recent addition to our list is a microwavable plate for heating up leftovers - often not available and we found ourselves always adding a plate to our collection each trip).


The second section are things you don’t want to forget in advanced of your trip, meaning not just the day before but further out (such as 1 to 2 weeks).

This list tends to be short but can be stuff like doing a fresh computer backup, making sure you have any necessary sitters coordinated (for pets or children), or setting up your mail on Hold (a great idea so the USPS holds your mail until you come back and you don’t have to worry about it).

TO-DO’s the day of/before:

Last, the things you want to remember to do the night before and morning of your trip. It SUCKS to forget a little detail that can be essential - Like “did I close the garage door?” A simple checklist makes everything easy.

I have about a dozen things on my custom list. Think about things like:

  • Having your luggage fully packed
  • Do you have a security system, lights, and blinds set up a certain way while you are gone (perhaps timers for lights or plants that need blinds at least partially open).
  • Pets - Make sure they are fully set up with food, water, and (for cats at least) a nice clean litter
  • Electronics - NO reason to leave everything running, so you can shut down and unplug (for safety) your computers, TV’s, consoles, etc…
  • Set an alarm - Make sure your alarm is set and ready to go for when you have to be up (as a trip usually has a start time not matching to your normal routine)

The list may seem like a lot to make at first, but pop it into Google Docs, work on it over time, and it will be a life saver for each trip. Keep it up to date and print it out 2 weeks before your trip so you can start checking things off.

There it is. That is my official guide to planning a trip, from someone who both LOVES to travel and LOVES to plan.

Comment below what trip YOU are most excited about for 2022 and beyond!


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About the Author

Nicholas Klein

Founder and visual artist, specializing in all aspects of a businesses presence from imagery and video to graphics and web. A graduate of IPFW with a Bachelor in Fine Arts, Concentration Photography as well as an Associates Degree in Business. His personal photography works are focused on landscape, travel, and aerial photography.

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